Delegating When you Don't Feel Ready

Avoiding the trust trap and learning to scale your leadership potential

There’s a peculiar yet common trap that emerging leaders can fall into when it comes to delegating. It’s the one where you know you should be delegating more, but every time you try, you end up stepping back in. Maybe you’ve been burned before. Maybe you see gaps in the team’s judgment. Or maybe you feel like the stakes are too high to let something slip.

Ultimately, you want to trust your team more, but maybe you just don’t feel ready yet. The problem is that trust isn’t something that just shows up. It grows through doing the work together. And delegation—real delegation, not just task-passing—is one of the ways it grows.

Let’s explore what makes this so hard, what it costs you to avoid it, and how to get better at it even when trust still feels like a leap.

Why Trust Feels Risky

If you’ve been in leadership long enough, you’ve seen your share of bad calls. Maybe it was the developer who spent weeks chasing a refactor that wasn’t really needed. Or the product manager who pushed a feature that didn’t solve a real problem. Or perhaps there was a teammate who said they had something covered, but didn’t.

Experiences like these leave a mark. They shape how much slack you give the next person. Sometimes it can feel safer to do it yourself—or at least to stay close enough that you can step in if things go sideways.

But that safety is only skin-deep.

Underneath, there’s a bigger risk playing out: you end up building a team that doesn’t grow, because you never gave it the room. You become the bottleneck, not the backstop, and your team ends up not learning, not growing, and not trusting you to teach them.

The Real Cost of Doing It All Yourself

Let’s name what’s at stake here. When you try to stay involved in every decision, every deliverable, and every piece of work, three things happen:

1. You burn out. No one can hold everything forever. If you try, you either work nights and weekends or you drop some of the balls you have in the air. Usually both.

2. You slow the team down. If people need your input to move forward, progress gets stuck in your inbox. They wait, or they guess—and neither outcome is good.

3. You miss the upside. The more time you spend managing the work, the less time you have to think about the big picture. You lose the chance to plan, coach, and lead.

That last one is easy to overlook, but it’s important. Leaders who fail to delegate often

get stuck in the middle layers of work. They never fully step into their leadership role, because they’re still doing the job they used to have. That’s not just bad for them—it’s bad for the business.

How to Build Delegation Muscle

Delegation is a skill. It takes practice. You don’t have to go from being a control freak to a Zen master of delegation in one week. You just have to start where you are and move one step forward.

Here are some ways to do that.

1. Define “safe to fail” areas

Not every decision needs your sign-off. Start by identifying parts of the work where mistakes are low-cost and can be easily recovered. These are the best places to start handing things off.

For example, let your team choose the order of tasks in a sprint. Let them decide how to break down a feature or communicate progress to stakeholders. These aren’t trivial decisions, but they’re typically not life-or-death either. If something goes wrong, it’s a chance to learn, not a crisis to fix.

The goal is to give your team space to build judgment in lower-risk areas so you feel more confident expanding that trust over time.

2. Share context, not just tasks

People usually don’t make bad decisions because they’re careless. They make them because they’re working with limited information.

If you hand off a task without explaining why it matters or how it fits into the bigger picture, you’re setting the other person up to guess. And when they guess wrong, you start to believe they’re not ready. It’s a vicious cycle.

Instead of just saying what needs to be done, explain why. What are you optimizing for? What are the tradeoffs? What would success look like? Sharing this context gives your team a better shot at making decisions you can stand behind—even if they’re not the ones you would have made.

3. Check-in vs. micromanaging

It’s okay to check in—you should. Delegating doesn’t mean disappearing. It means moving from doing to supporting.

The key is to shift your questions. Don’t ask, “Are you doing it the way I would?” Instead, ask, “Do you have what you need to keep going?” or “What’s been harder than expected?”

This keeps you in the loop without taking the wheel. It also gives your team a chance to surface problems before they become real issues, which builds your trust in them over time.

4. Use a simple framework

Here’s a lightweight framework that works:

Delegate > Observe > Feedback > Iterate

• Delegate a specific piece of work.

• Observe how it goes through check-ins, deliverables, or outcomes.

• Give feedback that’s timely, specific, and focused on learning.

• Adjust the level of support, scope, or guidance next time.

This helps you grow trust in a structured way. You’re not just hoping they’ll get better. You’re coaching them through it—and giving yourself the evidence you need to feel more confident letting go.

Let Go (of One Thing at a Time)

Here’s a simple call to action: pick one task this week that you usually keep close. Delegate it fully. Don’t just assign it—share context, agree on outcomes, and step back. And to make sure you follow through, tell someone who can act as an accountability partner, such as a coworker, mentor, or coach.

Then let it play out.

Resist the urge to jump in. Let the person learn. Let yourself learn, too.

Because the truth is, you don’t have to feel like you trust your team completely to start delegating. You have to trust them enough. Enough to let them try. Enough to believe they’ll get better. Enough to bet that growth is possible—for them and for you.

And that’s how trust is built. Not all at once. Not on faith alone. But one step at a time, in the work itself.

You’re not failing if delegation feels hard. It is hard. But it’s also the only path forward if you want to lead something that scales.

So take the first step. Let go of one thing. Watch what happens. You might be surprised by what your team is ready for.