Here’s my favorite list of provocative questions I’ve collected—and asked my clients—over the years.

1. What’s on your mind?

2. Where should we go today?

3. What’s the dream and desire in us working together at this moment?

4. Where do you want to go? Turn this into a single question for me.

5. If there was one question I could answer for you today…what would it be?

6. Why are you here?

7. Why are you really here?

8. What do you want?

9. If they struggle to answer #8, have them fill in this sentence stem: Wouldn’t it be cool if…

10. What are you longing for?

11. What’s whispering to you?

12. If I could wave a magic wand and solve the ONE thing that would have the biggest impact for you right now…what would it be?

13. If we waved a magic wand and gave you x (their answer from #12)...what would you want next?

14. What do you want to take away from this no matter what occurs?

15. Was there something that stood out or rippled out from the time we spoke last?

16. What crossroads do you face right now?

17. What does your heart want you to know? What does your gut (intuition) want you to know?

18. What’s the real challenge in that?

19. Why did you ask that question, what does that mean to you? (curiosity)

20. Why are you driving forward with the handbrake on? (curiosity)

21. What’s energizing you?

22. What’s draining you?

23. What are you proud of?

24. What are you confident about?

25. What are you excited for?

26. What big leaps have you made? In the past month or past year? Personal or professional.

27. What setbacks have you faced?

28. And are they recurring problems or real problems?

29. Are there some boundaries you’d like to put around that?

30. What do you need to tell me?

31. What do you need me to tell you?

32. What do you make of that?

33. What do you mean by that?

34. What’s no longer serving you?

35. Are you taking care of you?

36. If you knew you couldn’t fail, what would you do?

37. What are you afraid of?

38. Are you really afraid of that?

39. What makes you feel alive?

40. What do you want to do?

41. If you could be selfish and have one thing you wanted today…what would it be?

42. What do you love to do more than anything else?

43. What do you hate doing more than anything else?

44. What was going on in that silence?

45. Does that voice in your head belong to you or someone else? A parent? Teacher? Boss?

46. What’s your best idea for solving this?

47. What if it were easy?

48. What do you need to say YES to right now?

49. What do you need to say NO to?

50. What is the goal that, thinking about achieving it brings tears to your eyes?

51. What do you need to do to make that happen?

52. Who do you need to be?

53. What are you doing now that you’ll regret in five years if you are still doing it?

54. Who is the person most likely to pay you money right now? (Money)

55. How does it feel to have the idea that you can be paid by some people and nothing from others? (Money)

56. What if you had it the wrong way around and that if the more money you make, the more of those things (freedom, fun, time with family - what they most want but are afraid making more money would hinder them from having it) …would occur? (Money)

57. How would you coach a client on this very issue?

58. What is your biggest insight or take away from anything that’s happened here today?

59. How will you apply it?

60. Finish the sentence stem: “It’s XXYY (one year into the future) and the most amazing thing about my business is…x”. Repeat 10 times.

61. New sentence stem: “One tiny thing that intimidates/scares me about an amazing business is?” Repeat 10 times.

62. Where do we go from here?