Questions Database
260 questions across 7 categories
Personal
1. What’s something I continue doing a certain way even though I know there are more efficient alternatives?
2. Do I actually like myself or do I just like when other people like me?
3. Who would I miss if I stopped reaching out first?
4. What’s the biggest irrational fear that you have besides being unsuccessful?
5. Who are you afraid of disappointing and how would your choices change if you released that fear?
6. If a competent CEO took over your life, what’s the first thing they’d eliminate?
7. Where would I be if I were 3 times more courageous?
8. What are the emotions I’m afraid of feeling?
9. If money and status were no object, what would I do?
10. If I was less afraid of other people’s judgment, what would I say?
11. What is my definition of success if money was taken out of the equation?
12. What is the hidden price I’m paying for inaction?
13. What is something you deeply believe but rarely live out?
14. What would you do if you had no fear?
15. Who is a person I should be thanking/complimenting?
16. What is the most destructive habit in my life right now that I’m ignoring? What is the solution?
17. Where is the third door that the industry is ignoring?
18. Who/what exists in the shadow of my mind that is silently guiding my decisions?
19. What would it take to make this a yes?
20. What are you afraid of happening?
21. If I had $50M in the bank, how would my day-to-day change?
22. What are my 3 rules for success/happiness?
23. How will being anxious about this serve me?
24. Do I really need to answer this text or email right now?
25. Am I really happy? Or am I just really comfortable?
26. Am I really trying my best or am I just telling myself I am?
27. What is it that I can think of, read, watch, listen and talk about for hours on end without tiring of it?
28. If I had to describe who I wanted to be in 3 words, what would those words be?
29. What would it take to snap me out of my bad mood immediately?
30. What’s the first thing you think of when you wake up most days? Is that what you want to be thinking?
31. How do I want my life to be different in one year?
32. Is this project making me a better person?
33. What is the less-stressed version?
34. If I do [this], will I respect myself more?
35. Assume that more than one path exists to achieve your ideal life. What would some of the alternative routes look like?
36. Are you inventing things to do to avoid the important?
37. Where am I seeking comforting lies over inconvenient truths?
38. If you were writing the autobiography of your life, what would your next decision be?
39. How do I win, even if I lose?
40. What am I missing that a more humble person might see?
41. If there was one goal to commit yourself entirely to, what would it be?
42. Does this take me toward or away from my goal?
43. What is my 1 year, 2 year, and 25 year vision?
44. If I had all the money in the world, what would I do with my life?
45. What gives me the most energy? And how can I do more of it?
46. What drains me? And how can I do less of it?
47. What actions do I do repeatedly that doesn’t align with the person I want to become?
48. How would I like to be spoken about at my funeral?
49. How can I complete my 2 year goal in the next 3 months?
50. What friendship have I let die due to being ‘too busy’, and how can I get it back?
51. How would my daily schedule change if I did a little more of what I’m great at and a little less of what I’m not great at?
52. If you could spend 30 minutes today creating whatever you want, what would you create?
53. What has been the best hour of my week? How can I make it easier to have more hours like that?
54. What can I do today to improve by 1%?
55. Are the results I am expecting aligned with the habits I am following each day?
56. How can I make situations more magical for those around me?
57. When was a time in the past you successfully adapted and made a change? What is a change you would benefit from making right now?
58. What can you do in the next 30 days to build momentum and finish the year on a high note?
59. How can I use the negative experiences in my life to drive me? What fuel can I draw from my failures? What lessons can I take from my grief? What insights can I extract from my embarrassments?
60. The question is not, ‘Will I succeed?’ but rather, ‘What should I attempt?’
61. What’s something good to ‘go a little overboard’ on? What’s something you could benefit from caring less about?
62. What’s true about my life today that would make my 18-year-old self disappointed?
63. Are you being too passive or too aggressive right now?
64. Is taking things so seriously improving my performance? How can today feel like play?
65. What will happen if I don’t do this?
66. What career would you realistically pursue if you wanted the most money? What career would you realistically pursue if you wanted the biggest impact? What career would you realistically pursue if you wanted to have the most fun? What career offers the best combination?
67. When was the last time you felt a sense of wonder and awe? What can that experience teach you about how to spend your time?
