Last week, I returned home after taking 9 flights, 3 rental cars, and 1 ferry in the last 30 days. As I write that sentence, it hits me how exhausting it was (and how delusional I was to book that amount of travel, in hindsight!)

Vacation is a true privilege, and travel for pleasure even more so. And yet even in my immense gratitude for that privilege, I cannot deny the deep depletion that only shuttling to and from airports can initiate.

I’m ironically more tired after my vacation than before.

The fatigue was obvious to me last week. My focus was like the sputtering sprinkler in our back garden: Trying to spray haphazardly at everything but also not getting at any one thing fully in particular. All my internal gears grinding, not gliding, against each other, trying to find some rhythm.

I found myself tempted to plan another vacation, this time more relaxing, of course…

But that too is a farce. I remember coming back from my honeymoon, a few years ago — likely the most relaxed and truly recharged I’d ever felt on a trip — and finding the reentry into work like a slap in the face. The whiplash of changing context so quickly, from barely checking Slack for a few weeks to facing a mountain of DMs and to-dos once I returned. It was disorienting.

Yes, I had rested, but I sure as hell was not recovered.

In reflecting on all of this, I’ve realized: Vacation, travel, time away from work, no matter how relaxing or non-relaxing it might be, is simply that — time away. True restoration comes in our orientation when we return.

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Someone much wiser and thoughtful than me once remarked that the reason we go away from work and travel is usually not just pure escapism or needing to turn “off” etc. But in fact, it’s usually to learn something. To gain some distance on your life as it was, and to find a different point of view. A new perspective.

To learn that the flamenco music you heard in Granada rekindles your interest in dusting off your old guitar. Or to have the conversation with your mom in the kitchen childhood home in Rhode Island reminds you why you’re extremely partial to stargazer lilies.

Or, as I did recently, you revisit your old high school and realize it’s smaller than you thought… and that a lot of things you thought were important then were also much smaller as well.

This perspective, this capture of a new angle, a new discovery is, in a way, sacred. It likely couldn’t have come about any other way. It anchors into us, and then expands, like a growing seed, nourishing other parts of us.

Take note of this, and dare to widen the aperture and bring that new perspective into your work life. Ask yourself: What can I look at differently today?

Perhaps it’s the project that you felt needed to be solved in one way, actually might have another way of tackling it. Or the direct report you were very frustrated by before you left on this trip, you now see a different approach to try in your conversation.

For me, personally, I came back from this most recent vacation and changed up some staffing in our company in a healthy way, that I’m not sure I would have done with as much conviction, prior to this.

The power of the time away isn’t necessarily the experience in itself, but the new vantage point we gain and can apply once we return.

If we don’t expect renewal, we can perhaps find what is even more rare: Perspective.

I hope you find a slice of that perspective as I did, in writing this for myself.

-Claire

If you resonated with my writing this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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If you found this helpful and you’re looking for ways to deepen your growth as a leader, here are ways you can work with me, Claire, directly:

• 🧭 Explore 1:1 executive coaching with me personally, as you navigate a new leadership role or new organizational dynamics. (I’ve had the privilege of coaching leaders at Apple, Uber, and fast-moving organizations, and have helped over 50,000 managers grow through Canopy’s trainings.)

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on this very topic of coaching + developing your team.

• 🚂 Partner with me to roll-out a leadership training program for your managers.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

If you find my writing helpful, please consider sharing with a friend or colleague who you think might enjoy as well (and so also subscribe yourself, if you haven’t already!)…

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When you ask the question, “How can I help?” to your team, what’s the most common response you hear back?

Usually, it’s some variation of:

“I'm good.”

“Can’t think of anything.”

“Nothing, really.”

Perhaps there really is nothing that we as a leader can do to help.

But even if that were the case, you’ve likely felt the same frustration I have: You’re reaching out your hand to help someone out, but all your hand is grasping is air. You want to help as a leader but aren’t exactly sure how — even when you ask the question directly to your team.

Here’s the irony: The very question, “How can I help?” often doesn’t help much at all.

When we ask it, we unintentionally create more work for the other person. All of a sudden, they need to scan their to-do list, imagine your availability and context, then figure out what's appropriate to suggest. Many feel awkward about directing tasks to their manager or simply don't know what to ask for.

So, what to ask if we do want to be helpful? Instead of creating unintended mental load, we can proactively anticipate their needs by asking targeted questions.

Here are 24 other questions you can start with and ask instead:

Vision + Priorities

• Am I giving you enough information to do your job well?

• Would you like more or less direction from me right now?

• Do you feel clear on where we're headed and why?

• Are there any priorities I can clarify for you?

Work Style

• What part of my communication style makes your job harder than it should?

• Is there a decision I've made recently that you disagreed with—or didn't understand?

• What's something I could stop doing that would make things easier for you?

Support + Load-Balancing

• Do you feel like you're spread too thin right now?

• Is there anything I could take off your plate this week?

• Have I been mindful enough of timelines and bandwidth?

• Would it help to reprioritize anything?

Coaching + Development

• What aspect of your role would you like more coaching on?

• Are there any skills you've been wanting to build but haven't had time?

• Is there a challenge you're facing that we could unpack together?

• What's a decision you're stuck on that we could talk through?

Work Conditions

• Am I interrupting you too often with meetings or requests?

• Do you feel like you have enough focus time to get real work done?

• Is there any tool, resource, or system that's making your job harder than it needs to be?

Team + Dynamics

• Are there any relationships or team dynamics that have felt tricky lately?

• Is there a conversation we haven't had yet that we probably should?

• What's something you wish people talked about more openly on the team?

Efficiency + Frustrations

• What's one thing that's been frustrating you the past few weeks?

• What are your biggest time-wasters right now?

• What's something you wish we did more efficiently as a team?

The next time you feel the urge to ask, “How can I help?” pause and pick one of these questions instead. You may find the answers more helpful, more actionable, than you previously imagined.

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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If you found this helpful and you’re looking for ways to deepen your growth as a leader, here are ways you can work with me, Claire, directly:

• 🧭 Explore 1:1 executive coaching with me personally, as you navigate a new leadership role or new organizational dynamics. (I’ve had the privilege of coaching leaders at Apple, Uber, and fast-moving organizations, and have helped over 50,000 managers grow through Canopy’s trainings.)

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on this very topic of coaching + developing your team.

• 🚂 Partner with me to roll-out a leadership training program for your managers.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

If you find my writing helpful, please consider sharing with a friend or colleague who you think might enjoy as well (and so also subscribe yourself, if you haven’t already!)…

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Arguably the hardest thing to do as a leader isn’t telling someone they’re underperforming, giving feedback on a touchy subject, or even firing someone — it’s doing any and all of those things when you’re also friends with the person. 

When you’re friends, things get, well, complicated.

You have history. This person has been through thick and thin with you. They know what you’re really like after the Zoom call has ended. They laughed at your jokes before you’d gotten your fancy “Director” title.

You have a shared outside-of-work life. You see them on weekends at the tennis court. You regularly call them up to go for a run. Perhaps your kids even go to the same school.

You likely have mutual friends — a friend circle, who you might regularly hang out with. So you’re not just applying your own self-judgment to the situation: You anticipate the judgment of others you care about, too.

This inevitably colors your leadership. Not necessarily worse or better, just different. Imagine if this person you were leading were someone else. Someone who didn’t know you in college, who didn’t participate in the same soccer league as you on weekends.

This difference is sometimes what makes delicate situations especially hard: When you need to tell your friend they came unprepared to the meeting, or when you need to tell your friend they didn’t get that promotion.

The good news is, being an effective leader and being friends with someone doesn’t have to be as daunting as it seems.

At the core, when we’re managing friends, there’s one thing to keep in mind…

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Two roles, two approaches

The most helpful grounding point is this: The role of a leader and the role of a friend are two distinct roles.

To remind yourself of this, ask: What is the true purpose of a leader?

The true, ultimate purpose of a leader is to help a group of people (a team) accomplish something together that an individual typically couldn’t achieve alone. A leader exists to make that end outcome happen.

Now, I want you to consider: What is the true purpose of a friend? Is it to “accomplish” anything? No, no — I think most of us would say that a true friend is someone who supports us no matter what, who brings us joy and laughter, who help us feel good.

A leader is there to help the team get something done. A friend is there to help you feel good. Those are different things.

And that’s precisely why combining the two roles is so challenging.

It also underscores this truth: If we want to be a great leader and a great friend, we need to avoid conflating the roles. Instead, we need to keep them distinct and clear — and know which role we’re operating from, and when.

Here are a few ways to do that…

“Can we switch gears here?”

One of the trickiest parts of leading friends is figuring out when one role ends and the other begins.

Let’s say you saw your friend (who’s also your direct report) over the weekend at a basketball game. Monday morning rolls around, and you realize they’ve missed a critical deadline. You know you need to hold them accountable, just as you would anyone else — but it feels weird when you were just swapping stories 24 hours ago at Chase Center.

What do you do?

You acknowledge that the roles are shifting: That you’re now at work, and stepping into your role as a leader.

A simple phrase to signal this shift is: “Can we switch gears here?”

In this example, you might say:

“Hey, now that we’re back at work, can we switch gears here? I noticed we’re overdue on this deadline. Can we figure out how to move this forward so we can deliver on it as soon as possible?”

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“I know you value that we can have an honest conversation”

One of the most beautiful, incredible aspects of friendship is the inherent trust that is built in. When you’re friends with someone, you trust them to have your back, to look out for you, and to have your best intentions in mind.

Because of this trust, you should in fact feel more empowered to have a difficult, honest conversation with your friend. They already trust your intentions — and so when you’re in the leader role, you’ll want to affirm that.

You might say:

• “I know you value that we can have an honest conversation…”

• “I know you trust me to give you real feedback…”

• “I value that I can be super frank and open with you…”

I know many of us fear saying the wrong thing and negatively affecting or hurting our friendship in a work environment — but if we can lean in and highlight the trust that is already there, then we mitigate that risk almost completely.

“The work requires…”

I once worked with a CEO who had a co-founder who was a close friend of his. While they were trying to recruit and hire employees for meaningful, senior roles, the CEO noticed that his co-founder would show up, unprepared and ask questions that were “off script” and led the candidate is a totally different direction than what the interview was supposed to focused on.

“I don’t know exactly how to steer my co-founder back on course because (1) he’s my co-founder, not my direct report, and (2) he’s a good friend of mine and I don’t want to hurt his feelings,” this CEO told me.

Here’s what I shared with the CEO: The quickest path to course-correction is to focus on what the work itself requires, not on what you think the person is or isn’t doing. When you anchor your request in the needs of the work, the project, or the company, people who care about those things are more likely to adjust.

In this case, the company requires top-level talent — and that means interviews need to be tightly edited and focused, rather than sprawling and unpredictable. When the CEO communicated this to his friend, the co-founder, he almost immediately changed his behavior in the next interview.

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“Can I put my ‘friend’ hat on?”

The nature of duality is that it is indeed two-sided: Sometimes, we must inhabit both roles at once, and some situations require that we switch our roles.

I worked with a senior leader once who needed to let their direct report (a close friend of theirs) know that they didn’t get a promotion. Stomach in knots, the senior leader just couldn’t imagine how they’d be able to share this information with a straight face, knowing that their friend had tried their very best and would be gutted by this news.

I understood. In moments like this, both roles are called upon: Leader and friend.

Here’s what I recommended to the senior leader: Deliver the news professionally and clearly, as you would for any team member. Then, when you want to show empathy as a friend, name the shift.

A helpful phrase to do this could be: “Can I put my ‘friend’ hat on?”

You might say:

“You weren’t selected for the promotion this time. The feedback I received was [insert reason]. I know you gave it your all, and I believe more opportunities will come. That said… can I put my ‘friend’ hat on? Ugh. This freaking sucks. I’m so sorry.”

This way, you honor your role as a leader by calmly and fairly sharing the difficult news — while also creating space to show up as a friend and honor your friend’s experience.

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You don’t have to be everything everywhere all at once

I love that we have friends in the workplace. I personally know the feeling of working alongside close friends — it makes the time at work richer and more rewarding. Yes, it can also feel a little more precarious, a little more sensitive... But to me, that’s a signal we care. We care about these relationships.

And with that care comes clarity: You don’t have to cram the role of “leader” and “friend” into one voice, one moment, one interaction. You can choose which one you need to step into, which hat to wear, when the situation requires.

They are two roles. And when you treat them as such, you’ll show up as both a better friend and a better leader.

-Claire

If you resonated with my writing this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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In case you missed ‘em, here are two other recent pieces I wrote to help support your team’s performance (whether or not you are close friends with each person 😅)…

If you found this piece helpful and are looking for deeper guidance as a leader, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics for leaders including “Avoiding Leadership Pitfalls” and “Giving Difficult Feedback Well.”

• 🚂 Partner with me to roll-out a leadership training program for your managers to avoid key mistakes such as being overly nice and hard performance conversations.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well…

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Underperformance doesn’t hit like a tidal wave. It creeps up slowly, like the gentle rise of water along the shoreline. Often, you only notice once the water level has shifted.

You notice a team member who isn’t quite their normal self. It’s the small things: They are typically early to meetings and they’ve been late to the last few. Usually the first person volunteering ideas, now they stay quiet. They are close-to-flawless when knocking out to-dos and all of a sudden you start to see errors on even basic tasks.

It’s not necessarily a disastrous slip in performance — but that’s what almost makes it more precarious. You’re not sure if you’re seeing just a temporarily blip on the screen, or the first indicators of a larger nose dive to come. You’re concerned that tolerating the so-so performance might devolve into perpetual underperformance… and the project you’re working on right now can’t afford that right now (or, ever, really).

It would almost be easier to address if they had completely blown a project or missed a critical deadline. But these smaller, subtler issues feel trickier to bring up, especially with someone who has historically done well.

You’re concerned about appearing nit-picky or “hovering.” Worse yet, you’re worried about seeming insensitive, especially if you later discover a deeply personal issue affecting them. (No one wants to be the leader who criticizes an employee’s performance just after they’ve learned their dad’s cancer is back.)

If you find yourself nodding along here, I get it. There’s a part of you that should applaud that instinct: It’s beautiful that you care deeply about your employee’s experience. Your first impulse is understandably to avoid rocking the boat unless absolutely necessary.

However, if we truly care about our team members, it’s essential to speak up compassionately when we notice changes. We’re not rocking the boat — we’re ensuring it’s still headed in the right direction. The sooner you discuss these concerns, the better. Addressing performance early gives them a genuine chance to correct course, which may be the most compassionate act of all.

You’ll want to ask questions that open up dialogue without projecting assumptions about the cause. This isn’t an interrogation or a probe into their personal life. Instead, create space for them to share openly about what’s affecting their performance, allowing you both to collaborate proactively.

Here’s a starting point with the 9 best questions to troubleshoot performance:

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1. “How’s your energy level these days?”

This is a deceptively simple question that reveals what factors might be affecting their work, without pressuring them or assuming it’s one thing or another. We all show up to work each day with different energy levels, whether that’s an external factor (e.g., kids have been super sick lately, dog sadly passed away) or something related to the work itself (e.g., unclear on priorities overloaded with projects, need some support and training). But rather than butting in and brusquely asking, “Are you sick, or what’s bugging you lately?” this question helps them space to share what they feel like is responsible to share, on their own terms.

2. “How’s your workload and bandwidth lately?”

As leaders, we often check-in on the work itself, the timeline, the deliverables — but we forget to check-in on the capacity that our team members have. Do they have space to hold all stuff in the first place, or has too much been piled on? This is particularly a great question to ask the person when you have sort of a silent soldier who usually says “all is fine” and they tend to take a lot on.

Then, I suggest kindly sharing a few observations of where you’ve noticed drops in the quality of their performance…

3. “I’ve noticed some things falling through the cracks lately, like [INSERT SPECIFIC EXAMPLES]. How might we work together to address this moving forward?”

It’s important to not pretend that things aren’t just hunky dory — that you’re observing some things different in their performance, specifically. Notice though I don’t say vaguely “some things have been missed”. You’ll want to be as specific as possible, so the other person isn’t confused by what you mean that you feel performance has dropped.

You’ll also notice that I didn’t sugarcoat and say “and it’s all okay,” nor did I linger on “you used to do things like this…” You’re focusing on the future, and you’re focusing on what can you BOTH together do differently. Because of course, as their leader, there are always things that you can and want to do better to support them.

Which leads me to my next suggested question…

4. “I’d love to be as helpful as I can here. Can I clarify priorities, take something off your plate, or provide more context on anything?”

You are offering something specific as a way to help — not just, “Anything I can do?” When you offer specifics, then the other person is more likely to take you up on your offer. You can always offer something specific: More prioritization, more context, taking something off a plate, connecting the dots on something, streamlining an initiative, communicating something to upper leadership, getting clarity on something.

If the employee is uncertain about why their performance is slipping, consider asking these questions that prompt deeper reflection…

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5. “What feels harder lately than it should?”

I love this question because it is really about the delta — the difference between what is expected vs. reality. You can identify performance blockers and friction points more easily this way.

6. “What feels clear or unclear to you?”

Oftentimes, the source of slipping performance has to do with something not being clear: The expectations aren't clear, the context isn’t clear, the stakeholders aren’t clear, the level of detail isn’t clear, etc. And so you’ll want to ask upfront, what does or doesn't feel clear?

Additional helpful questions you may want to ask, to get to the root cause of the underperformance…

7. “What part of the project feels draining for you right now?”

Identifying where the greatest burden in the project can often lead you to where the greatest opportunity for support is.

8. “What part of the project feels energizing for you?”

Understanding what motivates them can help realign tasks to connect to what they find energizing, and help to turn performance around.

9. “Do you have any pointers for how I’ve been communicating?”

Crossed wires and communication breakdowns often are obstacles to performance that we’re not always cognizant are present. As a result, you’ll want to invite their perspective on how communication between the two of you can be improved.

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Your conversation, of course, is with a real human — not a block of text. And so when you ask these questions, listen actively, thoughtfully, and kindly to understand what’s genuinely happening and how you can help.

You don’t want to assume reasons for underperformance, but you do need clear and upfront expectations. Respecting the person and respecting the work go hand-in-hand. You care about how this person is feeling and you care about the work getting done. These two things are not mutually exclusive. And your effort to get this conversation right is proof of it.

I look forward to hearing how the conversation goes.

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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Looking for more ways to strengthen your abilities as a leader? Here are ways you can directly work directly with me, Claire, CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on this very topic: “What To Do When Someone is Underperforming.”

• 🚂 Partner with me to roll-out a leadership training program for your managers that covers raising performance.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Would love to know what you think of this piece, and if you find it useful, please consider sharing this piece with a friend or colleague who you think might enjoy as well…

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Imagine asking someone to sprint uphill with a backpack on.

How loud should you yell to get them to go faster?

If you cringed at the visual — the idea of shouting at someone in an attempt to spur better performance — I'm with you.

And yet, as leaders, it sadly can feel like “the only option” when the pressure's on. When you're launching a new product, entering a new market, or facing an unfamiliar challenge, the instinct is to issue the directive and hope it gets done: “Go faster.” “Do more.” “Step up.”

But what's the alternative?

This is the question I've been hearing more often from senior leaders lately, especially those facing high-stakes moments at their companies. We need our teams to rise to the occasion… but many of our team members have never done what's being asked. We don't want to push people so hard they collapse under the weight.

It's a precarious position. Stakes are high, margin for error feels slim, and your team is tired.

How in the world do you raise performance, without burning people out in the process?

Why this is genuinely hard

The challenge of trying to increase team performance, especially if we feel the team is at risk for burnout, is particularly complex for two reasons:

1. The obvious answer doesn't work.

The default approach — telling your team to “step up” — is merely saying you want a thing to be true, without recognizing any of the complexity required for the thing to be true. For instance, imagine saying, “We need to double our customer outreach this quarter.” Even if that's true, it's insufficient. Directives don't address the complexity of the work, or the internal motivation needed to do it well.

Furthermore, reality always subverts even the best-laid plans. There will always be something different from the original directive, an obstacle, a shift in the market, that means you and your team will need to adjust and reorient. A team that is copy-and-pasting everything you say may inadvertently overlook a blindspot, and not get you the results you were looking for.

2. Too many tools, too little focus.

From OKRs to coaching frameworks to feedback rituals, there's no shortage of trendy hacks and techniques to try improve performance. But when used in isolation or applied like a checklist, they create noise, not progress. These tools are undoubtedly helpful, but often don’t address the underlying drivers of successful, sustained performance in the long-run.

And so, we end up asking ourselves as leaders: What should I actually be focusing on? And how do I know it's working?

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The 3 Pillars of Performance

I've found that focusing on these three pillars enables the highest likelihood of successful performance, while also honoring your team’s capacity so burnout can be minimized…

Pillar #1: The Shape of Success

What exactly does success look like?

But I’m not talking about generic metrics or motivational catchphrases. I’m talking about painting a specific, descriptive picture your team can visualize and aim for. Something tangible, something tactile.

For example, instead of “We need happier customers,” say:

“We'll know we're successful when customer complaints drop by 50% and positive reviews increase by 30%. Customers will proactively share positive testimonials in our support exchanges, rather than us asking for them. We’ll start to hear more and more new customers coming to us and saying they heard about us from a peer.”

This means you will want to answer these questions for your team:

• What will success look like?

• How will we know we're on track?

• What obstacles should we expect — and not be discouraged by?

• How does this connect to what each person finds energizing?

