How To Build Stronger, Empowered Teams

Through my work, I’ve found that many founders and CEOs are deeply lonely.

They struggle to find someone they can think out loud with. Someone who can challenge their assumptions, see the big picture, and help develop effective strategy. An intellectual sparring partner if you will.

Perhaps this is you.
Perhaps you feel like every meaningful decision rests on your shoulders.
Perhaps leadership feels isolating, even when you’re surrounded by people.

It doesn’t have to be this way.

But first, let’s talk about WHY this happens.

This isolation often shows up when the leader has a strong presence, deep experience, and a proven track record. Over time, trust erodes. Not always intentionally, but subtly. The leader begins to believe the team cannot see the full picture or operate at the same level.

Where trust weakens, distance grows.
And the gap between the leader and the next layer widens.

Many leaders tell me, “Dean, I’ve tried to delegate. I’ve tried to empower my people. They didn’t step up. The work didn’t get done. So I took it back.”

That creates a cycle. And it rarely ends well. Everything funnels back to the leader.

Look at your org chart. If every major line connects directly to you, that’s a warning sign. This is not sustainable leadership. So how do we fix it?

Most leaders think the answer is growing their team. The real answer is growing their leadership.

That means understanding where your people truly are and giving them responsibility that matches their current capability. Then gradually increasing the weight and importance of those responsibilities as they grow.

We already understand this concept intuitively. We use it with our kids. You don’t hand a five-year-old a hundred dollar bill and hope for the best. You start with a piggy bank. You teach saving. Capacity grows over time through responsibility.

Leadership development works the same way. You must give things away.

A useful guideline is the “two pizza rule.” If your leadership team can’t be fed with two pizzas, it’s probably too large. In practical terms, five to eight direct reports is a healthy range, whether your organization has fifty people or two hundred.

In meetings, demand participation. If people are quiet, ask for their thoughts. Then stop talking. You might even track how much you speak compared to your team. The data can be humbling.

Yes, there will be bad ideas. That’s a good thing. Innovation requires contribution. Effective leadership teams create space for thinking, not just execution. Psychological safety is not optional if you want growth.

Here’s the real benchmark.

Six months from now, your people should be better thinkers than they are today.
You should be able to ask harder questions. They should be able to give better answers.

And every six months, ask yourself this honestly. “How isolated do I feel as a leader?”
If that answer hasn’t changed over time, that is not your team’s fault, it’s yours.