Manager's Toolkit #8: The Delegation Dilemma: Why High Performers Struggle to Let Go (And How to Help Them)
High achievers often make rubbish managers because they can't stop doing the work themselves. Here's how to help them break free from their own success trap.
Sarah was the best developer we'd ever hired. She could debug complex systems in her sleep, shipped features faster than anyone else, and clients loved her work.
So naturally, we promoted her to team lead.
Six months later, she was working 70-hour weeks, her team was frustrated, and she looked ready to quit. "I can do it faster myself," she'd say, taking back every task she'd tried to delegate. "They just don't get it the way I do."
Sound familiar? You've probably got a Sarah or two in your organisation. High performers who've been rewarded for their individual brilliance but struggle when they need to achieve results through others.
The problem isn't that they're bad people. It's that the skills that made them excellent individual contributors are the exact ones that can sabotage their management success.
Why Brilliant People Make Terrible Delegators
What makes someone a high performer? They're usually perfectionists. They have high standards. They can see problems coming from miles away and know exactly how to fix them.
These are brilliant qualities when you're working alone. But when you're managing a team? They become obstacles at best and work against you at their worst.
High performers often struggle with delegation because they've built their identity around being the person who gets things done. They've been praised for their individual output for years. Their whole sense of worth is tied up in being the smartest person in the room who can solve any problem.
When they delegate, they feel like they're losing control. And perhaps more importantly, they worry they're losing their value to the organisation.
I remember working with one manager who told me, "If I'm not the one writing the code, what exactly am I being paid for?" That fear is real and it's common.
In other spheres, this can be called a “productivity trap” - if I’m not actively being productive and generating output, am I valuable? I bet you, dear reader, suffer from this occasionally too, huh?
There's also the time factor. Teaching someone to do something well takes longer than doing it yourself. In the short term, delegation feels inefficient. High performers, who are used to quick wins and immediate results, find this delay frustrating.
And then there's the quality issue. When you're used to producing excellent work, watching someone else do it differently (or not quite as well) is painful. It feels easier to just do it yourself than to accept "good enough" from someone else.
The Actual Cost of Not Delegating
But here's what these managers don't realise - by not delegating, they're not just hurting themselves. They're holding back their entire team.
When managers don't delegate properly, team members don't get the chance to grow. They become demotivated because they're only given the boring bits while their manager keeps all the interesting challenges. Some of your best people will leave because they feel underused and undervalued.
The manager becomes a bottleneck. Everything has to go through them, which slows down the entire operation. They become stressed and burnt out, which affects their decision-making and their relationships with the team.
And ironically, the organisation loses the very thing that made this person valuable in the first place. They're so busy doing the work that they can't think strategically or focus on the bigger picture.
How to Help High Performers Learn to Delegate
The good news is that delegation is a skill that can be learned. But it requires a different approach for high performers than it does for other managers.
Start with mindset, not tactics. Before you teach them how to delegate, you need to address why they're not delegating. Help them understand that their role has changed. Their value now comes from multiplying the effectiveness of their team, not from their individual output.
One exercise I find helpful is asking them to calculate the cost of their time. If they're spending their day doing work that someone earning half their salary could do, what's the opportunity cost? What strategic work is not getting done?
Address the perfectionism. High performers need to understand that "good enough" often is good enough. Help them identify which tasks actually need their level of expertise and which ones just need to be completed to an acceptable standard.
Create a simple framework for this. Tasks that are high-risk, high-visibility, or require deep expertise might stay with them. Everything else is fair game for delegation.
Make delegation gradual. Don't expect them to hand over their most important projects immediately. Start with smaller tasks where the stakes are lower. Let them build confidence in their team's abilities gradually.
Change how you measure their success. If you're still evaluating them based on their individual output, you're encouraging them not to delegate. Instead, measure them on their team's results. Make it clear that developing others is now part of their job.
In fact, this is probably the key lever in helping your high-performer get over themselves. Their job is to make each of their team as good at their tasks as they are - measure them on that.
Teaching the Mechanics
Once they're mentally ready to delegate, they need to learn how to do it well. Poor delegation is often worse than no delegation at all.
Teach them to be specific about outcomes, not methods. Instead of "Make this presentation better," try "This presentation needs to convince the board to approve the budget. The key points they need to understand are X, Y, and Z."
Help them understand that delegation isn't dumping tasks on people. It's about matching the right work to the right person and providing the support they need to succeed.
They need to learn to ask, "What do you need from me to make this successful?" rather than assuming people will figure it out on their own.
Make sure (oh boy, this feels to obvious to say) that they’re asking for the OUTCOME they want to see and not the PROCESS to deliver the outcome.
Supporting Them Through the Transition
This transition is hard. High performers are used to being confident and competent. Learning to delegate means accepting that they'll feel uncertain and potentially unsuccessful for a while.
Be patient with them. Expect some backsliding. When they're under pressure, their instinct will be to take control again.
Celebrate small wins. When they delegate something successfully, make sure they know you've noticed. Help them see how delegation creates better outcomes, not just for them but for their team. My word yes this will be exhausting for you, but, well, you know, it’s your job, right?
And be honest about the timeline. Becoming good at delegation takes months, not weeks. It's a fundamental shift in how they work and think about work.
The Long Game
The best managers I've worked with all went through this transition (and you probably did too, OK). They learned to find satisfaction in watching their team members grow and succeed. They discovered that teaching someone to solve a problem is more rewarding than solving it yourself.
But it takes time, patience, and support. Your job is to help them see that letting go of the work doesn't mean letting go of their value. It means multiplying it.
The key is remembering that you're not trying to change who they are. You're helping them apply their talents in a new way. Their drive for excellence can make them brilliant managers - once they learn to channel it through other people.