Question 1: What Is the Hardest Part?
Migicovsky: The first question is — what is the hardest part about doing the thing that you're trying to solve? You begin an open-ended conversation trying to extract information about how that person currently works.
The best startups are looking for problems that people encounter on a regular basis, or that are painful enough to warrant solving. This question helps confirm whether the problem you're working on is actually one that real users feel is a pain — something they actively want to solve.
What is the hardest part about doing the thing you're trying to solve?
Question 2: Tell Me About the Last Time
Migicovsky: The second question — tell me about the last time you encountered this problem. The goal is to extract context around the circumstances. When did it happen? Who were they working with? What were they doing?
Try to extract as much information as you can about the context in which they began solving this problem. As you develop your product, you'll be able to reference real-life examples of past problems and overlay your solution to see if it would have helped.
Tell me about the last time you encountered this problem. Extract the context around the circumstances.
Question 3: Why Was This Hard?
Migicovsky: The third question — why was this hard? You'll hear many different things from different people. The benefit is not just identifying the exact problem you may solve, but you'll also begin to understand how you market your product.
Customers don't buy the what — they buy the why. They won't be overjoyed at having a file syncing tool. But they'll say — this product will help with this exact problem I had two weeks ago. The answers to this question may actually inform your marketing and your sales copy.
Customers don't buy the what. They buy the why. Answers to this question may inform your marketing.
Question 4: What Have You Done to Solve This?
Migicovsky: The fourth question — what, if anything, have you done to try to solve this problem? If potential customers are not already exploring solutions to their problem, it's possible the problem you're trying to solve is not a burning enough problem for them to even be interested in your better solution.
You want to ask this for two reasons — one, to figure out whether people are already looking for solutions. Two, to understand the competition. What will your product be compared against?
If customers aren't already exploring solutions, it's possible the problem isn't burning enough.
Question 5: What Don't You Love About Existing Solutions?
Migicovsky: The fifth question — what don't you love about the solutions you've already tried? This is the beginning of your potential feature set.
Note — this is not 'what features would you want in a new product?' That's a hypothetical question. Users are not great at identifying the next features they want. Like the old Henry Ford quote — our users would have wanted a faster horse rather than a car. This question specifically targets what's wrong with existing solutions. You can begin to figure out the differential between your new solution and what's already in the market.
This is not 'what features would you want?' — that's a hypothetical. Ask what's wrong with what they already tried.