I watched a founder grill ChatGPT last week.
Three attempts. Three terrible responses. Each time, he muttered about how AI was overhyped, how it didn’t understand nuance, how he’d wasted his money on the subscription.
I looked at his prompts. Each one was a single sentence. Vague context. No specifics. The digital equivalent of walking into a strategy meeting and saying, “So… what should we do?”
The tool wasn’t broken. The question was.
We do this with people too. I’ll ask a team member something I’ve spent weeks thinking about-something perfectly clear in my mind-and expect them to instantly grasp the full context, implications, and desired outcome.
Then I’m disappointed when they miss the mark.
Here’s what I’ve learned coaching founders through their hardest decisions: The quality of your answer is determined by the quality of your question.
Not just clear questions. Specific questions. Questions that do the work upfront.
When a founder asks me, “How do I scale?” I know we’ll spin our wheels. When they ask, “How do I scale our sales team from eight to twenty people without losing our culture of accountability?”—now we’re getting somewhere.
The right question contains half the answer.
It forces you to clarify what you actually need. It respects the person or tool you’re asking. It acknowledges that good answers require good setup.
Before you blame the response, interrogate the question.
Is that not where the real work lives?
