The three questions I ask every new coaching client

The first session with a new coaching client follows the same rhythm. After the small talk, I ask three questions. They sound simple. They aren’t.

One: what’s the business actually for? Not the mission statement. The reason the business exists for you. Cash flow? Legacy? A platform for the next thing? I’ve had clients stare at me for two minutes on this question. The good ones eventually answer with something honest that would never make it onto a website.

Two: what would have to be true for you to sell this in five years? I don’t ask because I think they should sell. I ask because the answer reveals what they actually believe about the business. People who couldn’t sell even if they wanted to have a different business than the one they describe.

Three: what’s the thing you know you should be doing and aren’t? Everyone has one. Most people have three. The shape of the answer tells me where the real work is — not the work they’d like to do, the work they’ve been avoiding.

These three questions do something useful even without me in the room. Put them in your notebook. Answer them for yourself, honestly, once a quarter. Compare the answers across quarters. The places your answers shift are the places you’re growing. The places they don’t shift are either bedrock or avoidance. Your job is to know which.