Try phrases like:

• “We'll know we're successful when…”

• “Here's how our customers' lives will improve…”

• “This directly impacts X, which I know you feel connected to…”

Then ask yourself:

• Have I been specific enough in describing what “great” looks like?

• Have I made it feel relevant to each person?

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Pillar #2: The Shape of Strong Performance

What does it look like to perform well day-to-day?

This is where many of us assume that it's self-evident what great performance looks like (“well obviously people should be checking in with other teams,” or “well obviously people should be sharing their progress each week”)…

And then we end up disappointed and frustrated by the quality of the work or lack of communication. Strong performance isn't only the outcomes: It includes the detailed day-to-day actions required.

For instance, instead of just telling people, “Be more proactive,” say:

“Please share one quick sentence in Slack about your project status at the end of each day, to help us catch bottlenecks early.”

This means you’ll want to define for your team:

• What actions and routines lead to success?

• What does excellent collaboration and communication look like?

• How does this align with how your team likes to work?

Use phrases like:

• “Day-to-day, here's what I'd recommend…”

• “Here's how I'd expect us to communicate and collaborate…”

• “I know you like X, and this aligns with that because…”

Then ask yourself: Have I described strong performance clearly enough? Or am I hoping they'll figure it out?

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Pillar #3: Connecting the Dots

You've defined success. You've described strong performance. But then reality throws cold water on our face. There will always be something unexpected that doesn't go 100% according to plan.

This is where you close the gap between what you've defined as success and strong performance, and the current reality of what's happening on the ground.

When YOU notice a gap:

Let's say you defined strong performance as “proactive communication with stakeholders,” but you're seeing team members working in isolation. Instead of saying “You need to communicate more” which is vague and could be interpreted in multiple ways, try:

“I noticed we've had some surprises in our stakeholder meetings that could have been avoided. I'm thinking we need more regular check-ins, but I may be missing something about your workflow. What's making it hard to loop people in earlier?”

Or if your shape of success included “delivering on time,” but the project is clearly running late:

“I noticed we're two weeks behind schedule. I know there may be factors I'm not aware of. What's going on, and how can we adjust?”

When YOUR TEAM notices a gap:

Equally important, if not more important, is to ask for the gaps your team sees. They're noticing things on the frontlines you might not be, and the quicker these gaps are identified, the quicker they can be addressed.

This could be your account manager realizing the client feedback process is adding two weeks to every iteration. Or your engineer notices that the database structure won't scale for the growth targets you've set. Or your project manager sees that the team is spending hours in meetings that could be async updates.

Don’t assume these gaps to be laid at your feet for you — you’ll want to directly ask your team about these gaps on a regular basis. Your team (understandably) won't always tell you on their own volition: Not because they don't care, but because they don't want to derail momentum or fear their input won't be valued.

Regularly ask your team questions like:

• What feels harder than it should be?

• What surprises you about how this project is unfolding?

• Where do you feel most and least confident?

• What seems like a waste of time or resources?

• How's your bandwidth and the workload feeling?

These shouldn't be one-off check-ins, something you ask once and then never ask again. They should be part of a weekly or biweekly rhythm. (I talk about this more in detail in the “Putting this into practice” section.)

And critically, when you hear these gaps, make sure to address them and do something about them. Or if it doesn’t make sense to prioritize closing the gap at this moment, at least say, “Got it, we can't do anything about that one for the time being, but thank you for letting me know.”

Otherwise, your team will wonder if you actually care about knowing the gaps in the first place.

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Why this works (and what it prevents)

Applying these pillars consistently helps prevent the most common failure modes of high-stakes projects. Let me know if any of these issues feel a little too familiar, you’ve seen them up close before…

• Building the wrong thing happens when the shape of success is unclear. Teams may execute strongly… but on the wrong priorities. By explicitly defining success, you steer effort toward what truly matters.

• Poor quality output arises when the shape of strong performance is assumed rather than articulated. People work hard but miss the mark on standards or approach. Defining strong performance helps your team calibrate to what “great” actually looks like.

• Lack of urgency emerges when the picture of success isn't connected to what your team personally cares about. Without that connection, even high performers may disengage. Tying success to what energizes them builds intrinsic motivation.

• Silent struggles take hold when feedback flows only one direction. Team members may notice obstacles, inefficiencies, or issues… but hesitate to share them, either because they don't want to derail momentum or they doubt their perspective will be valued. Encouraging two-way feedback, with specific questions, helps surface these insights before it's too late.

I’ve both seen and experienced each of these failure modes, personally. They’re pernicious — but avoidable. What I appreciate about the three pillars that I described above, though, is that they address each of these potential failure modes: When you have (1) clarity on success, (2) clarity on strong performance, and (3) connect the dots, you give a clear picture of what needs to be accomplished, raise the floor for performance, and create a feedback loop that supports alignment.

Putting this into practice

The key to making these pillars work isn't perfection: It's consistency. Here's how to weave them into your existing work rhythm without adding overhead…

Weekly touchpoints

During your regular 1:1 meetings, spend 10 minutes on:

• Reinforcing the Shape of Success: “Here's how what you're working on connects to our bigger picture...” or “I want to remind you why this matters, especially given what I know energizes you...”

• Shining a Light on the Gaps: This could be around how they’re tracking toward success and/or their performance: “One thing I wanted to bring your attention to…” or “Quick pointer here…”

• Connecting the Dots: Ask 2-3 specific questions about gaps they might be seeing:

  • “What's been harder than expected this week?”

  • “What would you change about how we're approaching this?”

  • “Where are you feeling stuck or unclear?”

The goal isn't to solve everything immediately. It's to create a rhythm where problems surface quickly instead of festering.

Monthly touchpoints

In team meetings, deeper 1:1s meetings, or performance conversations, carve out 20 minutes for:

• Reflecting on Strong Performance: “Let's talk about what great looks like on this project, day-to-day...” Share specific examples of strong performance you've observed, and ask what they're noticing about what works well. Also, point out where you see gaps between their current performance: “One thing I’m noticing…”

• Acting on the Dots: “Based on what you've all shared about X challenge, here's what we're changing...” Show that the feedback loop actually leads to action.

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An implementation mindset

Remember: You don't need to have perfect clarity on all three pillars before you start (especially if you’re also waiting on senior leadership to share further context with you, of if you’re already in the middle of a project). Begin with what you know, and refine as you go.

Start by asking yourself:

• If I had to describe success on our current project in two sentences, what would I say?

• What does strong daily performance look like from each person on my team?

• What gaps am I seeing that I haven't addressed directly?

Then pick one pillar to focus on this week. Perhaps it's painting a clearer picture of success in your next team meeting. Or it's having an overdue conversation about performance expectations with someone. It could even be simply asking, “What's harder than it should be right now?”

Again: The magic isn't in doing all three perfectly. It's in doing them consistently, so your team always knows where they're headed, what good looks like, and that you're paying attention to the reality on the ground.

Sprinting up the hill

None of us want to shout at our team.

If our team is sprinting up the hill with a heavy backpack, we want to make sure they know where they're going, and what to expect in the terrain. We want to help them carry the right weight, wear the right shoes. We want to check in on their stride, and give them information when things are changing.

That's what the three pillars do.

They offer clarity when pressure tempts us to default to control. They offer connection when urgency risks turning into burnout. And they offer alignment when effort alone isn't enough.

Rest your voice, lean on these three pillars, and the steep hill with that heavy backpack will become a lot easier for your whole team to climb.

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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Is raising performance top of mind for your team? Some ways you can connect with me directly, Claire, Founder & CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on this very topic: “Raising Performance””

• 🚂 Partner with me to roll-out a leadership training program for your managers that covers raising performance.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Would love feedback on this piece and if you find me sharing scripts like this helpful. And, do consider sharing this piece with a friend or colleague who you think might enjoy as well…

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Most feedback never gets said.

We hesitate. Overthink. Soften the edges so much that by the time the words come out, they barely land.

Or we convince ourselves we’re being “kind” by not saying it at all… when really, we’re just avoiding discomfort.

I’ve been there. I’ve written (and rewritten, woof!) feedback drafts that sit unsent. I’ve left meetings realizing I didn’t actually say the thing I meant to say.

But over time, I’ve learned this: The kindest, most respectful thing you can do as a leader is to be clear.

Not cruel. Not performatively blunt. Just clear.

In this spirit, I pulled together 7 of the most common situations where feedback often gets delayed, watered down, or avoided entirely. For each, you’ll see two versions:

• Version #1: The vague or sugarcoated way it usually gets said

• Version #2: What real, respectful feedback actually sounds like instead

These scripts are by no means perfect. But I hope they serve as a starting point for finding your own voice in giving direct feedback, rather than staying silent.

They’ve helped me say the thing, especially when it’s hard.

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Situation #1: The well-liked team member who’s underdelivering (and doesn’t know it)

They’re confident. Speaking up in meetings, friendly and responsive on Slack. They seem genuinely invested.

But… they consistently miss small details. The quality isn’t there. And when you give feedback, they nod along like they’ve already nailed it.

That disconnect is one of the hardest to navigate. You don’t want to deflate their confidence — but it’s time to close the gap between how they see their performance and what their performance is in reality.

Don’t say:

🔴 “You’re doing great — I just want to make sure you’re double-checking your work more closely.”

(It’s too soft. It reinforces their self-perception without helping them course-correct.)

Do say:

🟢 “You bring a lot of energy to the team and it’s clear people enjoy working with you. What I’m noticing, though, is that some of your recent deliverables have missed the mark — such as [INSERT A SPECIFIC EXAMPLE]. I want to be transparent with you about this gap, because I know your intentions are strong, but right now the execution isn’t meeting expectations.”

Clarity doesn’t crush confidence. It builds it, when it’s paired with care and specifics.

Situation #2: The infamous brilliant jerk

You know the one. The person who delivers results (arguably better than anyone else on the team). But they roll their eyes in meetings, and interrupt others. You get the sense they make people feel small.

And here’s the hardest part: They think they’re being efficient. Focused. Honest.

So they’re confused when their influence starts to wane, when other team members stop being as collaborative with them as they once were.

This is where being vague — or just asking them to “be nicer” — won’t cut it.

Don’t say:

🔴 “You have great ideas. I just think you could work on your tone a bit.”

(It’s too vague. They’ll either dismiss it or feel personally attacked.)

Do say:

🟢 “You’re one of the sharpest thinkers on the team, and I don’t want you to lose your influence. What I’ve observed is that the way you’re sharing feedback — like jumping in before someone finishes, or dismissing ideas quickly — is making teammates less likely to bring things to you. Your ideas are strong, but the delivery is inadvertently hurting you.”

You’re not asking them to be softer. You’re asking them to be more effective.

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Situation #3: The top performer who’s burning out

They’re still delivering, and reliable. But their energy is off. They’re more withdrawn, less proactive, perhaps even a bit cynical. You can tell they’re at the edge.

You don’t want to push — but you also don’t want to ignore the signs.

Don’t say:

🔴 “Let me know if you need anything.”

(This puts the burden on them to ask, and doesn’t name what’s happening.)

Do say:

🟢 “You’re still doing great work, and I’m grateful for that. I also want to check in on your bandwidth and capacity right now. You’ve seemed a little more tapped lately, and I want to make sure we’re not pushing past what’s sustainable. What’s feeling most heavy right now, and how can I help?”

Even top performers need someone who not only notices, but asks.

Situation #4: The “busy” contributor who isn’t making progress

This person is always in meetings, always working on something. But the strategic work is lagging. Deadlines keep slipping. And you can’t quite pinpoint where the time is going… It’s definitely not going toward what matters most.

Don’t say:

🔴 “You’ve been working hard. Just try to be a little more focused on the bigger picture.”

(It’s too abstract. And it reaffirms only the effort without addressing results.)

Do say:

🟢 “You’ve been juggling a lot, and I can see how much effort you’re putting in. What I want to name, though, is that effort and impact aren’t quite lining up right now. For example, [INSERT A SPECIFIC EXAMPLE]. I’d love to talk about how we can make sure your time is going toward the things that will really move the needle, not just the things that feel urgent in the moment.”

This isn’t about calling them out. It’s about helping them recalibrate.

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Situation #5: The high performer who’s coasting

They’re hitting their targets. The competent team member you can always rely on. But they’re no longer stretching themselves, or raising their hand proactively. They seem to be just… cruising.

At first, you’re relieved they’re not a problem. But over time, you’re concerned the stagnation will become the new norm, evolve into ambivalence, and set a precedent for the rest of the team.

Don’t say:

🔴 “You’re doing a great job — just wondering if you’ve thought about what’s next?”

(It makes it sound like they should be the one 100% bringing ambition to the table.)

Do say:

🟢 “You’ve been consistently strong in your role, and I think this opens up a beautiful challenge for you. You’ve mastered what’s in front of you. I’d love to explore what it might look like to push yourself into something new: Perhaps leading a new initiative or mentoring a junior teammate. How does that feel to you?”

Stretching isn’t just about promotions. It’s about deepening their growth and engagement in the team.

Situation #6: The manager who’s avoiding conflict or too hands-off

If you’re a manager of managers, you’ve likely seen this person on your team before: A well-intentioned leader. Someone who trusts their team, at their core, wants nothing more than to empower, not control, others.

But you notice their team drifting. Confusion and inconsistent results appear more and more often on the horizon. It’s clear a stronger leadership presence is missing.

Don’t say:

🔴 “You might consider being a little more involved — just to make sure nothing falls through the cracks.”

(It’s vague and easy to dismiss.)

Do say:

🟢 “I know you want to empower your team, and I respect that. What I’m seeing, though, is that the team seems unclear on direction and expectations, such as when [INSERT SPECIFIC EXAMPLES]. Your role isn’t just to support: It’s to steer. Let’s talk about what that could look like without feeling like micromanagement.”

You’re not hovering, when you say this. You’re helping to course-correct, when it matters.

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Situation #7: The well-meaning person who always has a (legit) reason things didn’t get done

Sick kids. Migraines. A tech issue. A teammate who dropped the ball. This person is not making excuses to be difficult. You believe them… But the work keeps slipping.

This is where compassion and accountability feel like they’re at odds. But they don’t have to be.

Don’t say:

🔴 “I totally understand, life happens. Just try to get it in when you can.”

(It unintentionally signals that expectations are flexible, even when they’re not.)

Do say:

🟢 “I know you’ve been navigating a lot, and I believe you’re doing your best with what’s on your plate. At the same time, I want to be honest with you: Your delays are affecting the team. So I’d love to figure out together, what needs to shift so that we can meet expectations more consistently going forward?”

This isn’t about questioning their integrity. It’s about keeping trust — and forward momentum — intact.

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Okay, now the hardest part…

You still have to say the thing, yourself 😅

None of these scripts will do this hard part for you: The emotional courage it takes to speak up when it would be easier to stay quiet.

But my hope is the above notes will help you feel just a little more ready. A little more equipped. A little more willing to trade perfection for progress.

If one of these resonated and you saw your own reflection in one of these situations, give it a shot in the coming days, even if it feels awkward or abrupt at first. Don’t wait for the timing to feel ideal. Just say the thing. (And feel free to read this piece if you’re a self-identifying nice person, in advance.)

Remember: Clarity isn’t cruelty. It’s what’s required for good leadership. And it’s what helps teams — and people — ultimately grow.

– Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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If you’ve always wanted to get better at delivering difficult feedback, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics that help leaders with communicating clearly, including “Executive Communication” and “Giving Difficult Feedback Well.”

• 🚂 Partner with me to roll-out a leadership training program for your managers to help them master hard performance conversations.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well…

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“What in the world am I supposed to offer them?”

A senior leader said this to me recently — bewildered and stumped about what to do.

They had a high performer on their team, someone who delivered consistently exceptional results, and their quarterly check-in with this person was around the corner. In most settings, this would be the obvious moment where the leader would praise their top performer and offer them some kind of promotion.

But their organization isn't scaling right now. It's stable (which in today's market conditions is its own victory), but it means there's no new rung for the direct report to climb, no title change on the horizon, no significant raise in the budget.

The leader confessed to me: “I know I can't offer something I can't give. But I'm also super worried that if I don't offer something, I'm going to lose this person.”

It's a sentiment I've heard across many companies I've been working with. With economic uncertainty, flattening hierarchies due to AI, and tightened budgets, the traditional “work hard, move up” promise feels increasingly hollow. Yet we still need our teams to be engaged, not just passing time until the market improves.

So what do we do when the standard playbook of promotions and raises is temporarily closed?

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An instinct that backfires

If you're in this situation, typically the first natural reaction is to avoid the topic entirely. You kick the can down the road and skip the “growth conversation” part in your quarterly one-on-one meeting.

You convince yourself that you're being humane: Why remind people of what you can't give them? Why set expectations you can't meet?

But avoidance creates a vacuum that people fill with their own narratives: “They don't value me,” “There's no future here,” and “I'm stuck.”

So then, you might try a different tactic: Vague reassurances about “when things pick up” and “future opportunities.”

Unfortunately, this is worse. When you offer hazy notions that might never materialize, you create false hope rather than genuine clarity.

You need something different. What I've observed through my work with thousands of leaders is that when traditional advancement is off the table, we need to change the conversation entirely. Not with platitudes about “growth mindset” or generic development plans, but with something more fundamental and surprisingly more powerful.

Beyond the promotion proxy

Most career conversations center around promotions because they're convenient shorthand. Tangible, visible, easy to explain. But they're also mere proxies for what people truly seek.

Think about your own career for a moment. When you've wanted a promotion, what were you really after? Status? Certainly. Money? Often. But dig deeper and you'll usually find something more fundamental: You sought a sense of mastery, autonomy, purpose, recognition, challenge, and perhaps even security.

The promotion is simply one pathway to these deeper needs — and when that pathway is blocked, we need to find others.

The secret isn't finding alternatives to promotions: It's uncovering what promotions were alternatives for in the first place.

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A different framework when promotions aren't available

After working with leaders who've faced this exact challenge over the past decade-plus, I've developed a different approach to career development that holds true even when promotions aren't on the table:

1. Uncover the real drivers (not just the career aspirations)

Skip the standard “Where do you see yourself in five years?” Instead, try questions that get to underlying motivations of your direct reports:

• “What parts of your work make you lose track of time?”

• “When have you felt most energized and fulfilled in your role?”

• “If money and titles were off the table, what would make your work most satisfying?”

In one company I worked with, when a leader asked these questions to their high performer, it revealed something crucial: What she really craved wasn't the next title but deeper expertise and external recognition. The promotion was purely her assumed path to those things.

This shift in understanding changes everything. When we see that a team member craves expertise and recognition rather than simply the next role level, completely different options emerge: The leader in this situation offered their direct report ownership of a tough, new project and presenting it to the rest of the company — and it was something that the top performer later remarked was “a highlight of my career.”

2. Create growth within roles, not just between them

Most career development focuses on preparing people for the next role. But the richest growth often happens by expanding and evolving current roles.

For each team member, try to identify:

• Which aspects of their role can be deepened

• Which new dimensions could be added

• Which parts could be shed to make room for growth

For example, if your top performer is seeking expertise and recognition, you might map out how they could:

• Take ownership of the most technically complex projects

• Develop thought leadership content that would build their industry profile

• Mentor more junior team members, solidifying their own knowledge

None of these require a promotion or budget approval, yet all push your team member toward genuine growth.

3. Connect individual work to larger impact

When traditional advancement is limited, people often lose sight of how their work contributes to something meaningful. They feel stuck in place, spinning their wheels.

Counter this by constantly connecting day-to-day tasks to broader impact:

• How does their work affect end customers?

• How does it influence company results?

• How does it create value beyond the immediate deliverables?

One leader I work with took this even further by instituting monthly “impact conversations” where they explicitly discuss these connections. For people craving purpose, this creates meaning even when titles aren't changing.

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4. Engineer recognition beyond advancement

Promotions often signal public acknowledgment of value. As a result, without them, we need to be intentional about creating other forms of recognition.

This goes beyond casual “Good job” comments dropped in Slack. It means:

• Creating formal opportunities to showcase work to leadership

• Facilitating cross-team visibility so peers can see the work they're doing

• Finding external validation through client interactions or industry participation

For example, for your team member, you could arrange for them to present their approach at a client workshop and/or lead your department's knowledge-sharing series — both providing the expert recognition they crave.

5. Build skills with tangible milestones

Without promotion timelines, development can feel nebulous and never-ending. Counter this by creating concrete skill development plans with clear checkpoints.

For instance, you can work with each team member to identify:

• 2-3 specific skills to develop over the next six months

• How you'll know they've made progress (concrete deliverables)

• How these skills serve both current performance and long-term growth

These become your focus in one-on-ones, giving a sense of forward movement even when organizational advancement isn't available.

The questions that actually matter

The framework above transforms career conversations from your employees asking, “When can I move up?” to questions that drive engagement regardless of advancement opportunities:

• “How can I achieve mastery in areas that energize me?”

• “Where can I have meaningful impact that I care about?”

• “How can I gain more autonomy over my work?”

• “Where can I get recognition for my contributions?”

Focus on answering these questions together with your team member. With one leader I worked with, these questions led to a development plan with a key performer that had nothing to do with their next title and everything to do with what actually drove their engagement. Six months later, despite no promotion in sight, the employee told the leader that he felt more invested in his role than ever before.

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The unexpected advantage of constraint

There's an uncomfortable truth I've come to appreciate: Sometimes, the absence of traditional advancement creates space for more meaningful growth.

