Difficulty Delegating? Here’s What’s Actually Going On

Reading time: 7 minutes

You should delegate more.

You know that. You’ve probably even said it out loud.
Maybe in a performance review. Maybe to a coach. Probably to a very patient significant other who was trying really hard not to roll their eyes because they’ve heard you say it many times before.

“I really should delegate more,” is your go-to line when things feel overwhelmingly busy.
And you mean it. You honestly intend to delegate.

And then you go back to doing everything yourself anyway.

This is not a time management problem. Nor is it a trust problem. Those are part of it, but not exactly.

The real reason you have difficulty delegating is a bit more uncomfortable than any of those reasons.

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The Delegation Myth

Most advice about difficulty delegating, treats it as a lack of skillset. If only you were better at breaking down tasks, giving clear instructions, setting expectations or following up without micromanaging.

If you only just tried harder… right?

Wrong.

That’s bad advice.
It’s not the reason you’re still doing tasks you probably shouldn’t be doing.

Here’s the thing: difficulty delegating is almost never about capability.
You know how to explain a task and you know how to set a deadline.
If you couldn’t do those things, you wouldn’t be in your role in the first place.

What you don’t know how to do – and what most leaders with this problem can’t do – is tolerate the feeling of not being the person who gets it done.

That’s a different problem entirely.
It’s not a skillset problem, it’s an identity problem.

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What’s Actually Happening When You Can’t Let Go

Think about the last time you handed something off… and then took it back.

What happened in your head?
Was it really that the other person was failing? Or was it that they were doing it differently than you, and that felt, on some level, wrong?

For most leaders with difficulty delegating, the answer is the second one. The work wasn’t bad. It just wasn’t yours. And they don’t know how to stop micromanaging.

That’s the trap.

Because somewhere along the way, doing the work became part of how you see yourself. You’re the one who figures things out. You’re the one who can be counted on. You’re the one who makes sure it gets done right.

That identity doesn’t happen by accident – it’s probably why you got promoted in the first place.

But it’s also why delegation feels like loss, instead of relief. Consider it a shadow of all that’s happening in your leadership blind spots.

When you hand something off, you’re not just transferring a task. You’re giving up a piece of how you prove your value.
Your brain, which is very good at keeping you safe, treats that like a threat.

So it finds reasons to convince you to take the task back.
I know that voice inside your head. I hear it too.
(And my voice also whispers sweet nothings about being a perfectionist leader. Yours might too – it’s a common side-product of people who have difficulty delegating)

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The Stories We Tell Ourselves About Difficulty Delegating

The brain is creative. When it wants to take something back, it doesn’t say “I feel threatened by not being needed.” Instead, it says something that sounds completely reasonable.

Here are some things I’ve heard that voice say, and maybe you do as well:

“It’s just faster if I do it.”
Sure, sometimes you can do it faster. But most of the tim it’s a just a way to justify your actions. The 20 minutes you saved today cost you the 2 hours of learning that person needed to eventually stop having you take over their work.

“They’re not ready yet.”
Maybe they’re not. But how long have they been “not ready”? And who’s responsibility is it for getting them ready? If the answer to that second question is “me”, and you’re also the one who has difficulty delegating the work, you’ve got a problem. Those 2 things are in direct conflict.

“This one is too important to delegate.”
This one is sneaky, because it’s sometimes true. Sometimes some things are too important to delegate. But not nearly as many things as you think. Leaders with difficulty delegating hear this voice on about 80% of the items on their task list. But if everything is too important to delegate, you don’t have a priority problem – you have a letting-go problem.

“If I delegate this, I’ll lose visibility.”
At least this excuse is honest. Leaders who struggle with difficulty delegating often fear becoming less visible and less involved. That’s really just a fear of being less needed. And that’s really a fear about your identity.

See how it always comes back to the same place?
Crazy, I know.

Don’t even get me started on imposter syndrome in leadership.

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The Cost Nobody Talks About

Difficulty delegating is expensive.

