Disappointing your direct reports
How to tell your team the one thing they don’t want to hear.
What’s the hardest message you’ve ever had to communicate to your team?
I remember chatting with a CEO a few years back about what he felt like was his hardest message to communicate in his career…
The company had drastically overestimated their revenues, and now would have to move to severe cost-cutting. For the first time in the company’s history, they’d have to do layoffs. He was devastated. A feeling of failure, of guilt and responsibility for it all, and of regret in not taking action sooner.
But the overwhelming feeling he told me was eating at him was this:
“Disappointment. I don’t want to disappoint my employees.”
More than anything, for this CEO and for so many of us as leaders, we fear disappointing our team.
Falling short. Not helping them get to where they want to be.
For better or worse, disappointment in the workplace is unavoidable. Perhaps it is in all of life. You don’t always get what you want. Your expectations sometimes don’t match up with reality.
And so, communicating disappointing news becomes necessary. It’s part of the path we all travel as leaders.
But it doesn’t have to be so bleak. Communicating a disappointing message can also become an opportunity.
Done well, and you can help your team transition to a new season. In a dire moment, you can unexpectedly uplift and reorient your team, making way for better days ahead.
How exactly can you do this?
Below, I detail some of the hardest conversations of around disappointing your team, and how to handle each…
Telling your direct report they’re not ready.
An engineering manager once shared with us here at Canopy: “I have a junior team member who is new to the company and has a lot of opinions on the overall organization and processes. They have told me that they feel as though they are meant to be weighing in on bigger decisions, but just don’t have the experience yet. What do I do in this situation?”
Yes, you will be disappointing them by letting them know that they’re not ready to weigh in on those bigger decisions. But the key thing here is to not shutdown their initiative (they may never want to demonstrate it again), but rather to redirect their eagerness.
There is usually positive and well-intentioned energy behind a junior employee’s desire to contribute more. Address and highlight that energy — and then redirect it.
To do this, you might try saying something like:
“I deeply appreciate your desire to want to contribute to the organization in a greater way. And I have no doubt you’ll do so in the future. I also want to take this time to align on where your milestones moving forward are. Here's where I see you right now and here are the next steps to get to where you want to go. It’s essential that we don’t skip over these steps, as they are essential to building your foundation of leadership.”
Here’s why this can work:
You recognize the intention behind their ask — that they want to be helpful. (“I deeply appreciate…”)
You show confidence that this is an area they could contribute to be helpful. (“I have no doubt you’ll do so in the future…”)
You realign on what reality is and the steps to get to their desired reality. (“I want to take this time to align on where your milestones moving forward are…”)
Telling your direct report they didn’t get the promotion.
This is one of the trickiest conversations to have as a leader — especially if you feel like your direct report deserved the promotion, and the decision was out of your hands.
Regardless of the context and reasons, the main thing to focus on in this conversation is a hopeful path for the future. You don’t want this person to give up – you want to give them fuel to be resilient.
Here’s what you might say:
“I recognize this is not what you wanted the result to be. And I completely understand how you may not feel it’s reflective of your growth and effort you’ve poured into the past year. However, the road doesn’t end here. I can assure you this one event will not define the rest of your career. There is always another opportunity, and I’d love to support you in that journey.”
Here’s why this can work:
You demonstrate empathy on a specific level and address their disappointment head on, not sugar-coating it. (“This is not where you wanted to be…”)
You make it clear this is NOT the “end all be all”. (“The road doesn’t end here…”)
You provide optimism in the next opportunity and you volunteer your support. (“There is always another opportunity…I’d love to support you…”)
To help an employee see career growth as more than just a promotion, you may want to check out our “Effective Career Development Conversations” webinar.
Sharing that your team failed.
You may have winced at that word, “failure.” It’s natural. We don’t like to linger on when things don’t go our way….
But, in order to talk about it well, we must be willing to face it. Steel yourself. Failure is inevitable. Not achieving something will happen. Sometimes in small ways, other times in big ways. It happens to everyone. And just because your team didn’t meet a goal, or a major mistake was made – that does not mean you are a failure.
