Here are questions to consider asking entrepreneurs when you interview them:

  1. What ignited the spark in you to start a new business venture or to make significant changes in an existing business? How did the idea for your business come about?
  2. How do you find people to bring into your organization that truly care about the organization the way you do?
  3. How important have good employees been to your success?
  4. What three pieces of advice would you give to college students who want to become entrepreneurs?
  5. If you had the chance to start your career over again, what would you do differently?
  6. What would you say are the top three skills needed to be a successful entrepreneur?
  7. What have been some of your failures, and what have you learned from them?
  8. How long do you stick with an idea before giving up?
  9. How many hours do you work a day on average?
  10. Describe/outline your typical day?
  11. How has being an entrepreneur affected your family life?
  12. What motivates you?
  13. How do you generate new ideas?
  14. How far are you willing to go to succeed?
  15. What is your greatest fear, and how do you manage fear?
  16. What are your ideals?
  17. How do you define success?
  18. What is the best way to achieve long-term success?
  19. Is your company profitable or what is your profit for last year?
  20. Where did your organization's funding/capital come from and how did you go about getting it? How did you obtain investors for your venture?
  21. How do you build a successful customer base?
  22. How did you decide on the location for your business?
  23. Do you believe there is some sort of pattern or formula to becoming a successful entrepreneur?
  24. If you could talk to one person from history, who would it be and why?
  25. Who has been your greatest inspiration?
  26. What book has inspired you the most? (OR What is your favorite book?)
  27. What is your favorite aspect of being an entrepreneur?
  28. To what do you most attribute your success? What would say are the five key elements for starting and running a successful business?
  29. What has been your most satisfying moment in business?
  30. What do you feel is the major difference between entrepreneurs and those who work for someone else?
  31. How do you go about marketing your business? What has been your most successful form of marketing?
  32. What kind of culture exists in your organization? How did you establish this tone and why did you institute this particular type of culture?
  33. In one word, characterize your life as an entrepreneur.
  34. What are some of the biggest mistakes you've made?
  35. How can you prevent mistakes or do damage control?
  36. What are your hobbies? What do you do in your non-work time?
  37. What makes you happy?
  38. What sacrifices have you had to make to be a successful entrepreneur?
  39. Excluding yours, what company or business do you admire the most?
  40. Where you see yourself and your business in 10 years? 20 years?
  41. If you were conducting this interview, what question would you ask?
  42. How did you get started in this business?
    Did you found the company?
  43. Is this your first business? (If not, ask what the others were, and what happened to them.)
  44. Were you exposed to entrepreneurship as a child (say, from family members or friends)?
  45. How did you finance your business? What have been your most effective sources of financing over the years?
  46. What are the revenues of the business? (They may or may not answer this.)
  47. How many employees do you have? Full- or part-time? (This gives you some idea of the company size in case they didn't answer the revenue question.)
  48. What is an average workday like for you?
  49. Who are your customers? What are your most significant products or services?
  50. How has your market changed in the past few years? How has your business changed to keep pace?
  51. How have sales grown in the last few years? (gives you an idea of how successful the business is.)
  52. Is the business profitable? What kind of profit margin does it have?
  53. What are the most crucial things you have done to grow your business?
  54. What plans do you have now to expand your business further?
  55. What systems have you used to automate your business to give you more time for business planning and development?
  56. What outsiders have been most important to your business success? (e.g., bankers, accountants, investors, customers, suppliers, mentors, etc.)
  57. Do you have a business plan? A marketing plan? When was it last updated? (gives you some idea of how sophisticated their planning process is)
  58. How do you market your products or services?
  59. What has been your most effective marketing tactic or technique?
  60. What’s the worst business advice you’ve ever received?
  61. 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.”
  62. How long do you plan to keep operating this business? Do you have an “exit” strategy for getting out of the company?
  63. If you were to start another business, what might it be?
  64. Do you believe business has any obligation to make the world a better place?
  65. How does your business “give back” to the community or to society?