What an Executive Coach Is Actually Listening For

Before I coach a senior leader, I hold 8 to 10 confidential conversations. Board members, peers, direct reports. Thirty minutes each.

Under every question I ask sits one more: what does this leader need to hear that nobody will say to them directly?

That post drew more attention than I expected, so this edition goes further into the process behind it.

Two versions of the same leader

Every senior leader walks into coaching with a version of their situation. It usually sounds reasonable, and it usually sounds like this:

"I'm just so busy." "My team isn't taking ownership." "I don't get honest feedback." "I need to be more strategic."

None of these are false. They're the part of the story the leader can see from where they sit.

The interviews give me the other part. A direct report describes decisions that get reopened after the meeting ends. A peer mentions that disagreements go around the leader rather than to them. A board member says, carefully, that they like the leader and worry about the team's energy.

When I hold both versions side by side, the coaching changes. We stop working on the problem the leader brought in and start working on the one the organization is living with.

Step one: the mirror

A leader tells me, "My team won't take ownership."

I don't diagnose the team. I ask, "What is this giving you?"

The question usually lands with a pause. Then the honest answers come. Being the one who knows. Getting it right. Not having to trust a call to someone else when the stakes are high. Not having the conversation with the direct report who keeps missing commitments.

Patterns stay in place because they give us something. The work starts when a leader can see what the pattern is protecting.

While they talk, I'm tracking more than the words: what they return to, what they skip over, what happens in their voice when a certain name comes up, and what protective strategy once served them and what it costs them now.

Step two: the structural work

This is where I spend most of the engagement, and it's the least cinematic part.

We redesign how decisions get made. Who owns which call. Where trade-offs have to be named out loud instead of settled quietly by whoever has the most seniority in the room. Where the leader has been absorbing conflict that belongs to someone else.

That last one shows up constantly. A leader becomes the translator between two peers who stopped talking to each other months ago. It feels like good leadership. It also means the conflict never gets resolved, and the leader's calendar fills with meetings that exist only because two people won't have one.

A breakthrough moment in a session feels good. A decision-rights change that holds for six months changes the organization.

Step three: measuring the echo

The measure I care about is what holds after the leader leaves the room.

• Are issues getting raised earlier, while they're still small?
• Do people know what they own without checking?
• Does the team execute without the leader stepping back in?
• When the leader is on vacation, does work move or wait?

A session can feel smooth and change nothing. A session can feel uncomfortable and change the next quarter. I watch the echo.

What leaders don't expect

Most senior leaders arrive expecting coaching to feel like insight. Some of it does.

More of it looks like telling the truth, sitting with discomfort, and changing how the leader and the team actually operate.