John Bennett/ January 3, 2022/ Development, Executive Coaching, Leadership

Skills-Focused Coaching Questions

In Coaching for Change, Mary Wayne Bush and I define coaching skills that are used in the change-coaching process. Below are some questions that support five specific skills that are used in the change-coaching process. While questions are used in all six steps of the coaching for change process, these five often present the most challenges for executive coaches. Powerful questions in the context of executive coaching share some common characteristics:

  • They are related to the client’s situations and support their goals for the coaching conversation
  • They build on what the client says and does
  • They are brief (15 words or less is a good rule of thumb) and direct
  • They are asked in language that the client understands
  • They do not require much contextualization or explanation
  • They minimize defensiveness and usually do not begin with “why”

Following are some examples of questions that should be used throughout the change-coaching process.

Listening for Understanding

Listening for understanding is more than making simple sense of what the client says. It involves detecting what is not spoken and making sense of it by connecting data observed and gathered from various sources. It involves seeking deeper understanding for the client, and for the coach.

  1. What are you trying to say?
  2. Is ___ what you are saying?
  3. Do you think I understand you?
  4. What happened?
  5. Tell me more.
  6. I hear you say X, yet I see you doing Y. What does this mean?
  7. What else?
  8. What are you thinking?
  9. How do you feel?
  10. What is an example?
  11. Is this what you mean?
  12. Help me understand____
  13. What does that mean to you?
  14. What I hear you saying is ….
  15. Are you saying…?
  16. I imagine that made you feel ____.

Providing Feedback

While feedback is usually delivered in the form of statements, questions can also be used to help the client gain awareness and test possible actions.

  1. How can you be more open to feedback?
  2. What feedback have you received?
  3. How do you respond to feedback?
  4. What feedback are you willing to consider?
  5. What is your reaction to the feedback you received?


Reframing involves encouraging, guiding, and supporting coaching clients to discover different or multiple perspectives. It is particularly useful when a client is trying to make sense of a circumstance or trying to develop strategies for action. Reframing may be used at any point in the coaching process; however, it will most likely be used in the ‘Information Gathering’ and ‘Action Planning’ steps. Reframing supports challenging assumptions and beliefs, discovering new perspectives, and envisioning a new future. It helps the client develop and understanding multiple perspectives, learn new perspectives, develop new insights, get “unstuck,” and shift from tactical to strategic thinking.

  1. Are you following the compass or the calendar?
  2. What are you afraid of?
  3. What would that look like?
  4. Do you see people or problems?
  5. Are you the same in public as you are in private?
  6. What is your relationship with conflict?
  7. What is stopping you?
  8. Which do you believe first—the best or the worst?
  9. How could you have approached those circumstances differently?
  10. If you were in a helicopter hovering above your life, what would you see yourself doing?
  11. What would it look like if you reached your goal?
  12. What would the relationship look like if it were healthier?
  13. What is stopping you?
  14. Is your recent behavior helping you reach your goals?
  15. If you succeed, what would that look like?
  16. When you look back __ (days/months/years) what change will you wish that you’d made?
  17. What other perspective can you consider?
  18. What other angles can you think of?
  19. If you look back ____ (months/years) from now, what would you like to stay you accomplished?
  20. What assumptions can you let go of?
  21. Let’s assume you will be successful. How does that shift your perspective and ideas about what to do next?
  22. What has worked for you in the past?
  23. What could happen if you ___?
  24. What have you seen or experienced others doing in similar situations?
  25. What’s the best/worst thing that could happen?
  26. In what ways can you see this as an opportunity versus a problem?
  27. What makes investing time, money and other resources in this make sense for (you, the business, the community, the customer, etc.)?
  28. How might this look if you stepped into other shoes, or looked at it from a different perspective?
  29. What would the younger version of you tell you right now?
  30. What might an older version of you tell you right now?
  31. Imagine the future, what do you see?
  32. If you were the (owner, employee, manager, stockholder, etc.), how might you interpret the situation?
  33. If you were the (owner, employee, manager, stockholder, etc.), what possibilities can you imagine?
  34. What patterns do you see?
  35. What are you not aware of that if you were aware might make a difference?
  36. What are you accepting as fact that might not be true?
  37. Who could you talk with that has a different perspective?
  38. What if ____?
  39. What would you attempt to do if you knew that you could not fail?
  40. What if you could not fail?
  41. If you had a magic wand and could make any change, what change would you use it to make?
  42. If you woke up tomorrow and the issue was resolve, what would that look like?
  43. What would you like to be true?
  44. What if the opposite it true?
  45. If none of the current options were available, what would you do?
  46. What would an outsider do?
  47. What might I notice about X if I were seeing it for the first time?
  48. If you were to start over, what would you do first?
  49. What are you willing to abandon?
  50. What would happen if you shortened your timeline?
  51. What would happen if you extended your timeline?
  52. What would you do if half of the resources you have were taken away?
  53. What would you do if you got twice as many resources as you currently have?
  54. What would your great-grandchildren think of the decision you are making?

Providing Insight

Coaching is typically non-directive; however, it involves challenging the client to gain clarity, discover blind spots, gain understanding of meaning, and test assumptions. Providing insight may involve drawing on the coach’s knowledge and experience to help the client discover for themselves solutions, insights, and resources. Insights should be offered in a non-judgmental and non-directive manner.

  1. How is that working for you?
  2. What is stopping you?
  3. What does your response to feedback communicate to others?
  4. What keeps you from pausing?
  5. How do you talk to yourself?
  6. From whom could you seek that information?
  7. What do you avoid in leadership?
  8. What do you avoid in conflict?
  9. What do you avoid in relationships?
  10. When are you at your best?
  11. How did you reach that conclusion?
  12. What do you fear most?

Building Support

One goal of coaching is to support clients in their independence from the coach and to foster independence and interdependence with a network of support. As the client is exploring possible actions, developing action plans, or establishing partners for accountability, it may be useful to help them identify individuals or groups with whom they can access information, role models, resources, and feedback.

  1. Who can support you?
  2. What support do you need?
  3. What will you do to get their support?
  4. What is important for you in an accountability partner?
  5. Who can be your accountability partner?
  6. Who else needs to be involved?
  7. Who do you know that can help you?
  1. What resources will you need to access?
  2. Who have you relied on when you’ve faced similar issues/opportunities?
  3. What feedback do you need? From whom?
  4. Who are your trusted advisors and how can they support you?

What other questions would you add to (or, maybe even delete from) these? I’m interested in your thoughts and ideas, so please leave your comments, feedback, and suggestions below.

Photo by airfocus on Unsplash


References and Additional Resources

Bennett, J. L., & Bush, M. W. (2014). Coaching for change. Routledge.

Berger, W. (2014). A more beautiful question: The power of inquiry to spark breakthrough ideas. Bloomsbury.      

Berger, W. (2018). The book of beautiful questions. Bloomsbury Publishing.    

Brookfield, S. D., & Preskill, S. (2016). The discussion book: 50 great ways to get people talking. Jossey-Bass.         

Fadem, T. J. (2009). The art of asking: Ask better questions, get better answers. Peason Education.   

Morgan, N., & Saxton, J. (2006). Asking better questions (2nd ed.). Pembroke Publishers.      

Raker, J. (2021). Now that’s a great question. Walsh, J. A., & Sattes, B. D. (2005). Quality questioning: Research-based practice to engage every learner. Corwin Press.


© 2022, John L. Bennett. All Rights Reserved.

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