100 Questions Every Coach Needs in Their Back Pocket

‍Because great coaching isn’t about having answers—it’s about asking great questions. A well-timed nudge toward clarity. And at the heart of it all? Questions.

The kind that make you pause mid-sentence. The kind that open doors you didn’t even know were there. The kind that shift perspectives, unlock possibility, and maybe—just maybe—change a life.

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So, whether you’re a seasoned coach, a leader looking to inspire your team, or just someone who loves a great conversation, this list is for you.

Use them in your coaching sessions. Reflect on them for yourself. Steal a few for your next dinner party and watch the conversation actually get interesting.

Ready? Here we go.

Foundational Questions (The Big Picture)

1. What do you really want? Like, really?
2. If you weren’t afraid, what would you do next?
3. What’s been whispering to you lately?
4. If your life were a book, what’s the title of this chapter?
5. What are you resisting?
6. What’s the invitation hidden inside this challenge?
7. What’s the question beneath the question?
8. Where do you feel most alive?
9. What’s your next brave yes?
10. And what’s your next necessary no?

Finding Clarity (Uncovering What Matters)

11. What’s yours to carry, and what never was?
12. What if you stopped waiting for permission?
13. If you could only work on one thing for the next six months, what would it be?
14. What have you been tolerating for way too long?
15. What if your current frustration is actually a clue?
16. If your life had a soundtrack, what song would be playing right now?
17. When was the last time you felt fully engaged in something?
18. What’s the thing you keep saying you should do, but never actually start?
19. Where do you need to create more space?
20. What’s trying to emerge in your life right now?

Courage & Change (When It’s Time to Move)

21. What’s one small action that would change everything?
22. If you don’t do this now, when will you?
23. What’s the worst that could happen? What’s the best?
24. Where are you playing it safe?
25. What’s more important—certainty or possibility?
26. Who would you be if you let go of that story?
27. What if you actually did the thing?
28. What’s the next right step?
29. What’s waiting for you on the other side of fear?
30. What’s the cost of staying where you are?

Exploring Limits (Deepening Awareness)

31. What have you outgrown?
32. What’s keeping you small?
33. What do you need to unlearn?
34. If this were easy, what would it look like?
35. What rules are you following that you never agreed to?
36. What’s the limiting belief you’re ready to retire?
37. Who taught you that success looks like this?
38. What’s the deeper fear underneath all of this?
39. If you could fully trust yourself, what would you do?
40. What’s one story about yourself that isn’t true anymore?

Wisdom & Integration (Living It Out)

41. How do you know when something is right?
42. What would it look like to honor what you already know?
43. What practices keep you grounded?
44. What’s calling you forward?
45. What if you didn’t have to earn rest?
46. Where are you making things harder than they need to be?
47. How do you want to show up in the world?
48. What’s the simplest way to get started?
49. What rhythms in your life need adjusting?
50. What’s one way you can embody your values today?

Relationships & Connection (Human Stuff)

51. Who are your people?
52. What kind of friend do you want to be?
53. What’s unsaid that needs to be said?
54. Who needs to hear you say ‘thank you’?
55. Where do you need to practice better boundaries?
56. How do you want to be remembered?
57. What’s the hardest thing about asking for help?
58. Where can you offer more grace—to others, or yourself?
59. What’s one thing you wish people knew about you?
60. Who do you need to forgive?

Creativity & Possibility (Dreaming & Making)

61. What wants to be created through you?
62. If you weren’t worried about getting it right, what would you try?
63. What does inspiration feel like in your body?
64. What’s an idea that won’t leave you alone?
65. What if you experimented instead of aiming for perfection?
66. What’s the most playful way forward?
67. Who needs to hear what you have to say?
68. What would your 10-year-old self tell you to do?
69. What happens when you follow your curiosity?
70. What’s something you want to try just for fun?

Life & Meaning (The Bigger Stuff)

71. What does enough look like?
72. Where do you find wonder?
73. What does it mean to be fully alive?
74. What’s been life-giving for you lately?
75. How do you measure a good day?
76. What’s the lesson life is trying to teach you right now?
77. What’s sacred to you?
78. If you could write your own job description for life, what would it say?
79. What’s your relationship with time?
80. What would change if you believed your life was unfolding exactly as it should?

Inner Work (The Questions Behind the Questions)

81. What if you didn’t have to prove anything?
82. What if this isn’t a problem to solve, but a mystery to live?
83. What are you avoiding?
84. Where do you feel resistance in your body?
85. What’s beneath the surface of this feeling?
86. What’s your relationship with failure?
87. What if you were already enough?
88. What would happen if you fully trusted yourself?
89. What’s the fear that’s holding the megaphone right now?
90. How are you making this more complicated than it needs to be?

Future & Legacy (Looking Ahead)

91. What do you want to be known for?
92. How do you want to feel at the end of this season?
93. What’s one thing you want to tell your future self?
94. What’s a dream you’re willing to bet on?
95. What’s one habit that would change everything?
96. What do you want more of in your life?
97. What’s the invitation of this next season?
98. How do you define success?
99. What’s the story you want to tell when you look back on this?
100. What’s the next question you need to ask yourself?

Bookmark this. Use it. Let it spark something.

And if one of these questions landed for you, sit with it. Because sometimes, the right question is all it takes.

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