The Question Behind the Question
Why the right questions are the unit of strategy
A friend asked me two questions this weekend that I’ve been sitting with ever since.
The first was simple. The kind of question people ask when they’re not playing around.
Are you really committed to building a venture firm?
The second question had teeth.
With so much changing in the venture world, do you genuinely believe you can deliver top-decile returns?
In my younger years, questions like that would have triggered the chip-on-the-shoulder version of me. The part that wants to prove something before it wants to explain something. I know that guy well. He has helped me in some moments.
But he’s not the best positioned to build for the long haul.
This year, I’ve been trying to approach questions like this differently: not as an attack to defend against, but as curiosity to honor. That shift has done more for my conviction, my relationships, and my clarity than almost anything else I practiced in 2025.
Because here’s what I’ve learned, slowly and repeatedly:
The quality of your outcomes is usually downstream of the quality of your questions.
A good question is like a great journal entry
A great question does what a great journal entry does.
It forces you to say what you actually believe.
It exposes gaps and assumptions.
It makes the fuzzy parts visible.
