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100 Questions Every Founder Must Ask Themselves

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I’ve spent the past 5+ years building a company I love and believe in. It has all the hallmarks of being a success – the team is happy, challenged and able to innovate on a daily basis. It’s profitable, community oriented and has unlimited opportunities for growth in the coming years.

With that context in mind – there are so many questions I should have asked myself from the onset.

I did ask some of the following questions of course, but I think if you’re going to start a company, or you have a young one, you’ll be greatly served by answering the following for yourself.

Find an hour or two to really focus on these questions and see what your answers are. They’ll change over time. Here it goes:

100 Questions Every Founder Must Ask Themselves (download)

1. What do we want to be?

2. What do we want to do?

3. What does the next 10 years look like for us?

4. What’s our mission and common vision?

5. What do we need to achieve our mission?

6. What does the plan look like?

7. What resources do we need?

8. How long will it take to implement the plan?

9. How much will it cost?

10. What does success look like to us?

11. What does it look like to me?

12. Do you want to make money or an impact or both?

13. Can you have both?

14. What’s the best way to have both?

15. Who are you competing with?

16. How are they better than you?

17. What don’t you know that you know you need to know?

18. How are you going to figure out how to uncover what you don’t know you need to know?

19. Are you capable of doing this job?

20. What are you good at?

21. What are you bad at?

22. Who/what are you jealous of?

23. What are you proud of?

24. What does swimming upstream look like?

25. What does swimming downstream look like?

26. What happens when you get to the ocean?

27. What does your product/service offering look like from a blue ocean POV?

28. If you could build this company for the next 10 years where would you do it and why?

29. How much less successful will you be if you don’t build it there?

30. Is that trade off worth it?

31. Is the mission you’ve been on the right mission for you anymore?

32. What will happen over the next decade w/ or w/o you in your community?

33. What is the culture of our company?

34. What is your personal set of values?

35. What values do you look for in others?

36. How would you describe your character?

37. How successful are you in your own eyes?

38. Who are you trying to impress?

39. What are you trying to prove?

40. When will you know if you’ve impressed them/proved it?

41. What is failure for you?

42. What the probability you’ll fail?

43. What happens if you fail?

44. What else do you want to do if there’s an “after this company”?

45. What is holding you back?

46. Who is holding you back?

47. How good a leader are you?

48. What do you do poorly as a leader?

49. What do you do well as a leader?

50. What do you need to do to be a better leader?

51. Can you name 5 people who’d be great mentors for you? Name them.

52. Is it feasible to have them as mentors?

53. What is your process for getting them to mentor you?

54. What do you want to accomplish by 30/40/50/60?

55. Is the current community you’re in a good thing in your life?

56. Why aren’t you happy in the community if not?

57. Are you living a life of mediocrity?

58. What’s so bad about mediocrity?

59. What’s making you mediocre?

60. When have you not been mediocre?

61. How mentally healthy are you right now?

62. How physically healthy are you right now?

63. How emotionally healthy are you right now?

64. What have been your biggest mistakes?

65. What have been your biggest good calls?

66. Could you have done a better job over the last 5 years? How?

67. How have others faired in your peer group over the past 5 years?

68. What should you stop doing?

69. What is a distraction?

70. What is worth investing in over the long term?

71. What would you do with $500k in extra cash?

72. What would you do with $1m?

73. What would you do with $3m?

74. What would you do with $10m?

75. What will the state of the world be in 1 year?

76. What will the state of the world be in 2 years?

77. What will the state of the world be in 3-5 years?

78. What will the state of the world be in 10 years?

79. What is the biggest risk you can think of taking right now?

80. What is the biggest risk you have the stomach for?

81. What happens if you take theses risks and fail?

82. What happens if you don’t fail?

83. What’s your emergency going broke plan?

84. What offer would someone have to make today to make you sell your company?

85. What offer would they have to make to hire you away?

86. What do you lose if you lose your company?

87. What do you gain if you lose your company?

88. Have you taken enough risks?

89. Is 5 years a long time in this business?

90. Why does time matter?

91. What is arbitrary?

92. What can you do to remove the arbitrary pressures?

93. Do you have enough pressure on you?

94. Do you have clear measures for success?

95. What do you need to achieve before you die?

96. How much of this is about you vs. everyone else?

97. Do you give a fuck? About what?

98. What is missing from your life?

99. What is missing from your company?

100. What will you do to live the life you want to live and grow the company you want to grow?

Let me know what you think in the comments. Were these helpful?

6 Responses to “100 Questions Every Founder Must Ask Themselves”

  1. Aaron says:

    I feel like I just grew up at least 5 years trying to answer these questions. It’s very cool that many of them challenge and define those intersections between professional versus personal areas in life – which are certainly important areas to address, especially when trying to start your own company. These questions are straight-to-the-point-no-bullshit kind of questions and way better than the standard business plan. Thank you for taking the time to think of these and for posting them!

  2. Misha says:

    Wow. Thats good. You guys should make a mobile app and call it the founder checklist. I think many of us tend to jump into a project without fully thinking it through. Definitely printing this and keeping it on my wall.

    Thanks!
    - M

  3. My favorite question: 18. HOW ARE YOU GOING TO FIGURE OUT HOW TO UNCOVER WHAT YOU DON’T KNOW YOU NEED TO KNOW? Thanks for this list. It’s inspiring, scary, comforting and thought provoking.

  4. kem says:

    Awesome list! Downloading, will work on answering all these questions this summer!

  5. RangerMK says:

    Brilliant. The psychology of congruence for Founders. This is like blending start-up coaching, Meyers Briggs on steroids, and Lean Launchpad. Thanks for sharing.

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