There is one thing that every guest I’ve invited to the podcast has told me:

I’m not an expert on decision-making.

That’s because no one is. There are just too many variables for anyone to ever make perfect decisions all the time. However, we have plenty of tools to improve our process, our thinking, and our lives as a result.

One of these tools is asking the right questions. I’ve compiled this list of 100 of them to help us both see as many angles as possible, to widen our view, challenge our assumptions and catch ourselves when our thinking gets hooked on a bias.

These questions are a result of the conversations I’ve had while recording the podcast, while doing research for the weekly newsletter and while reading on the topic. In doing so, I came across some great resources that I’ve linked to (some more than once) below, so you can take your explorations further.

If these questions help you in any way, I’d love to hear from you, equally so if you have others that can fill in the gaps.

  1. What is this decision for? Define your objective.
  2. Who is this decision for? Is it for you or someone else?
  3. Who is this choice NOT for? Set your constraints.
  4. Why do you have to make this decision (now)? Figure out your motivations, purpose and timeliness.
  5. Why did this decision become necessary? Figure out where and how it all started.
  6. How much time will you give yourself to make this choice?
  7. Are you trying to make this decision quickly or wisely?
  8. What is your role in this decision?
  9. What is your responsibility as a decision-maker?
  10. Is the question you’re asking yourself framed correctly?
  11. What does success look like for the decision you’re trying to make?
  12. How will you evaluate if your decision is successful or not after you’ve made it?
  13. What will you NOT be doing as a result of this decision?
  14. Is this in your control?
  15. What is the most important thing for you about this decision?
  16. What are you missing?
  17. What happens if someone makes this decision for you?
  18. How have you made similar (and successful) decisions before?
  19. Could you be remembering your choices as better than they actually were? Read about the choice-supportive bias.
  20. Who makes similar decisions that you can talk to about the choice you have to make?
  21. Have you reconsidered decisions like this one before? What happened?
  22. On a scale from 1–10 where 10 is very confident indeed, how confident are you right now of making the right decision? Learn more about the scale of confidence.
  23. How come it’s a 4 and not a 3 or a 2? What’s helping you to be confident already?
  24. What would be the first tiny signs that your confidence had increased to a 5? What else?
  25. How could you manage to have ‘both’? What might it mean to do ‘neither’?
  26. Who does this decision affect/impact?
  27. How are your habits influencing the decisions you make and how you make them?
  28. What are the risks you associated with the decision you’re trying to make?
  29. Are you amplifying risks by making them more “vivid, personal and immediate” than they need to be?
  30. What is the worst thing that can happen as a result of this decision? Do some fear-setting.
  31. What can you do to minimize the chances of your worst fear coming true (related to this decision)?
  32. If the worst-case scenario happens, what could you do to repair the damage?
  33. What would you decide if you knew you couldn’t fail?
  34. What will happen if you don’t make this decision (now)?
  35. What will happen if you postpone this decision?
  36. What would you choose if you did it right now?
  37. Can you make this choice with the information you have?
  38. What are you suffering from right now that’s making this decision necessary?
  39. What is the best decision according to your values and principles?
  40. How does this decision align with your priorities?
  41. What long-term effects does this decision have on you?
  42. How does this decision fit into your plan?
  43. What is the acceptable alternative for this choice?
  44. How you define what’s “acceptable” or “best” for the decision you have to make?
  45. If you do X, what will it really cost you? (Don’t think just about the money.)
  46. What is this cost made of?
  47. Is the best choice you have at hand worth the time/effort/money/cost involved?
  48. What is the cost of choosing an option against the other? Figure your the opportunity cost.
  49. What are you willing to suffer/take/cope with to make the most of your choice?
  50. How will you feel about it in 10 minutes? Try the 10/10/10 method.
  51. How will you feel about it in 10 months?
  52. How will you feel about it in 10 years?
  53. Imagine that the option you’re currently leaning toward simply vanished as a feasible alternative. What else could you do? Avoid the “narrow frame”.
  54. Imagine that the alternative you are currently considering will actually turn out to be a terrible decision. Where could you go looking for the proof of that right now?
  55. What would you tell your best friend to do, if he/she was in the same situation?
  56. Six months from now, what evidence would make you retreat from this decision? What would make you double-down?
  57. What are the pros and cons of this decision?
  58. Are you looking towards the future or the past when making this decision?
  59. Which sunk costs are holding you back from making this decision?
  60. What are you resisting to in making this choice?
  61. What is great about having to make this decision?
  62. What are the secondary consequences you expect your choice to have?
  63. Does this decision have permanent consequences? Why does it/doesn’t it?
  64. How will you feel if you give up making this choice?
  65. If you only had a day/an hour to make this decision, what would you do?
  66. What is one thing you can to today to make it easier to choose a path?
  67. Are you the right person to make this decision?
  68. How would this decision look like if it were easy?
  69. Which cognitive biases could be distorting my perspective regarding this decision?
  70. Is the anchoring effect keeping you from evaluating your options as objectively as possible?
  71. Are you avoiding the options that you don’t have enough information about to stay clear from more ambiguity?
  72. Are you only taking into consideration the information that supports your beliefs or are you challenging your assumptions? Check yourself for the confirmation bias.
  73. Is this decision leading you to recall unpleasant memories more intensely than positive ones? Learn more about the negativity bias.
  74. Are you at risk of misjudging your options because of the availability heuristic?
  75. Which mental models could help me see different perspectives of the choice I have to make?
  76. Could you change your mind after making this decision? What would that look like?
  77. What could happen if you make the wrong decision?
  78. What do you really care about in this decision-making process?
  79. Sit in a quiet place for a few minutes and think about the choice at hand. How does it make you feel?
  80. What is the safest decision? Why?
  81. What is the riskiest choice? Why?
  82. Are you basing this decision on analyzing just the top layer and assuming that what’s underneath matches it?
  83. How do you make decisions? Map out your process.
  84. What are your strengths in making this decision?
  85. What commitment will you be making as a result of this decision?
  86. Which versions of your dream or objective are you comparing for this choice?
  87. In which ways does this decision make you rethink your future?
  88. Do you feel peer pressure to lean towards one choice versus another/others?
  89. Are you basing your decision on the current context or is something from your past holding you back?
  90. Are you trying to avoid something or are you trying to achieve something by making this choice?
  91. Is this decision urgent or important or both?
  92. What change are you trying to make by this decision?
  93. Do your hunches match the data you gathered and analyzed to make this choice? Look for counterintuivite insights.
  94. How would pausing for 300 seconds change your current reaction to the context and information you have?
  95. What are the complications or complexities involved this in this decision? Map them out.
  96. What can you do to avoid allowing the lizard brain making the choice for you?
  97. What is the smallest choice you can make to work your way up to a more complex decision?
  98. How is one option better than the other?
  99. How does this decision influence the legacy you want to build?
  100. How will this decision make you a better human?