The power of asking stupid questions.

When I was younger, a teacher once told me to stop asking stupid questions.

I still think about that sentence because a surprising amount of work gets better when somebody is willing to ask the question everyone else assumes has already been answered.

Obvious questions are often diagnostic

Why do we do it this way? Who actually uses this? What happens after the pilot? What would have to be true for this to work?

None of these questions sounds sophisticated. That is precisely why they are useful. They force a conversation away from vocabulary and toward assumptions.

Curiosity is practical

My work puts me between different groups: business teams, technology companies, founders, consultants and executives. Each group has its own shorthand. Asking basic questions is often how I translate between them.

I would rather look uninformed for thirty seconds than spend three months executing against an assumption nobody tested.

So I kept asking questions. Some of them are probably still stupid. I am fine with that.