The Delegation Dilemma: Why Good Leaders Struggle to Let Go

linnearader
Oct 29
7 min read

Listen to the audio version here!

Here's something nobody tells you when you step into leadership: the very skills that made you successful as an individual contributor, your ability to execute flawlessly, your attention to detail, your commitment to excellence, can become your greatest liability as a leader. And nowhere is this more apparent than in delegation.

I see it constantly. Talented, dedicated leaders drowning under the weight of tasks they should have handed off months ago. They're working late, skipping lunch, answering emails at 10 PM, all while their teams sit with capacity and capability that's going completely untapped. It's not that these leaders don't know they should delegate. They do. But knowing and doing are two very different things.

Let me share something personal. I have a hard time saying no. I genuinely don't want to disappoint anyone, so for years I just kept accepting projects and duties until I couldn't see the light of day anymore. That created a fear in myself that I would cause that same drowning feeling in my team. So my solution? Keep trying to do everything on my own and not delegate. Brilliant strategy, right?

The result was predictable: I was exhausted, burned out, and drowning. But here's what I didn't see coming, my team wasn't growing either. They were capable, talented people sitting on the sidelines watching me struggle. After a few honest conversations and some very careful planning, my team actually asked me to delegate more to them. They wanted the opportunity to step up. I practiced, stumbled through it, learned what worked, and the rest is history. Life is much better now, both for me and for my team.

But why was it so hard in the first place? Why do good leaders struggle so much with something that seems so straightforward?

The Perfectionism Trap

"Perfect execution of everything means perfect execution of nothing."

Let's start with the elephant in the room: perfectionism. Many leaders built their careers on being the person who gets it right, who delivers quality work, who never drops the ball. That identity becomes deeply ingrained. When you delegate, you're essentially saying, "Someone else can do this well enough." For perfectionists, "well enough" feels like failure.

The truth is, leaders under a lot of stress struggle even more with delegating. When people are looking to you to be perfect, or worse, when you feel that internal pressure yourself, you won't want to take the chance that the person you delegate to doesn't do a good job. The stakes feel too high. Your reputation feels too fragile. So you hold on tighter, convinced that doing it yourself is the only way to ensure quality.

But here's what I've learned: perfect execution of everything means perfect execution of nothing. When you're spread too thin, even the work you keep suffers. Your best work requires focus, and focus requires choosing where to invest your limited energy.

The Trust Paradox

Woman with red hair and striped shirt screaming with hands in the air. Her nails are painted red and black; she looks frustrated. — The weight of potential consequences makes letting go feel reckless

Delegation requires trust, but trust requires evidence, and evidence requires opportunity. It's a circular problem that leaves many leaders stuck. You can't fully trust someone with a task until you've seen them handle it, but they can't demonstrate their capability until you give them the chance.

This paradox is particularly strong in organizations where mistakes have consequences beyond just missed deadlines. In public service, where I've spent my career, a mistake might mean an angry resident, a board member asking pointed questions, or worse, a safety incident. The weight of potential consequences makes letting go feel reckless, even when logically you know your team is capable.

The solution isn't to eliminate risk, that's impossible. It's to manage risk strategically. Start with lower-stakes tasks where mistakes create learning opportunities rather than crises. Build trust incrementally through success, not by throwing people into the deep end and hoping they swim.

The Control Illusion

"Real leadership isn't about being irreplaceable."

Here's something leaders rarely admit: sometimes we don't delegate because we like being needed. There's a certain satisfaction in being the person everyone comes to, the one with all the answers, the indispensable expert. It feels validating. It feels important.

But this is an illusion of control that costs everyone. When you position yourself as the only person who can handle certain tasks, you create organizational fault lines. What happens when you're sick? On vacation? Dealing with a crisis that requires your full attention? Everything grinds to a halt or worse, falls apart, because you've made yourself the single point of failure.

Real leadership isn't about being irreplaceable. It's about building a team that can function excellently with or without you in the room. That might feel like diminishing your importance, but it's actually the ultimate measure of leadership success.