When promotions are readily available, they become the default metric of success. Development becomes transactional: Check these boxes, wait your turn, move up.

When that expected path is unavailable, we're forced to look deeper. To understand individual drivers for what motivates people, rather than assuming it's the new title. To consider each person's development as personal to them, rather than copy-and-paste. To view growth as something within the role itself, not just between roles.

This isn't meant to sugarcoat tough realities. Limited advancement opportunities create real challenges for sustained motivation when the worker market is as competitive as it is. But they also push us toward a more nuanced understanding and deeper respect for what our team members may actually care about.

Start the conversation you're not having

If you're avoiding career conversations because you don't have promotions or raises to offer, you may be missing an opportunity to address what your team members truly need.

You may want to try this: In your next one-on-one, acknowledge the elephant in the room…

“I know we're not in a position to offer promotions right now. But that doesn't mean your growth isn't important. I'd like to understand what aspects of your work matter most to you, and how we can create meaningful development even within these constraints.”

This honesty creates space for a different kind of conversation — one that might reveal opportunities for engagement and growth you hadn't considered.

Because while we can't always offer our teams the next step on the ladder, we can help them find meaning, mastery, and forward movement right where they are. And sometimes, that's what they were really after all along.

In the end, your most valuable currency as a leader isn't titles or compensation packages — it's your ability to see what truly drives each person on your team and create pathways to those deeper needs, regardless of organizational constraints.

-Claire

If you found my writing this week useful, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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If you’re looking for more ways to coach your top performers, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 🌳 Partner together to create custom trainings for your senior and frontline leaders to help them coach their top performers and enable team growth, even if promotions aren’t on the table.

• 📣 Invite me to deliver team keynotes and workshops at your next offsite, remotely or in person, on topics such as “Growth Conversations” and “Coaching Top Performers.”

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you with coaching your top performers. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

This week, I’m reacting to something I read the other day — would love to hear what you think in the comments, too. And, do consider sharing this piece with a friend or colleague who you think might find the piece interesting as well…

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The other week, Uber employees exploded in anger at their CEO during an all-hands meeting. But what caught my attention wasn’t the pile on Uber — it was the painful reminder of a lesson many leaders, myself included, inevitably face:

The hardest test of leadership isn’t giving — it’s taking away.

Uber’s senior leadership team recently announced they were rolling back certain employee benefits, notably increasing mandatory in-office days and raising eligibility for their popular month-long sabbatical from five years to eight. Employees nearing their five-year mark weren't grandfathered in, leaving many feeling betrayed. One employee's comment particularly resonated with others:

“How is five years of service not a tenured employee? Especially when burnout is rampant in the org.”

The anger spilled into the press, turning a private internal dispute into a public spectacle.

Reading this story, I felt deeply for the employees worn thin. This sabbatical felt like a rare recognition of their hard work — only to have it abruptly deferred, seemingly arbitrarily.

I also imagined that senior leaders likely didn’t enjoy making this decision. Driven by challenging realities of market conditions and financial pressures, these are arduous decisions, stressful if not haunting. And usually, they’re chosen as the best option from grim alternatives.

Yet I do believe Uber's situation didn't have to spiral into such backlash. If you feel like you have to take something away from your team, there are worse and better ways to do it.

A few notes on a better way…

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Be transparent about what’s truly at stake.

Why now? Why not before? There's a reason why Uber’s leadership team decided that now, not say two years ago, was the time to change the company's benefits. Uber’s CEO shared how the company needs to go from being “good” to “great”...

But what does “good” to “great” actually mean? What’s really at stake? For example:

• Is it about financial stability?

• Avoiding layoffs?

• Positioning for long-term growth?

Transparency about the gravity of the situation doesn't scare employees — it respects their intelligence. Without context, tough decisions feel arbitrary and unfair.

Communicate what's being gained — not just what's lost.

When you take something away, it's going to cost you. But you do it because you feel like there's something to gain.

In Uber's case, it was clear what the cost was. But what was the gain? Senior leadership could have clarified what they were hoping to achieve:

• Will reduced benefits mean greater job security?

• More resources for critical projects?

• Enhanced long-term opportunities?

Based on the reaction shared publicly, from the employee perspective, it felt like all pure cost to them — and nothing to be gained. They were given no other reason to feel differently.

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Offer a sliver of choice, even when some choice is being taken away

Resentment builds not when you’re just taking something away — it’s when you’re removing a sense of autonomy that people have. And that removal of a sense of autonomy, a sense of control, can in fact be sometimes more infuriating than the loss of the thing itself.

Offering choice — even the smallest sliver you can imagine — is most helpful in these situations. Even when you’re faced with the tightest of constraints, there is often some small semblance of optionality or flexibility you can provide. For example, specific to Uber’s sabbatical benefit in question, you could:

• Grandfather in people within a certain time range of meeting the five-year requirement.

• Allow alternatives, like choosing between benefit options (e.g., opt-in for the eight-year sabbatical redemption mark or a pay raise or a leveling or growth opportunity)

• Provide some flexibility for those eligible for the sabbatical to rotate on timing, so not everyone takes it all at the same time

Even the most minimal of optionality can inject some sense of agency.

Plain old heart ‘n empathy.

Take a moment to put yourself in the shoes of the Uber employee who’d already booked their sabbatical:

“I’ve worked so hard. Felt like I’ve given the company my best. This sabbatical was a few weeks out. The trip was booked, I’ve made plans with my family. And then, all of a sudden, it’s torn out from under me and I’m told I need to wait a few more years.”

My sense is that this was not a scenario the leadership team had internalized. They likely had not embodied what it might actually feel like to have something taken away from them. It’s easier to think: “Well I've never taken a sabbatical, but here I am not complaining. We're lucky to even have this as an option. People are entitled if they want to complain...”

This is of course my own projection — I'm not in the heads of the Uber senior leadership team. But I did notice the CEO's reaction to the angry employee: “it is what it is.”

When I hear that phrase, I can almost see his shoulders shrugging, arms held up.

“It is what it is, it's not my problem...”

That's apathy — as we all know, the antithesis to empathy.

This is what employees reacted to. This is why employees were so angry. This is why someone leaked audio and memos around the meeting with CNBC: They felt this lack of empathy. They felt they weren’t being treated as people anymore.

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Now of course, there are other factors beyond what I listed above that dictate how well your team receives you taking something away. For example, if you regularly are not treating your employees with respect, than no amount of giving choice is going to help.

Yet, Uber’s unfolding highlights an important reminder for all of us:

How we implement difficult changes matters as much as the changes themselves.

When leaders have to make painful decisions, the effort to minimize harm isn’t optional — it is the essence of leadership, itself. We must re-root in the humanity of our decisions as much as possible, and remember as leaders the degree of direct impact we have on the quality of other people’s lives.

Sure, we all want to avoid the negative PR that Uber is bearing. But, above all, I hope what we want most is to make sure we’re not causing undue harm to others.

Even when we have to take something away, we can still honor the humanity of the people we work alongside.

-Claire

If you resonated with my writing this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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If you’ve made difficult decisions in your org lately and are hoping to integrate some of the practices I mentioned, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 🌳 Partner together to create custom trainings for your senior and frontline leaders for easing and mending organizational friction points: For example, “Communicating Difficult Decisions” and “Leading Through Change and Uncertainty.”

• 💡Consider inviting me as an advisor to your HR and/or L&D teams as you navigate large-scale organizational change and introduce / recover from difficult decisions.

• 🌿 Use Canopy, our lightweight leadership learning app, as a reference point in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you through times of uncertainty and difficult decisions. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Eager to hear any and all feedback on my writing. And, do consider sharing this piece with a friend or colleague who you think might enjoy as well…

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Recently, several leaders have asked me: “How do I get better at strategy?”

“Strategy”— I wince at that word. It’s evolved into one of those all-encompassing buzzwords attached to virtually anything business-related requiring forethought.

Strategic planning. Strategy session. Strategic objectives.

I'm reminded of a CEO who kicked off quarterly “strategy” meetings by distributing 15 projects to his team with 12-week deadlines, and then told them: “Go reach for it!”

But what he issued wasn’t a strategy — it was a to-do list, plus a half-hearted attempt at a motivational pep talk.

A few years later, I learned that the company sadly had filed for bankruptcy. They hadn’t been able to adapt to the changing demands of the market, and their competitors had gained ground. I reflected on the CEO’s to-do list and pep talk that was prepared each quarter: What was touted as a “strategy” hadn’t addressed any of the specifics of the challenges in the market, and most importantly, how to address those challenges. And it cost the company everything.

My hope is this fate isn’t met by other leaders. When we’re tasked with “figuring out the strategy” or “getting good at strategic thinking,” we shouldn’t jump straight to OKR-setting mode or planning tactics or aspirational speeches. Nor should we use the word “strategy” as a broad attempt to justify the goalposts we feel like we need to go after…

Effective strategy dictate what goals, tactics, and messaging we pursue — not the other way around.

With this, I compiled my thoughts. From my research on strategy (see my list of recommended books on strategy below), as well as my own direct experience and what I’ve seen firsthand from leaders I’ve worked with, I wanted to share my observations here:

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Centering on a definition

As consultant and scholar Richard Rumelt writes in his seminal book Good Strategy/Bad Strategy: “The core of strategy work is always the same: discovering the critical factors in a situation and designing a way of coordinating and focusing actions to deal with those factors.” This means…

Strategy is:

• Identifying the most critical challenge in a situation

• Addressing this challenge with some kind of coherent approach

• Having coordinating actions focused on overcoming this challenge

Strategy is not:

• A catchphrase (“Whatever it takes.”)

• A vision (“Helping our customers live happier lives.”)

• A mission (“To be the market leader in our industry.”)

• A goal (“We'll reduce our costs by 20%.”)

Strategy is a distillation of what the exact challenges are, keying into what is most critical, and then coming up with an approach and set of coordinated actions to address the specific challenges with that approach.

This very definition of strategy actually denotes what is important to do well if you want to be good at strategy…

What to focus on

Single out the specific challenge

A strategy is not just saying you want things to be better. It's about understanding what's going on: Deep observations of the market, the competition, potential driving forces for change. It's about investigating underlying problems and the root-cause of those problems. After all, a strategy is only helpful for a problem if you’re precise about the problem you’re solving.

When Netflix shifted from DVD rentals to streaming, they didn't just identify a vague notion of “digital disruption” as their challenge. They specifically realized their core challenge was: “How do we maintain our customer relationships when physical media becomes obsolete?” This specific identification of the market challenge led them to invest in streaming technology and original content rather than trying to extend the life of their DVD business.

Key question to ask yourself:

• “What is the true, critical challenge here that we're looking to solve?”

Inspect the dirty corners of the mirror

It's impossible to actually know the real challenges if you're not honest about all of the factors involved. This means having a desire to look at information that you may not want to hear. To peer at your own self-reflection and/or your company’s reflection when the mirror isn’t quite so pristine. A relentlessness for rooting out information from all crevasses. An openness to hearing things that are not always optimistic.

Consider Kodak's story. Despite inventing the first digital camera in 1975, they avoided confronting how digital photography would impact their profitable film business. This reluctance to face an uncomfortable truth cost them their market leadership and eventually led to bankruptcy when digital photography became mainstream.

Key questions to ask yourself:

• “What information or scenario have I been avoiding?”

• “What's the one thing I don't want to think about that I should probably think about?”

• “Anything I've found myself glossing over, postponing, or ignoring altogether?”

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Be hungry for the insight

The most effective strategic leaders are ones who are always looking for some kind of hidden insight. Something that's obvious at first glance, but in reality much more difficult to execute on. Or, the insight is derived from a slight adjustment to the current frame or approach. This hidden insight could also be a practice pulled from another analogous industry or leverage of a certain power and competitive advantage.

Airbnb famously demonstrated this principle well. Their founders spotted an opportunity others missed: During conferences when hotels were fully booked, people would pay to stay in someone's spare room. This insight — that unused living space could be monetized — led to a platform now worth billions. All from a hidden, unlikely insight.

Key questions to ask yourself:

• “What's something others are overlooking?”

• “Why hasn't this been done before?”

• “How do we get leverage here?”

Work with the obstacle, not against it

If a strategy is in fact a set to overcome a specific challenge, then we need some kind of maneuver(s) to go around the obstacles. We can't just butt our heads against it. We must acknowledge the constraints as reality — rather than pretending we can brute force our way, or hope we get there by the strength of our ambition. The obstacle cannot be ignored.

Toyota's development of the Prius illustrates this principle well. In the 1990s, they recognized that while fully electric vehicles were the environmental ideal, significant obstacles existed — battery limitations, costs, and infrastructure. Rather than waiting for these to be solved or just pretending these obstacles didn’t exist, Toyota asked: “What would have to be true to reduce emissions with today's constraints?” Their answer was the hybrid system that became the Prius in 1997 — the first mass-produced hybrid vehicle ever. It was a direct result of working with their obstacle, not against it.

Key question to ask yourself:

• “What would have to be true?”

Seek rhythm and coordination

What makes strategy work well, including the execution that flows from it, is if the actions themselves are coordinated. If the actions are connected in some way, and building on each other, they reinforce each other. And if they reinforce each other, that in fact makes the strategy stronger.

Apple exemplifies this principle in how their ecosystem functions. Their hardware (iPhone, iPad, Mac), software (iOS, macOS), and services (iCloud, App Store) all reinforce each other. When they release a new iPhone feature, it typically coordinates with software updates and service enhancements, creating a rhythm where each component makes the others more valuable.

Key question to ask yourself:

• “Are the steps we’re looking to take coordinated with one another and work together to accomplish what we want to accomplish?”

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Simplicity is key

The best strategies are focused. They're not overwhelming. They're not unwieldy. Effective strategy cuts through complexity to find the essential path forward, making it easier to communicate and execute.

Apple is a perennially, classic example. When Steve Jobs returned to Apple in 1997, he found a company with dozens of overlapping product lines. His first strategic move was radical simplification — cutting the lineup to just four products (two desktops and two laptops). This clarity of focus allowed Apple to concentrate its resources on making those few products exceptional rather than spreading itself thin across many mediocre offerings.

Key question to ask yourself:

• “How can I keep things simple?”

Make a choice

The only way to keep things simple is to not do everything. There is real power in saying “no” — it opens up the space, energy, and resources to then concentrate on what you say “yes” to. In your strategy, you’ll want to make sure you’re not saying yes to everything, and actually turning your back on some things.

In-N-Out Burger exemplifies this principle. While competitors constantly expanded their menus with breakfast items, chicken options, and limited-time offerings, In-N-Out has maintained essentially the same simple menu for decades. By saying “no” to menu expansion, they've maintained quality, operational efficiency, and a cult-like customer following that values the consistency and focus (out-of-state friends of mine seek out In-N-Out first thing when they land in California).

Key question to ask yourself:

• “What am I / what are we saying 'no' to?”

These principles provide a foundation for effective strategic thinking. However, even with these guidelines, there are common traps that can derail even the best strategic intentions.

Let's examine what to watch out for…

Strategy pitfalls to avoid

1. Mistaking goals for strategy - Setting targets alone is the equivalent of setting stretch goals. You need a coherent approach for how you’ll achieve those targets, and a clear articulation of the problem you’re addressing that explains why you’re reaching for those targets in the first place. That’s strategy.

2. Analysis paralysis - Yes, you should gather data to help define the challenge and approach — but be wary of when it becomes the excuse for not yet deciding on what path to move forward on.

3. Ignoring implementation - Your strategy must meet reality where it’s at — and this includes the execution capacity of your team. Don’t forget this as a factor.

4. Following trends blindly - Especially in this age of AI, we’re eager to watch and mimic others closely out of fear of being “left behind.” But be prudent to not over-adopt what seems to be working well for others, without considering your own context first.

5. Refusing to adapt - Things change. And when your market conditions change, your strategy should change with it too.

Have you been following into any of these pitfalls? Here’s a quick self-check you can use to calibrate areas of growth for yourself…

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Quick strategy self-assessment

Rate yourself from 1-5 on each of these strategic thinking dimensions:

• How well do I identify the core challenge beneath surface problems?

• How comfortable am I confronting uncomfortable truths?

• How often do I spot insights that others miss?

• How effectively do I work within constraints rather than fighting them?

• How well do my strategic actions reinforce each other?

Your responses to these questions can highlight where you might focus your development efforts.

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But perhaps most importantly, you’ll want to keep in mind the following…

Immersion in the patterns

Above all, I've noticed that leaders who are best at strategy tend to be:

1. Rigorous in their search for information to inform an insight

2. Effective at distilling what is most important to form that insight

The ability to do both I wish I could tell you was as easy as just asking ChatGPT or reading this article — but in reality, these powers are only found through broad and deep exposure to frameworks. That is, the most strategic leaders have been receptive to numerous ways of doing something, they've seen the shape of many problems, they've learned about many people's different ways of approaching things and the outcomes. It's an immersion in patterns.

To help increase your exposure to these patterns, here are some further resources you can explore…

Further reading resources

For foundations of strategy:

• Good Strategy/Bad Strategy, by Richard Rumelt - Probably my favorite overall primer on strategy.

• Playing to Win, by A.G. Lafley and Roger L. Martin - A solid look at another framework for strategy creation.

For strategic thinking development

• Deep Dive, by Rich Horwath - A nice read on the specific mechanics of getting good at strategy.

• The Opposable Mind, by Roger L. Martin - More of a book on decision-making but still helpful for seeing alternate paths and options.

For competitive advantage building and understanding

• 7 Powers, by Hamilton Helmer - One of my favorite books on durable business advantages.

• The Innovator's Dilemma, by Clayton Christensen - A classic for a reason, I love this as a reminder for one of the most helpful and counterintuitive understandings of innovation.

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Returning to you

Remember that CEO who conflated a to-do list with strategy? His company's bankruptcy wasn't inevitable — it was the result of failing to identify and address their core challenge.

True strategy isn't about knowing everything or having perfect foresight. It's about developing the discipline to identify what matters most in your unique situation and coordinating your actions to address it.

As Rumelt reminds us: “Strategy is discovering the critical factors in a situation and designing a way of coordinating and focusing actions to deal with those factors.”

It’s your situation. It’s up to you to discover what is most critical.

You can start today: Take 15 minutes to write down what you believe is the single most important challenge facing your business right now. Not symptoms, not aspirations —the fundamental obstacle. Then ask: “What would have to be true to overcome this?” That question alone will begin to shift your thinking from tactical to strategic.

After all, strategy isn't just for CEOs or consultants — it's for anyone who wants to move beyond reactivity toward purposeful action.

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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If you’re looking to improve your own or your team’s strategic thinking, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics that help leaders with communicating clearly, including “Strategic Thinking” and “Strategy Translation.”

• 🚂 Partner with me to roll-out a leadership training program for your managers to help them coach and keep their top performers.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well…

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This email lands in your inbox at 9:43AM on Monday:

After some consideration, we need to implement a cross-functional AI-augmented human connection initiative across all departments immediately. Can you incorporate this into your team's OKRs for Q2 and pull together a plan by Thursday, for us to review?

-Your CEO

You stare blankly at the screen. The coffee next to you grows cold. The quarterly roadmap was just finalized last week. Your team is already stretched thin on three different priorities. Everyone’s already a bit paranoid of their jobs getting replaced by AI… And honestly, what does a “cross-functional AI-augmented human connection initiative” even mean?

Your eyes dart to the clock on your screen: In less than three hours, you have your team’s weekly sync meeting, and twelve team members will be looking to you for clear direction on what this means for their daily work. You've become the interpreter — responsible for translating this abstract vision into concrete action steps without revealing your own uncertainty.

Sound familiar?

As a CEO myself who has also trained thousands of managers who’ve found themselves in similar situations, necks sore from the proverbial whiplash, I feel deeply for everyone involved. These strategic pivots coming from upper leadership usually emerge from a prudent place: The CEO has seen genuine signals about market changes or competitive pressures that haven’t yet filtered throughout the organization…

But these seemingly out-of-nowhere directives wreck havoc on the frontline leaders who have to find a way to share them with the rest of the team — and implement them.

Your CEO’s good intentions doesn't make your job as the interpreter any easier. You still face the challenge of interpreting abstract vision into concrete action while maintaining your team's trust and momentum.

Let's talk about exactly how to do this effectively.

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Beyond parroting

The temptation after receiving a directive like “implement a cross-functional AI-augmented human connection initiative” is to simply repeat those exact words to your team. (That is what they told you, after all!)

But as you've likely discovered, simply parroting executive language rarely leads to meaningful action.

For your team to perform at a high level, they need to somehow internalize what needs to get done. You want folks to act with a sense of ownership, accountability, and proactivity.

After all, the best teams don't just follow directives from the top — they understand the underlying purpose and apply their own expertise to bring the vision to life.

Resonating with a directive, not just replicating it, is an approach that benefits everyone. The senior leader doesn't need to micromanage every detail. Instead, they can focus on demonstrating the shape of what “good” looks like and reinforcing why the work matters. Your team can also feel more freedom to try new ideas, push limits, and in fact come up with even better outcomes that the original directive dictated.

Then, something even more remarkable, and dare I say beautiful, emerges: Work becomes less externally dictated and more internally motivated. Intrinsic motivation arises, which is in fact the strongest source of motivation for anyone.

This is what we aspire to cultivating in our team, as leaders.

The question is, though of course, how do we do that amidst a handed-down senior-level directive?

Here are 5 steps for turning an abrupt and/or vague executive-level directive into team action:

1. Unpack the underlying intent

When executives issue broad directives, there's almost always a deeper strategic reasoning behind them. We must identify that underlying intent, if want any hope of our team internalizing that intent as well.

