John Bennett/ June 10, 2021/ Development, Executive Coaching, Leadership/ 0 comments

“A beautiful question is an ambitious yet actionable question that can begin to shift the way we perceive or think about something—and that might serve as a catalyst to bring about change.”

(Berger, 2014, p.8)

Questions Are Powerful

In every aspect of our lives, questions are powerful. Whether as a parent, friend, colleague, manager, leader, or professional coach questions serve many purposes, including:

  1. Opening up thinking
  2. Directed and focused thinking
  3. Prompting understanding
  4. Clarifying _____
  5. Encouraging creative thinking
  6. Demonstrating interest and curiousity
  7. Fostering divergent and convergent thoughts
  8. Calling to action
  9. Helping us understand and empathizing with others
  10. Discerning choices and making decisions

As human beings, we tend to delete most of what we see, categorize the rest, and then file it away in long-term memory using categories. When provided new or different data, we quickly make judgements and develop assumptions, and tend to dismiss what doesn’t fit with what we already know, believe or assume. This is the opposite of having a “beginner’s mind”. Assumptions and biases may be embedded in the questions we ask. Our mental models help us to both process data and dismiss data. And, remaining curious is critical to gaining understanding, developing possibilities, making evidence-based decisions, and taking action. 

Asking questions requires trust and vulnerability. Too often, leaders are expected (by themselves or others) to have answers. Saying “I don’t know”, or “I don’t understand” may be perceived as a sign of weakness. Yet, being trusted and willing to be vulnerable opens the possibilities for curiosity, exploration, relatedness, and creativity. 

Naguib Mahfouz, 1988 Nobel Prize for Literature, said, “You can tell whether a man is clever by his answers. You can tell whether a man is wise by his questions.” Be wise! And, as Bertrand Russell said, “In all affairs it’s a healthy thing now and then to hang a question mark on the things you have long taken for granted”. A good coach or manager doesn’t tell you what to do; they facilitate a discovery process to help you figure it out for yourself. The coach helps their client to get from where they are to where they want to go. This means the focus is on the client’s priorities, not the coaches. 

We need to formulate questions that invite honesty, dignity and revelation. There are many forms and purposes of questions. Below are some examples, along with a brief definition and example for each:

  • Application: A question that focuses on how an idea, skill, opinion, etc. can be used in service of the desired outcome. Example: “How will you use this?”
  • Close-ended: A question with a specific answer. These questions are particularly useful in gaining commitment, clarifying points, ending a step in the coaching process before moving to the next step. Example: “Which of those three topics would you like to focus on first?”
  • Commitment: A question that seeks commitment for a decision or course of action. Example: “What will you do by Tuesday?”
  • Contextual: A question to understand the background of what is happening or being discussed. Example: “What was happening when you made that decision?”
  • Convergent: A question that focuses on reducing the focus of the conversation. Example: “Which of those options would you like to pursue?”
  • Divergent: A question intended to shift away from a particular line of thought or feeling to consider another seemingly different perspective. It is a recombination of existing elements or ideas and combining them to create something new and original. Example: “What is possible if you look at X and Y, then combine them into something different?”
  • Expansion: A question to expand thinking and consideration. Example: “What other possible actions can you identify?”
  • Open-ended: A question with no specific answer. Highly effective leaders and coaches use a lot of these types of questions. Example: “What are some options you might consider?”
  • Reflective: A question that focuses on what is happening, what has happened or will happen in order to make sense. Example: “What does this mean for you?”
  • Reframing: A question to prompt a shift of perspectives. Example: “What would you do if resources were unlimited?”
  • Why: A question to understand meaning, purpose or value. Be careful with “Why” questions. They can prompt defensiveness or philosophical answers. Example: “Why did you take that particular approach?”

When asking powerful questions, it is essential that you allow sufficient time for the answers. This may require seconds, minutes, days, weeks or even longer. If your question is worth asking, then it is worth waiting for an answer. “By ‘living with’ a question, thinking about it and then stepping away from it, allowing it to marinate, you give your [or the other person’s] brain a chance to come up with the kinds of fresh insights and ‘What If’ possibilities that can lead to breakthroughs.” (Berger, 2014, p.109.) 

