Fifty Questions to Ask a Startup Founder During an Informational Interview

What’s an informational interview? It’s when you sit down to talk to someone for the purpose of learning from them. It can be formally stated that that’s the purpose or informal and naturally brought up, but usually it’s a good idea to at least give the person a head’s up that you’ll be asking for advice. There are lots of resources online that describe more about what they are and how to schedule them, and I’ve also written a bit about them in the context of networking here:

Knowing what to ask can be tricky, especially when you’re first starting out— there are a lot of “unknown unknowns.” So I present this incomplete list to you— some are questions I get asked a lot, some are questions I ask others a lot. Some are questions about ethics and life fulfillment, others are about the nitty gritty of tax law. Some questions are meant to give you answers when you read between the lines, others are for useful direct information. I hope it helps.

This particular set of questions focuses on business within running a startup.

  1. What motivates you to keep running a business?

  2. What is your end goal with the business?

  3. What are your thoughts on bootstrapping vs fundraising?

  4. What was getting your first customer like?

  5. How did you build a network for sales?

  6. How did you come up with your pitch?

  7. How did you find your co-founder?

  8. What advice do you typically give people who are thinking of co-founding a company with someone else?

  9. Do you focus on selling to one industry? If so, how would you say that industry differs from others?

  10. How has your experience been selling to large companies?

  11. Is there anything you can tell me on how companies differ from each other, in terms of sales strategy needed?

  12. How does your ethical framework influence the way you run your business?

  13. How do you see charity and nonprofit work overlapping with your business?

  14. What’s been important for you to hone/focus on when negotiating?

  15. How did you come up with your pricing scheme? What were the factors you considered?

  16. How did you manage uncertainty in early stages of business? Were you ready to pivot if needed? Did you keep it a very lean MVP?

  17. How have you been affected by cash flow, as opposed to revenue/profit? Has that been pretty smooth or a challenge?

  18. How did you choose your pricing model (yearly, monthly, per project, support/services, etc)?

  19. If you have different tiers to pricing, how has that evolved over time?

  20. Was there any strategy that worked well early in the business that isn’t so useful now?

  21. What are some business challenges you’re facing now?

  22. What are you currently learning about in business?

  23. Why did you choose to design your website the way it is now?

  24. How has your marketing evolved over time?

  25. Are there any clauses you’ve found especially important in contracts?

  26. What are the most contested clauses in your contracts?

  27. Do you have any terms you don’t budge on, are willing to lose big deals over?

  28. About how many hours a week do you work?

  29. How has your workload/work schedule changed over time?

  30. How are your hours spread throughout the week? Have you had to set any boundaries around time?

  31. Do you have any advice around taxes, things to be careful of or be sure to prepare for?

  32. Has your business made you happier and more fulfilled in life, compared to how you felt before starting it?

  33. Where do you see yourself in 10 years?

  34. What are your thoughts on cooperative structures?

  35. What are your thoughts on benefit corporations?

  36. What are your thoughts on LLCs vs S corps vs C corps?

  37. What are your relationships with your customers like? Does it vary greatly depending on the customer?

  38. Do you offer support? What’s the structure like?

  39. How does support differ between customers?

  40. Do you offer any hard time constraints in your contracts around resolving issues? What’s the legal language like around that? How to you lead a balanced life within that?

  41. How do you protect your IP? What’s your strategy around that?

  42. What are some complexities/challenges within your IP strategy?

  43. What are your thoughts on patents, trade secrets, copyright, and other legal IP protections?

  44. What clauses in your contracts help protect IP?

  45. What are your thoughts on NDAs/MNDAs? When do you sign them and when do you not?

  46. What’s your public relations strategy?

  47. What’s your marketing strategy?

  48. Do you have any advice specific to my scenario/business challenges?

  49. Do you know anyone else I should talk to about this?

  50. Can I follow up with you in a few months to check in and talk again if needed?

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