Questions are in no particular order ..
1. What assumptions are being made? [This one is my favorite question to ask, so I wanted it to be first]
2. Why are you making those assumptions?
3. Who is “we”?
4. Do all the people who you define as “we”, know that they are part of “we”, and what part they are?
5. Who is “them” / “they”?
6. How is the past influencing you? Should it?
7. If you never encountered that person before, how would you approach them?
8. Why is this necessary?
9. Was this necessary last year, and if it was, what has changed to really make it necessary this year?
10. If you do that, what will happen?
11. If that happens, what will it affect and how?
12. What is relevant about this situation?
13. If you think the glass is half full, how do you get it to be completely full?
14. If you think the glass is half empty, how do you get it to start filling again?
15. What do “faster”, “more”, “better”, “soon”, “ASAP” mean?
16. Why is what you described a problem?
17. If this problem and/or situation has been around for a long time, and it is important, how come it wasn’t’ addressed / solved before?
18. I know this has been tried several times before, but is it possible that there is a solution; it just hasn’t been found yet?
19. Is it possible that what is impossible to you, might actually be possible?
20. Are you responsible for figuring out the solution, or are you responsible for ensuring that a solution is figured out?
21. Are you sure? If you’re not 100% sure, what would you have to do to be 100% sure?
22. How can you validate those assumptions?
23. What if those assumptions are not true?
24. What other assumptions might there be?
25. What caused this?
26. What else may have caused this?
27. What, even though improbable, could have caused this?
28. What is impossible, but if it were possible, it could have caused this?
29. Is there any component of the impossible, which is actually possible, and could have caused this?
30. Why do you care?
31. How does that action contribute to the goal?
32. What other actions are necessary that will contribute to the goal?
33. What are the variables that affect the outcome?
34. What variables can be controlled?
35. What variables can you control?
36. Is this a show stopper? If it is, why?
37. What other ways can you solve the problem, given the constraints of the show stopper?
38. How would you find out?
39. Who can you ask who might know?
40. What assumptions can you make that allow you to continue, and you can validate or invalidate later?
41. Is your experience, “the” experience?
42. What other experiences might there be that will support or contradict your experience?
43. How do you know that’s a fact .. it is absolutely true?
44. How can you validate what you just read and/or heard?
45. Is there a way to gain confidence in this information without knowing that it is actually true?
46. What is the vision, the end state, i.e. what does the world look like after you solve that issue?
47. What about You, your values, your core beliefs, that are influencing you in this situation?
48. What other experiences from others might be important in this situation?
49. What makes you so confident in your conclusion (solution)?
50. If you were presenting to a group of skeptics, what experiences, facts or information might they question?
51. What is the meaning of this information?
52. How does that information affect others?
53. If the data could talk, what would you hear?
54. What would it mean if the value increases or decreases?
55. Your project plan has green, yellow and red. What are you doing to prevent yellow from becoming red and making them green?
56. How will you make sure your green initiatives stay green and not turn yellow or red?
57. How does this information affect you, your department, others, the company?
58. Do you have a good idea as to what is next?
59. Do others who are responsible for what’s next, know what is next?
60. If you were leading the other departments, and you knew what you’re thinking regarding what is next, would you do anything different?
61. Can you anticipate a future outcome, reaction or barrier?
62. Given this outcome, what could you do to prevent or leverage it?
63. What metric can you track that can provide insight to a future outcome?
64. What are the consequences of what you are doing?
65. What are the downstream effects?
66. How are others affected?
67. Can you describe a broader issue that this issue belongs to?
68. How much of the broader issue will the solution to this issue accomplish?
69. What other issues exist regarding the broader issue?
70. What and where are the handoffs in the current process?
71. Is there a way to eliminate some of the handoffs?
72. Is the math correct? Are the formulas correct? Are they applied correctly?
73. Are there any subjective overrides, i.e. beliefs, that might be affecting the thinking?
74. What are the criteria you will use to make a decision?
75. Why do you think those criteria are sufficient?
76. Does the decision need to be made now? If not, when?
77. If you were to present a case to support the other ideas that people have, what would that look like?
78. So you want to think “outside-the-box”? What’s the box?
79. How might your experience hinder your ability to think of new ideas?
80. How can you leverage the thinking of others?
81. What is the downside of making that decision?
82. What’s the probability of the downside occurring?
83. If the downside occurs, what would happen?
84. If the downside occurs, how could you mitigate it?
85. What is the upside and the probability of obtaining it?
86. Is the upside and probability worth the downside and its probability? Why?
87. What would happen if this issue wasn’t solved?
88. Why do you think you’re not accomplishing some of the things on your to-do list (besides the excuse of “I don’t have time”).
89. What did you learn from this?
90. When you made that decision, what was your thinking like?
91. What things on your to-do list are time dependent?
92. If you had a "great day", what made it so great.
93. What actions can you take to get future days to be like the one that was great?
94. You just said something, and I’m not really clear on how that affects this other thing we’re talking about, so can you say this another way so that I can see the connection?
95. How do you know that what you read or what you were told is information that you can rely on?
96. If you take that action, who is it going to impact?
97. If you take that action, what will be the impact on others?
98. If that action is taken, what is going to change?
99. If that changes, what will the reactions be, why, and how will you address them?
100. Why haven’t you signed up for a HeadScratchers Critical Thinking Class? Oops, that’s an advertisement, so this one won’t count as a question … although it’s a really good question :)
101. What other questions can you ask to Get Clear on an issue, come to a Conclusion (solution) about the issue, and Decide to take action?