For example, when your CEO mentions an “AI-augmented human connection initiative,” they're likely responding to industry trends about balancing technological advancement with meaningful customer relationships. Perhaps they've spotted competitors leveraging AI while losing the human touch that differentiates your company.

But it’s hard to know exactly without asking :-)

As a result, instead of accepting the directive at face value, schedule a follow-up conversation with questions like:

• “Just so I can align on supporting the outcomes we want, what would things would look like if we were successful at this?”

• “To make sure we execute well on this, may I ask what market insights you noticed that prompted this new direction?"

• “To understand how we want this to fit together, how do you view the prioritization and alignment of this with our other current priorities?”

These questions help you understand not just what needs to be done, but why it matters. You’ll then get the context you need to make implementation decisions that align with the true intent of the directive.

You’ll also notice that I suggest a opening to these questions, such as “Just so I can align...” and “To make sure we execute well on this…” This preface gives your CEO context as to why you’re asking the question. You’re not trying to question their judgment or authority — you’re merely trying to gain the information you need to make things happen.

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2. Breakdown the abstract, ground in the concrete

Once you understand the underlying intent, your next challenge is to turn the abstract concepts into concrete steps your team can execute.

You may want to start by breaking down the initiative into its component parts. In the case of the example above:

• What does “cross-functional” mean in practical terms? Which departments need to collaborate, and how?

• What specific AI capabilities are we leveraging, and for what purpose?

• How do we define and measure improved “human connection”?

Then, you can begin to create some structure that connects high-level goals to specific actions. This might be the flavor of your company’s specific goal framework, such as OKRs. But just to illustrate a more framework-agnostic example:

• Goal: Improve customer sales and renewal through AI-human partnership

  • Action: Implement AI systems to handle routine inquiries and data collection

  • Action: Develop customer stewardship training program for support team members

  • Action: Create customer journey maps identifying key moments for human guidance

  • Action: Establish metrics that measure relationship depth, not just resolution time

Again, this is merely an example. The key thing here is to breakdown the abstract into components — and then find ways to ground those components into actions.

3. Connect to what’s compelling and relevant

It's one thing to share the actions and distribute the to-dos, but it's another for those tasks to actually matter and connect with your team. You need to find a way to make this initiative personally relevant and compelling to them — and non-threatening.

For instance, your customer support team might understandably worry that an “AI-augmented human connection initiative” signals the beginning of the end for their roles. Instead of brushing past these concerns, address them directly: “This initiative isn't about replacing you — it's about elevating your role from handling repetitive tickets to becoming true customer stewards and guides, especially during critical moments like onboarding.”

Connecting these dots won't happen automatically — not because your team isn't smart, but because there are so many signals in a company that if something isn't explicitly stated, it gets lost in the noise. You need to make these connections clear, relevant, and compelling.

Relevant means how this applies to their job and connects to what motivates them. For your support team, emphasize how AI handling routine inquiries creates space for them to develop deeper customer relationships and more strategic skills.

Compelling means it feels like it matters and is interesting. Something has to be at stake. People don't change their behavior unless there's a clear upside. The best way to make something compelling is to share concrete examples, numbers, and a vision of the future.

For example: “Once we implement this initiative, three months from now our support team will transition to spending 70% on personalized onboarding experiences and proactive customer success. A year from now, we'll have transformed our support team into a strategic consultative function with advanced skills in customer relationships for both new sales and retention — making your roles both more secure and more valuable.”

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4. Anticipate and preview how things will feel

As leaders, we sometimes focus so much on the strategic benefits that we forget to address how changes will actually feel day-to-day for our teams. All change includes natural friction.

With this in mind, anticipate what those friction points might be, and be transparent about what the journey will look like:

• The transition period: “For the first few months, you'll be doing double-duty — both handling some routine support tickets while also developing your customer stewardship skills. This might feel overwhelming at times, but we'll adjust workloads to make this manageable.”

• The learning curve: “Becoming true customer guides requires new skills in consultative communication, product expertise, and relationship building. We're investing in training programs specifically designed for this transition.”

• The changing metrics: “We'll be shifting from measuring ticket resolution times to tracking customer success metrics like adoption rates and expansion opportunities. This means your performance will be evaluated differently.”

• The emotional journey: “It's natural to feel unsure about giving up tasks you've mastered for new responsibilities that might feel unfamiliar. We'll celebrate small wins along the way and create opportunities for you to share your experiences.”

This level of honesty about the transition builds trust and resilience. Instead of glossing over challenges with vague promises about a better future, you're acknowledging that change is difficult while still maintaining confidence in the direction.

You might even explicitly project how their role might be impacted: “Here's what your typical customer interaction looks like today... and here's what it might look like six months from now as a customer steward.” This concrete visualization helps team members picture themselves in their evolved roles.

By anticipating and acknowledging the full range of experiences — from discomfort with new tools to excitement about more meaningful customer relationships — you demonstrate empathy while keeping the team focused on the journey ahead.

5. Consider your communication format

Remember that your team is bombarded with information from all directions. For any transition to resonate, you'll need to communicate consistently across multiple channels, each serving a different purpose.

For your AI-augmented human connection initiative:

• Team meetings: Use these for dialogue, not just announcements. Present a customer journey map showing where AI will handle routine inquiries and where human stewardship becomes critical. Leave time for questions and collaborative problem-solving.

• Visual roadmap: Create a simple timeline showing the gradual shift from traditional support to stewardship roles, with key milestones and training opportunities clearly marked.

• One-on-ones: These are crucial for addressing individual concerns. Some team members might worry about their technical abilities to work with AI, while others might question if they have the consultative skills for deeper customer relationships. Tailor your message to each person's specific situation.

• Peer learning circles: Establish small groups where team members can discuss their experiences during the transition, share tips for working with the AI system, and practice their new stewardship skills.

• Success spotlights: Use your team chat or email updates to regularly highlight examples of effective customer stewardship, creating visible models of what “good” looks like in this new paradigm.

Different team members will connect with different aspects of the message. Technical people might want to understand the AI's capabilities and limitations. Customer-focused folks might need examples of what meaningful stewardship conversations look like in practice.

The key is consistency in your core message: “We're augmenting your capabilities with AI so you can evolve into true customer guides, especially during critical moments like onboarding.” This should be the thread running through all communication channels, repeated often enough to stick, but varied enough to stay fresh and relevant.

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The most important aspect: Enrollment

The most important thing when translating senior leadership directives is remembering that for people to take action in a lasting way, they have to choose it themselves. They have to enroll.

As Peter Senge discusses in his work, shared vision isn't imposed — it's something people actively choose. Your job as a leader isn't to force compliance but to create conditions for meaningful commitment.

Let's return to that Monday morning email about the “cross-functional AI-augmented human connection initiative.” After following the steps above, imagine this conversation with a senior support team member:

• Before interpretation: “So... we're implementing AI. Does this mean half our team is getting replaced?”

• After interpretation: “Believe it or not, I'm actually excited about building our customer stewardship program. Having AI handle the basic troubleshooting and billing queries means I can finally develop those onboarding workshops I've been talking about for months.”

That's the power of effective interpretation. You've transformed a threatening directive into an opportunity that team members willingly embrace. You haven't just clarified what needs to be done — you've created a context that allows your team to see themselves as active participants in an exciting evolution, not passive recipients of an imposed change.

The next time you receive a vague directive from above, remember: Your role isn't just to repeat the message from above, or simply assign the to-dos. It's to create the context for your team to operate at their highest level.

And perhaps most importantly, be sure give yourself grace during this process. Even the most skilled interpreters need time to process sudden changes. Do take a moment to absorb the directive yourself before attempting to translate it for others.

I look forward to hearing how it goes for you.

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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If you’re looking for ways to help yourself + fellow managers translate and incorporate senior-level directives to your team, you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics that help leaders with communicating clearly, including “Effective Communication,” “Operationalizing Vision,” “Setting & Implementing Goals” and “Managing Up.”

• 🚂 Partner with me to roll-out a leadership training program for your managers to help them coach and keep their top performers.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well…

Subscribe now

Last year, I gave what I believed was thoughtful, effective feedback to a team member. This was his response to me:

“Claire, please don't be so nice about it. I want you to be even more direct — and don't spend so much time writing it up. That's a waste of time. Just tell it to me quickly, bluntly.”

I almost laughed out loud because of how marvelously helpful it was for me. It revealed an important truth: My “niceness'“ wasn't serving either of us.

How about for you?

If you've ever canceled a feedback meeting last minute because “now isn't the right time,” spent an hour crafting an email only to save it in “Drafts” in perpetuity, or found yourself nodding and smiling when you should be addressing performance issues — this article is for you. You might even have a mental list of conversations you know you need to have but keep pushing off week after week.

Your “niceness” isn't actually nice. It might be your biggest liability as a leader.

If you're nice, you typically fall into this pattern when giving feedback:

• You fear judgment: What if they think you're harsh, nit-picky, or unreasonable?

• You protect your “nice person” identity: You've naturally want to be liked (who doesn’t!) and are more comfortable avoiding conflict.

• You over-empathize: You imagine how hurt they might feel and talk yourself out of delivering the message.

• You downgrade the issue: “Maybe it's not that big a deal” or “Perhaps I'm overreacting” becomes your internal monologue.

The result? You either say nothing at all or deliver something that sounds suspiciously like praise:

“Keep doing what you're doing, just maybe consider...”

“This is good work, but when you have time...”

Then comes the confusion: Your team member hears something positive, continues the same behavior, and you're left wondering why nothing changes while your frustration silently builds.

This pattern doesn't just damage your effectiveness as a leader — optimizing for niceness actively harms the people you're trying to protect.

That's why nice people (I'm right there with you!) need to remember these crucial truths about feedback…

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This is your job.

Remind yourself that this is, in fact, a huge part of what it means to be an effective manager. The other person needs to know where they stand and where they can improve. If you don't tell them, they simply won't know and will continue making the same mistakes.

Think of it this way: If you hired a gym trainer who never corrected your posture or exercise form, would they be doing their job properly? Of course not. And so the same thing goes for being a leader. Providing regular, meaningful feedback is one of the core responsibilities of an effective leader.

When you withhold necessary feedback, you're essentially doing your job half-done.

The other person WANTS to know.

No one wants to silently suffer. Your team members don't want to look incompetent in front of others, and they don't want you to think they're incapable. They want to know what they could be doing better.

A 2014 study published in Harvard Business Review by Jack Zenger and Joseph Folkman found that 57% of people prefer corrective feedback to praise, and 72% said their performance would improve with more corrective feedback. It's more disrespectful to mince words or try to soften feedback because it implies that they can't handle it or don't have an appetite for hearing what they need to improve.

Early in my career, I once worked with a team member who was consistently making small errors in client communications. After months of gentle hints that weren't working, I finally had a direct conversation.

Her response? “Why didn't you tell me sooner?”

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Direct is kind.

If you really care about being nice, remind yourself that being direct is a form of kindness. It shows that you respect the other person enough to be forthcoming. That you've put in the thought and consideration to articulate exactly what you want to change. It also means you care enough to take the time to actually communicate openly with them.

The kindest thing you can do is be clear. Ambiguity creates anxiety, while clarity — even when challenging — provides a path forward. Consider this: Would you rather spend months wondering why you keep getting passed over for opportunities, or have one uncomfortable moment of truth that allows you to improve?

Here's how this works in practice…

🔴 Don't say: “The presentation looked nice! Maybe when you have some extra time, you might want to double-check some of those numbers?”

🟢 Say this: “The data on slides 5 and 8 contained errors that I had to correct before the client meeting. We need all presentations to be fact-checked before submission.”

🔴 Don't say: “I noticed the report was a bit delayed. No big deal, but whenever you can try to be more mindful of timelines...”

🟢 Say this: “I need you to submit reports by their deadlines. The last three reports were late, which delayed our team's analysis. What support do you need to meet Friday's deadline?”

(I have more tips for being clear in this article here.)

Recognize what you're trying to avoid/optimize for.

Often, as nice people, we hesitate because we don't want to be seen as “an asshole.” But this is actually a distraction from what's really happening. When we're overly nice, we're trying to please the other person and make them think favorably of us. In other words, we're prioritizing our reputation over telling the truth or having a hard conversation. We're optimizing for ourselves — rather than the other person. And that's inherently not a very nice thing to do.

Take a moment to ask yourself: “Who am I really protecting with my silence? The team member or my own comfort?” Research from organizational psychologists shows that this self-protective behavior often stems from our own past experiences receiving harsh feedback. We overcompensate by going too far in the opposite direction.

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You cannot control their reaction — but you can control your own preparation and execution.

The way to overcome the niceness that's holding you back is to come properly prepared — you can control this. You can come to the conversation fully prepared to give direct and kind feedback.

Before a difficult feedback conversation, try spending 5-15 minutes with this preparation:

• Write down the specific behavior that needs to change

• Note the impact this behavior has on work outcomes

• Decide on one clear request you'll make

Research has shown that leaders who prepare specific examples and focus on behaviors rather than personality traits report more successful feedback conversations and less emotional aftermath.

I talk more about how to prepare for giving feedback well here — but know that you can put in the upfront work.

Make sure to say the thing!

I remember the Co-Founder of Intercom, Des Traynor, telling me on a podcast we did together a few years ago, how he'd once written out feedback he wanted to give to an employee on a Post-it note. Then, he amped himself up for a difficult conversation... But after the conversation was over, realized he hadn't said the very thing written on the Post-it note 😅

Des, like so many of us, was betrayed by his own niceness.

It's easy to dance around the issue — but you absolutely need to make the clear, descriptive ask. You can absolutely share your intention and context for the feedback… But don't forget to say the thing. For example:

🔴 Don't say: “Just wanted to mention that clients sometimes like more detailed updates, so whenever you think it might be helpful, consider adding a bit more information to your emails.”

🟢 Say this: “Our client has expressed confusion about our project status twice this month. I need you to send weekly updates that include specific milestones completed, current challenges, and expected deliverables for the coming week.”

I've seen leaders firsthand spend 7 minutes of a 10-minute feedback conversation on preamble and only 3 minutes on the actual message. If you can't summarize your feedback in a single, clear sentence, you're not ready to have the conversation.

One way to do this is to make sure you have a “headline first” for all feedback. Start with the main point before providing context or examples. This way, you make sure you always say the thing.

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Perfect is not possible, and it's also not the goal.

Accept that you might flub. That you might accidentally add more words than necessary or use a tone that you didn't intend. But perfection isn't the goal. The goal is to give it your best. There's no alternate reality where things could have gone better or worse. There's only the reality you have, and it is your job as a leader to face it, address it, and do everything in your power to help support this person to be better – that includes giving feedback.

Countless research has supported that delays in feedback hurt performance and learning, especially around course-correction. A perfect message delivered too late is worth less than the good-enough message delivered on time.

Before your next feedback conversation, try this perspective shift: Ask yourself, “If I were in their position, would I rather hear this imperfectly now or perfectly never?'“

Re-read this when you need to

As a self-identifying “nice” person, I know I need to read this too. I needed to be reminded by the team member who told me, “Claire, please don't be nice about it. I want you to be even more direct.”

What I thought was kindness was actually making both our jobs harder. My carefully crafted, time-consuming “nice” feedback wasn't what he needed to improve.

Not every employee will be quite so welcoming or self-aware, but the sentiment remains true: People want clarity, not cushioning. They want a path forward, not protection from the truth.

The next time you catch yourself writing and rewriting that feedback email or rehearsing a conversation that never happens, remember: Your niceness isn't serving either of you. The truly kind thing to do is to say the thing.

After all, that's what you'd want someone to do for you.

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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If you’re hoping to become more direct (while not losing your kindness) as a leader, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics that help leaders with communicating clearly, including “Executive Communication” and “Giving Difficult Feedback Well.”

• 🚂 Partner with me to roll-out a leadership training program for your managers to help them coach and keep their top performers.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I periodically have spots upon up throughout the year — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well…

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“I'm in repair. I'm not together but I'm getting there.”

I've always loved this lyric from John Mayer. (He admittedly might have quite a bit to apologize for in his personal life!) Yet, the struggle he describes in this song — the pain of broken trust in a relationship — is resonant beyond just his own foibles.

Broken trust is an unwelcome reality that can reverberate in any relationship…including work relationships.

Trust is as fragile in the workplace as it is anywhere else. An announcement of layoffs that blindsides your team. A reorganization that leaves people cautious and questioning their future. A strategic pivot that seems to sideline the company's core values. Even a routine process handled poorly can fracture the foundation of trust you've spent years building as a leader.

When trust breaks, the silence in the room is deafening. Team members who once freely shared ideas now guard their thoughts. The energy that used to fuel a collectively confident “carpe diem!” is now frenetic and anxious. Collaboration gives way to self-preservation.

I've sat with leaders in these moments, watching them grapple with what feels like an impossible task. “How do I rebuild what's broken?” they've asked me.

Here's what I tell them: There is a path forward. After working with thousands of leaders, I've discovered that a window for repair exists — though, the window is often narrow and demands swift, intentional action. The journey to rebuilding trust isn't about quick fixes or surface-level balms. It requires fundamental shifts in both thinking and behavior, as a leader.

If you're ready to dig deep, let's dive in.

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1st Key Shift: Trust doesn't equal likability

After a major restructuring, one CEO I worked with immediately arranged an elaborate team retreat with premium perks and ample social activities. She was stunned when this approach made her team even more withdrawn.

Why? Because she was trying to solve a problem about trust with a solution about optimizing for likability. It's the wrong solution for the problem at hand.

When trust fractures, our instinct as leaders is to reach for what we think might curry a sense of likability or good will: Surprise bonuses, team-building retreats, positive compliments. But consider this: You can like someone without trusting them. And the reverse is also true… You can trust someone you don't particularly like.

Trust does not equate to likability. And so these remedies aimed to foster greater likability don't just fail — they often deepen the wound. When employees notice leaders organizing happy hours while avoiding difficult conversations about why trust was broken in the first place, it reads as inauthentic at best and manipulative at worst. The team's frustration grows because these gestures feel disconnected from the real issues at hand.

What you're attempting to repair is what scholars call "affective trust" — the emotional connection and rapport between people. While this is certainly one dimension of trust, when organizational trust breaks, the issue usually runs much deeper than whether people feel a personal connection with you as a leader.

The fundamental misunderstanding here is conflating rapport with reliability. Rebuilding genuine trust requires looking beyond whether your team members feel comfortable around you to whether they believe you'll do what you say you'll do… which brings us to our second key shift.

2nd Key Shift: Trust = Intentions matching actions

When a senior executive announced a new “collaborative decision-making process” but then made three major decisions without any team input the following week, the disconnect was glaring. What disintegrated wasn't personal rapport — it was the alignment between stated intentions and observable actions.

What's truly damaged when trust breaks is what researchers call “cognitive trust”— the fundamental belief that your words and actions align. At its core, your team needs to believe that what you say matches what you do. Trust erodes rapidly when people perceive a gap between these two elements: Intentions and actions.

Let’s take a look at how this has played out in real life…

I worked with an organization whose senior leadership team genuinely intended to help employees feel valued and heard. The company's stated commitment was that leadership would support team members and ensure their voices influenced decisions. However, when they implemented an aggressive performance management system without any context, people interpreted it as a thinly veiled excuse to eliminate staff and undermine even high performers.

This perception — regardless of whether it matched leadership's actual intentions — shattered trust throughout the organization. The critical fracture wasn't about whether people liked their leaders, but that they no longer believed the leaders' actions reflected their stated intentions.

To begin repairing trust, you must ask yourself this essential question: What was your original intention as a leader in the initiative that's causing distrust? And what specific actions might people be interpreting differently, as not matching that intention?

This gap — between how you intended your actions to be perceived and how they're actually being interpreted — is precisely where trust reconstruction begins.

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3rd Key Shift: Clarify intention, align actions

Once you've recognized that broken trust stems from misalignment between intentions and actions, the path forward becomes clearer. Rebuilding trust requires deliberate work on both sides of this equation.

The repair process isn't complex in theory, but it demands courage and consistency in practice:

Clarify your intention with transparency

Don't just restate your original intention — acknowledge where things went wrong. For example, "Our intention with the reorganization was to create more growth opportunities for everyone, but we failed to explain how these changes would benefit each of you." This vulnerability signals authenticity and opens the door to real dialogue.

Realign your actions to visibly match your intention.

Words alone won't rebuild trust. Every decision, policy change, and communication must reflect your stated intention. When you say employee well-being matters, ensure your next decisions prioritize it in visible ways.

The key is consistency across every touchpoint. One misaligned action can undo months of trust-building efforts. Think of trust as a bridge you're reconstructing: Each plank must be solid and secured before the next is added.

Remember that timing matters as well. In the wake of broken trust, your team will scrutinize your actions with heightened sensitivity. This vigilance isn't personal — it's a natural protective mechanism. Respond not with defensiveness but with patient, persistent demonstration that your intentions and actions are now in lockstep.

This alignment work isn't a one-time fix but rather a continuous practice that gradually rebuilds the foundation of trust. With each aligned action, you lay another plank to rebuild what's broken.

Applying this to real scenarios

With the gap between intention and action in mind, the process of rebuilding trust requires three steps:

1. Define your intention with personal honesty: Get clarity within yourself first about what you truly intended.

2. Identify the gaps: Recognize where actions didn't align with these genuine intentions.

3. Let actions do the talking: Implement visible changes that demonstrate your intentions, rather than just explaining them.

