101 Questions

Here is a set of 101 of my favorite questions that I draw from, whether it’s to shape my day, solve a problem, figure out next steps, or get “on path.”

1. What’s the way forward?
2. What do you want your life to be about?
3. Who do you want to be and what experiences do you want to create?
4. How does that serve you in terms of who you are and who you want to be?
5. Are you giving your best where you have your best to give?
6. What do you want to accomplish?
7. What do you want to do more of each day? What do you want to spend your time doing more of?
8. What do you want to spend less time on?
9. If this situation were to never change, what’s the one quality I need to truly enjoy it?
10. If not now, when?
11. If not you, who?
12. What’s right with this picture? (if you always ask, “What’s wrong with this picture?” this is a nice switch)
13. How can you make the most of the situation? If there are no good options, what’s the best play I can make for this scenario?
14. Who else shares this problem? Who would solve this problem well? (a great way to find models and learn from the best)
15. What would do?” How would I respond if I were Bob Hope? Leonardo da Vinci? Guy Kawasaki? Seth Godin? etc. (this is a great way to come up with new ideas or plays for your situation)
16. What are you pointing your camera at? (a simple way to direct your day on a scene by scene basis)
17. What’s good enough for now?
18. What can you be the best at in the world?
19. What’s the most effective thing for me to focus on?
20. Are you asking the right question? Is that the right question?
21. How is that relevant?
22. What’s that based on?
23. What’s the goal? What are the goals?
24. What would success look like?
25. What do you need to be successful? What do you need to be successful in this situation?
26. Is it working? Is it effective?
27. What do you measure? What are the metrics?
28. What are the tests for success?
29. How do you know it’s working?
30. How do you know when you’re done?
31. What did you expect?
32. Are you creating the results you want?
33. Does it matter?
34. Will it matter in 100 years?
35. Is it worth the effort?
36. What actions have I taken? What steps have I tried? ( a great sanity check when you’re testing your ability to take action)
37. What’s next?
38. What do you want to do?
39. What’s best for you?
40. What’s the best thing for now?
41. What’s your next best thing to do?
42. Is that a good idea?
43. So what? Now what?
44. What’s the problem?
45. What’s the threat?
46. What’s the concern?
47. When do you want it by? You want what by when?
48. Who needs to do what when?
49. Who needs to do what differently?
50. Who should do what when?
51. What would you have them do differently?
52. What’s wearing you down?
53. What’s lifting you up?
54. Why do you get up in the morning and come to work?
55. What do you want to experience? What do you want to experience more of?
56. What are you trading? What are you trading up for?
57. What did you learn that you can use next time?
58. What would you do differently next time around?
59. Where’s the growth?
60. What would people pay you for?
61. Do you want to run towards or away from the problem?
62. How big is the pie, how big is your slice?
63. Does it make business sense?
64. Is it business critical?
65. What’s our capacity?
66. What’s our constraint?
67. What are the KPIs (Key Performance Indicators)?
68. What’s our core business?
69. What does the market want?
70. Is it push, pull or indifferent?
71. What’s the trend?
72. What to cut back on?
73. What does the pro know that you don’t? (this is a good way to figure out if knowledge or insight can make a difference)
74. Now what are you going to do about it?
75. Can you teach it to someone else?
76. How can I use this?
77. What do you want to say?
78. What’s the right thing to do?
79. Is now the right time?
80. Is this the right forum?
81. How much time do you have?
82. What are you making time for?
83. How much time should you make for it?
84. What can you do all day long?
85. What are you spending the bulk of your time on?
86. Does your schedule reflect your priorities?
87. If you had all the time in the world, how would you spend your time?
88. If you had all the money in the world, how would you spend it?
89. Where are we on the map?
90. What would make life more wonderful for you?
91. How can you chunk it down?
92. How fast can you do it?
93. What’s the impact?
94. What would you like to have happen? What would you like instead?
95. What’s the opposite of that?
96. How might that be true?
97. What are you seeing that I’m not?
98. What did you see, what did you hear?
99. What’s the writing on the wall?
100. What’s their story?
101. Who’s stopping you? What’s stopping you? What’s holding you back?