One of the biggest challenges for entrepreneurs running the customer development process (watch the explanation video) is leading the witness. What I mean is that entrepreneurs are so passionate and eager for potential customers to see the same vision they see, the entrepreneur asks leading questions that don’t allow for true understanding of both the severity of the problem as well as potential solutions.
Here are a few ideas for customer development questions:
- How do you currently do X?
- What do you like about it?
- What do you dislike about it?
- How have you tried to improve X?
- If you could wave a magic wand and have a new solution, how would it work?
- How much of an issue is this problem/opportunity?
Now, this is a simple starting point but the idea is to ask open-ended questions to learn from the potential customer without steering them in a specific direction. Entrepreneurs that are able to validate their ideas without leading the potential customers will have a stronger conviction that they’re headed in the right direction.
What else? What are some other customer development questions for entrepreneurs to ask while validating an idea?
David Cummings on Startups 
Two questions I would certainly add:
“When doing X, what do you usually do right after (or right before)?” -> to check how your solution fits in the user’s workflow and to see which possible integrations might be interesting.
“How often does X occur?” -> to measure the frequency of the pain/opportunity
A good read on this subject is Cindy Alvarez’s Lean Customer Development!
-Y