50 Informational-Interview Questions for Entrepreneurs

1. How did you get started in this business?
2. Did you found the company? 
3. How did you make your first sale? 
4. How did you get credibility quickly?  
5. How did you develop key partnerships?  
6. How did you get funded or what creative strategies did you use to execute on minimal cash flow?  
7. What habits helped make you successful? 
8. What mindsets helped make your successful? 
9. How did you distinguish yourself from your competitors? 
10. What was your biggest mistake? 
11. What do you think will be our success metrics? 
12. What would a prototype look like? 
13. How do you think we could provide 
14. Who should we talk to?  
15. Who would you recommend we talk to? 
16. How do you re-make yourself?   
17. What would you do in our shoes? 
18. How did you deal with failure? 
19. How did you learn from failure? 
20. What was unexpected? 
21. What did you learn? 
22. What would you have done differently? 
23. How did you test your assumptions?  
24. How can you minimize the unknowns?
25. If you had the chance to start your career over again, what would you do differently? 
26. What would you say are the top three skills needed to be a successful entrepreneur? 
27. What have been some of your failures, and what have you learned from them? 
28. How long do you stick with an idea before giving up? 
29. How many hours do you work a day on average? 
30. Describe/outline your typical day? 
31. How has being an entrepreneur affected your family life? 
32. What motivates you? 
33. How do you generate new ideas? 
34. How far are you willing to go to succeed? 
35. What is your greatest fear, and how do you manage fear? 
36. What are your ideals? 
37. How do you define success? 
38. If you were conducting this interview, what question would you ask? 
39. Is this your first business? (If not, ask what the others were, and what happened to them.)
    Were you exposed to entrepreneurship as a child (say, from family members or friends)? 
40. What three pieces of advice would you offer entrepreneurs starting out today? (asking for three is a lot, but it forces your subject to dig deeper than just saying , “Just do it,” or “Hire good people.” 
41. How long do you plan to keep operating this business? Do you have an “exit” strategy for getting out of the company?
42. How did you get started with Visitors Cafe?
43. What is an average workday like for you?
44. Who are your customers? 
45. What three pieces of advice would you offer entrepreneurs starting out today? 
46. Do you have an “exit” strategy for getting out of the company?
47. What are the most crucial things you have done to grow your business?
48. Do you have complementary skills on your team?
49. Can you eliminate all distractions to making your business work?
50.  Whats your next step, do you dream to be a Big Brand like Amazon or MC-Donald ?

The open-endlessness of the question allows the interviewee to focus in on what they deem as being the key insights rather than "leading the witness" towards answering questions you think are important. Framing it as a time travel experiment eliminates abstraction and gets them to think in terms of specific failures & epiphanies that occurred during the course of their startup's development. And by putting constraints on the visit (only 15min to tell to yourself anything) it forces them to prioritize the most pivotal advice first and go as deep on any point as they felt it merited.