Why Leaders Struggle to Delegate (And the Hidden Fear Behind It)
“Micromanagement is a function of distrust. Letting go is an act of trust."
— Brené Brown
Over the last four weeks, I witnessed the biggest transformation I've seen in a client in a very long time.
As you might remember from my last newsletter, an old client of mine initially came back to coaching looking for help with his morning routine after a promotion to his dream job.
What we found instead, just two sessions into our work, was not only what neither of us had anticipated, but it revealed a connection I hadn't seen as clearly before: between the inner shift in a leader and the external expressions of their leadership.
If you missed the previous newsletter, in a nutshell, finding an internal indicator of stress had already helped my client reconnect to himself and to manage his levels of overwhelm. You can read the full version here.
A Deeper Transformation
After the internal shift from our previous sessions, he came into session three not just calmer; he looked excited and free. It seemed like something had reorganised inside him.
Following a very positive update about how things had been going at work, I asked him what had been the main shift that had made such a difference.
He didn't need to think. He replied almost immediately.
"I'm delegating unapologetically.”
There was a newfound freedom in his voice:
"I was afraid to let go of control. Mostly afraid of what would happen if one of my team members couldn't deal with the work. So I was keeping it to myself."
I see this time and again in leaders I have worked with following a promotion. They hold on to work out of fear. Both the fear of their team making mistakes, and the fear of losing the identity that has made them feel valuable. I wrote an article on this process which you can read here.
My client had found a way to move past those fears. When I asked him to identify exactly what he had done, he smiled and said:
“I'm just... letting go. Letting go. Letting go!"
The Real Reason Leaders Don't Delegate
During that session, we uncovered the main reason why he wasn’t delegating. In his own words, my client said
"Up until now, I've been delegating based on what I think my team can do; only giving them work I was confident they could handle."
He paused.
"But if my boss only delegated to me based on what she thought I could do, I'd feel... disrespected. Like she didn't believe in me. Like she was keeping me contained."
That was the insight that completely shifted his mindset about delegation and his relationship with his team.
He wasn't holding back because his team wasn't ready. He was holding back because he wasn't ready to trust them. And, underneath that, he wasn't yet ready to trust himself to handle anything that might go wrong.
He could now see it clearly.
He had been keeping his team small.
And himself overwhelmed by not delegating.
The Unfounded Fear
I've seen this pattern in almost every leader I work with at a similar point in their journey.
The usual fear is: "My team isn't ready."
But more often than not, when I speak to their teams, the opposite is true.
That’s exactly what happened with another senior leader I recently worked with. As part of our coaching engagement, I ran a 360 degree stakeholder interview process including several of her colleagues.
Every single one of her direct reports told me they wanted more responsibility and felt they could take on more.
When I asked them to rate my client on a scale from 1 to 10 on delegation, they said she was at a 5 or a 6. However, when I asked my client to rate herself, she gave a score of 8 or 9.
I share this example as leaders often feel that their teams have less capacity than they actually have.
The good news is, you don't need to guess. Just ask your team. What I have seen consistently is that leaders who sit down with their direct reports to check in honestly on workload and capacity discover their team is hungry for more.
The insight is clear:
The unfounded fear around delegation isn’t about your team’s capacity; it’s about your ability to trust both your team and your capacity to support them if and when things go wrong.
The Unapologetic Truth
When my client sat with that realisation, something shifted in his body.
He straightened. His shoulders opened. As if he'd just found a new superpower. Then he said:
"So I'm just going to delegate above their capacity."
He paused, then added:
"Not too far above. Just slightly. Enough that they have to stretch and grow."
He had intuitively found what research confirms:
We all grow best when we're slightly outside our comfort zone. Challenged enough to stretch, but not so far that we become overwhelmed.
In many ways, the job of a leader is similar to that of a coach.
You need to believe in your people more than they believe in themselves.
Challenge them in ways that keep them engaged and at the edge of their growth.
And trust that if something goes wrong, you'll be there to support them.
A confident leader doesn't keep people small out of their own fear.
A confident leader trusts their team to rise to the next challenge.
But first, they need to trust themselves in their new leadership role.
Delegation With Intention
To help my client find that sweet spot for growth for his team, we spent the last part of our session developing a growth plan for each of the key members of his team.
Some needed more challenge. Others needed more support.
Some were ready to take on bigger projects. Others needed more coaching first.
This is what I call delegating with intention. Not a blanket approach, but a conscious, personalised one. Knowing your team well enough to understand where each person is, what they need to grow, and how much stretch is the right amount.
From self-awareness to conscious leadership
During our last session, my client gave me an update on how his team was responding to his newly found letting go, letting go, letting go approach.
Instead of drowning, as he had feared, his team members are rising to it. They're engaged and growing. They're coming back to him with solutions, not problems.
And because of this shift, my client has stepped back from most of the day-to-day operations, which is giving him more time for strategic thinking and for coaching his team.
In other words, he's actually leading.
Remember the red sphere from Part One?
He continues to use it as his inner check-in. It's smaller than it's ever been.
And some of his original practices are making their way back. He's meditating again. Going to the gym a couple of times a week.
Which, if you remember, was his original goal when he first reached out.
He didn't find his way back to the gym by focusing on the gym.
He found his way back by learning to trust himself and then learning to trust others.
That's the connection I hadn't seen as clearly before working with him:
Delegation wasn't just a leadership strategy.
It was the thing that gave him back his life.
And it only became possible when he stopped holding on out of fear and started letting go with trust.
Practice for the Week: Delegating With Intention
Think of two or three people on your team.
For each person, ask yourself: how much challenge do they need right now, and how much support?
Reflect on where you might be keeping them small and what would stretch them just beyond their comfort zone.
Then delegate to each of them this week a task or project just above their current capacity.
How might this two-part journey be useful in your own leadership?
Do you need to spend more time building self-awareness and reconnecting to yourself?
Or do you need to take more risks in your delegation and trust that you and your team will rise to the new challenges?
Comment below and let me know, or forward this to a leader who might find it useful.
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