When coaching (as a manager or professional) here are a few things to keep in mind:

  1. Take time to develop your question after the other person stops speaking.
  2. Questions should be based on what the other person said and you observed.
  3. Use questions to facilitate the conversation through the steps in the change coaching model.
  4. Be cautious of your own assumptions, values, and mental models and their impacts on your curiosity.
  5. Avoid too much contextualization. If you are in synch with the person you are asking, the questions shouldn’t need to be contextualized. Just ask it. 
  6. Keep your questions as brief as possible. 15 words or less is a guide.
  7. Wait for an answer. Seven seconds may seem like a long time to wait; however, a thought-provoking question requires time to process.
  8. Experiment with questions; you don’t have to hit a homerun each time you ask a question. Some questions may not be a powerful as you wished. 
  9. Be prepared for the answer to your question to take a different direction. In this case, your question had an impact, just not the one you imagined. 

6-Step Coaching Conversation Model

In our book, Coaching for Change, Mary Wayne Bush and I describe a six-step coaching conversation model that can be used in formal as well as informal coaching conversations. We believe that all coaching is about change. Coaches, whether a professional or a manager or peer, can apply this dynamic framework.

The steps flow in a sequence; however, due to the discovery nature of coaching, it may be necessary to move backward in order to move forward. In a coaching conversation, for example, as the client identifies and explores possible action, additional information may be needed taking the conversation back to the “Information/Gathering” step. Or, while in the “Action Planning” step, it may be necessary to return to the “Possible Actions” step to identify additional possible actions before narrowing on the action plans that will support the client’s agenda or goals for the session.

The following examples of questions are arranged to correspond with each of the six steps in the coaching framework. They are not intended to be prescriptive, a menu to follow, or an exhaustive list of possibilities. They should be used to help you develop your own questions. It is important to note that agility is essential. While the coach is facilitating a conversation using the steps, it is critically important that you move through the coaching process and adjust to the flow of the conversation. 

Context & Situation

“The focus of this step is to establish or reestablish the coach-client relationship, obtain and update from the client recent occurrences in the context of the coaching goals, assess progress on previous action-items, and acknowledge success and breakthroughs that may have occurred.” (Bennett & Bush, 2014, p.69)

  1. How are you today?
  2. What has happened since we last met?
  3. What’s the most significant thing that happened for you today?
  4. What have you been able to accomplish related to your action plans from the last time we met?
  5. What progress have you made since we spoke?
  6. What accomplishments (or setbacks) have you experienced since our last coaching session?
  7. What’s your story?
  8. What are you concerned about?
  9. What are you excited about?
  10. What is giving you energy?

Goal Setting/Desired Outcomes

“The focus of this step is for the coach to gain an understanding of the client’s current reality, understand and agree on the goals for the coaching session, align those goals with the overall goals of the coaching engagement, and, if necessary, adjust the goals of the engagement.” (Bennett & Bush, 2014, p.62)

  1. Given your overall goals for the work we are doing together, what would you like to focus on right now?
  2. What are we going to focus on in this coaching session today?
  3. Of the __ things you mentioned that we might focus on today, which do you want to start with?
  4. What is most important for you to accomplish in our coaching work today?
  5. If this coaching session is a huge success for you, what will you have accomplished?
  6. One a scale of 1-10 (10 being most important), how would you rate this goal?
  7. If we were to “hit a home run” in this coaching session, what would that look like?
  8. For this coaching session, what will success look like for you?
  9. What are your goals?
  10. What do you want?
  11. What are the gaps between where you are today and where you want to be in ___ months/years?
  12. How would you like things to be different?
  13. What makes this focus important for you?
  14. What challenges are you facing that you want my help with?
  15. What opportunities are you facing that you want my help with?
  16. What do you not have time to work on that you would like to be working on?

