The Delegation Trap

And Why It’s Costing You More Than Time

Let’s talk about delegation.

Not the theoretical kind you read about in leadership books. I mean the kind that separates good managers from scalable leaders. The kind that feels a little uncomfortable at first—like handing over your future to someone else and hoping they don’t screw it up.

Because here’s the truth: the people who move up the corporate ladder are usually the ones who know how to get things done. They’re the workhorses. The go-to problem solvers. The ones who figure it out, pick up the slack, and quietly (or not so quietly) make things run.

Until they don’t.

Because somewhere along the way, what got them there starts holding them back.

Instead of empowering their teams, they keep “doing”. They hold onto tasks below their pay grade, convince themselves they’re “helping,” and slowly become the bottleneck they used to complain about. And then they wonder why they’re always in meetings, have no time to work on strategic initiatives, and why their best people aren’t growing—or worse, are leaving.

It’s a vicious cycle. One I’ve seen over and over.

And yes, I’ve lived it too and occasionally still fall into the trap (hey, I can still do some things better).

There’s a classic Harvard Business Review article called “Who’s Got the Monkey?” If you haven’t read it, I’ve attached it for you. It’s a simple metaphor: employees show up with problems (monkeys), and instead of helping them feed their monkey, most managers just let the monkey jump on their back. Now you have the problem, the task, the next step. And your team? They walk away lighter, waiting for you to solve it.

It’s not management. It’s monkey adoption.

Article Link: HBR - Who's got the Monkey

Delegation isn’t about offloading work. It’s about scaling leadership.

Here’s why this matters:

1. If you don’t delegate, you can’t scale.

There’s no version of business growth where you’re personally involved in every decision, every fire drill, or every tactical move. You’re either building a machine—or you are the machine. And the second one breaks down.

2. You block your people from growing.

When leaders hoard responsibility, they unintentionally signal that their team isn’t ready—or worse, not trusted. You end up with frustrated employees stuck in neutral while you keep doing their job and yours. No one wins.

3. You burn out. And you lose sight of your real job.

Your job is to focus on vision, strategy, and long-term value creation. If you’re still approving vendor invoices, running down quality complaints, or answering the RFP, you're playing the wrong position.

4. You create dependence, not accountability.

When people bring you problems and you solve them, they learn to rely on you. When you coach them through it—ask questions, guide decision-making, and let them own the outcome—they build confidence and capability.

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I know the fear. “What if they mess it up?” “It’s faster if I just do it.” “I don’t have time to explain it.” We’ve all said it.

But here’s the reality: if your team can’t handle it, that’s not their fault—that’s on you. Either you hired the wrong people, you haven’t trained them, or you haven’t let go long enough to find out what they’re capable of.

Delegation isn’t about perfection. It’s about progress. Sometimes the handoff will go sideways. That’s okay. It’s still worth it. Because every time you delegate with intention, you’re investing in your team’s growth—and your organization’s future.

So if your calendar is full of tasks that someone on your team could (and should) be doing, ask yourself:
Is this really mine to own—or did I just let another monkey jump on my back?

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Your turn: Take inventory of what’s on your plate this week. Circle anything that’s below your pay grade. Then ask: who should own this? And how do I support them to succeed?

That’s not stepping back. That’s leadership.

Lastly, let me know what you delegated and how it felt to get some time back!