The Hidden Ways Leaders Unintentionally Punish Their Top Performers
How to identify the subtle behaviors that drive away your top performers, and what to do instead
👋 Howdy! Claire here, Founder & CEO of Canopy. I've spent the last decade studying 50+ years worth of leadership research and training 30,000+ leaders. I distill all my learnings in this weekly newsletter.
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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:
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.
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.
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.
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:
Is my vision clear enough that my top performers can navigate without constant direction? If not, am I honest about that gap?
When was the last time I removed something from my top performer's plate rather than just adding to it?
Do I truly give ownership? Or am I still backseat driving while claiming to delegate?
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…” 😉)
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 💚
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