Information Gathering

“The focus of this step is gathering information that serves the client’s agenda, gaining a mutual understanding of that information, and identifying needs for additional data — which may become an action item for later consideration.” (Bennett & Bush, 2014, p.69)

  1. How can you see this with fresh eyes?
  2. What does the feedback you have received tell you about your strengths (growth opportunities)?
  3. What expectations does your manager have of you?
  4. What data do you have to support your perceptions (or understanding)?
  5. What are your career goals?
  6. How important is that to you?
  7. How is your behavior impacting others?
  8. What would others tell me about you?
  9. What are your key development areas?
  10. What does that feedback mean to you?
  11. In what, if any, ways are you rushing to judgement?
  12. What are you missing?
  13. What matters most?
  14. What are you inclined to believe about ___?
  15. What did you once believe that is no longer true?
  16. What prompts you to believe what you believe?
  17. What would you like to be true?
  18. What if the opposite is true?
  19. How strong is the evidence you have?
  20. What are you being told by others about ____?
    Does what you are hearing/seeing fit together logically?
  21. What is the opposing view?
  22. Which of the conflicting views has more evidence behind it?
  23. What are you afraid of and why?
  24. What activity or theme do you keep coming back to?
  25. What resistance are you facing?
  26. What is current working well that you want to keep doing?
  27. What is your impression of ___?
  28. How does that fit into your plans?
  29. What additional information do you need to explore before we move on to thinking of possible actions?
  30. What have you already tried? How did it work? What did you learn from that experience?
  31. What are you curious about?
  32. What is an example of ____?
  33. What assumptions are you making?
  34. What’s the best outcome you can imagine?
  35. What contributed to the situation?
  36. What’s working right now?
  37. What does _____ exist?
  38. How does this ____ present a problem, create a need, or present an opportunity for ____?
  39. What makes investing time, money and other resources in this make sense for (you, the business, the community, the customer, etc.)?
  40. How do you know that? 
  41. What evidence do you have to support that conclusion?
  42. What does it matter?
  43. If you were the (owner, employee, manager, stockholder, etc.), how might you interpret the situation?
  44. What patterns do you see?
  45. What are you not aware of that if you were aware might make a difference?
  46. What are you accepting as fact that might not be true?
  47. What is your responsibility?
  48. What is your authority?
  49. What are your interests?
  50. What might you be assuming?
  51. What are you missing?
  52. What matters most?
  53. What are you inclined believe in this situation?
  54. What prompts you to believe what you believe?
  55. What would you like to be true?
  56. What if the opposite it true?
  57. What are you defending? Why?
  58. What are you not being told?
  59. What are you afraid of?
  60. What about this is exciting for you?
  61. What might you notice if you were encounter this for the first time?
  62. What would (any admired leader or creative thinker) see in this?
  63. What feedback have you received?
  64. What might I notice about X if I were seeing it for the first time?
  65. What part(s) of this do you own?
  66. Why hasn’t this been addressed already?
  67. Have you ever dealt with an issue like this before? If so, what do you do?
  68. How are other people experiencing you?
  69. What have you tried?
  70. What’s motivating you?
  71. What’s demotivating you?
  72. What would your great-grandchildren think of the decision you are making?
  73. How is that working for you?

Possible Actions

“The focus of this step is to explore possibilities for action that will serve the client’s needs and desired goals for the coaching session. In this step, the client generates ideas for possible action, establishes criteria to evaluate those options, considers barriers to implementing them, and establishes priorities for action.” (Bennett & Bush, 2014, p.69)

