The Art of Asking the “Wrong” Question

There’s a subtle power in asking a question you already know the answer to.

Sometimes, it’s a test. Sometimes, it’s a mirror. Sometimes, it’s a trap- one not for harm, but for truth.

I’ve asked the “wrong” thing on purpose before. Not to be clever. Not to show off. But to see who corrects me. Because how someone responds when they think you’re mistaken says a lot more about them than about you.

In business, this is a useful tool. Ask a question with a small, intentional flaw- something factual but slightly off. Watch who speaks up, who hesitates, who defers. You’ll find out quickly who’s paying attention, who’s knowledgeable, and who’s just nodding along. The correction might be kind and collaborative. It might be smug. It might be silent. That reaction is data. Although it is always unfortunate when your boss corrects you in a negotiation with another business.

This tactic used to work when using search engines or AI tools. Ask your question the way you’d expect a beginner to ask it. Don’t optimize. Don’t overthink. Just throw the “dumb” version into Google. Why? Because if the system can’t understand the obvious, it’s not very useful.

It’s not about playing dumb. It’s about running diagnostics.

In high-stakes conversations—negotiations, interviews, even first meetings- I’ve found that asking a “naïve” question reveals more than a smart one. It invites people to show who they really are when they think they know better. And if you’re paying attention, you’ll learn exactly what you need to.

Sometimes, the best way to get an honest answer is to ask a dishonest question.