A Real Conversation About Delegation, Growth, and Getting Unstuck

What it is: A real-life story of an emerging leader ("Colin") learning how to delegate more effectively—not just to lighten his load, but to grow his team. This field note draws from coaching conversations and explores key insights like the Delegation Ladder, context over control, and the mindset shift from "doer" to "developer."

Why it matters: Most managers struggle with delegation because they were never taught how to do it well. Poor delegation leads to burnout, bottlenecks, and underdeveloped teams. Great delegation—rooted in clarity, trust, and shared decision-making—unlocks scale, team growth, and stronger leadership cultures. This story shows how it happens in real time.

When I first met "Colin," he was days away from starting a new leadership role. He had just accepted a management position at a respected creative agency known for high-quality work and intense deadlines. The job was a big step up—more money, more visibility, and more responsibility. But Colin wasn’t strutting. He was thinking.

“I’m excited,” he said. “But I’ve never had a team this size before. I’m trying to figure out how not to become a bottleneck.”

That one sentence captured the central leadership challenge we see again and again: a good human, trying to do good work, caught between wanting to support their team and the fear of letting go.

Over the next few sessions, our conversations kept circling back to the same tension:

• How do I delegate without dumping?

• How do I challenge people without overburdening them?

• How do I set high standards without micromanaging?

Lesson #1: Delegation is not a task transfer. It’s a trust-building process.

When we introduced the Delegation Ladder (inspired by David Marquet’s work), Colin immediately saw himself stuck between levels 2 and 3: still approving every decision, still fielding status checks, still responsible for more details than he had time to manage.

What changed things was a simple insight: Delegation isn’t just about handing off work. It’s about transferring decision-making authority along with context.

The more context your team has—what matters, what tradeoffs are acceptable, what the end goal is—the better their decisions. The more decisions they make well, the more trust you build. The more trust you build, the less you have to approve. That’s the delegation flywheel.

Lesson #2: To scale your impact, you have to give away your Legos.

We talked about the classic metaphor from Molly Graham’s work: “Give away your Legos.” In a growing company, if you want to take on bigger challenges, you have to give up things you used to own. And it’s hard, especially when you like your Legos.

Colin was managing several client accounts and leading a team of creatives. He was good at both. But being good at something doesn’t mean you should keep doing it forever.

We mapped out which responsibilities he could let go of in the next 90 days and framed the conversation with his team around growth: “I want you to lead this area because I believe you can. I’ll support you—but I won’t take it back unless you ask.”

Lesson #3: Leadership isn’t about having all the answers. It’s about asking the right questions.

As Colin stepped more fully into the role of leader, one of the biggest shifts wasn’t tactical—it was mental. He realized he didn’t need to be the hero, the fixer, or the person with the best idea. He needed to be the person who asked, “What do you think we should do?”

That question changes the game. It invites ownership. It invites learning. It invites the team to step up.

The Takeaway: Delegation that doesn’t suck starts with a mindset shift.

The truth is, most of us were never taught how to delegate well. We learned to either dump and disappear—or hover and micromanage. But great delegation lives in the middle. It’s thoughtful, intentional, and rooted in trust.

Here’s what we saw with Colin:

• His team started stepping up in visible ways.

• He had more time to think strategically.

• The culture of the team began to shift from dependency to ownership.

It didn’t happen overnight. But it started with a conversation.

And if you’re reading this wondering if you’re ready to delegate more—you probably are. Start small. Share the context. Let them try. Catch them doing it right. And then keep climbing the ladder together.