Every task you do that someone else should be doing has a cost, whether you recognize it or not. The person who should be doing the task doesn’t develop the skill. They don’t build the confidence. They don’t get the reps that would eventually make them genuinely capable of doing it well.

More importantly, they learn that you don’t actually trust them. Even if you never say that. Even if you’d be genuinely offended if someone suggested it.

Regardless of whatever words you use, the “lack of trust” message is clearly delivered through your behavior.

Over time, the team learns to wait for you. They stop bringing critical thinking and creativity to their work, because they’ve learned their ideas will be changed by you. They start managing upward instead of solving problems downward. Before you know it, they’ll be better skilled at looking busy, while they wait to find out what you actually want.

In the end, all you’ve got is a team that feels like it’s underperforming.
You’re right – it is.

That’s usually when people call me to help with leadership coaching.

Because they think the underperformance is their team’s fault. It isn’t. It’s yours, and it’s due to that Unconscious Operating System your running that created the environment that rewards underperformance. And if you don’t decide to change things, you may very well see leadership burnout in your future.

[Interesting fact: Leadership teams also work off a joint Unconscious Operating System, which is an amalgamation of what all members bring to the table, layered in with the interpersonal dynamics between each team member. It’s common for leaders to explore senior leadership team coaching to help understand and address this.]

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What Difficulty Delegating Actually Requires

Getting better at handing off work isn’t the actual way to address your difficulty delegating. I mean, it will definitely help, but it probably won’t last long. Eventually you’ll start taking on the tasks again and sucomb to your difficulty delegating.

To permanently overcome this behavior, you have to change how you measure your own value as a leader.

The leader who does everything, measures their value by output. A winning day is judged by how many boxes you’ve checked off your to-do list (even though the important stuff never gets done.)

On the other hand, a leader who has learned to delegate effectively, measures their value by what the team produces. A winning day is a productive team.

That shift sounds simple.
It isn’t.

It requires you to sit in the discomfort, while someone does something less well than you would have. And you don’t get to fix it.

It requires you to find your value in something you can’t directly control. That means, you need to trust the idea that building someone else’s skillset is more valuable than demonstrating your own.

Most leaders with difficulty delegating have never been explicitly challenged to make that shift.
They’ve just been told to delegate more. Which is a bit like telling someone with a fear of heights to just get closer to the mountain’s edge.

The fear won’t go away until the belief is addressed, and you feel comfortable in your safety.

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A Different Way to Think About It

Your job, at the level you’re operating, is not about doing all the work.

Your job is to build the environment where the work gets done well, by people who are growing their skillsets. And to do it all without you at the center of every decision.

Every time you do something someone else should be doing, you are actively working against yourself, the person who should be doing it and the company.

Let me be clear with this: you are not being a better leader by staying in the weeds.

You are being a more comfortable leader and there’s a big difference between better and more comfortable. Difficulty delegating is what the comfortable choice looks like from the outside.

The leaders I work with, who break through this, don’t do it by getting better at task management. They do it by accepting what their job actually is at this stage of their career, adjusting their identity, and then letting that clarity be more important than the discomfort of letting go.

That’s the work.
And, I guarantee, it’s harder than any task you’re currently refusing to hand off. But it’s also infinitely more rewarding. (And it usually doesn’t take a lot of time!)

If you have difficulty delegating in your leadership role, and you want to understand what’s actually driving it, that’s a good conversation to have with someone who’s heard the voices before and learned to quiet them down.

I put on a workshop for people like you who want to better understand the unconscious patterns holding them back. Learn more about the Leadership Diagnostic Workshop.

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Jeff Matlow is a leadership coach, mentor and 3x entrepreneur who helps senior leaders spot the unconscious patterns keeping their teams dependent on them – then redesign the environment so everyone can actually perform. He’s spent 25+ years working with leaders at Disney, Porsche, Nestlé, and hundreds of high-growth companies. Think Ted Lasso meets Brené Brown meets a Navy SEAL. Learn more about working with Jeff or subscribe to The Best Leadership Newsletter Ever.