68. What’s my favorite way to fail? What am I willing to struggle for?
69. How can I make this process more enjoyable?
70. What am I saying no to by saying yes to this opportunity?
71. What do you want? What’s the price? Are you willing to pay that price?
72. What do you believe stands between you and complete happiness?
73. If you could write a note to your younger self of 10 years ago, what topics would you focus on?
74. What does a perfect day look like to you?
75. What’s something you thought you’d grow out of but haven’t?
76. What’s something you’re self-conscious about and how does that affect your life?
77. What’s something you’d like to do well, but never have been able to?
78. Are you willing to see how the opposite of your story might be just as true?
79. What do you love about yourself that has nothing to do with your money or success?
80. What have you been wrong about lately?
81. What are you optimizing your life for at the moment?
82. What are you good/bad at saying ‘no’ to?
83. Does the amount of attention I’m giving this match its true importance?
84. Can my current habits carry me to my desired future?
85. How can I create an environment that will naturally bring about my desired change?
86. What game am I playing? Is it worth the prize?
87. How do I want to spend my days?
88. What can I do today that will make life easier ten years from now?
89. Where am I taking shortcuts that may hurt me in the future?
90. How can I 10x the speed of my decisions?
91. How can I better listen to the wisdom of my body and emotions?
92. Where am I copying others that I don’t want to be or shouldn’t be?
93. For the things I want to get better at, have I been deliberately practicing or just going through the motions?
94. Am I making space for stillness, silence, and solitude?
95. What am I putting off? What would happen if I just did it now?
96. Am I sticking to the plan or am I letting life get in the way?
97. What’s the real goal here? Is there a better way to approach it?
98. Who do I need to connect with to gain access to the opportunities I want?
99. What if I did the opposite for 48 hours?
100. What if I created my own real-world personal MBA?
101. If you win at whatever game you’re playing right now, would you be happy?
102. How many people do I admire that are actually miserable?
103. What would this look like if this was fun?
104. How is this person going to treat me when they have the opportunity to be selfish?
105. If life were a video game, whose stats would be maxed?
106. What do I believe is true only because believing it puts me in good standing with my tribe?
107. Is this thing I’m worried about actually a problem, or am I looking for problems to worry about because they make me feel in control?
108. What do I think is a universal truth but is actually just a norm unique to my own culture?
109. What was true a generation ago that no longer is, and who is clinging to that old truth?
110. Are there things going well in my life today that I will look back on and wish I had quit while I was ahead?
111. If someone could only see my actions and not hear my words, what would they think my priorities are?
112. What are you excessively curious about — curious to a degree that would bore most other people?
113. What could you not be paid a billion dollars to stop doing? What would you do if the only reward for doing good work is more work?
114. If I could only learn from 3 books for the rest of my life, what would they be and why?
115. What are the opportunity costs behind X decision?
116. What are the second and third order consequences of this decision?
117. How much time do I spend thinking & learning each day? How can I create more of it?
118. What makes me feel anxious? How can I do less of it?
119. What are my 5 core values?
Conversation
1. What is the kindest thing anyone has ever done for you?
2. What is a moment in our relationship that changed how you see me?
3. What are you hesitant to ask me and why?
4. What’s something you stress about but know you shouldn’t?
5. What’s something you’d like to be remembered for?
6. Do you live more in the present, past, or future?
7. If you could pause time for one day, what would you do?
8. Who is the most high energy person you know?
9. What do you have ‘unreasonably’ high standards for?
10. What was that like for you?
11. What’s interesting to you right now?
12. Is there closure you never got to have?
13. What’s the first thing you think people notice about you?
14. So what do you do with your money?
15. Are you afraid of dying?
16. What title would you give this chapter of your life? Why?
17. What do you miss about your childhood?
18. What movie has had the biggest impact on you?
19. What job would you pick if money didn’t matter?
20. What’s one thing about yourself that you hope never changes?
21. If you are in a bad mood, do you prefer to be alone or be with someone to cheer you up?
22. What one quality in others bothers you the most, and what does that say more about you or them?
23. What is something you could never truly forgive yourself for?
24. Is your perception of self closer to who you are or who you’d like to be?
25. What would you rather change: your past or your future?
26. What’s the biggest difference between who you are and who you pretend to be?
27. How did you two meet?
28. Assume you get paid $1M per year no matter what you do, but you still gotta work 40 hours a week. What would you pick to work on?
29. When was the last time you had so much fun you lost track of time?
30. What’s the kindest thing someone has ever done for you?
31. What usually takes people a long time to figure out about you?
32. What traits do you share/don’t share with your parents or siblings?
33. What do you mindlessly collect?
34. What outfit would you wear everyday if you knew no one would notice that you repeated it?
35. What’s your fighting style?
36. What would you do if you knew you’d be successful at it?
37. What are you borderline overconfident about?
38. What’s your long-term/end goal?
39. Would you rather… A or B? Why?
40. What challenge, personally or professionally, are you facing that if I helped you, could change your life?
41. If you could set a good morning ritual for you, what would it be?
42. Who’s having the most fun?
43. If you could give a TED talk on anything, what would it be?
44. If you crack open your YouTube right now, what are the 20 videos it recommends you watch next?
45. What are you getting most excited about right now?
46. What’s something you’ve changed your mind about?
47. What’s your worst self sabotaging behavior?
48. What’s something that’s always been different about you?
49. What’s something you’ll never understand?
50. What do you get most jealous about?
51. What can I do to make your life easier?
52. What is not being said that needs to be said?
53. What’s one big thing you want to change about yourself?
54. What’s something simple that makes you smile?
55. Fill in the blanks with the first thing that comes to mind: Life is ______. People are ______. I am ______.
Mentor
1. What did it cost to be you?
2. What is something most people think is important that I can skip entirely?
3. What’s something important in your daily routine you wish you started sooner?
4. What channels led to the development of your highest-quality relationships?
5. What is something you did differently than your peers 5 years ago that led to pushback, but served you in the long run?
