Why Leaders Struggle to Delegate—and How to Change That

Posted On: March 31

Delegation is something leaders know they should do. But they often struggle. It’s not about holding on to power—it’s about fear. Fear that the work won’t be done right and that it won’t meet their standards. Fear it won’t be delivered on time.

So, instead of trusting their team, they make a significant leadership error: they do the work themselves. Not a good strategy.

I’ve seen this firsthand. As an executive coach, I hear the same reasons over and over: “It takes too long to explain.” “I don’t know if they have the skills, but I know I do.” Or the classic, “If I delegate and they fail, it will make me look bad.” When the project is high-stakes, the instinct is to keep it close.

If this sounds familiar—and your calendar is overloaded with tasks someone else could handle—you’re not delegating effectively.

That’s not just a time-management problem. It’s a leadership problem. Failing to delegate leads to burnout, frustration, and micromanagement. But more importantly, it holds your team back and limits your impact. Delegation isn’t about getting things off your plate. It’s how you grow your people and how you focus your time. It’s how you make your greatest impact.

Leadership expert Emily Morgan calls delegation “your personal energy management system.” Dave Kerpen, author of Get Over Yourself, says the actual barriers are emotional— perfectionism, control issues, and, as I pointed out, fear of failure. Left unchecked, these create bottlenecks and wasted potential. As Kerpen reminds us, “Delegation is about how you choose to spend your time, your focus, and ultimately, your life.”

To make this practical, I created a simple delegation framework: Prioritize, Assign, Clarify, Empower, and Review.

First, prioritize what only you can do.

Where do you create the most value? Focus there. Set strategy. Guide your senior team. Be the face of the company in critical conversations. Let go of the rest. You don’t need to be in every interview. You don’t need to approve every purchase. Once the right people are in place, trust them to lead. That’s what you hired them for.

Do the work ONLY you can do. Let someone else do everything else.

Second, assign the right task to the right person.

Don’t hoard the work you’re good at just because it makes you feel important. That might feed your ego, but it starves your team of growth.

Third, clarify the task.

Set expectations. Define success. Be specific about deadlines and outcomes. And wherever possible, create binary goals. Ambiguity breeds mediocrity. If the goal is measurable, there’s no debate—it was either achieved or not. No politics, favoritism, or guessing. Just data. That’s why Kerpen advises: “Delegate outcomes, not tasks.” 

Fourth, empower them.

Provide the resources, tools, and support they need—and trust them to deliver. Start small. Build momentum with quick wins. Mistakes will happen. That’s how people learn.

Finally, review.

Stay in the loop without hovering. Check-in regularly with focused questions: “How’s it going?” and “What are your roadblocks?” Offer coaching. Share feedback. Celebrate progress. Create a simple system to track how things are going. A dashboard can work well—something visual and easy to understand. Green means you’re on track. Yellow signals struggle. Red means we’ve got a problem. This lets you spot issues early and offer support before things go off the rails. Once your team sees that tracking doesn’t equal punishment—it equals help—they’ll welcome it.

If someone on your team can do the task 80% as well as you, delegate it.

Free yourself up to focus on the things that truly require your leadership. And if they stumble? Consider whether the failure was in execution—or in how you delegated. Most delegation breakdowns are upstream, not downstream.

You can’t do it all. You shouldn’t try. The best leaders focus on what only they can do—and trust their teams with everything else.

You can either be a control freak or a great leader. You don’t get to be both.


2025 is already underway, and this video is here to help you make it a standout year.  In it, I share six key insights about what you should focus on that will have a strong positive impact on your organization. Six important ideas to make you more successful.

I’m confident you’ll find it valuable.

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