Use a single sentence: For [specific person], when [trigger], [problem] prevents [desired outcome], causing [cost]. Then add observable evidence you expect to hear. Precision avoids generic interviews and encourages stories grounded in time, place, and consequence, which you can verify without tools or budget.
Ask which belief, if disproved tomorrow, would kill the project. Prioritize that. New founders often chase easy questions that confirm hopes. Replace comfort with clarity: one tough question, one short script, ten attempts. Treat each failure as saved runway, not a verdict on your potential.
Define ahead how you will know learning happened: a scheduled call, a shared screenshot, a forwarded invoice, a calendar invite, or a testable commitment. Choosing concrete signals prevents overfitting anecdotes and keeps you honest when enthusiasm rises faster than truth during early excitement.
Open with, Walk me through the last time this happened. Ask for timestamps, tools used, people involved, and the moment frustration peaked. When Ana, a first-time founder in Madrid, tried this, she uncovered a billing workaround costing teams hours weekly, unlocking a clearer opportunity.
After a strong answer, pause for three seconds. People often continue, revealing sensitive details like budget caps, internal politics, or deadlines. Mirroring their last phrase invites depth. Those unprompted additions weigh more than rehearsed opinions and frequently point to testable commitments you can observe later.
If someone asks for your solution, say you are still collecting stories and will share a summary later. Selling breaks honesty and narrows answers. Stay curious. You are gathering reality, not approval. Opportunities multiply when people feel safe exploring problems without pressure or premature promises.