My Worst Delegation Mistake
And what it taught me about trust, control, and letting go
The Setup
I still remember the day I thought I had delegation figured out. I had just been promoted, eager to prove I could “lead” instead of doing everything myself. A big client project came in, and I saw the perfect chance to show my team I trusted them.
So, I handed it off.
At least, that’s what I thought I was doing.
Where It Went Wrong
I gave my teammate the task but… I never really let go.
Instead of setting clear expectations up front, I offered a vague overview and said, “Ping me if you need anything.” What I actually meant was: I’ll be watching over your shoulder the whole time.
Over the next week, I checked in daily, corrected small details, and even rewrote sections of their draft. My teammate grew quieter in each meeting, and by the deadline, the work wasn’t what I’d hoped for.
But here’s the uncomfortable truth: the failure was mine, not theirs.
The Real Mistake
Looking back, my worst delegation mistake wasn’t assigning the wrong person. It wasn’t even the missed deliverable.
It was failing to give clarity, then failing to give trust.
I didn’t define what success looked like.
I didn’t set constraints or milestones.
And when my teammate hesitated, instead of coaching, I swooped in to “fix” it.
I thought I was helping. In reality, I was suffocating the very ownership I wanted them to have.
The Turning Point
After that project, my teammate pulled me aside. They said, “I don’t know what you actually want from me. It feels like you don’t trust me to do it right.”
It stung. But they were right.
That moment forced me to rethink delegation completely. Delegating isn’t about dumping work. And it isn’t about micromanaging either. It’s about creating clarity, then stepping back enough for people to succeed on their own terms.
The Lesson I Carry
Since then, I’ve followed a simple mental checklist every time I delegate:
Context: Why this task matters. How it connects to the bigger picture.
Constraints: What’s non-negotiable (budget, deadline, format).
Milestones: When we’ll check in—not to nitpick, but to align.
Ownership: Making it clear this is their work, not mine in disguise.
When I stick to this, I notice two things:
The work gets done better, often in ways I wouldn’t have thought of.
My team members grow in confidence—because they know I actually trust them.
And honestly? I grow too. Each time I let go a little more, I prove to myself that leadership isn’t about control. It’s about enabling others.
Why This Matters for You
If you’re stepping into leadership for the first time, delegation will test you. You’ll want to jump in, to re-do, to prove yourself through the work. But the real proof is in your team’s success, not your corrections.
Your people don’t just need your direction—they need your trust.
Reflection Question
What’s one task this week you could delegate with more clarity and trust—and then step back from?
Hit reply and let me know—I’d love to hear your story.
P.S. Next week, I’ll share the feedback mistake that almost broke trust with my team—and the exact script I wish I’d used instead. Subscribe now so you don’t miss it.