Of course, doing this in real life is much more nuanced and trickier than what any 3-step framework can capture. As a result, here are some scenarios as examples to help anchor you, as you consider repairing trust in your own team…

A Reorganization: Rebuilding trust after a structural change

Your team was promised clearer paths to growth and better collaboration through reorganization. Yet months later, confusion reigns and skepticism has replaced optimism. People are questioning if this was just change for change's sake.

Step 1: Define your intention honestly, with yourself

• Before involving others, ask yourself: "What was our true intention with this reorganization? Was it really about improving work-life for everyone, or primarily about efficiency and cost-cutting?" This honest self-assessment is crucial for authentic next steps.

• After grounding yourself in your own personal sense of clarity, you’ll want to also make sure you’re aligned with your leadership team on the genuine purpose of the reorg.

Step 2: Identify the intention-action gaps

Reflect on where the roll-out of the reorg may have contradicted your desired intentions. For instance:

• People’s roles remain unclear, despite promises of improved clarity around responsibilities.

• Frontline manager have been so frequent, it suggests disorganization, not strategy.

• Benefits of the reorganization remain theoretical for most employees — work currently feels harder to get done, not easier.

Step 3: Let actions do the talking

Rather than relying on lengthy explanations about how the reorg is “supposed” to work, implement visible changes that address the intention-action gaps. For example:

• Create and distribute clear role documentation that actually solves confusion.

• Establish stability in reporting structures with a commitment to consistency, and when another change might be anticipated in the future, and why.

• Focus on identifying and fixing specific pain points around workflow and cross-functional collaboration that the reorganization was meant to address.

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A Reduction in Force (RIF): Reassuring the remaining team

The difficult decision to reduce headcount has left surviving team members shaken. Backchannel conversations revolve around “who's next” rather than future opportunities. Productivity is suffering as anxiety rises.

Step 1: Define your intention honestly, with yourself

• It’s time to ask yourself some difficult questions: “Was this truly unavoidable? Was there anything in our control earlier, as a company, that could have prevented this RIF from happening in the first place? What was my (and our leadership team’s) primary concern — the business, the employees, or both??

• As painful as it might be to even consider these questions, they can help you cut through your own fog. The more real you can be with yourself, the more real you can be with your team. Your honest self-assessment will prevent hollow messaging later.

• Once you’ve let yourself be real with yourself on the intentions of the RIF, then of course align with your leadership team, with what your learnings from this are, going forward.

Step 2: Identify the intention-action gaps

Then, consider how the intention of the RIF to put the company in a position for long-term success may in fact contradict the actions surrounding the RIF. For example:

• Current messaging is forcibly optimistic and not reflective of the somber and hard decision this was.

• In hindsight, departures were handled too brusquely, in contrast with state company values.

• The workload that remains from departed employees and falls onto the lap of existing employees is in direct conflict with the company’s claims about valuing employees.

Step 3: Let actions do the talking

Demonstrate your true intention and values through concrete actions. For instance:

• Adjust communications to acknowledge the difficult moment and give current employees time to process the decision by extending or removing deadlines.

• Find ways to immediately reduce workload for teams on the remaining work, or communicate a clear plan for how the remaining work will be tackled.

• Make visible changes to company operations to ideally prevent a RIF in the future — or at the very least, changes to how RIF departures are handled in the future.

A Strategic Change: Realigning trust after a pivot

After years of focusing on one direction, your company has announced a significant strategic shift. Long-time employees are struggling to see how their expertise remains relevant, while others wonder if this is just another fleeting idea that leadership is over-excited about.

Step 1: Define your intention honestly, with yourself

• Ask yourself: "What is truly driving this change? Is it market conditions, competitive pressures, or something else?" This honesty ensures your subsequent actions come from an authentic place.

• After gaining personal clarity, then align with your leadership team.

Step 2: Identify the intention-action gaps

Reflect on potential contradictions of a strategic change that undermine trust. For instance:

• The new strategic direction could seem like a departure from the original company values.

• Past patterns of strategy shifts further contributes to a sense of inconsistency about the company’s long-term vision.

• Statements on the new direction are abstract and don’t give any concrete clarity on roles, projects, prioritization for teams.

Step 3: Let actions do the talking

Show through tangible actions that the new strategic direction underscores your intention. For example:

• Give specific examples of projects of how the new strategic direction in fact supports the original company values.

• Create visible connections between past projects and new priorities — how what was worked on before and what will be worked on in the future is all building toward the long-term vision.

• Provide write-ups and documentation of the exact implication for team around what will now be prioritized, how projects will change, and the impact this has on each person’s role.

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Rebuilding a bridge you didn't break

“But what if I didn't cause this?” I hear you. When you’re not the one who precipitated the rupture in trust, you are merely left with the destruction in the aftermath. It’s not your intention and actions you’re dealing with — it’s someone else’s.

Your hands are tied. Whether you're implementing a reduction in force you didn't plan or announcing a reorganization you just learned about, you’re also likely upset about these changes as well.

In these moments, focus on what you can control:

• Your authenticity matters. Be honest about what you know and don't know. Your team respects candor more than corporate lines that ring hollow. For example, you can say: “I don’t have the information but will do my best to get it.”

• Your sphere of influence is holds weight. While you can't change organizational direction, you control how changes unfold within your team. Create clarity around new expectations and provide psychological safety for honest conversations. For instance, you might say: “In the coming weeks, I’d love to have a 1:1 with each of you so we can discuss what you’re thinking and feeling in light of these changes.”

• You're a translator, not just a messenger. You help your team make sense of chaos by connecting larger changes to their daily work — perhaps your most valuable contribution during trust breakdowns. For example, you might say: “As disruptive that this new change is, the work you do day-to-day still matters to our customers in this way…”

Remember, too, that you're also experiencing this breach of trust. Your own relationship with senior leadership may be strained. Acknowledge this reality for yourself rather than suppressing it, and so you don’t put more pressure on yourself that you’re already bearing.

You cannot single-handedly rebuild what's broken at the organizational level. But within your sphere of influence, the alignment between your own intentions and actions can create an island of trust in a sea of uncertainty.

Sometimes, that island is enough to keep your team afloat until larger repairs can be made.

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Getting there

“I'm not together, but I'm getting there.”

The lyric continues to resonate: “I’m getting there.”

You are getting there. You are reading this newsletter. You are thinking about ways to strengthen trust in your team and mend what was broken, even if you weren't the person who broke it. And in that effort, in your courage you gather to be honest about your intentions, and in the discipline you muster to align your actions with your intentions, you make more progress toward trust than ever before.

As the cliche goes: It's a journey, not an event. Some days, the trust gap may still feel impossibly wide. Other days, you'll glimpse the emerging structure of what you're rebuilding. Both experiences are part of the process.

The value of repair doesn't come from certainty that you'll fully succeed, but from the conviction that the relationship is worth the effort. Your team doesn't expect perfection — they just need to see that you're genuinely committed to the work of rebuilding.

Your team will be grateful for that commitment.

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

If you’re keen to rebuild trust in your organization, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 🧠 Consider having me advise you and/or your leadership team on navigating trust post-RIF, reorganization, or strategic direction.

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics that help leaders with rebuilding trust, especially post-reorganization or acquisition or strategic change.

• 🚂 Partner with me to roll-out a leadership training program for your managers to help with building and restoring greater team trust.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day, that include primers and reminders on how to build trust in a team.

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well…

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I've worked with hundreds of teams, and the #1 request that team members consistently make of their leaders surprises me every time.

No, they don't wish their bosses were more warm toward them.

No, they don't wish they gave them more compliments.

What they actually want is much simpler:

“I really wish my manager was more clear.”

They want to know where they actually stand in terms of performance, rather than some weird mind voodoo about “growth opportunities.”

They want to know exactly what they could be doing better rather than some vague, passive-aggressive notion of “be more collaborative” or “take more ownership.”

They want to know if their ideas are actually being considered and would prefer an outright “no, not this time,” rather than some blanket corporate speak of “we're processing everything...”

Above all, what teams crave is clarity:

• “I wish I knew where I stood”

• “I wish I knew what I could exactly do differently”

• “I wish I knew where we were going with the overall strategy”

• “I wish I knew what the rest of the team was working on and what is going on”

They want to know what you actually mean, rather than what you think they want to hear.

It's harder than it looks

The irony of clarity? It sounds simple but is arguably the hardest leadership skill to master.

One reason it's so difficult is that, sometimes, we ourselves aren't clear on what we're trying to communicate. We're vague about company vision because we haven't fully defined it yet. We say "keep doing what you're doing" because we haven't properly assessed if someone is meeting performance standards.

But there's another challenge: Being clear requires work. Real work. You need to determine not just what to say, but how to say it in a way that's simple, compelling, and something the other person will internalize. Whew. No wonder it feels easier to postpone these conversations…

Yet, postponement means the conversation likely never happens at all.

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4 steps to be more clear

To make clarity feel a little less effortful, here are four critical steps you can return to whenever you need to communicate something important:

#1: Set up a topic marker

Signal that something important is coming.

One of the hardest parts about being clear is signaling to the other person that you're about to say something worth listening to. Give them a heads up so they don't mistake your significant message for “just another thing I should be roughly aware of.”

For example, when you want to be clear about a person's performance:

🔴 Don’t just say this: “It'd be great if you could try this next time.”

🟢 Try saying this: “Let’s take a moment to check in and get on the same page about your performance.”

Or, when you want to be clear about team direction:

🔴 Don’t just say this: “Here's what we're working on.”

🟢 Try saying this: “I want to emphasize what our overall direction is and why.”

You'll notice in the ineffective examples, you're rushing into talking about the topic without first signaling its importance.

Set the stage. Flag their attention. Mark the topic.

#2: Have a headline

Make your main point concise and unmistakable.

Just as journalists craft headlines to grab attention, your key messages need a clear headline. The most effective ones are short, direct, and free of corporate fluff.

For instance, when you want to be clear that someone is not meeting expectations:

🔴 Don’t say this: “I was thinking it might be good if we could tweak a few things and maybe you could consider trying some different techniques the next time around.”

🟢 Try saying this: “Currently, you are not meeting expectations.”

And, when you want to be clear that the org is changing strategy:

🔴 Don’t say this: “I think there might be some things that the leadership team ends up thinking through and processing to decide whether or not we should maybe change some things potentially.”

🟢 Try saying this: “We are shifting our strategy.”

Notice how the “Try saying this” headlines mirror your actual intent without softening or obfuscating. Your team craves this concreteness, rather than vague phrases that evaporate and hold no meaning.

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#3: Describe the specific impact

Connect the dots between your message and its consequences.

Don't leave your team guessing about how your feedback or information affects them. Make the connection explicit to prevent assumptions.

For example, when you want to be clear about poor performance:

🔴 Don’t say this: “I think it'd be great to clean up some of those mistakes in client communications, as I think it looks sloppy.”

🟢 Try saying this: “The mistakes in client communications impact how likely a client is to renew — so it directly affects business revenue.”

Or, when you want to be clear about a shift in strategy:

🔴 Don’t say this: “We're evolving and trying to improve our recurring sales.”

🟢 Try saying this: “This new strategy means that, as a team, we need to prioritize existing customers rather than new customers.”

“Sloppy” is vague. “Recurring sales” could mean a lot of things. When you focus on describing the actual impact, your message becomes more concrete and actionable.

#4: Invite commitment

Ask for specific, actionable next steps.

For change to happen, you need the other person to commit to specific actions. Don't leave your conversation hanging — extend an invitation that creates mutual accountability.

For instance, when you want to be clear about performance:

🔴 Don’t just say this: “It'd be great if you could take more ownership.”

🟢 Try saying this: “Could you be the owner on writing the to-dos, prioritizing them, and then distributing them?”

When you want to be clear about the overall team performance:

🔴 Don’t just say this: “I'd like us to move with a sense of urgency.”

🟢 Try saying this: “Could we aim to give ourselves at least 2 days of buffer before the deadline?”

The invitation for commitment comes in the form of a direct ask that allows the other person to make their own decision and take ownership.

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Reinforcement through repetition

Clarity isn't a one-time event but an ongoing practice. Remember that your team is bombarded with information daily — what seems clear to you may be missed entirely by others.

Share important messages through multiple channels:

• Follow-up performance discussions with written summaries

• Reinforce strategy changes in team meetings and written communications

• Review key points in one-on-one meetings to ensure understanding

There's a leadership platitude about, how as a leader, you should communicate things enough times that you’re get sick of hearing it yourself. In this case, it's a platitude that gained prominence because of how true that actually is.

Nothing should be said just in passing. Intentional repetition helps ensure your message is actually received.

Upfront investment, long-term payoff

I want to acknowledge that this takes effort. Even with the four steps I've shared, you'll have to put in a bit more work upfront and be more conscious and intentional about what you're saying.

But while clarity may require some work initially, it actually saves tremendous time and energy in the long run.

Hours spent clarifying misunderstandings, managing disappointment, or dealing with missed expectations — clarity prevents these issues before they start.

Keep these four steps in mind to make clarity a bit easier to incorporate, day-to-day:

1. Set up a topic marker

2. Lead with a headline

3. Describe the specific impact

4. Invite commitment

It's an upfront investment, but there's a long-term payoff. And when you do choose to invest, you're able to give your team what they truly crave more than anything else: The clarity to know where they stand, what success looks like, and how they can get there.

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

Share

If you’re hoping to become more clear + adept in your communications as a leader, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics that help leaders with communicating clearly, including “Effective Communication” and “Communicating Change Well.”

• 🚂 Partner with me to roll-out a leadership training program for your managers to help them coach and keep their top performers.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I’ve had a few spots open up for 2025 — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well…

Subscribe now

You overhear someone apologizing to someone else:

“I'm sorry if you interpreted things that way.”

It seems like a real apology at first listen. (They are saying they’re sorry, after all!)

But the qualifier “if” suggests that perhaps the other person could've interpreted things differently. They’re subtly implying it's on the other person, not themselves.

Whether or not they intended to, they’re absolving themselves from responsibility.

This is what I call a “non-apology” — an attempt to subvert your true culpability in a situation. Usually, it's not because we're ill-intended, but because we’re trying to keep a semblance of forward-momentum with our team.

For instance, I sometimes find myself issuing a non-apology when I'm in a rush (“Let's just focus on the future...”) or when I don't want the team to dwell on a mistake I made (“This was out of my hands...”).

Initially, a non-apology may seem innocuous. But it's death by a thousand cuts — the more you use them, the more it deepens the hurt. The shifting of blame can even become a cultural norm, and infect the entire organization.

One CEO I worked with would buffer mistakes with phrases like, “We're working on it...” without admitting any error or fault on his fault. A top-performing employee confided to me how this drove him “crazy,” because it meant errors would constantly be brushed under the rug, stalling the team. He eventually left the company.

To avoid a similar fate for each of us as leaders, I've identified several common types of non-apologies that we should be conscious of…

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Types of non-apologies that create resentment

Deflecting Non-Apologies

These non-apologies actively push blame away from the leader:

1. "Mistakes were made" - The passive voice acknowledges error but doesn't assign responsibility.

2. "I was advised by my team" - You're subtly shifting blame to unnamed others.

Minimizing Non-Apologies

These non-apologies downplay the significance of what happened:

3. “This was an unforeseen circumstance" - Sometimes, of course, things are unforeseen. But be wary of using this in your apology as it makes it sound like unforeseen equates to unavoidable.

4. "I regret if anyone was offended" - Similar to the example shared at the beginning of the piece, this frames the problem on others' reactions rather than your actions.

Distraction Non-Apologies

These non-apologies attempt to shift focus away from the mistake:

5. “Let's focus on moving forward" - Be wary that this attempts to shift attention away from accountability toward future actions. You can encourage folks to move forward, separately — not attached to your apology.

6. "This is a learning opportunity" - Be mindful in how you use this phrase, as it can sound like you're ignoring any harm caused under the guise of "growth."

Escapist Non-Apologies

These sound like real apologies but contain subtle escapes:

7. "I take full responsibility, but..." - The "but" usually negates the responsibility you may have claimed to take.

8. "This has been taken out of context" - When you use this as part of your apology, it sounds like you're trying to wriggle out of accountability: That everyone else is misunderstanding or misrepresenting what happened.

(Note, if something in fact has been taken out of context in a meaningful way, address that separately as part of an explanation for a decision or situation — but not as part of the apology itself.)

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Trust me, I've been as guilty as anyone for using these phrases. I reach for them because they feel easy and convenient. Subconsciously, we’ve heard others say the same words, and so take them on as our own. Perhaps that contributes to why they sound hollow and inauthentic on the other end…

But we can stop. We don't have to continue to rely on these non-apologies. Here are the steps we can take to actually give an apology and rebuild trust with our team…

The anatomy of a real apology

Step 1: Say the exact words, "I'm sorry"

Few phrases are more powerful than a simple, unqualified “I'm sorry.”

Not "I'm sorry, but..." or "I'm sorry if..."

Just "I'm sorry." These two words signal genuine remorse and open the door to reconciliation.

A corporate PR team might direct us to use “I apologize”… But remember, we’re not animatrons. We’re human! “I'm sorry” connects on an emotional level that “I apologize” rarely achieves.

Example: “I am truly sorry for my reaction in the meeting.”

Step 2: Own the failure completely

As the leader, the buck stops with you. Even when factors were outside your control, the outcome still falls under your responsibility. This means no finger-pointing, no qualifiers, no deflections.

The harder part is making sure you genuinely feel this ownership internally. If you go off in private and mutter to your executive team, “Well, it wasn't really my fault...” your team will sense the disconnect between your words and beliefs, even if they weren’t in the room to hear your disclosure. Take time to process your own feelings about the mistake before attempting to apologize.

Example: "I take full responsibility. This was my decision, and I own the outcome."

Step 3: Address specifics

Details prove you've reflected deeply on what went wrong and aren't just offering generic platitudes. When you articulate exactly what went wrong and why it mattered, you demonstrate respect for those affected.

Be concrete about what you did wrong. This isn't about self-flagellation, but about clarity and honesty. Avoid the temptation to softly bring others into sharing the blame.

Example: "Here specifically, I made three mistakes: First, I ignored early warning signs. Second, I didn't consult with the team. Third, I rushed the decision."

Step 4: Share your learning

A real apology includes insight: What you've learned and how you'll approach similar situations differently. This provides evidence that you're actually going to change rather than repeat the same errors.

This isn't about irrational self-criticism or dramatic promises. It's about thoughtful reflection that examines both personal actions and systemic factors. The goal is to demonstrate that this experience has created meaningful change in your understanding.

Example: "What I've learned is that I need to listen more carefully to dissenting voices. My desire for quick resolution sometimes silences important concerns."

Step 5: Commit to specific actions

An apology without changed behavior is just empty words. The final step to a real apology is committing to specific actions that will prevent similar mistakes and create better outcomes in the future.

These commitments should be prompt, concrete, and meaningful. This is also the time to address systemic factors that may have contributed to the problem: Incentives, processes, or cultural elements that need adjustment.

Example: "Going forward, I'm implementing three changes: Weekly check-ins with our finance team, a new approval process with documented risk assessment, and hiring a business coach to help me get better at these decisions."

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But, what if…?

In an ideal world, you could just follow these 5 steps every time you needed to apologize, and all would go smoothly. But, alas, reality makes things complicated :-) And so here are tips for when you run up against the challenges of reality, in giving your apology…

When you don't actually feel sorry

• The obstacle: Sometimes, you genuinely believe you made the right call despite negative outcomes.

• The solution: Separate outcome from intent. You can authentically apologize for the impact while acknowledging your reasoning: "While I made this decision based on what I believed was best at the time, I'm genuinely sorry for how it affected the team. The outcome wasn't what any of us wanted."

When you're only partially responsible

• The obstacle: The situation involved multiple parties and factors beyond your control.

• The solution: Own your part completely without qualification. "While several factors contributed to this situation, I'm taking full responsibility for my role in it. Specifically, I..." This demonstrates integrity without requiring you to shoulder blame for things truly beyond your influence.

When you've apologized before for similar issues

• The obstacle: You've apologized for similar mistakes previously, making this apology feel less credible.

• The solution: Acknowledge the pattern directly: "I realize I've apologized for something similar before, which likely makes my words seem less meaningful now. That's why I've created this specific plan with clear accountability measures..." Then follow with concrete, verifiable actions.

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Getting to the heart of the apology

If you're finding this a bit difficult to put into practice, especially in the heat of the moment, that's completely understandable. It doesn't mean you're a terrible person—it’s likely that you’re tired, depleted, and/or balancing many variables as a leader. The weight on your shoulders is heavy, and the guilt of not apologizing well doesn’t lighten the load.

Instead, keep this in mind: What matters most isn't perfection, but authenticity.

For instance, consider how differently these two approaches land…

“I'm sorry if anyone felt confused by the change in direction.”

Versus…

“I'm sorry. I changed our priorities without proper communication, and that created unnecessary confusion. I've learned I need to bring the team into these decisions earlier, and I'm implementing a new process to ensure that happens.”

The true heart of apologizing well is to feel it genuinely — to recognize the impact of our actions and care deeply about making things right. It's not about diminishing your leadership, it's about strengthening it through vulnerability.

So, the next time you're tempted to say, “I'm sorry if you interpreted things that way,” pause. Apply the anatomy of a real apology, rather than a non-apology.

When you do, our apologies can heal, rather than unintentionally hurt.

