A few years ago I stopped giving advice at dinners. Not because I ran out of it — the opposite. I noticed the advice never landed. People nodded, wrote nothing down, and went home to do what they were already going to do.
What did land was a question. Usually a plain one. “What would you do if the money weren’t a problem?” “Who are you still trying to impress?” “What are you pretending not to know?” Asked at the right moment, over a second glass, by someone with no stake in the answer.
I think this is because advice is about the adviser. It comes wrapped in their story, their timing, their luck. A question has none of that. It leaves the room for the other person to fill, and they fill it with something true, because there’s nowhere else to get the material.
So most of what I do now — coaching, dinners, the odd walk — is arranging the conditions for a good question to be asked, and then keeping my mouth shut long enough for the answer to arrive. It’s harder than it sounds. It’s also the whole job.