  1. How might you improve the situation?
  2. What possible actions have you not explored?
  3. What have you seen others do that might work here?
  4. If none of the current options were available, what would you do?
  5. What is the counterintuitive choice?
  6. What would an outsider do?
  7. What ideas do you have for addressing this?
  8. How will you decide which step to take next?
  9. What has work for you in the past?
  10. If a friend/colleague had to make this decision, what advice would you give them?
  11. What would you try if you knew you could not fail?
  12. If you did fail, what would be the likely causes? What new possibilities does that prompt you to identify?
  13. Let’s assume you will be successful. How does that shift your perspective and ideas about what to do next?
  14. If you succeed, what would that look like?
  15. When you look back __ (days/months/years) what change will you wish that you’d made?
  16. What other perspective can you consider?
  17. What other options can you imagine?
  18. What assumptions are you holding that may be impacting your approach?
  19. What other possible actions can you think of?
  20. What have you seen others do in similar situation?
  21. What have you done in the past that work when you faced a similar challenge/opportunity?
  22. What needs to happen to move you forward?
  23. If there were something else you could do, what would it be?
  24. What will help you achieve your goals?
  25. What resources are available to support you in this quest?
  26. What will you do about that?
  27. What are the one or two things you can do to meet this challenge?
  28. Are there other possibilities you can think imagine?
  29. What have you seen or experienced others doing in similar situations?
  30. What is on the horizon for your (field, industry, market, etc.)?
  31. What could happen if you ____?
  32. What’s the best/worst thing that could happen?
  33. What “experiment” might you run?
  34. If you were the (owner, employee, manager, stockholder, etc.), what possibilities can you imagine?
  35. What if ____?
  36. Who could you talk with that has a different perspective?
  37. What did you love doing as a child that if you did now would give you joy?
  38. What would you attempt to do if you knew that you could not fail?
  39. What if you could not fail?
  40. What if you fail, how will you recover?
  41. What if you succeed?
  42. What’s worth doing, whether you fail or succeed?
  43. What do you want to do/say?
  44. What if you could say/do it in a way that has never been said/done before? How might you say/do that?
  45. If you had a magic wand and could make any change, what change would you use it to make?
  46. If you woke up tomorrow and the issue was resolve, what would that look like?
  47. If none of the current options were available, what would you do?
  48. What would an outsider do?
  49. If you succeed, what will that look like?
  50. What would a beginner do?
  51. If you were to start over, what would you do first?
  52. What are you willing to abandon?
  53. What would happen if you shortened your timeline?
  54. What would happen if you extended your timeline?
  55. What would you do if half of the resources you have were taken away?
  56. What would you do if you got twice as many resources as you currently have?
  57. Which of the options you’ve described interests you the most?
  58. What have you always wanted to try?

Action Planning

“The focus of this step is to develop action steps (what the client will do, by when, with what outcome, and with what support), ensure accountability and commitment for implementation, and determine resource and support needs as well as how those resources will be acquired.” (Bennett & Bush, 2014, p.69)

  1. What could be your first step?
  2. What is one small step you could take?
  3. What’s a giant step you could take?
  4. What action will you take? 
  5. What support do you need?
  6. What are you committed to do? By when?
  7. What support do you have that you will call on to accomplish you action plan?
  8. What challenges or barriers do you anticipate and how will you address them?
  9. What support will you access to accomplish your action plans?
  10. What support do you have in place to help you?
  11. What support do you need? What will you do it secure it?
  12. What resources will you need to access?
  13. When will you get that completed?
  14. What barriers can you foresee that will need to be addressed as you implement you action plan?
  15. Who will you speak with?
  16. What are the one or two things you can do to meet this challenge?
  17. Where will you find that?
  18. What support will you need from ____?
  19. What, if any, negative consequences are there for the course of action we discussed?
  20. Who can be your accountability partner?
  21. Who else needs to be involved?
  22. If a friend/colleague were in a similar situation, what action would you advise them to take?
  23. Will you still love this action plan next week?
  24. Who are your trusted advisors and how can they support you?
  25. How will you implement your plan?

Summary & Agreement

“The focus of this step is to review insights and commitments gained from this coaching session, identify possible agenda items for future coaching sessions, and reinforce that ownership of the coaching agenda and actions are held by the client.” (Bennett & Bush, 2014, p.69)

  1. What have you gained from this conversation?
  2. What are your key “take-aways” from our work today?
  3. Did you achieve your goals for this coaching session?
  4. What are your next steps?
  5. What are you committed to do?
  6. What will you do as a result of this coaching session?
  7. When we get back together what will you be able to share?
  8. What was most impactful for you in our work today?
  9. Did we meet your goal(s) for this coaching session?