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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If you’re a recovering non-apologist and would like to share this framework with others, here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on topics that help leaders with apologizing well, including “Uncovering Leadership Blindspots” and “Communicating Change Well.”

• 🚂 Partner with me to roll-out a leadership training program for your managers to help them coach and keep their top performers.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I’ve had a few spots open up for 2025 — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well…

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Judith was, dare I say, the perfect employee.

Always early, always prepared. Diligent, proactive, and constantly generating new ideas. Creative and bold, she was the cultural heart of the company, lifting spirits while pushing the edge of innovation. Her work quality consistently surpassed her peers, and the CEO often handed her tasks knowing she'd solve them better than he would.

The CEO, Jeremy, saw Judith as the future. She was so good that he could envision her leading the company someday. From their conversations, he knew she was invested in the company's future and loved a challenge. She was bought in.

So you can imagine his shock when Judith submitted her two weeks' notice. Jeremy, caught completely off guard, immediately tried to keep her. “Higher pay,” he said. “We'll do 50% on top of whatever they're offering!”

But Judith politely declined and left for the other company, leaving Jeremy flabbergasted.

I spoke with both of them separately once the flames of the situation had died down (I’ve changed the names and details here for confidentiality). When I asked Judith why she left, she didn't mention leadership toxicity or strategic problems with the organization. She simply disclosed that the company had grown complacent and she was bored. The new offer promised new challenges and boundaries to push.

She might have stayed if Jeremy had suggested interesting projects instead of just throwing money at the problem.

“I was almost offended that his only solution was more pay,” she told me. “Money was never the issue. It was the lack of meaningful problems to solve. I got bored, and I feel like the company got bored too.”

Judith isn't alone. Many top performers are driven away because their leaders punish them without realizing it. In Judith's case, her excellence actually worked against her— the company grew complacent about challenging her.

I’ve unfortunately seen this, time and time again, with the thousands of leaders I’ve worked with. As leaders, we need to recognize how we accidentally push our best people away when all we want is for them to stay.

Here are the key behaviors to be wary of that can accidentally drive your top performers away:

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1. Not having a clear vision

“I'm so confused about what exactly our CEO wants.”

This refrain has echoed through countless conversations I've had with top performers. They're eager to excel, ready to carry the organization forward, but they can't figure out what their leader actually wants. They're looking for that picture of a better future and the path to get there.

Why is this so common? Often because as a CEO, you yourself might not have perfect clarity on where you're headed. You started this journey for a reason, but the future remains fuzzy.

This uncertainty isn't inherently problematic — unless you pretend it doesn't exist.

The real damage happens when you avoid the vision conversation entirely, or when you keep shifting direction without explanation. Your top performer begins to assume you simply don't care about having a coherent direction. To someone who craves purpose and impact, that's deeply demoralizing.

What to do instead:

• Be transparent about the status of your vision. If you have one, share it clearly. If you're still developing it, admit that openly. (There’s nothing wrong with vision being a work-in-progress!

• Schedule a dedicated vision conversation. Make time specifically to discuss where the company is headed and how their work contributes.

• Invite their perspective. Ask directly: “Can I get your input on what direction we are heading in?” Their insights might sharpen your own thinking.

• Document and revisit. Write down the vision elements you agree on and reference them regularly to maintain consistency.

Top performers would rather work with someone who's honest about the vision —even if it's still evolving — than someone who avoids the topic entirely or shifts direction without explanation.

2. Stacking on more, without taking anything off

Your top performer consistently delivers exceptional work. Naturally, you give them your toughest challenges — the problems no one else can crack, the initiatives you believe could transform the business. You keep adding to their workload because they've never let you down before.

This approach solves the boredom problem that drove Judith away… But it also creates a new one: Overload. You can't continually stack responsibilities without creating unsustainable pressure. Without trade-offs, you're setting up your star performer for inevitable burnout.

Worse, this pattern sends a toxic message: Excellence is punished with more work.

I've watched promising leaders get rewarded for their outstanding performance by working evenings and weekends while their more moderately-performing colleagues maintain work-life balance.

What to do instead:

• Practice the “one in, one out” rule. Before adding a new responsibility, identify something that can be deprioritized, delegated, or delayed.

• Make capacity conversations normal. Try: "Before I add this to your plate, what's your current bandwidth like? What could we shift to make room?"

• Conduct regular work inventories. Periodically review everything they're responsible for and assess what's still relevant versus what's become lower priority.

• Recognize their invisible work. Remember top performers often handle unofficial mentoring, troubleshooting, and cross-functional collaboration that doesn't appear on any project list.

This approach fuels sustainable high performance rather than setting up a burnout cycle. It demonstrates that you value quality over quantity and respect their humanity beyond their productivity.

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3. Asking this person to do parts of your job

We've all heard the truism, “effective leaders delegate.” Top performers want stretch assignments. Developing future leaders means giving them increasingly challenging work….

This advice isn't wrong — but there's a crucial boundary that's often crossed.

I recently spoke with a top performer whose CEO had such confidence in them that they'd publicly mentioned this person as a potential future company leader. But behind the scenes, this “vote of confidence” translated into the CEO offloading so many of their own responsibilities that the top performer was effectively doing two jobs: Their own VP role PLUS significant portions of the CEO's work.

The result wasn't growth. It was frustration and anxiety.

This wasn't development. It was dumping.

As a leader, you need to honestly assess: Are you delegating to develop, or are you simply offloading the parts of your job you don't want to do? Are you asking this person to substitute their judgment for yours in areas where your perspective is still essential?

What to do instead:

• Frame it as intentional development. If you want someone to take on parts of your role, position it as deliberate skill-building: “I'd like you to handle investor updates because it will develop capabilities you'll need for future leadership roles.”

• Articulate the learning purpose. Explain specifically what they'll gain: “Taking this on will give you visibility into how board members think and what drives their questions.”

• Create space by adjusting other expectations. Acknowledge explicitly: “While you're handling these strategic initiatives, I expect your direct production to decrease by about 20%.”

• Provide a scaffolded handover. Don't just delegate — create a structured transition with the appropriate context, resources, and decision ownership.

This approach ensures your top performer feels developed rather than exploited. It transforms what could be overwhelming into an opportunity for meaningful growth.

4. Telling this person that they have control, but then jumping in and hijacking the details

“They told me I owned the project, but then wanted to dictate every detail.”

This complaint surfaces repeatedly in my conversations with frustrated top performers. The leader explicitly grants ownership, but when the work unfolds, they can't resist micromanaging everything. The message becomes painfully mixed: “I trust you completely — except I actually don't.”

If you see this pattern in yourself, it's perhaps worth examining what's driving it. Maybe you've spotted genuine errors or gaps. Maybe the project is heading in a direction that makes you uncomfortable. Whatever the trigger, your intervention undermines the ownership you promised.

Over time, this inconsistency trains your top performer to wait for detailed instructions rather than exercise real judgment — precisely the opposite of the ownership you wanted to encourage.

What to do instead:

• Define "ownership" with specificity. Clarify upfront which decisions they can make independently versus where they need input: “You have full authority on timeline and staffing. For budget and messaging, let's review together.”

• Schedule structured check-ins instead of random interventions. Rather than surprising them with critiques, set regular touch-points where course correction is expected and less disruptive.

• Focus on outcomes, not methods. Ask yourself: “Are they achieving the right results, even if they're taking a different approach than I would?”

• Frame feedback around principles, not preferences. Instead of, “I don't like this approach,” try, “This approach seems to conflict with our commitment to simplicity.”

This clarity helps your top performer genuinely own their work while still benefiting from your experience. It prevents the whiplash that comes from having authority seemingly granted and then withdrawn.

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5. Assuming you know what they're motivated by

Remember Judith from my opening story? It'd be tempting to say that she left simply because she was bored — but that was merely a symptom of the greater ailment. She left because her fundamental motivation (to be intellectually challenged) wasn't understood or addressed.

Even when she resigned, Jeremy's response revealed how little he grasped what drove her. He offered more money to solve a problem that had nothing to do with compensation.

This happens constantly. We project our own motivations onto others or fall back on conventional wisdom: “Everyone wants more money” or “Everyone wants a promotion.” But our top performers are individuals with unique drivers that may surprise us.

When we miss what truly energizes our best people, we inadvertently create an environment they want to escape rather than one where they can thrive.

What to do instead:

• Ask direct questions about motivation. Try: “What aspects of your work do you find most energizing?” or “When have you felt most fulfilled in your career, and what specifically made that experience satisfying?”

• Study their excitement patterns. Notice which types of projects generate their most enthusiastic responses and highest engagement.

• Observe their discretionary effort. Where do they naturally invest extra time and energy when not directed?

• Offer varied opportunities and watch what resonates. Present different types of challenges and observe which ones they tackle with the most passion and effectiveness.

• Make motivation a regular conversation. Discuss what drives them periodically, not just during annual reviews or when they're already halfway out the door.

Understanding what truly motivates your top performers lets you create conditions where they want to contribute their best work — rather than seeking those conditions elsewhere.

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Hold the mirror steady

For those of you who recognized yourself more than you’d like to in the description of these actions… It’s okay! Take a deep breath. Don’t demonize yourself. Hold the mirror steady. I’m right there with you — I wrote this piece very much with my own reflection in mind. Your willingness to even admit that you might be participating in these actions is enormously salient for supporting your top performers.

The antidote is simple, but powerful. You must keep these hidden forces within your scope of awareness. You must ask yourself:

1. Is my vision clear enough that my top performers can navigate without constant direction? If not, am I honest about that gap?

2. When was the last time I removed something from my top performer's plate rather than just adding to it?

3. Do I truly give ownership? Or am I still backseat driving while claiming to delegate?

4. Have I ever directly asked what motivates my top performer? Or am I projecting what would motivate me?

We all have our own “Judith” on our team. Think of them, as you ask these questions to yourself. Small shifts in how you lead can dramatically change their experience —and whether their story with you ends differently than what happened with Judith and her CEO Jeremy.

Remember: Your top performers aren't just valuable assets. They're people whose growth and fulfillment in part rest in your hands. The fact that you're reading this suggests you're the kind of leader who wants to get this right.

-Claire

A note for the top-performer reading this: If you’re on the other side of this and you've been thinking, “I wish I could anonymously send this article to my boss,” I feel you. I am currently working on a future article on how to address these forces as a top performer. If you'd like to receive that piece once it’s published, make sure that you're subscribed to my newsletter. (In the meantime, perhaps you can forward this article to a colleague who perhaps can gently DM this to your CEO “just for interesting reading of course…” 😉)

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Looking to do more to keep your top performers (and help others in your org do so too)? Here are ways you can directly work directly with me, Claire, Founder & CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on “Coaching Top Performers” or “Uncovering Leadership Blindspots.”

• 🚂 Partner with me to roll-out a leadership training program for your managers to help them coach and keep their top performers.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day, and dive in to our module specifically on coaching top performers.

• 🤝 Explore 1:1 executive coaching with me personally to help you elevate your leadership keep your best people. (I’ve had a few spots open up for 2025 — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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Do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well…

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My team was falling apart under pressure, and I was furious.

The quality of work had plummeted. Deadlines were slipping. People seemed disconnected from our goals and were making careless mistakes. Week after week, I watched my once-bold team grow increasingly cautious and unfocused.

Desperate to solve this mystery lapse in performance, I took a weekend to reflect. A question came to mind from famed executive coach Jerry Colonna, whom I'd had the privilege of speaking with years earlier. He’d asked me:

"What are the conditions that you don't want to create that you are in fact complicit in creating?"

The answer drove through to my spine: The problem was me.

I was responsible for my team's condition. I was complicit.

My anxiety was creating frenzy. My shifting expectations were impossible to follow. My failure to provide context was setting everyone up to fail. While searching for solutions everywhere else, I had missed the most obvious place to begin with — myself.

After a decade of training thousands of leaders, I've discovered this pattern repeats endlessly. Our greatest workplace challenges often stem from conditions we've unknowingly created. The problems we blame on our teams frequently trace back to our own blindspots. It’s never the answer we want to hear, but it’s the answer we need.

Here are the ten critical leadership blindspots I've seen derail even the most well-intentioned leaders, myself very much included…

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Blindspot #1: "What our team doesn't know doesn't hurt them."

Headcount changes, compensation decisions, strategic pivots — the territory of our work as leaders is often riddled with landmines. Not everything can nor should be fully transparent. However, the absence of information creates its own problems.

When I've seen this blindspot play out:

I recall an organization where two key leadership members were dismissed for performance reasons, but no explanation was provided for their departure. Without context, rumors spread about potential layoffs and a giant re-org. Fear rippled throughout the organization. Even a few top performers approached me, wondering if they should start looking for another job — all because of the information vacuum leadership had unintentionally created.

This doesn't mean throwing all discretion out the window. Rather, when you choose not to be transparent, you must take responsibility for the speculation and uncertainty that follows.

Self-assessment questions:

• When you can't share everything, how do you provide enough context to prevent harmful speculation?

• How might your team be filling in the blanks about situations where you've been vague or silent?

Action to try:

Identify one area where you've been less than forthcoming. Find a way to share more context that doesn’t include sensitive details — or be explicit in why you can’t share more context — and observe how it affects team trust and performance.

Blindspot #2: "Everyone should share my sense of urgency."

Leaders are prenatally impatient. We always want things done better or faster. And while that’s not necessarily a bad thing, we often forget that our own sense of urgency stems from our own experience. We feel in the importance of the mission in our gut, we feel the needs of our customers in our bones — but that urgency isn't automatically transferred to our team.

How I've fallen victim to this blindspot:

About a decade ago, I was helping our team prepare for a product launch — one that had taken 3 months to prepare. Two weeks before launch, I became increasingly concerned about the remaining tasks. In a meeting, I found myself chastising a team member for focusing on minor details rather than "the critical stuff." Later, I realized they never received information about what constituted as critical. I apologized immediately, but never forgot this egregious oversight.

Our team doesn’t embody urgency in the same way we do, by default. And, as leaders, we shouldn’t expect them to. If you have an expectation of urgency, recognize that it's your responsibility to communicate effectively, not your team's failure to intuit.

Self-assessment questions:

• When you feel impatient with progress, do you first check whether you've provided the context needed for urgency?

• How often do you explain the "why" behind urgent requests, not just the deadline?

Action to try:

Ask each team member to rank what they see as top priorities, and see if it aligns with what you had in mind. If there is a discrepancy, it’s on you (not them) to clarify the required level of urgency.

Blindspot #3: "As long as my team likes me, they trust me."

You give someone a compliment ("I really like the sweater you're wearing") or highlight a commonality ("I'm a huge Minnesota Timberwolves fan too")… But that doesn't necessarily signal that you would rely on them for an important task. A critical part of trust is this sense of reliance, that your team feels they can count on you. (Researchers call this "cognitive trust," which is the most sustained and lasting form of trust.) Someone liking you is very different than someone trusting you.

When I've seen this blindspot occur:

A leader might spend the first ten minutes of every one-on-one asking about weekend plans and family updates, believing these personal connections are building deep trust. Meanwhile, their team is frustrated because this same leader consistently misses deadlines for providing feedback on their work.

Of course, building positive report on a team is absolutely helpful for building trust. But it should not be seen as the only form of trust you should be focused on cultivating. Make sure that you are a leader that your team can rely on — that is the strongest form of trust you can build.

Self-assessment questions:

• When was the last time you made a commitment to a team member and then didn't deliver on time?

• Can you identify three promises you made to your team in the past month and whether you kept them?

Action to try:

Rate yourself on a scale of 1-5 on the following statement: "When I say I'll do something, my team can count on me to deliver without needing reminders."

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Blindspot #4: "I don't play favorites with my team."

We all have preferences — including who we enjoy working with. The problem arises when these natural affinities turn into favoritism, filtering into opportunities, support, and recognition. Pretending that you don't have these preferences is where you run into trouble: You're then not being truthful enough to recognize how they might be playing out.

When I've seen this happen:

A leader has two equally talented team members: Amy and Jordan. The leader finds Amy's communication style more aligned with theirs and enjoys their conversations. Over time, they assign Amy the high-visibility projects, provide more detailed feedback on her work, and mention her contributions in executive meetings. Meanwhile, Jordan's equally valuable work receives less recognition, fewer growth opportunities, and less attention.

These imbalances create resentment and dysfunction. Team members notice favoritism long before leaders realize they're displaying it, and it erodes trust throughout the organization.

Self-assessment questions:

• How do you ensure your personal preferences don't affect who gets challenging assignments or recognition?

• When's the last time you praised the work of someone whose style differs from yours?

Action to try:

Review your calendar for the past month. Note how your time was distributed across team members and ask yourself whether allocation patterns reveal unconscious favoritism.

Blindspot #5: "I treat everyone the way that I want to be treated."

Most of us were taught the Golden Rule: “Treat others as you want to be treated.” In theory, it's well-meaning. But in reality, not everyone is “you” :-) We each have our own proclivities and preferences for how we want to do things… And so we should take that into consideration, rather than assuming those preferences are the same as ours.

When I've made this mistake myself:

A couple of years ago, I wanted to ensure our team was adequately taking vacation. With our unlimited vacation policy, I worried folks weren't taking enough time off. I suggested we have one Friday every month that the entire company takes off, thinking that's what I would personally prefer, and the team would love the idea. It wasn't until our CTO pointed out that this wasn't helpful for him or several others because they preferred taking time off during the middle of the month on a more flexible schedule. I’d mistakenly projected my preferences — I’d assumed everyone wanted something just because it's something I wanted.

Remember: True empathy isn't about projecting our own preferences onto others.

Self-assessment questions:

• What aspects of your management style are based on your personal preferences rather than your team's needs?

• What management practices do you avoid because you personally dislike them, without checking if they might benefit your team?

Action to try:

During your next one-on-one conversation this week, ask: "How can I better support your work style?" Listen closely to the details of what their preferences are. Then implement at least one suggestion from each person.

Blindspot #6: "I'm the only one who can solve this problem."

Sometimes it’s true: We are the only person who can solve a particular problem. But other times, it’s not. As leaders, we can find ourselves assigning ourselves to problems that we enjoy tackling or we fear others messing it up, rather than enabling our team to solve them and become more self-sufficient.

When I've seen this happen:

A team consistently brings customer escalations to their leader because the leader has a knack for handling difficult situations. While this works in the short term, the leader becomes stretched thin and unavailable for strategic work. Meanwhile, the team never develops these crucial skills, creating a dependency cycle that limits everyone's growth.

Yes, as leaders, we have valuable expertise and experience, but we don't want that expertise and experience to be purely isolated. We want to be replaceable. A sign of great leadership is helping our team solve problems themselves rather than solving all the problems ourselves.

Self-assessment questions:

• How often do team members come to you with problems versus proposed solutions?

• What expertise do you have that you haven't systematically shared with anyone else?

Action to try:

This week, when someone brings you a problem, resist solving it. Instead, consider teaching them how to solve it. Coach them through their own solution.

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Blindspot #7: "Some problems will work themselves out."

I thought this to myself before, especially if I've been facing a particularly draining problem. It's understandable, given how delicate or tricky a situation is to untangle. Yet it is also wishful thinking. Usually, the problem that we're avoiding is the problem only we is the leader have the power to address. It's up to us to confront it.

When I've seen this occur:

A high-performing team member consistently interrupts and dismisses ideas from junior colleagues in meetings. Instead of addressing it directly, the leader hopes they'll recognize the issue themselves after seeing the leader's positive model of inclusivity. However, six months later, two talented junior team members resign, citing "lack of voice" in their exit interviews.

These situations almost never resolve themselves. Intervention is needed that only a leader can take: Having a conversation about changing behavior, coaching the person to success, or making the difficult decision to let someone go. These problems tend to get worse when we turn a blind eye to them. Don’t fall for the myth that they'll magically disappear.

Self-assessment questions:

• What issue on your team have you been hoping will improve without your direct intervention?

• What's the potential cost to your team if you wait another month to address this issue?

Action to try:

List one problem you've been avoiding and commit to a specific date this week to take the first step toward addressing it.

Blindspot #8: "My team has the same context I do."

As leaders, we consistently underestimate the information gap between ourselves and our teams. Because of meetings your team members aren't in, or experiences they haven't had, you as a leader naturally know more and have greater perspective on the big picture.

When I've observed this happening:

After six months of strategic planning sessions with all leaders, an executive team announces a major pivot to the organization. Leaders are then confused when frontline employees seem resistant and ask "unnecessary" questions — forgetting they haven't been part of the lengthy discussions that led to this decision and haven't processed the change like leaders have.

Keep in mind that as a leader, you have more context than you might be aware of. It's up to you to help fill in those gaps for your team.

Self-assessment questions:

• When was the last time you explicitly connected your team's day-to-day work to the organization's bigger objectives?

• What information do you have access to that your team doesn't? How much of that would help them do their jobs better?

Action to try:

At your next meeting, ask team members to briefly articulate the current top priority and why it matters. The alignment (or lack thereof) in their answers will reveal your context-sharing effectiveness.

Blindspot #9: "My team doesn't know how hard I fight for them."

Leadership can feel thankless. We work hard behind the scenes, fighting for resources, navigating politics, and removing obstacles to set our teams up for success. When team members complain about minor issues ("Why can't we have more days off?") after we've secured hard-won victories, resentment naturally builds.

