Without questions, there is no quest to take you from where you are to where you want to be. The movement of a quest prevents stagnation.


old thinking results

Questions invite you into the unknown.

The best coaching relationships I have had are like a game of ping pong. The coach will start by sending a question over the net. This creates a response, which invites another question. Nobody knows where the conversation is going to go, because it’s guided by the improvisational responses that are uncovered as you play.

Over the past few years, I’ve collected some of my favorite questions into a swipe file that I refer to in the middle of a coaching conversation. Next to my Zoom window, I keep this list of questions open throughout the call. This has been extremely helpful in making sure the rhythm doesn’t falter, and every pause can be punctuated by a pivot.

Feel free to use these questions to deepen your own conversations.

101 Great Questions for Coaching

Note: I’d like to give a quick tip-of-the-hat to the many coaches I’ve hired and studied in the past. This list is neither original nor plagiarized. I have reused and rewritten questions I have been asked in the past, instead of copy-pasting from others, and I invite you to do the same.

  1. What would be the best outcome of today’s call for you?
  2. What’s happening right now with this issue?
  3. If you could start this over again, what would you do differently?
  4. How much control do you personally have over the outcome?
  5. If it doesn’t work out, what will you do?
  6. What’s the worst that could happen?
  7. Would that be so bad?
  8. What has held you back in the past?
  9. How can you prepare for this?
  10. What have you done so far?
  11. Are you getting the results you want?
  12. What is it you are hoping will happen?
  13. And what’s the goal of this?
  14. I want you to set a goal that is so big, achieving it would blow your mind. What will your life be like when that happens?
  15. Whats the best way to do that?
  16. Why do you think that is?
  17. Why does that matter?
  18. How so?
  19. Why are you doing that?
  20. How much does that cost you?
  21. What would make the biggest difference?
  22. What happens if we take this seriously?
  23. Do you believe this is possible for you?
  24. If your idea was a flyer on a bulletin board, what would it say?
  25. How is your business brand different than you?
  26. What’s the worst that could happen?
  27. What happens if you do nothing?
  28. Who does what you do really well?
  29. How can you learn from them?
  30. How can you differentiate yourself from them?
  31. What results have you created so far?
  32. What problems keep you up at night?
  33. Why is that important?
  34. What’s this really about?
  35. What would happen if you just leave it the way it is?
  36. What do people expect from you?
  37. What’s been the most successful so far?
  38. What do you think would be most successful in the future?
  39. Do you have any evidence to support this view?
  40. What’s the worst thing about this?
  41. When was the last time something like that happened to you?
  42. Why was that so hard?
  43. How could this be easier?
  44. What are the points of friction or delay?
  45. How will you know it’s time to change focus?
  46. How important is this to you?
  47. What are you committing or re-committing to accomplishing in the next two weeks?
  48. What might get in the way of you achieving these goals?
  49. Who can you reach out to for support?
  50. What was the most valuable thought or takeaway you had during our time together today?
  51. Was there anything missing that you wanted to get clarity on?
  52. What should people know about you that you haven’t shared?
  53. What would you like to be acknowledged for?
  54. What does your instinct tell you to do in this situation?
  55. Can you ask your question another way?
  56. What’s your own answer to this question?
  57. What will happen if you do not solve this problem?
  58. Why are you uniquely qualified to do this?
  59. What are you pretending not to know?
  60. How is that a problem?
  61. How can you use this to your advantage?
  62. What if it could be easier?
  63. What would be the ideal solution?
  64. How did that feel?
  65. How do your customers find you?
  66. What are the stages of their journey?
  67. How do you currently automate your systems?
  68. What are the points of friction in that process?
  69. How could those be smoother?
  70. If everything goes perfectly, where do you see yourself in three years time?
  71. What would be the choice of someone who handles this type of thing really well?
  72. What else could you do?
  73. If you were confidently in your highest power, what would the best response to this be?
  74. Who can help you?
  75. Who will need to be convinced?
  76. What would it take for you to get the results you want?
  77. On a scale of one to ten, how do you feel about this?
  78. What would it take to get a ten?
  79. What are the positive and negative impacts of success for you?
  80. What changes would this make in your life?
  81. What resources do you already have?
  82. What other resources do you need?
  83. How will you measure success?
  84. How will you keep yourself on track?
  85. What is the next thing you will do?
  86. What support can I give you?
  87. When do you want to begin?
  88. What if this could be easier?
  89. So what’s this really about?
  90. How is that a problem?
  91. What is it you are hoping will happen?
  92. What would be the ideal solution?
  93. How did that feel?
  94. What would be good for your self-care today?
  95. If you were to take this seriously, what is the first change you would make?
  96. How would you feel about doubling your goal?
  97. How could you make your goal more specific or measurable?
  98. What would be the impact on your life if you achieved this goal?
  99. Why is that important?
  100. What’s the next step?
  101. Are you committed to this?

Any answers to these questions can be followed with ‘Why?’ or ‘Why not?’ to encourage the dialogue to continue.

Sometimes, an answer sounds like it is only the tip of the iceberg. When you see it floating into the conversation, acknowledge it, and look deeper.

I often say to my clients, ‘Say more about that.’

This is my favorite thing to say in a coaching session, because I know I’m about to get a passionate and detailed download of something really close to their heart.

Being present for moments like that – that’s why I do this work.

If you’d like to answer some of these questions with me, I’m offering 10% off my coaching rates for anyone who applies for a Discovery Call by the 15th of January, 2022.

testimonial roger wolkoff

During this free, no-obligation Discovery Call, I will not talk to you about my coaching programs.

We are going to talk about you, your plans, your goals, and the obstacles sitting in your way.

I’ll ask you a bunch of questions, and give you some insight on your quest. After that conversation, if you want to continue on your quest with me as your coach, I’ll invite you to a second call to talk about the specifics of my 3-month and 12-month coaching programs.

Anyone who fills out the application for a Discovery Call before the 15th is eligible for a 10% discount off my program rates.