Stop pitching, start interviewing
The instinct is to describe your idea and watch their face light up. This is the worst thing you can do, because the moment you pitch, the conversation becomes about your feelings, and the polite human across from you will protect them. They will say I would totally use that, which is a compliment, not a commitment, and you will walk away falsely encouraged.
Flip it. Do not mention your idea at all for as long as you can. Ask them to walk you through the last time they hit the problem you care about. What were they doing, what did they try, what did it cost them, what happened next. You are a detective collecting facts about their past behavior, not a salesperson collecting reactions to your future product.
Ask about the past, not the future
Anything someone says about what they would do, or would pay, or would love, is a guess about a hypothetical, and people are terrible at predicting their own behavior. Anything they tell you about what they already did is a fact. So aim every question at the past. Not would you use a tool that does this, but what did you do the last time this happened. Not would you pay for this, but what do you currently spend to deal with this.
The best signal is evidence they have already tried to solve it: a spreadsheet they built, a freelancer they hired, three apps they downloaded and abandoned. Someone who has spent time or money on a problem has shown you it is real and that they will reach for a fix. Someone who has done nothing about it, no matter how much they nod, is telling you it does not hurt enough.
- Good: talk me through the last time this happened.
- Good: what do you use today, and what is annoying about it?
- Good: what does this problem cost you, in time or money?
- Bad: would you use an app that solved this? (a hypothetical they will answer kindly)
Dig for the commitment, not the compliment
Compliments feel great and mean nothing. That is so cool, I love it, you should build it, are all fluff, and when you hear them you should get suspicious, not happy. Real interest shows up as commitment: they ask when they can have it, they introduce you to a colleague with the same problem, they offer to pay, they give you their email and actually open the follow-up. Anything that costs them something is signal. Anything free is noise.
If the conversation stays warm and complimentary but produces no commitment, that is your answer, and it is a useful one. Push gently for a next step. Can I show you what I am building next week. If they will not give you twenty minutes or an email, the enthusiasm was politeness. Better to learn that now than after you build.