When I've seen this happen:

A leader spends three months negotiating with executives to get their team a budget increase and prevent layoffs during a difficult quarter. Rather than appreciation, the leader faces complaints about the small end-of-year bonuses. The frustration boils over, and the leader lashes out in passive-aggressive ways, thinking, "Do you have any idea what I had to do to even get you those bonuses?"

The blindspot emerges when this resentment seeps into your interactions. The problem isn't your team's lack of appreciation — it's the expectation gap you've created by not communicating your efforts effectively.

Self-assessment questions:

• How often do you share context about the effort that went into decisions or resources you've secured?

• What would happen if you were more transparent about your own challenges and victories?

Action to try:

Create appropriate transparency around your behind-the-scenes work. This isn't about seeking praise — it's about providing context that helps your team understand organizational realities and appreciate the full picture.

Blindspot #10: "It's personally important to me that I'm seen as a good leader."

This might be the most dangerous blindspot of all: Believing your worth as a person is connected to your "goodness" as a leader. I'll be the first to raise my hand as someone who has fallen prey to this blindspot time and again.

How I've personally fallen into this trap:

A few years ago, I worked with a team member who put tremendous effort into their work. They wanted to be successful, but their output didn't meet expectations. Rather than having direct conversations about performance, I became preoccupied with being seen as a “good leader” and only offered encouragement instead of real feedback. When the subpar results had gone on for over six months, I decided to let them go — and they were very surprised. I'll never forget that shocked reaction and how the root cause was my attachment to be being seen as a “good leader.” I failed to have hard conversations because I was trying to play the role of being "supportive" and "encouraging.”

When our identity is wrapped up in being a "good leader," we are resistant to seeing our shortcomings, often using our identity as a shield for what we don’t want to face about ourselves. Our ego protects our self-image by filtering out contradictory information. This creates the largest gap between intention and impact.

Self-assessment questions:

• How do you typically respond to critical feedback about your leadership?

• When was the last time you were genuinely surprised by how someone experienced your leadership?

Action to try:

Ask a trusted colleague who works closely with you: "What's one assumption I make about my leadership style that might not match reality?" Listen without defending or explaining.

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It doesn’t feel good to read, but it feels good to change

This wasn't the most fun piece for me to write. I've made each of these mistakes listed in these blindspots, myself, I’m sure at least twice over. I winced, thinking about the negative effects that I might have had on my team. And I felt fear creep up in me: Maybe there are even more blind spots that I am not aware of as well… What does that mean?

It means that I am human. I am fallible.

But most importantly, it also means that I can get better.

While it might not feel good to read, it does feel good to change. I assure you that the redemption comes in your efforts to overturn these blindspots. Instead of treating this article like a list of faults or source of self-conscious cringe, view it as project list or work-in-progress list: Areas for you to explore, create accountability around, and choose to be better.

Here's an approach to try:

1. Choose one blindspot. Don't try to fix everything at once. Select the single blindspot that resonated most strongly or that your team would benefit most from you addressing.

2. Create accountability. Share your focus area with someone you trust — a colleague, mentor, or even your team. Say: "I've realized I might have a blindspot around [X]. I'm working to improve this over the next month. Would you be willing to give me candid feedback on my progress?"

3. Set a concrete timeframe. Give yourself 30 days of deliberate focus on this one area. This is long enough to create momentum but short enough to maintain focus.

4. Build in regular reflection. Schedule a 15-minute calendar appointment with yourself every Friday to assess your progress. Ask yourself: What situations triggered this blindspot this week? How did I respond differently? What impact did I observe?

5. Celebrate progress, not perfection. Leadership growth isn't linear. You'll have days where old patterns emerge. That's normal. Acknowledge the setback, recommit to awareness, and keep going.

Remember, even after a decade of studying and teaching leadership, I still catch myself falling into these blindspots. That's why I wrote this piece — as much as a reminder to myself as a resource for you.

A meaningful shift starts with the courage to see ourselves clearly. Which blindspot will you tackle first?

- Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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Keen to work through some of these blindspots, yourself? Here are ways you can directly work directly with me, Claire, CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on “Biggest Leadership Mistakes and How to Avoid Them” or “The Accidental Bad Boss.”

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day, and dive in specifically on uncovering blindspots & leadership foundations. (This specific module is in fact 100% free.)

• 🚂 Partner with me to roll-out a leadership training program for your managers to help them avoid and overcome these blindspots.

• 🤝 Explore 1:1 executive coaching with me personally to help see your own blindspots more clearly, and work through them. (I’ve had a few spots open up for 2025 — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

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Buried in a box at my mom's house, I recently came across my collection of school yearbooks — each from a different state. Growing up, I moved around quite a bit: Georgia to Washington state, Ohio to Minnesota, and then to Chicago for college.

Each move represented a complete reset of my world. New faces, new rules, new geography. In retrospect, this constant change proved valuable for my development. But in the moment? It was disorienting to my core.

I still recall the stomach-dropping sensation of walking into yet another new cafeteria, lunch tray in white-knuckled hands, scanning for a friendly face among strangers. That feeling of the ground shifting beneath me as my entire universe transformed…again.

This visceral memory informs how I empathize with what happens when our teams face significant change. The physical manifestations are remarkably similar: Quickened pulse, scattered focus, the undercurrent of nagging questions. What will change next? Am I safe here? Do I still belong?

If your team has recently weathered significant change, they're likely experiencing this same internal turbulence. Their professional identity — the story they've been telling themselves about their work — has been disrupted.

The good news? You can create islands of stability amid these choppy waters. As someone who's both experienced and led through significant change — as well as worked with thousands of leaders in high-growth organizations — I've discovered four specific approaches that help teams regain their footing when everything feels suddenly uncertain.

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#1: Predictability

When the ground shifts beneath us, we instinctively search for patterns and consistency. As humans, we naturally crave a sense of predictability — an understanding of what's coming next. However, as Howard H. Stevenson and Mihnea Moldoveanu wisely noted, "The need for predictability is not a need for guarantees." We seek the reassurance of knowing there's solid ground ahead, even if we can't see the entire path.

Perhaps this explains our love of games and sports. The outcome isn't guaranteed, but the rules are predictable and constant. This allows us to calculate probabilities and act accordingly.

Similarly, when significant organizational change happens, we don't expect guaranteed outcomes, but we do want the potential paths forward to feel clear and understandable. Predictable.

To establish predictability during change, take these deliberate actions:

Create a communication cadence

• Weekly check-ins with a consistent format.

• Monthly updates that happen regardless of news volume.

• Clear expectations about when and how information will flow.

Example: After a reorganization

"In light of the restructuring, I'll host a weekly Friday meeting at 10am to discuss our team's current state and address any concerns that have emerged during the week. You'll always leave knowing what to expect for the coming week."

Do scenario planning and share potential paths

• Best and worst case scenarios with realistic probabilities.

• Conservative, moderate, and optimistic projections with timelines.

• Emphasis on what remains unchanged despite the broader shifts.

Example: After team downsizing

"As our team just went through a significant reduction, I know things feel uncertain. Let's talk through all possible paths forward. Here's what remains stable, here are the variables, and here are the decision points we'll encounter in the next three months."

While predictability provides the framework, clarity fills in the details — preventing people from sketching their own troubling scenarios in the blank spaces. I'll talk about this next.

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#2: Clarity

I'll never forget advising a team experiencing organizational change. One direct report confided in me, "I'm really worried they're going to let a bunch of people go. They haven't said it, but I can just tell."

That last sentence is revealing: This person's fear and anxiety didn't stem from anything the company or leaders had said. It was the absence of clear communication that led them to suspect the worst.

When things are unclear, we tend to assume the worst. Confusion breeds frustration. Therefore, it's crucial to be as specific as possible when sharing your current reality. Otherwise, people fill in the blanks with alternative realities that are often far worse than the actual situation.

Here's how to create clarity that fosters stability:

Explain the "why" specifically

• Elaborate on how a company-wide change affects your team directly.

• Don't assume implications for your team are obvious to your team members.

Example: After a strategic shift

"I know you attended the meeting where our new strategic direction was discussed, but I want to explain specifically how this impacts our team and why."

Make next steps explicit

• Don't just discuss long-term ramifications. Address immediate steps.

• Be concrete about what happens next.

Example: After downsizing

"With our smaller team, our goals will need to change. I've been thinking through our priorities, and I want you to do the same. Then in our next team meeting..."

Keep it simple

• Avoid vague phrases like "things are evolving" or "trust the process."

• Use clear, simple language about what's actually happening.

Example: When cutting previously important projects

"The company is focusing purely on growth. This means we're prioritizing projects that directly impact current revenue."

#3: Control

Much of why we humans dislike change is because it makes us feel out of control. As leaders, we can create stability by finding ways to give some control back to our teams.

While we may not be able to control the change itself, we can often influence how that change unfolds:

Give options where possible

• Identify areas where choice is still available.

• This might be in the form of meeting duration, frequency of updates, etc.

Example: After a reduction in force

"Given the weight of these changes, should we adjust the frequency or length of our standing meetings? I want to give you space and flexibility to process this change."

Offer autonomy to shape their environment

• Allow team members to influence how work gets done.

• This might be in the form of communication, preferences, workflow, preferences, etc.

Example: After a shift in priorities

"As we navigate this change, how might we adjust our meetings or status updates to better serve our new focus?"

Invite contribution to the path forward

• Ask for input, perspectives, and ideas.

• Give team members agency in determining next steps.

Example: After a reorganization

"I'd like you to spend the next week thinking about what you see as the best path forward."

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#4: Care

Through it all, we of course care about our teams. However, during times of significant change, it's not enough to say we care — we need to show it through our actions.

Here's how to demonstrate authentic care:

Take accountability

• Acknowledge your role, especially in communication gaps.

• This is your this is your opportunity to show where you wish you would have been a better leader in certain moments.

Example: When priorities change unexpectedly

"Here's the role I played in this not being communicated well. This is on me..."

Give grace and space for reactions

• Recognize that people will process change differently.

• Normalize taking some time to process.

Example: After layoffs

"I want to make sure you have time and space to process this..."

Remember, this isn't all about you

• Focus on supporting your team, not just grinding through.

• Consider processing with peers, rather than adding to your team's burden and doing your own live processing with them.

• Make yourself genuinely available.

Example: During any significant change

"Please let me know how I can best support you during this time..."

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What about YOU?

As you work to create stability for your team, don't forget to create it for yourself as well. Slow down. Create space. Give yourself time to prepare thoughtful responses and establish supportive systems based on these four principles — predictability, clarity, control, and care.

Your level of anxiety, stress, and panic sets the tone for your team. This isn't about putting on a false front or pretending to feel fine about difficult changes. Rather, it means ensuring you've lightened your own load before attempting to lighten others'.

Change will always be part of our organizational lives. But by intentionally creating stability through these four approaches, we can help our teams navigate even the rockiest waters with greater confidence and resilience.

-Claire

P.S. Because you read this far, my gift to you is a photo of kindergarten Claire from my very first yearbook… 🥹 The nostalgia of going through old yearbooks gets me every time!

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it for free 🫶

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Looking for some help in navigating change in your team? Here are ways you can directly work directly with me, Claire, CEO of Canopy:

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person on “Leading Through Change” or “Navigating Org Change.”

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day, and dive in specifically into our module on high-growth teams.

• 🚂 Partner with me to roll-out a leadership training program for your managers to equip them with tools for managing growth and change.

• 🤝 Explore 1:1 executive coaching with me personally to work through how you best can navigate change as a leader. (I’ve had a few spots open up for 2025 — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

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Below, I wrote a piece for when you feel you’ve done everything you can as a leader to support an employee (including examining how you might be unintentionally contributing to their behavior) — but there’s something particularly challenging, or even toxic, about the dynamic. You don’t know what to do anymore.

Hopefully, this piece is helpful to you in this moment…

“What in the world is happening here?

I remember the words running through my mind, almost a decade ago. A team member sat across from me, masterfully spinning a web of excuses about missed deadlines while I wrestled with a crucial question: How do you coach someone to success when they won't even acknowledge reality?

Luckily, I kept my cool. I stayed steady and calmly explained where I thought there was a gap between expectation and performance and what they could do better. They relented, and we were able to find a way to move forward, at least in that moment.

Eventually, we parted ways, perhaps to no surprise. But since then, it got me thinking: How as leaders can we handle the inevitably challenging employees we encounter?

Is there a way to approach the situation and positively coach difficult employees? Or is it lost to the wind and irrecoverable?

In working with thousands of leaders over the past decade, I’ve discovered patterns. You can indeed help bend the arc of performance to be positive — but only if you understand the pattern’s root basis, and how to respond effectively.

Here are the five most challenging employee archetypes I've encountered, and the specific strategies that can help you lead them successfully...

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Archetype #1: The Entitled Veteran

Meet the cultural cornerstone of your company – the person who remembers when the office was just one room rather than an entire building, and when original logo for the company was sketched out on a napkin. They carry invaluable institutional knowledge and deep relationships across the organization. They're often beloved, respected... and they know it.

But here's the challenge: This veteran status has morphed from an asset into a shield against change. When new initiatives roll out, you might hear them say something like: "Back when I was employee number 4, we just didn't do things that way. I don't know if that's what our company should be now..."

Their resistance isn't just personal stubbornness — it can ripple through the organization, swaying newer team members and quietly undermining important transitions. Their institutional influence makes this particularly tricky to navigate.

Here’s the key to understanding the Veteran mindset:

• Identity investment: Their long tenure isn't just about time served – it's core to their identity. When you challenge "how things are done," they feel you're challenging who they are.

• Memory as authority: They've seen initiatives come and go, leaders arrive and depart. This history becomes their source of power, leading them to view their experience as superior to current leadership directives.

• Loss aversion: Change threatens their status as the "keeper of culture." Their resistance often stems from fear of losing their unique value to the organization.

• Selective memory: They tend to romanticize the past ("when things were simpler/better"), forgetting the challenges and messiness of earlier days.

This means your task isn't just about managing their performance — it's about helping them find their place in the company's evolution without losing their sense of value and identity.

Here are the specific steps you can take as a leader:

1. Ground conversations in present reality. “I value your experience with our history, and I'd like us to focus on our current reality. What specific concerns do you have about this new direction?"

2. Create inclusive accountability. "While we've all been here for different lengths of time, these new standards apply to everyone equally – from our newest hire to our most seasoned veteran."

3. Connect past and present. Instead of dismissing their experience, help them see how their knowledge can actually support the change: "Your deep understanding of our core values could really help us implement this change in a way that stays true to who we are."

4. Be clear about role requirements. "This role now requires [specific new expectation]. This isn't optional – it's a core requirement for everyone in this position."

When do you reach the upper limit, and consider parting ways?

• Ask yourself: Is their behavior changing in a way that positively affects the team? Or it is net-neutral or even outright negative?

• Remember: Their cultural weight does NOT give them permission to override your actions and efforts as a leader. You don’t want the old corrosive culture of the past to subvert the new positive culture of the present.

Archetype #2: The Passive Resister

Picture this: You're in a meeting and your team member is nodding enthusiastically. "Yes, absolutely, I'm on board!" they say with conviction. Fast forward a week, and the work isn't done. Or worse, it's done poorly with a fresh set of excuses. This is the Passive Resister, the master of cheerful agreement followed by quiet inaction.

What makes this behavior particularly frustrating is its elusiveness. Unlike open resistance, which you can address head-on, this pattern of agree-and-avoid creates a maddening cycle of apparent commitment followed by mysterious under-delivery.

Here’s the key to understanding the Passive Resister:

• Success through avoidance: Their strategy has served them well, so far. By agreeing in the moment and failing quietly later, they've learned to dodge both confrontation and consequences.

• The accountability gap: Each missed deadline or subpar deliverable gets lost in a fog of vague explanations and renewed promises, making it hard to pin down the pattern.

• The time advantage: By the time you realize there's an issue, the moment for immediate correction has passed, creating a cycle of delayed feedback and response.

Here are actions you can take as a leader to break the cycle:

1. Create clear checkpoints."Let's break this down into specific milestones. I'd like to see a draft by Wednesday and get an update in our Monday meeting. How does that sound?"

2. Document agreements in real-time."I'm noting down what we've agreed to. I'll send a quick email after this meeting so we both have the same reference point."

3. Address patterns, not incidents."I've noticed a pattern where we agree on deadlines, but the work consistently comes in late. What obstacles are you encountering that we haven't discussed?"

4. Set explicit consequences."If we continue to miss these deadlines, it will impact your performance evaluation and our ability to assign you to key projects. What support do you need to meet these timelines?"

How do you know when it’s time to move on?

• Give them one clear chance with a specific timeline: "Over the next 30 days, I need to see these three specific improvements..."

• If after implementing clear checkpoints and consequences, you're still having the same conversations about missed deadlines and unfulfilled commitments, it's time to acknowledge that the pattern isn't changing.

• Remember: Each cycle of agree-and-avoid doesn't just impact deliverables — it erodes team trust and sets a precedent that commitments are optional.

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Archetype #3: The Brilliant Aggressor

Every organization knows this person: The technical genius whose brilliance is matched only by their ability to leave emotional wreckage in their wake. They consistently deliver exceptional results while creating a wake of demoralized colleagues and fractured team dynamics. Their technical work may be elegant, but their communication is anything but.

You might hear them say something like: "Look, I don't have time to hold everyone's hand. If people can't keep up or handle direct feedback, maybe they shouldn't be here. I'm just focused on getting results."

Here’s the key to understanding the Brilliant Aggressor:

• Success as validation: Their exceptional results have created a self-reinforcing belief that their aggressive approach is not just acceptable, but necessary for excellence.

• Learned behavior: Years of implicit rewards (promotions, praise, special treatment) have taught them that interpersonal costs are acceptable collateral damage for high performance.

• Superiority complex: They genuinely believe their technical excellence gives them license to bypass social norms and professional courtesies.

• Efficiency obsession: They view interpersonal niceties as inefficient obstacles to getting work done, rather than crucial elements of sustainable team performance.

Here’s the action you can take as a leader to address this:

1. Connect behavior to business impact."When you dismiss others' ideas in meetings, it doesn't just hurt feelings — it means we're missing insights that could make your solutions even better. We're actually losing efficiency."

2. Quantify the hidden costs."Your technical solutions save us 20 hours a week, but we're spending 15 hours managing team conflicts and rebuilding confidence. Let's talk about how to maintain your high standards while lifting the team up."

3. Create clear behavioral expectations."I need you to do three things: wait 10 seconds before responding to ideas in meetings, acknowledge one positive aspect before critiquing, and raise concerns privately first. Can you commit to trying these for the next two weeks?"

4. Leverage their logic."If you could improve team performance by 30% by making a few behavioral adjustments, wouldn't that be worth it? Let's approach this like any other optimization problem."

You may also find it helpful to set boundaries as a leaders in these ways:

• Document impact. Keep specific examples of both their technical contributions and the interpersonal incidents that undermine team effectiveness.

• Create measurement systems. "We'll be evaluating success not just on technical metrics, but also on team health indicators like collaboration scores and peer feedback."

• Define clear consequences."Continued interpersonal issues will affect your growth opportunities here, regardless of technical performance. Here's specifically what needs to change..."

When is it time to part ways?

After implementing these strategies, evaluate these critical questions:

• Have they shown genuine interest in modifying their behavior, beyond surface-level compliance?

• Has the ratio of their positive impact to team damage improved meaningfully?

• Is the emotional toll on the team worth the technical output?

• Are you seeing sustained behavior change or just temporary adjustments?

Remember: Technical skills can be rehired for, but a poisoned team culture can take years to rebuild. If this person show no real commitment to change after clear feedback and support, it's better to part ways sooner rather than later.

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Archetype #4: The Perpetual Victim

There's a pattern you start to notice: Every missed deadline has an elaborate backstory. Every piece of feedback triggers a cascade of explanations about why others are to blame. At first, some explanations seem legitimate – after all, we all face obstacles. But soon you realize that this person has mastered the art of dodging responsibility through an endless series of justifications and deflections.

You might hear them say: "I really tried my best, but Marketing didn't give me what I needed, and then Sarah was late with her part, and the client kept changing requirements, and honestly, I feel like I'm being singled out unfairly here..."

Here’s what to understand about the Victim mindset:

• External locus of control: They genuinely believe their success or failure lies completely outside their control, making them feel powerless and defensive.

• Pattern of self-protection: Victimhood has become their shield against criticism and their escape route from accountability.

• Confirmation bias: They actively collect evidence that supports their narrative of being unfairly treated or blocked by others.

• Fear of inadequacy: Often, beneath the excuses lies a deep fear of not being good enough, making it safer to blame others than risk taking full responsibility.

Here are the key leadership actions you can take:

1. Create objective benchmarks."Let's look specifically at what's expected in this role. Here are the measurable standards everyone on the team needs to meet..."

2. Focus on future solutions."Rather than discuss why this happened, let's focus on what you need to deliver different results next time. What specific actions can you take?"

3. Document facts, not stories."I'm noting that the project was delivered three days late. What specific actions will you take to meet our next deadline?"

4. Redirect to personal agency."I hear several external challenges. Of those factors, which ones can you influence or control?"

You may need to also set boundaries with them:

• Break the excuse cycle. Acknowledge their perspective briefly: "I understand there were challenges..." Then immediately pivot to accountability: "However, managing these challenges is part of the role."

• Create clear paper trails. This includes documenting agreements and deadlines in writing, following-up on verbal conversations with email summaries, and tracking patterns of explanations and missed commitments

• Establish consequence outcomes."If we continue to miss deadlines, regardless of the reasons, here's what will happen next..."

