[bbaumgar]

I usually will ask the person I'm interviewing to describe their job or the activity which I am posing a solution to. In the case of my startup, I'll ask them to describe their experience planning and running a conference as if I knew nothing. Their pain points will naturally emerge as they describe their processes, and their real issues usually become obvious by the way they describe their job (even if they don't know their issues consciously themselves!).

I usually go for long interviews (30 minutes to an hour) and look for commonalities between them after every batch of 5 or so.

If more than 2/3 of the people express a pain point, I know there's a real problem there. In my case, I'm trying to craft an MVP with 3 or so main features. Every person I've interviewed so far has expressed the same base 3 pain points (in addition to other needs which varied from person to person) so I know what I'm going to focus on solving with my MVP.

I usually use around 5 questions an interview, but sometimes I've asked as many as 10 or 15 depending on how talkative the person I'm interviewing is.