Questions that Work Throughout the Coaching Conversation

Some questions may be well-suited for use in multiple steps in the six-step coaching for change process. These include:

  1. What else?
  2. What are you thinking?
  3. How do you feel?
  4. What is an example?
  5. Tell me more.

Coaching Skills

In Coaching for Change, Mary Wayne Bush and I define six coaching skills that are used in the change coaching process steps defined above. Below are some questions that support three specific skills. While questions are used in all six skills, these three often present the most challenges for coaches:

  1. Listening for Understanding
    1. Is this what you mean?
    2. Tell me more…
    3. Help me understand____
    4. How do you feel?
    5. What are you thinking?
    6. What does that mean to you?
    7. What else?
    8. What I hear you saying is ….
    9. Are you saying…?
    10. I imagine that made you feel ____.
  2. Reframing
    1. What other angles can you think of?
    2. If you look back ____ (months/years) from now, what would you like to stay you accomplished?
    3. What assumptions can you let go of?
    4. Let’s assume you will be successful. How does that shift your perspective and ideas about what to do next?
    5. What has worked for you in the past?
    6. What could happen if you ___?
    7. What have you seen or experienced others doing in similar situations?
    8. What’s the best/worst thing that could happen?
    9. In what ways can you see this as an opportunity versus a problem?
    10. What makes investing time, money and other resources in this make sense for (you, the business, the community, the customer, etc.)?
    11. How might this look if you stepped into other shoes, or looked at it from a different perspective?
    12. What would the younger version of you tell you right now?
    13. What might an older version of you tell you right now?
    14. Imagine the future, what do you see?
    15. If you were the (owner, employee, manager, stockholder, etc.), how might you interpret the situation?
    16. If you were the (owner, employee, manager, stockholder, etc.), what possibilities can you imagine?
    17. What patterns do you see?
    18. What are you not aware of that if you were aware might make a difference?
    19. What are you accepting as fact that might not be true?
    20. Who could you talk with that has a different perspective?
    21. What if ____?
    22. What would you attempt to do if you knew that you could not fail?
    23. What if you could not fail?
    24. If you had a magic wand and could make any change, what change would you use it to make?
    25. If you woke up tomorrow and the issue was resolve, what would that look like?
    26. What would you like to be true?
    27. What if the opposite it true?
    28. If none of the current options were available, what would you do?
    29. What would an outsider do?
    30. What might I notice about X if I were seeing it for the first time?
    31. If you were to start over, what would you do first?
    32. What are you willing to abandon?
    33. What would happen if you shortened your timeline?
    34. What would happen if you extended your timeline?
    35. What would you do if half of the resources you have were taken away?
    36. What would you do if you got twice as many resources as you currently have?
    37. What would your great-grandchildren think of the decision you are making?
  3. Building Support
    1. Who do you know that can help you?
    2. What help do you need?
    3. What resources will you need to access?
    4. Who have you relied on when you’ve face similar issues/opportunities?
    5. What feedback do you need? From whom?
    6. Who are your trusted advisors and how can they support you?

My Magic Question

Use it when you don’t know what to ask – “what should I ask you next?”

References and Resources

Here are a few references and resources that were used as well as others that can be useful as you continue developing yourself as a curious question asker who is trying to be helpful to others.

Adams, M. (2004). Change your questions, change your life: 7 powerful tools for life and work. Berrett-Koehler.    

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

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

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

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

Dweck, C. S. (2006). Mindset: The new psychology of success. Ballantine Books.           

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

Hieker, C., & Huffington, C. (2006). Reflexive questions in a coaching psychology context. International Coaching Psychology Review, 1(2), 46-55.             

Kaplan, R. S. (2011). What to ask the person in the mirror: Critical questions for becoming a more effective leader and reaching your potential. Harvard Business Review Press.     

Leeds, D. (1987). Smart questions: The essential strategy for successful managers. The Berkley Publishing Group.

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

Ruiz, D. M. (1997). The four agreements. Amber-Allen Publishing.         

Schwarz, R. (2013). Smart leaders smarter teams: How you and your team get unstuck to get results. Jossey-Bass.            

Studer, Q. (2005). 101 Answers to questions leaders ask. Fire Starter Publishing.

Tippett, K. (2017). Krista Tippett: On generous listening and asking better questions

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© 2021, John L. Bennett. All Rights Reserved.

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