Most of the questions founders bring to me are not the real question.
They arrive with versions of: should I hire this person, should I take this deal, should I restructure now or wait? And these are real decisions, worthy of serious thought. But when we slow down and stay with them, something else begins to appear underneath — a quieter question, less comfortable, more generative.
The real question is almost never strategic. It is almost always about the person asking it.
What I mean by this
Last year I worked with a founder who was convinced she had a hiring problem. Her CTO wasn't performing, she said. She'd tried everything. Should she let him go?
We spent the first hour on the evidence. Then I asked: What would it mean about you if you let him go now?
She was quiet for a long time.
What emerged was a belief she'd been carrying without examining: that good founders don't give up on people. That loyalty was a non-negotiable, even when it was costing her the company. The hiring question was real. But it was sitting on top of an identity question she'd never surfaced.
We didn't solve anything that day. We found something better: the actual question.
On strategy and self
This is the part of advisory work I find most generative — not the strategy itself, but the way strategy and self are always entangled.
A business decision is never just about the business. It is made by a person with a history, a nervous system, a set of beliefs about what kind of person they are. The spreadsheet doesn't capture any of that. And the decision that looks optimal on paper can feel impossible to execute — because to execute it, you'd have to be a different person.
So the work is always two things at once: the decision and the decider. The plan and the person who has to carry it.
If you're sitting with a question that isn't quite resolving — that keeps coming back, that you've analysed repeatedly without it shifting — it might be worth asking: what question is this question protecting you from?
That one is usually more interesting.