Use this for problem interviews — the kind you run before you've built anything. Each question is open-ended; let them talk.
- "Walk me through the last time you did [task]." Get the story. Names, tools, friction.
- "What was the hardest part of that?" This is where the pain lives. Stay quiet after.
- "Why was that hard?" Push for root cause. Most first answers are surface.
- "What did you try to solve it?" Active searching = real pain. "I just lived with it" = mild pain.
- "What would solving this be worth?" Pause. Watch what they say (and don't say). Anyone who can't quantify isn't paying.
What you DON'T ask: "Would you use a tool that...?" — they'll lie politely. "Is this a problem you'd pay for?" — same. You're listening for stories, not pitching.