The Time Investment Excuse

"It's faster if I just do it myself." Every leader has said this, and in the short term, it's absolutely true. Teaching someone to do a task takes longer than doing it yourself. Explaining your thinking, answering questions, reviewing their work, providing feedback, all of that requires time you might not feel you have.

Hand holding a minimalist wristwatch with a white face and brown leather strap. The background is softly lit, creating a calm mood. — It's faster to do it myself

But this is short-term thinking that creates long-term problems. Yes, delegation is a time investment upfront. But it's an investment that pays dividends. Once someone learns the task, they can handle it indefinitely. You've multiplied your capacity. You've freed yourself for higher-level work that only you can do. You've created development opportunities that make your team stronger.

I had to learn this the hard way. Every time I chose to do something myself because it was "faster," I was choosing immediate efficiency over long-term capacity building. I was keeping my team dependent rather than developing their independence.

The Fear of Irrelevance

"You move from executing to enabling, from doing to developing, from managing tasks to cultivating talent."

Let's talk about something uncomfortable: sometimes leaders don't delegate because they're afraid of becoming unnecessary. If your team can handle everything without you, what's your role? This fear is particularly acute for leaders who've been promoted from individual contributor roles where their value was measured by their personal output.

But here's the truth: when your team can handle operations smoothly, you become free to focus on strategy, vision, and innovation. Your role doesn't diminish, it evolves. You move from executing to enabling, from doing to developing, from managing tasks to cultivating talent.

The leaders I admire most aren't the ones who have their hands in everything. They're the ones who've built teams so capable that the organization thrives in their absence. That's not irrelevance, that's impact.

The Growth You're Stealing

Here's the hardest truth about failure to delegate: it's not just hurting you. It's hurting your team. Delegation isn't just a time management strategy, it's a development tool. When you hold onto tasks your team could handle, you're stealing their opportunities to learn, grow, and stretch their capabilities.

Your team members need challenges to develop. They need the chance to tackle projects that push their skills, make decisions that matter, and yes, sometimes make mistakes they can learn from. When you insist on doing everything yourself, you're keeping them in a holding pattern, maintaining their current skill level rather than helping them reach their potential.

I saw this clearly once I finally started delegating. Team members who I thought were "not quite ready" for certain responsibilities proved incredibly capable when given the chance. They brought fresh perspectives I hadn't considered. They found more efficient approaches than my established methods. They grew in confidence and competence in ways that wouldn't have been possible if I'd kept holding on.

The Path Forward

"Make yourself available for questions, but resist the urge to hover or take over at the first sign of struggle."

So how do you break free from the delegation dilemma? It starts with honest self-reflection. What are you really afraid of? Is it about the work, or is it about you? Are you protecting your team from overwhelm, or are you protecting yourself from feeling unnecessary?

A path through trees — Create a path forward for yourself and your team.

Then, start small but start now. Identify one task you're currently handling that someone on your team could do with proper guidance. Not the most critical project, something with manageable stakes where mistakes would be learning opportunities rather than disasters. Delegate it completely, not just the execution but the ownership.

Provide the context they need. Explain not just what to do, but why it matters and how it connects to bigger goals. Make yourself available for questions, but resist the urge to hover or take over at the first sign of struggle. Give them room to figure things out, even if their approach differs from yours. I can attest to how truly hard this is!

And here's the crucial part: when they complete the task, even if it's not exactly how you would have done it, acknowledge what worked. Build on success. Help them learn from what didn't work. Create a feedback loop that develops capability rather than dependence.

The Liberation of Letting Go

The beautiful irony of delegation is this: the moment you accept that you can't do everything perfectly is the moment you enable everything to be done better. When you distribute leadership across your team, you multiply impact. When you develop others' capabilities, you elevate the entire organization.

Yes, it requires trust. Yes, it takes time. Yes, it means accepting that things might be done differently than you would do them. But different doesn't mean wrong, and perfect is the enemy of sustainable.

Your job as a leader isn't to be the best at everything. It's to ensure everything gets done well by building a team capable of excellence. That requires letting go, even when, especially when, letting go feels uncomfortable.

The question isn't whether you can afford to delegate. It's whether you can afford not to.

As always, carry social kindness with you everywhere you go. The world needs you and your positive mindset!