6. What can I expect to struggle with along the way?
7. What is something you believed 5 years ago that you had to ‘unlearn’ to take the next step?
8. What’s something you didn’t pay enough attention to early on, then had to learn the hard way?
Interview
1. What is the kindest thing anyone has ever done for you?
2. Give an example of a time you upheld your integrity under pressure.
3. Tell me about the last hard conversation you had and how you handled it.
4. Tell me about a time you faced a major challenge and how you handled it.
5. Imagine you had a really great day at work and you’re telling your partner all about your day. What is it that you’re telling them?
6. What feedback will I be giving you in your first performance review?
7. Tell me about a time that you delivered something that was impactful?
8. What’s something everyone believes that you disagree with?
9. Tell me about a time something went wrong? What was it and what did you do about it?
10. What would your sibling say about you?
11. Fast forward 3 years… what’s different about you then?
12. Tell me something you’re really proud of.
13. Describe to me a time when you were a part of a controversial decision?
14. What’s the hardest thing you’ve ever done?
15. To what do you attribute your success? (And you can’t say ‘luck’)
16. What’s your strategy for learning?
17. Fill in the blanks with the first thing that comes to mind: Life is ______. People are ______. I am ______.
18. What was the [core metric] when you started and what was it when you ended? What were the 3 things you did that most impacted that?
19. Ask a reference: On a scale of 1-10, what would you rate this person? What could they do to get to a 10?
20. On a scale of 1-10, how lucky do you think you are? Why?
21. Can you just screen share and show me your thinking process?
22. How did you prepare for this job interview?
Business
1. What’s the worst software that you use on a regular (at least weekly) basis as part of your job?
2. If you could pick 1 person and you could have 10% of their future earnings – who would you pick and why? How can you adopt the skills, beliefs, and character traits of the person you picked?
3. How can I be working on something that will last 100 years from now?
4. What metrics am I not tracking that I should be?
5. The 4-part career question
6. In your professional life, who do you admire most? In your personal life, who do you admire most? How can you surround yourself with them more?
7. What’s something controversial today that you don’t think will be tomorrow?
8. What is the work that keeps working for me after I stop working?
9. Where am I hunting field mice instead of antelope?
10. If I could only work 2 hours per week on my business, what would I do?
11. Am I doing things just because everyone else is or because it’s the right for me?
12. What might I put in place to allow me to go off the grid for 4 to 8 weeks, with no phone or email?
13. What would this look like if it were easy?
14. ‘If you accomplished your biggest goal, would it change your world or the world?’
15. Who’s playing chess when everyone else is playing checkers?
16. Who’s having the most fun?
17. What are the hard things you’re avoiding?
18. You can only keep 3 employees. Who do you keep?
19. What would my favorite entrepreneur(s) tell me I’m doing wrong?
20. If I decided to reinvest my earnings, where are the best leverage points?
21. What can I do to be different from my competition?
22. What is my competition doing that I can do better?
23. What is my competition not doing and why?
24. Over the past 2 years, what decisions led to the best results? Can I repeat them?
25. Over the past 2 years, what decisions led to the worst results? Can I avoid them?
26. If I could only get paid AFTER I got results… what would I be doing and who would I be doing it for/with?
27. What would you do differently if you increased your timeframe?
28. Where could you work harder not smarter?
29. Where am I approaching my business through a lens of scarcity?
30. What non-creative, repetitive tasks are taking up your time (and how can you remove them)?
31. If you had no fear, what steps would you take differently now?
32. What is my business optimizing for?
33. What area of my business is less than excellent right now? What steps can I take to improve it?
34. What would my favorite entrepreneur(s) tell me to do next?
35. What assets should I create this week?
36. Do I have a skill set that will be useful 5 years from now?
37. What problem have you solved this week?
38. How do I become so good I can’t be ignored?
39. What can I do to make your life easier?
40. What is not being said that needs to be said?
Audience
1. What is the transformation you provide to your audience?
2. What story am I telling my audience?
3. What core emotion do I want my audience to feel?
4. What core benefit am I delivering to my audience?
5. What’s the most valuable place I can direct this attention?
Content
1. Would I genuinely read this or am I chasing the wrong incentive?
2. How can I use my sawdust more effectively?
3. A chef invents recipes, puts new things together & creates new ideas. A cook follows recipes and does things that have been done before. Are you a cook or a chef?
4. What is no one else making?
5. What aesthetic is no one capturing?
6. What small details are up and coming?
7. What would you be most excited to share?
8. What are you seeing that no one else is seeing?
9. How can I find the synthesis between education and entertainment?
10. What important truth do very few people agree with you on?
11. What is something you’re trying to achieve?
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