The Five Great Questions

Migicovsky offers five questions that work in almost any early interview. One: what's the hardest part about doing the thing you're solving for? You want the problem to be one users themselves rank as painful, not one you've decided is painful for them.

Two: tell me about the last time you encountered that problem. This drags the conversation from abstract to concrete and surfaces the circumstances around the problem. Three: why was that hard? The answers here become your marketing, because users buy for their reasons, not yours, and different users will give different reasons.

Four: what, if anything, have you done to try to solve it? This is the brutal one. If they haven't tried anything, the problem may not be painful enough to build a business on. People with real problems hack together spreadsheets, hire help, or endure ugly workarounds.

Five: what don't you love about the solutions you've tried? Notice it isn't 'what features do you want.' Users are unreliable at specifying features but excellent at describing what frustrates them today. Their complaints about existing alternatives are your differentiated feature list.