The Pattern I See Every Time I Prepare an Executive Team for the Big Stage

I was in the middle of a two-day intensive with an executive team - ten leaders preparing for a massive company event. Thousands of employees flying in. Four days on stage. The kind of moment that can define a leadership team's presence for years.

The work with the team was going beautifully. They were leaning in, trying new things, pushing past their comfort zones. There's something special that happens when a group of leaders gives themselves permission to be in-process together. They stumble, they laugh, they sharpen each other. By the end of day one, I could already see the transformation taking shape.

And then the CEO walked up to me. Quietly. Almost like he didn't want anyone else to notice.

"I'm not quite ready yet," he said. And he pushed back his session.

I've seen this more times than I can count.

Here's what I've come to understand about CEOs in these moments. When I'm working with their leadership team, everyone gets to be a learner. That's safe. That's expected. The SVP can fumble through a practice run and nobody thinks twice - that's what coaching is for.

But the CEO doesn't get that same permission. They're the one everyone is looking to. They set the tone. And somewhere along the way, many of them have internalized a belief that they should already have this figured out. That asking for help - especially in front of their own team - means something is wrong.

So they watch from the edges. They see their people growing and improving. And the cruel irony is that the more their team loves the work, the higher the bar feels for them.

This is why I approach CEO coaching completely differently than I do team coaching.

With the team, I'm teaching. I'm pushing. I'm creating a space where they can experiment and fail forward together. There's energy, there's group accountability, there's the safety of being in it with peers.

With the CEO, I'm not there to teach. I'm there to partner.

I work with them privately. I lead with curiosity instead of curriculum. I'm not trying to correct anything - because usually there's nothing to correct. These are brilliant people who've built something real. My job is to make sure that when they step on stage, the room sees what I already see when I'm sitting across from them: the clarity, the conviction, the command presence that's already there.

They don't need someone to fix them. They need someone who understands the weight they carry and can help them trust what they've already built.

If you're bringing in coaching for your executive team before a high-stakes moment, consider this: your leaders need preparation, and they'll likely thrive in a group environment where they can grow together.

But your CEO might need something different. They might need a partner who works with them one-on-one. Someone who gets the loneliness of their seat. Someone who isn't there to evaluate them, but to amplify them.

That's the work I love most.

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