9 Delegation Mistakes That Keep Entrepreneurs Stuck (And How To Fix Them)

Have you ever had something on your to-do list that needed to get done—but it sat there, untouched, weighing on you?

You knew you weren’t the right person to do it. But you didn’t hand it off either.

So, you tried to tackle it yourself. It drained your energy. You squeezed it in between other priorities, compromised your sleep, and ended up with a mediocre result—not because you didn’t care, but because you were never the right person for the job in the first place.

Sound familiar?

This is what happens when delegation breaks down—or doesn’t happen at all. And for entrepreneurs, this is a huge roadblock to growth.

But the good news? It’s completely fixable.

Here are the nine most common delegation mistakes I see entrepreneurs make—and what you can do instead to create a more leveraged, energized, and productive future.

1. Not trusting your team to handle it.

Delegation isn’t just a skill—it’s a mindset. And often, it starts with one big shift: letting go of the belief that “I can do it better myself.”

When you don’t trust your team to take on more, you miss the opportunity to create space for what really matters—the activities you're best at and love doing, your relationships, and your vision.

So ask yourself: If I had more time in the day, what would I use it for?

That vision is your cue. It means something’s ready to be delegated.

2. Insisting everything be done your way.

Micromanagement is one of the fastest ways to drain both yourself and your team.

Yes, you care deeply. Yes, it’s your business. But insisting on doing things only your way creates a culture of control—not growth.

Empower your team to bring their ideas, judgment, and creativity to the table. Mistakes may happen—but so will learning, innovation, and ownership.

3. Delegating the wrong kinds of tasks.

Not everything should be delegated. And not everything should stay on your plate either.

At Strategic Coach, we use the ABC Model to simplify this:

• A activities = irritating → eliminate.
• B activities = okay → delegate or automate.
• C activities = fascinating + motivating → do more of these!

When something no longer excites you, or you’ve systemized it well enough for someone else to learn, it’s probably a B activity—and it’s time to hand it off.

4. Delegating to the wrong person.

Delegation isn’t dumping—it’s matching.

Before you assign a task, ask: Who has the mental energy, skill, and interest to run with this? Who would love doing this?

Don’t choose based on convenience. Choose based on talent. When you pair the right task with the right person, the results speak for themselves.

5. Not empowering your team.

Are your team members clear on how much authority they have?

Can they make decisions, spend money, adjust timelines?

Delegation without empowerment is just setting someone up to fail. Be clear about what they can own—and then give them the freedom to follow through.

When the task is brand new or complex, break it into steps and check in. Otherwise, step back and let them shine.

6. Not sharing your success criteria.

This is a big one.

You’ve probably done this task a hundred times before—it’s second nature. But what’s obvious to you might not be obvious to someone else.

Spell it out: What does success look like? What does “done well” mean to you? How long should it take to complete?

Clarity here saves time, frustration, and rework down the line.

7. Not letting people make mistakes.

Mistakes are not failures—they’re feedback.

The truth is, your team will get some things wrong at first. But that’s how they learn.

Make yourself available for questions. Offer guidance when needed. But let them take the lead. Growth happens in the doing.

8. Not tracking progress or being available.

Delegation isn’t “set it and forget it.”

Keep the lines of communication open. Let your team know how often you want updates and in what format. That way, you stay in the loop—and they feel supported without being hovered over.

Avoid “drive-by delegations” that leave people guessing.

9. Not showing appreciation.

Never underestimate the power of saying “thank you.”

When your team does a great job, say it—out loud and in detail. Recognition isn’t just nice—it’s fuel. It builds confidence, loyalty, and motivation.

If something didn’t go quite right, start by highlighting what did work before offering feedback. We all needed grace when we were learning too.

Final thought: You’re not supposed to do it all.

Entrepreneurs often wear too many hats for too long—and the cost is creativity, energy, and momentum.

Delegation is how you grow. It’s how you multiply your impact. And it’s how your team grows with you.

So let go of the idea that your value lies in doing it all—and start investing your time where it counts most.

Your future self will thank you.