What Happens in a 1:1 Coaching Session

The first thing most people are surprised by is how much talking they do.

A coaching session isn't a lecture. It's not a performance review, a strategy session, or a pep talk. The best description I've heard is this: it's a structured excavation. The coach holds the frame. The leader does the digging.

What the first few minutes actually look like

We usually start with one question: what's the most important thing to work on today?

That question does more work than it looks like. It forces the leader out of reactive mode — out of whatever fire was burning in their inbox an hour ago — and into a deliberate choice about what actually matters. A lot of leaders spend almost no time in that mode. The session starts by requiring it.

From there, we go deeper into whatever surface. Sometimes that's a specific decision. Sometimes it's a relationship that's become expensive. Sometimes it's a pattern the leader has noticed and hasn't had space to examine.

The questions do the work

I ask a lot of questions. Some of them feel obvious. Some of them are uncomfortable. The ones that produce the most are usually some version of: what are you not saying?

Not to be provocative — but because leaders are trained to communicate strategically, and sometimes that habit closes down the honest thinking. When I ask what they're not saying, the answer often contains the real problem.

I also push on assumptions. "You said they won't respond well to that. How do you know?" The leader usually has a story built on incomplete data, and examining the story is more useful than accepting it.

What you leave with

A good session produces clarity, not just conversation. That usually means the leader leaves with one to three specific things: a decision made, a reframe of a situation that was stuck, or an action they're committing to before the next session.

The accountability piece matters. What you said you'd do, and whether you did it, is how the work compounds between sessions. A coaching relationship without accountability is just interesting conversation.

I'll also say this: not every session is crisp. Some go deep into something the leader didn't expect to surface. Those sessions are often the most valuable, and they're also the hardest to explain to someone who hasn't been in one.

One format of many

One-to-one sessions are one way to do this work. Peer masterminds do something similar in a group format — you get honest reflection from people who aren't in your building and don't have skin in your decisions. The dynamic is different. For some leaders, the peer accountability is more powerful than the individual session.

What I'd say, regardless of format: the session is only as useful as what you're willing to bring into it. Show up with your real problems, not your presentable ones.

The presentable problems are fine. The real ones are where the work happens.