When is it time to go in different directions?

Monitor these key indicators:

• After establishing clear expectations, do they still default to elaborate explanations?

• Has their language shifted from "why I couldn't" to "how I will"?

• Are they beginning to take ownership of outcomes, even partially?

• Is their behavior affecting team morale or creating additional work for others?

Then, be on the lookout for these red flags that signal it’s time to move on:

• They begin creating preemptive excuses before projects even start.

• Other team members are increasingly hesitant to work with them.

• They react to support and solutions with more victimhood narratives.

• The energy spent managing their narratives exceeds the value they create.

Remember: Your role is to manage performance, not provide therapy. While you can support someone in developing a more empowered mindset, you can't force them to take responsibility if they're committed to their victim narrative.

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Archetype #5: The Performance Rollercoaster

One week they're your star performer, delivering work that exceeds all expectations. The next week, they're missing basic deadlines and making elementary mistakes. Their emotional state seems to swing just as dramatically — from euphoric enthusiasm to tearful overwhelm. This unpredictability keeps both you and the team constantly off balance, never knowing which version of the person you'll encounter each day.

You might hear them say: "I know I crushed that project last week... I just... I don't know what happened this time. I'm so sorry [fighting back tears]. I promise I'll do better — I'll stay late, work weekends, whatever it takes..."

Here’s the key to understanding the Rollercoaster:

• Pattern blindness: They often can't see their own performance swings, experiencing each high and low as an isolated incident rather than part of a larger pattern.

• Emotional amplification: Their self-assessment tends to magnify both successes ("I'm incredible!") and failures ("I'm terrible at everything"), with little middle ground.

• Crisis-driven performance: They often need emotional intensity to perform at their peak, making sustainable consistency difficult.

• Validation dependency: Their self-worth is deeply tied to their most recent performance, creating an exhausting emotional pendulum.

Here are the specific steps you can take as a leader:

1. Create visibility around patterns."Let's look at your last six projects together. Notice how the quality varies? I want to understand what's different between your high and low periods."

2. Establish baseline standards."We need to define what 'good enough' looks like. Not every project needs to be exceptional, but they all need to meet these basic requirements..."

3. Build performance guardrails."Let's create a checklist for each project type. This gives you a concrete way to verify quality before submission, regardless of how you're feeling."

4. Address emotional management."Being passionate about your work is valuable, but emotional stability is also a core job requirement. How can we help you find a more sustainable balance?"

You may also want to set boundaries with this person:

• Create consistent check-ins. Schedule regular brief check-ins to catch issues early. Use these meetings to calibrate their self-assessment with reality. Focus on concrete deliverables rather than emotional states.

• Define success metrics clearly."Success looks like meeting these five specific criteria consistently, not occasionally exceeding them while missing basics other times."

• Document performance patterns. Track both the highs and lows. Note any external factors that might correlate with performance swings. Include emotional impacts on team dynamics.

When is time to part ways?

Evaluate these key factors:

• After implementing structure and support, has the performance variance decreased?

• Are they developing better emotional self-regulation in professional contexts?

• Is the team's productivity being significantly impacted by the unpredictability?

• Do the exceptional periods justify the resources required to manage the low periods?

These signs will tell you, in particular, that it’s time to move on:

• The emotional volatility is spreading to other team members.

• Their inconsistency is creating unsustainable backup work for others.

• Despite support and feedback, the pattern remains unchanged or worsens.

• The emotional labor required to manage them exceeds their contribution.

Remember: While everyone has better and worse days, a baseline of consistency is necessary for team function. Your role is to support growth while protecting team stability — sometimes that means making the difficult decision to part ways.

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The most important question to ask

Whether you're dealing with one of these challenging archetypes or managing a blend of several, the most crucial question isn't just "Should they stay or go?" but rather:

“What’s in the best service of the team?

This question helps cut through the complexity. You don’t need to make a pro’s and con’s list. Instead, ask yourself, “What’s in the best service of the team?” and focus on three key considerations:

Impact assessment

• How much energy are you and your team spending managing this situation?

• Is this taking attention away from other team members who could be flourishing with more support?

• Are you seeing meaningful progress, or just temporary improvements followed by regression?

Resource reality

Every leader has limited time and emotional bandwidth. Sometimes the kindest thing — for yourself, your team, and even the challenging employee — is to acknowledge that the current situation isn't working for anyone.

Growth potential

• Has the employee shown genuine recognition of the issue?

• Are they actively participating in solution-finding, or merely reacting to feedback?

• Do they demonstrate the capacity and willingness to change?

Answering these questions will give you a truthful answer.

Give yourself permission to make the decision

If you’re like me, you resent this part of leadership. It’s excruciatingly hard. But it’s hard for all of us. Know that you’re not alone in finding these situations daunting — and every experienced leader has faced similar moments of uncertainty.

Take this writing here as a permission slip — whatever permission you need. Perhaps it's permission to make one final, structured attempt at turning things around. Or maybe it's permission to acknowledge that you've given it your best effort, and it's time to make a change.

Most importantly, know that being thoughtful about these decisions, and that feeling the weight and agony of them doesn't make you a weak leader. It makes you a conscientious one. The key is not to let that conscientiousness paralyze you from making necessary changes.

Your team is watching and waiting for your leadership. They may not know all the details, but they know when something isn't working. Taking action, whether it's a final committed attempt at improvement or a decision to part ways, shows them that you're committed to maintaining a healthy, high-performing team culture.

The path forward starts with your next step. What will it be?

-Claire

If you found my writing useful this week, feel free to “like” or “share” the post — it helps other folks who might find this piece similarly useful see it completely for free 🫶

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Eager for more helpful tactics like this, from me, Claire, CEO at Canopy? Here are ways we can work directly together:

• 🚂 Partner with me to roll-out a leadership training program for your managers.

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally. (I’ve had a few spots open up for 2025 — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

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Now, onto what’s on my mind this week…

Can you translate the following phrase for me?

“Things are evolving, and I’d like for you to step up more.”

Let’s say your supervisor says this to you. A few potential interpretations run through your head of what your supervisor might actually mean by this:

• A) “You might be getting a promotion, and so I need you to show some extra effort so I can go to bat for you.”

• B) “There is a lot change in the organization right now, and so you’ll likely want to put in more effort so you can make sure your job stays safe.”

• C) “I haven’t been great about upholding job standards as your supervisor, so I’m recalibrating, and need you to perform at a higher level.”

So which one is it? Hard to say without any context.

And the stakes of misinterpretation are high: If it's Translation A, you might want to start documenting your achievements for a promotion. If it's Translation B, you might need to increase your visibility on critical projects. And if it's Translation C, you might need to rethink entirely how you show up at work.

These aren't just different interpretations — they represent radically different implications for your career:

Translation A is about expecting a promotion.

Translation B is about making sure you keep your job.

Translation C is saying that your job is seriously at risk.

Yet, in reality, how often do we receive the context needed to select the accurate translation?

Think back to the times you’ve heard a team member say, “Wait I didn’t know that’s what you meant” or “I was not expecting this” or “I don’t understand where this is coming from.”

Most of what we communicate at work gets lost in translation.

However, it does not have to be this way. With more context, more specificity, more meaning shared, our team doesn’t have to blindly choose between Translation A, Translation B, or Translation C. Our intent can come through clearly on the other side of the translation.

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Here are 3 critical ways you can make sure to avoid getting lost in translation at work as a leader:

(1) Channel your energy into crafting a clear, direct topic sentence.

There’s a reason we were taught this rule in school. The ol’ standby works. If you don’t know the title, if you don’t read the topic sentence, the whole point of the story dissipates in the plot.

Avoid this by having your conversation start with a clear topic sentence that is direct and succinct.

This feels like an obvious tactic to employ, until we actually try it.

Here is one example…

• We usually say something like this: “I think growth is really important and I want us all to be improving…”

• Instead, try this: “Your performance is not meeting expectations.”

And another example…

• We usually say something like this: “After a lot of hard thinking and deliberation, we are making some changes in the organization...”

• Instead, try this: “Today is your last day at the organization.”

Now you may be thinking, “Hoo boy, but Claire, the latter part of your examples feel so… jarring. The first one is much easier to slide into.” Yes you’re right that the first one feels easier, but that’s why we do it. We tiptoe around the real point, because we’re worried about rocking the boat.

The reality is though, if we bury the lede, the other person will miss it entirely. I once worked with a manager who tried to let someone go, but structured the conversation so indirectly that it took 20 minutes before the direct report realized they were being fired.

The direct report's response? "Why didn't you just tell me straight away? The past 20 minutes feel like complete deception."

And in a way, they have been. Their leader avoided the key message, trying to contort it into something palatable, but the end result is something inedible entirely: Frustration that they couldn't just be direct with them.

You’ll notice a few things about the topic sentence examples above I provided as well:

• They are simple. Not more than 5 or 6 words, maybe 8 if you include prepositions. No flowery language. Simple, succinct.

• They are specific. “Today is your last day” — not “you’re being let go” or “we’re doing a lay off” where the latter is much more vague.

Which leads me to my next recommendation…

(2) Anchor everything in specificity.

When working with leaders, one of the most common requests I receive is a version of this:

“Claire, I want my team to be more ____.”

“Engaged”, “proactive”, “taking ownership”, etc.

I hear you. And trust me, as a business owner, I always want those things too! Over the past decade though, working with thousands of leaders and hundreds of teams is this:

We are never specific enough for the change we’re seeking.

For instance: Let’s say I want my team to be more proactive.

As a leader, what do I really mean by “proactive”?

To me as a leader, “proactive” might mean…

• Coming to meetings 5 minutes early

• Volunteering ideas in meetings

• Anticipating problems in a workflow and solving them

• Trying new experiments without asking their supervisor

• Asking to take on more projects when their workload eases up

• Or even, all of the above

Upon examination, “proactive” has many translations — not just one. And it’s on us as leaders to make it clear which translation we’re relying on.

If we mean coming more prepared to meetings and volunteering more ideas, then we should specifically say that. If we mean running more experiments independently, then we should say that instead.

Otherwise, without this level of specificity, our team is going to default to their own interpretation, and choose the translation that serves them best.

To make sure you’re being as specific as possible, try asking yourself:

“What is the observable behavior for what I’m ideally asking for?”

The answer to that question will give you your specificity.

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(3) Center on the consequence they care about.

The most powerful way to ensure your message gets through is to frame it around what matters most to your audience. When people don't seem to hear your feedback, request, or decision, it's often because you're speaking to your priorities rather than theirs.

“I can’t get this person to change their behavior,” a CEO I once coached lamented to me. “They’re a top performer, they have the organization’s best interest at heart — but I can’t get them to stop being so harsh and aggressive to the team. I know they mean well, but the rest of the team doesn’t receive it as well and I know it’s affecting overall morale.”

On top of this, the CEO leveled with me: “I’ve tried telling this person that their tone is affecting the team negatively already, and all I get is the response: ‘I think this is the only way they’ll hear me.’”

I empathized with this CEO tremendously. I’ve personally have worked with sharp, ambitious folks who are high-integrity people at heart — but come across as aggressive and rude to others. They have good intentions, thinking it serves the team’s overall goals, and justify their tone as ‘the only way to operate.’

How in the world do you get this person to hear what you’re saying and change their behavior, when they believe their behavior is the correct one?

I must say, no silver bullet answer exists, but the one that’s worked for me personally and other leaders who I’ve coached is this:

Talk about the consequence that the other person cares about.

In this situation, here’s what this leader cares about: How the rest of the team feels and overall team morale.

However, what the direct report cares about is this: How quickly will be able to meet our team goals and milestones. How well we are serving customers.

As a result, if you share your feedback in the lens of the consequence of only what you care about (team morale), then the other person of course isn’t going to hear what you’re saying.

You have to center on the consequence that the other person cares about (team goals). That if they can find a way to adjust their tone to be warmer to others, that in fact will help the team get closer to our goals and serve customers better.

In practice, it may look like this…

• Try this: “I think your tone could be a blocker to us achieving our goals. When folks are frazzled, it affects our work product. We need folks to perform at their highest level so that our customers’ aren’t let down.”

• Not this: “I think your tone leaves folks feeling frazzled. I don’t want folks to feel demoralized on the team. I’m worried about overall team morale.”

See the difference? The first translates better to the consequence that the other person cares about — and that will influence how they then choose to act.

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Translating billions of languages

There are roughly 7,151 known human languages that exist in the world. Yet I’d argue that in practice, each of us has our own perspective for how we interpret that language. Our own unique language, if you will.

And so, in some ways, it’s inevitable that what we say as leaders gets lost in translation somehow. Everyone is operating in their own context, their own perspective. Each person has their own language from which we’re speaking from.

Yet, if we can root in these three things — a topic sentence, specificity, and consequence — all of sudden, the translation becomes clearer. We have something common to align around. And there is less, “well I had no idea”, that our team is telling us.

To ensure your message comes through clearly:

1. Start with a clear, direct topic sentence that states your main point in 5-8 words.

2. Get specific about observable behaviors. What exactly do you want to see change?

3. Frame your message around the consequences that matter most to your audience.

When you combine these three elements, you create clarity where there was once confusion, direction where there was once doubt.

Let's go back to the original phrase we were trying to translate, at the beginning:

"Things are evolving, and I'd like for you to step up more."

Using these three principles here, it could become:

1. Clear topic sentence: "I want you to take on more senior responsibilities."

2. Specificity: "Specifically, I'd like you to lead the weekly team meetings and mentor two junior team members."

3. Consequence they care about: "This will help you develop the leadership skills needed for the senior role we discussed in your career planning."

Now there's no room for misinterpretation — just a clear path forward.

Give it a go yourself, with these three principles, and see what happens. Note how you slowly might start to bridge worlds, install a phone line, and cross a chasm where you previously weren't able to get your voice heard.

You don't have to leave it lost in translation.

-Claire

If you enjoyed my writing this week, feel free to “like” or “share” the post — it helps other folks who might find this piece useful see it completely for free 🫶

Share

Curious to improve your communication as a leader even further? A few ways to get your hands on more insights from me…

• 🚂 Partner with me to roll-out a leadership training program for your managers.

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally. (I’ve had a few spots open up for 2025 — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

Eager to now share this brand new piece I wrote below. And, to receive new writings each week in the future, be sure you’re subscribed…

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Imagine squeezing a tube of toothpaste at both ends.

Apply enough pressure, and at some point, the what’s inside is going to explode from the middle. (Yes, not the most pleasant of mental visuals.)

Now, can you hypothesize what it might feel like to be the toothpaste tube, itself ?

As absurd of a question it might be, if you’re a leader — caught in the middle between a layer of direct reports and supervisors — you might relate to the tube of toothpaste more than you’d like to. Squeezed at both ends, with no one concerned that what’s in the middle simply isn’t going to fit.

After working with thousands of leaders, I’ve observed that most leaders feel this way. And as a CEO and small business owner myself, I’m all too familiar with this reality.

What we feel most squeezed on is our time.

Oftentimes, this tension between the two sets of tasks is referred to as being a “player-coach.” On one end, you’re expected to map out team goals, hold 1:1 meetings (the “coach” role). At the other end, you’re being asked to deliver on tactical work such as writing code, designing a feature, or creating a marketing campaign (the “player” role).

This isn’t inherently always a bad thing. Doing some of the “player” work may keep you feeling connected to what you’re passionate about. Or, perhaps, the tactical work keep your knives sharp around the latest industry trends.

What feels bad is the lived experience of it. You’re overwhelmed, never knowing if the priority you’re chasing is the right one. You’re depleted, trying to keep up with requests from all angles.

You are the toothpaste tube, squeezed from both sides. How do we reconcile this?

From my work with leaders over the past decade, here are the do’s and do not’s for how to navigate this tension well, and allocate your time in the best way possible.

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First and foremost...

DO NOT: Chase balance, or believe a perfect distribution of time exists.

Balance is an illusion.

There is no magical formula for how to best distribute your time. So don’t beat yourself up that you feel like you’re not striking some “perfect mix.”

What is “best” highly depends on the context of the situation: What is required of you, your team, your organization in that moment in time.

This means...

DO: Figure out what is most high-leverage for your specific context.

Ask what would best serve the current context — and choose your allocation of time based on that context.

Some of these questions to ask yourself to help discern this:

• What is most urgent?

• What is team success most contingent on?

• What is most critical to your team and organization at this moment in time?

You might discover: You need to take a step back and nurture your team so they can adopt new processes better. Or, you may realize you need to double down fiercely on finishing your own personal deliverables first, so that the team then contribute their work around what you created.

Examine what role — “player” or “coach” — would truly be high leverage, and prepare yourself to then...

DO: Choose only 1 focus at a time, for a specific period of time.

Not two focuses, just one. Decide what role you’ll concentrate your energy on, and for what specific period of time. I call this “Fluid Focus.”

For example: Say, you’ll focus on being in the “coach” role to help your team navigate a reorg that’s happened. You set aside 1 month to focus on this. This means you intentionally will place your IC engineering work in the back seat for that 1 month.

You accept the trade and acknowledge that you’re not going to get as much (if any) progress done on coding during that 1 month and — here’s the important part — that’s okay. The “player” role of coding is something you’ll come back to.

In order to perform exceptionally well in one role, rather than subpar in both, you recognize you must pick one role to focus on at a time. And then remember, you can switch your focus later (hence, “Fluid Focus”)!

However, none of this works if you don’t communicate it.

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DO NOT: Assume that you can put your head down and just get the job done.

It may seem like a great idea to you to focus on purely the “coach” role for 1 month.

But if your team happens to think that receiving your part of the code was top priority, they’re going to be confused why you haven’t shipped it yet.

And if your supervisor had a deadline for that code in mind, they’re going to believe that you dropped the ball.

This means, you’ll need to...

DO: Communicate exactly the role you’re prioritizing and why — with both your team and supervisor.

While it may seem obvious to you to prioritize a certain role, no one will know unless you tell them.

Specifically, you’ll want to detail:

• The role you’re prioritizing (“player” or “coach”)

• What period of time you’ll be prioritizing that role

• Why you’re prioritizing this role

For instance, to your team, you might say:

“For the next 3 weeks, I’m going to be shifting my priorities to focus on the creation of a new marketing campaign. As a result, we’ll pause our 1:1 meetings we have, and team check-ins. Know that it may feel like I’m more absent than usual, but it’s merely a short phase to serve our company’s overall goals. The company’s growth targets require that I knock this out now, and I’ll need focus deep work time to do so. You can expect me to come out of this phase in 3 weeks, and we’ll pick back up our 1:1 meetings again.”

And to your supervisors, you might say:

“For the next 3 weeks, I’m thinking it makes sense to shift my priorities to focus on completing the creation of the new marketing campaign — that way we can hit the deadline you intended for Q2 growth goals. Are you okay with me prioritizing this? If so, I think some of the managerial updates I usually send to you will be on pause for those 3 weeks, but happy to resume them after this phase is completed. How does that sound to you?”

For the communication to your supervisors in particular, you’re also actively asking for their input on the prioritization of the role. This ensures you’re always aligned with their expectations and not superseding what your supervisor believes to be the most critical priorities.

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A few last caveats as well...

DO NOT: Underestimate the cost of context switching.

It’s little wonder we’re so tired as leaders. Context-switching consumers our energy. Studies have found in fact that 40% of productivity is lost when context-switching.

Because of this, accept that the switching of context itself is work. Build in the margin for that energy expenditure. Perhaps, for example, you place a 1 week buffer between modes as “catch up” time, where you don’t have a specific focus on “player” or “coach” role. This then gives you time to evaluate which role might be best to focus on in the next phase. Or maybe you decide to carve out a much needed break and take time off as needed.

DO NOT: Stay in 1 lane for too long... because you like it.

Be wary of your personal preferences for allocating your time as a leader. We all have a bias to a mode that’s more “fun.” For some of us, that’s relishing being a “coach,” helping our team solve problems and coaching them in their careers. For others, we’re most comfortable jamming in the deep work of our “player” role.

Either way, what we personally like is not always what the situation requires. We must be truthful with ourselves to not conflate the two.

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Putting it all together

A blog post may feel nice to read on a Thursday at 10AM — but it’s of course an entirely different thing to try to put into practice.

Because of this, to help you hold all these pieces in your mind, you can distill it down into what I call the “4 Steps of Fluid Focus”...

1. Stop chasing “balance.” Commit to making a trade.

2. Choose 1 role to focus on (“player” or “coach”) and the period of time.

3. Communicate this choice to your team and to your supervisor.

4. Readjust and reassess as needed.

As you go through these four steps, you’ll likely discover an inconvenient truth: The choice isn’t obvious. In fact, it’s excruciatingly, almost impossibly hard to decide on just one role. A part of you wishes that you could “cheat” and you could just do both roles at once. Well, sure, you absolutely could!

But remind yourself of the tube of the toothpaste: The reason you’re so exhausted and displeased in the first place is because you’re squeezing yourself from both sides. You’re trying to do too many things at once.

Embrace the trade-off. Relish your freedom to be fluid in your focus. You’ll start to notice some interesting side effects…

The cognitive load of doing two roles at once will slowly be relieved. You’ll find depth in your work, not just surface area covered. And the actual output of your work you’ll find more satisfactory.

After all, you deserve a far better fate than the squeezed tube of toothpaste.

-Claire

Looking to find more ways to be precise with your time as a leader? Here are few ways we can work together…

• 🚂 Partner with me to roll-out a leadership training program for your managers.

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally. (I’ve had a few spots open up for 2025 — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