74 Leadership Coaching Questions That Will Empower Clients

Are you a coach aspiring to enhance your leadership mentoring skills? Or perhaps you’ve recently assumed a leadership position and desire to guide your team in the most effective manner. Hang tight, you are mere moments away from uncovering potent leadership coaching questions that will amplify self-awareness, shatter self-imposed barriers, and inspire individuals.

Leadership is not easy. From effective decision-making and communication to performing and maintaining the right culture, a lot of responsibility lies on a leader’s shoulders. Often leaders are so busy, that they never find time to reflect on themselves and evaluate their actions at work. To help leaders cope with their positions and improve further, we are going to use the best coaching strategy.

Every successful coach will agree that asking questions is the core fundamental strategy of any type of coaching. Simple yet powerful questions can do wonders if they are asked correctly, and most of the time it’s all that coaches need to do. Remember, the client has a unique leadership experience, therefore he has all of the answers to his problems.

When asking questions, don’t try to infuse your beliefs, judgments, or agendas. Instead, ask open-ended questions in an honest and curious way, so the client can answer by guiding himself through all the uncertainties. Make a client observe himself, and reflect on his leadership approach and experience.

Let’s start with self-discovery leadership questions, and then move to organization-based queries:

Self-Discovery Leadership Questions:

1. Where are you now and where do you want to be?

2. How did you get where you are now?

3. What were the biggest challenges you had to face?

4. What were the most difficult decisions you made?

5. What is the biggest career goal you have ever achieved?

6. What makes you proud of yourself?

7. What are your biggest strengths?

8. What are your biggest weaknesses?

9. How opinions of others impact you?

10. How do you handle stress in your life?

11. What is more important for you – to be liked, or respected? And why?

12. How do you define a good leader?

13. What motivates you to be a leader?

14. What was your biggest joy while leading someone?

15. What qualities are necessary for successful leadership?

16. What qualities do you think you have for successful leadership?

17. What is the most difficult part of being a leader?

18. What is your favorite leader, and why?

19. What characteristics do you think today’s leader lack?

20. What are the most detrimental characteristics of a leader?

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21. What was your most satisfying leadership role? Why?

22. What do you think are the advantages and disadvantages of being a leader?

23. What do you do in your personal time to become a better leader?

24. What are your favorite leadership books?

25. What other resources do you rely on for improving leadership? (podcasts, shows, magazines, etc)

26. What do you think you need to learn about leadership?

27. What skills do you use most often in your leadership role?

28. How do you motivate a team?

29. What example do you demonstrate when leading your team?

30. What kind of criticism or praise do you most get?

31. How does criticism or praise affect you?

32. How do you handle conflicts in your life?

33. How important is emotional intelligence in a leader’s position?

34. How do you view work-life balance?

35. What is the most impactful mentor of your life, and why?

36. What advice you could give to a new upcoming leader?

Organization-Based Leadership Questions:

37. How do you perform in a team versus on your own?

38. What does your team think about you?

39. What are the biggest misconceptions your team has about you? Why?

40. What is working in communication with your team and what is not?

41. What special talents does each team member contribute?

42. What would you say your leadership style is?

43. How do you delegate tasks?

44. How do you give feedback to your team?

45. How do you respond to feedback?

46. How would you inspire someone who underperforms?

47. How do you persuade people to agree with your ideas?

48. What is the difference between the leader and the manager?

49. What was the biggest change you ever made to an organization?

50. How do you evaluate your work performance?

51. How do you contribute to a positive work environment?

52. How you should respond to ideas and suggestions from a team as a leader?

53. Describe the best leader you have ever worked with. Why do you consider that person to be the best?

54. What do you take into account before you promote someone?

55. What qualities should you prioritize when recruiting a new team member?

56. How do you handle disagreements between your team members?

57. How do you handle interactions with someone that is difficult to work with?

58. What situations do you most avoid, and why?

59. Should there be a competition inside the team, and why?

60. How do you foster creative thinking within your company?

61. How do you prioritize tasks?

62. How do you react to tasks you have never undertaken before?

63. How do you introduce good or bad news to the team?

64. How do you set a balance between thinking forward and being present for your team?

65. How often do you think team meetings should be held?

66. How often an organization should assess its strengths and weaknesses?

67. How often should an organization analyze its competition?

68. What are the biggest challenges your organization is facing?

69. How can you improve your company’s product?

70. What are your organization’s vision and values?

71. How do you convey the company’s core values to the team?

72. How would you motivate people in your company to share the core values?

73. What was the most difficult decision you’ve ever made at work? What did you take away from it?

74. When was the last time you were scared to make decisions? How did you overcome fear?

Related: 9 Best Books For Leadership Coaches


The leadership role is not an easy one, and often things get out of control when the pressure builds up. These powerful coaching questions will help leaders analyze and understand themselves more, so they can become better at making decisions, handling responsibilities, and most importantly – inspiring others.

Feel free to ask these questions when coaching clients or employees in your organization. These questions do not have to follow a specific order, and you can figure out and add your own open-ended questions on the spot. Remember, coaching is all about being present and curious about what the client has to say.