The Courage to Delegate: Why Letting Go Is the Hardest Part of Leading

There's a moment every emerging leader hits — usually within the first few months of a new role — where they realize they're doing two jobs at once. Their old job: managing. Hitting deadlines, overseeing deliverables, keeping the team on track. Work that's familiar, tangible, and measurable. Their new job: leading. Setting direction, developing people, thinking strategically about what comes next. Work that's less defined, harder to measure, and — if they're honest — a little uncomfortable. The problem? Most new leaders never fully make the transition. They keep doing the old job because it feels safer. Because they know they can do it well. And because — quietly — they're not sure their team will do it as well as they did. This tension shows up most clearly around one skill: delegation.

Why Delegation Feels So Hard

On paper, delegation seems straightforward. You have too much on your plate. Someone on your team can handle it. You hand it off. Done. In practice, it rarely works that way.

New leaders often struggle with delegation for reasons that go deeper than time management. There's a concern about quality — what if the work doesn't meet the standard I'd hold myself to? There's a worry about perception — will it look like I'm dumping work on my team too early? And underneath both of those, there's often a quieter fear: if I'm not the one doing the work, what exactly is my value here? These aren't signs of weakness. They're the natural growing pains of a leadership transition. But if they go unaddressed, they keep leaders stuck — still managing instead of leading, still in the weeds instead of looking ahead.

What Gets in the Way

In our Emerging Leaders Peer Group sessions, delegation comes up almost every cohort. And the pattern leaders describe is remarkably consistent: They hesitate to hand things off. They worry about quality slipping. They feel a quiet guilt about "burdening" their team. So they keep doing it themselves. It feels easier in the short term. But it comes at a real cost — their own leadership development stalls, their team doesn't grow, and over time, burnout becomes a real risk. According to DDI's Global Leadership Forecast 2025, only 1 in 5 manager candidates demonstrate strong delegation skills — even though delegation consistently ranks among the most powerful tools leaders have for preventing burnout and building high-performing teams. The gap between knowing you should delegate and actually doing it is where so many emerging leaders get stuck.

What It Takes to Break Through

Leaders who've moved past this pattern tend to describe the shift in similar ways. It's less about learning a new technique and more about a fundamental change in mindset.

It requires tolerating imperfection — at least at first. When you delegate, the work will sometimes come back not quite the way you'd have done it. That's not failure; that's the cost of developing someone. The goal isn't a perfect handoff. It's a process of coaching, feedback, and growing trust over time.

It requires believing your team wants to step up. Most leaders are genuinely surprised to discover how eager their direct reports are to take on more responsibility. The hesitation to delegate is often more about the leader than the team. People want to grow. They want to be trusted. When you give them the chance, they frequently rise to it.

It requires redefining what "good work" looks like for you. As a manager, your value came from doing excellent work yourself. As a leader, your value comes from enabling others to do excellent work. That's a different standard, and it takes time to internalize. The shift from I did a great job to my team did a great job isn't always comfortable, but it's essential.

It requires getting comfortable being uncomfortable. Leadership growth rarely happens inside the comfort zone. The leaders who develop fastest are usually the ones who lean into the uncertainty — who push through the discomfort with self-awareness, good coaching, and the support of people who've been there.

Delegation Is a Leadership Skill, Not a Management Shortcut

One of the most important reframes for emerging leaders is this: delegation isn't about offloading work. It's a core leadership capability. When you delegate well, you're not just freeing up your time (though that matters). You're developing your team's skills and confidence. You're building a culture of trust and ownership. You're creating capacity for your organization to grow beyond what any one person can do alone. And you're investing in your own ability to lead at a higher level. Done well, delegation multiplies your impact. It's one of the few leadership moves that benefits everyone — you, your team, and your organization — at the same time.

Making the Shift

If delegation is an area you're working on, a few practical places to start:

Start small, but start. Pick one task you've been holding onto and hand it off. Be intentional about setting clear expectations, providing the right context, and building in checkpoints — but resist the urge to take it back. Coach, don't rescue. When the work comes back imperfect, your job is to give feedback and guide improvement — not to redo it yourself. That's where the real development happens, for both of you. Reflect on what you're holding and why. Not everything you're doing needs to be done by you. Ask yourself honestly: is this something I should still own, or is this something I'm holding onto because it feels familiar? Find your people. The leaders who navigate this transition most successfully rarely do it alone. Peer communities, mentors, and coaches provide the outside perspective and honest feedback that's hard to get inside your own organization.

The Work We Do Together

This is exactly the kind of challenge we work through in the Emerging Leaders Peer Group — not in theory, but in practice, with a group of leaders who are navigating the same transition you are. Because the gap between knowing you should delegate and actually doing it isn't closed by reading an article. It's closed by practice, by accountability, and by the support of people who get it. If you're ready to make that shift, we'd love to have you in the room.

Interested in learning more about our next cohort? Get in touch — we'd be glad to tell you about it.