As a leader, you can share and talk about failure in a way is productive and forward-looking.
Here’s what you might say:
“We fell short, and that is on me. I take full responsibility for this. I’m committed to doing everything possible to make sure we learn from it. Here’s specifically our learnings, and what our course of action will be going forward toward a more productive future…”
Here’s why this can work:
You’re owning the failure, through and through. No minced words. The accountability will feel refreshing to your team, and help your team feel they can place their full trust in you. (“I take full responsibility…”)
You focus on learning from mistakes, not wallowing in self-pity or pointing fingers. (“I’m committed to doing everything possible to make sure we learn from it…”)
You’re specific about what you learned and how you’ll avoid failure in the future. (“Here’s specifically our learnings…”)
Depending on what the exact “failure” is, you’ll want to, of course, adjust some of these recommendations to best fit the magnitude of the event, and your role in it.
For example, if you’re a frontline manager needing to share news about a layoff and you were not a part of the decision-making process, it doesn’t make sense to “own” the failure.
Letting someone go.
I have personally found this to always be the hardest message to communicate. Few messages are emotionally and energetically taxing as firing someone – mainly because it is so unequivocal. The road does end here. It can feel cold and brutal, even if the person’s performance warranted. (Sometimes, it feels hardest when it was a performance issue because you feel complicit in their poor performance and wonder what more you could’ve done.)
The biggest thing most leaders forget to do when letting someone go is: Being clear. We try to be nice, and share the news softly – but the other person feels confused or felt “led on” in the conversation. The lack of clarity is most often what frustrates the person on the other side. They think to themselves, “Wait am I getting fired or what are they saying?” or “What does this really mean? When is my last day?”
With this in mind, here’s what you might say:
“Today is your last day. We are letting you go. It’s effective immediately. This is because of ______ [insert very short and clear reason, such as “performance issues” or “company-wide layoff”]. I want to thank you for all of your contributions, appreciate everything you’ve done for the organization, and know you will find success in your next chapter.”
Here’s why this can work:
You’re being extremely clear. There is no room for interpretation. (“Today is your last day…”)
You didn’t babble about how hard of a decision it was, or how you don’t want to do it: You kept it concise and focused on the other person. (“We are letting you go…”)
You showed gratitude and an eye toward the future. This is just one stop on their career journey. They may have a very different and brighter stop somewhere else. (“I know you will find success in your next chapter...”)
Keep in mind that this message may differ depending on what employment laws are for where you company is located, so be sure to check in with your legal counsel and/or HR team to make sure you are compliant.
It feels hard because it is hard.
I doubt you read any of this with a smile. Even with these frameworks and scripts, communicating disappointing news will almost never feel pleasant or convenient.
Reality also reminds us that we are only in control of ourselves: No matter how well you prepare and communicate the disappointing message, ultimately, the reaction of your team is something you cannot control. It’s out of your hands.
While this can feel defeating, I hope you also find it liberating. Know that you are doing the very best you can – and that is enough.
You’re choosing to take time to read this piece. You’re choosing to reflect on some of the suggestions above, and prepare thoughtfully. You’re choosing to gather courage to implement these suggestions in your own way.
You are putting your best foot forward. What more can you do?
I say, “Nothing.” Just keep going. Keep trying.
It feels hard because it is hard. But you’re strong enough to find a way through it.
-Claire
✨ For a deeper dive, be sure to check out “Leveling-Up Your Communication” in Canopy. And if you’re keen to share best practices like this with all your managers, we personally design custom leadership training programs, including on feedback and performance conversations. Learn more here.
💚 If you’ve been enjoying reading my original writing here, I wanted to share two other ways to gain even deeper leadership insights…
(1) Receive free daily leadership tips when you sign-up for Canopy (and receive them on your phone if you download our free iOS app along with it). Learn more about Canopy here 🌿
(2) Work with me personally and our team to implement a custom leadership training program for your internally-promoted managers, based on our past decade of research. Learn more about Canopy for Teams here 🏔️