Ask people about what they already did, not what they would do

In YC's Startup School lecture on talking to users, Eric Migicovsky warns against hypothetical questions such as "If we built this feature, would you be interested in using it or paying for it?" People are polite and optimistic about the future. Ask instead about specific things that already happened.

Questions from the lecture that work well:

1. "What is the hardest part about doing the thing you're trying to do?"
2. "Tell me about the last time you encountered this problem."
3. "Why was this hard?"
4. "What, if anything, have you done to try to solve this problem?"
5. "What don't you love about the solutions you've already tried?"

The fourth question is the strongest signal. If people have not tried anything, not even a spreadsheet, the problem may not hurt enough to pay for.