Startup School has a great video on this topic: https://www.ycombinator.com/library/6g-how-to-talk-to-users https://www.ycombinator.com/library/6g-how-to-talk-

Startup School has a great video on this topic: https://www.ycombinator.com/library/6g-how-to-talk-to-users https://www.ycombinator.com/library/6g-how-to-talk-to-users > The second mistake that we pretty much all make is we talk about hypotheticals. We talk about what our product could be. We talk about features that we want to build. We ask questions like, "If we built this feature, would you be interested in using it? Or would you be interested in paying for it?" That is wrong. Instead, talk about specifics that have already occurred in the user's life. This will give you stronger and better information in which to make product and company changing decisions. You also want to talk in general about the user's life. You don't want to just talk about the specific problem or, sorry, the specific solution that you're presenting. > Try to extract information about the users, the path that led them to encounter that problem. Ask them questions about their life in more broader ways to extract context around how they arrived at this problem. Learn about their motivations. Learn about why they got themselves into that problem in the first place. > The first question is, "What is the hardest part about doing the thing that you're trying to solve?" > The second question …, "Tell me about the last time that you encountered this problem." > The third question is, "Why was this hard?" > The fourth question is, "What, if anything, have you done to try to solve this problem?"