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10 powerful questions for facilitating coaching conversations

Jan 14, 2023
By: Tom Cox

In most organizations, talent development investments are restricted to the executive level, while first- and second-level leaders are largely left underserved. For these future leaders, the essential practice of coaching — helping the individual clarify and move toward a specified goal, higher level of job performance, improved state of being or other positive outcome — can increase employee satisfaction, improve communication and reinforce other forms of learning.

A coaching process that employs specific, progressive steps can help future leaders reach their full potential. Throughout the process, coaches should work with coachees to increase self-awareness, define and commit to target objectives, construct plans, develop potential options and be personally accountable for making the necessary changes required to achieve the coaching objectives.

These simple but powerful coaching questions enable you to facilitate dialogue, uncover issues and build a rapport with a coachee.

The following list provides sample questions you might pose at each stage of the coaching process (enroll, envision, establish, execute and evaluate).


  • What are you looking forward to with this coaching relationship?
  • What barriers to success do you anticipate? How have you overcome barriers in the past?


  • If you were able to dramatically improve in one area of your current role, what would it be?

    What would be different as a result?

  • What are some ways you would describe the benefits of that change?


  • What are the steps that you’ll need to take to make a change happen?
  • How can you make that you have a measurable outcome?


  • What were you able to accomplish since our last coaching session?
  • What happened that prevented you from completing the action as expected?


  • What’s working and what’s not?
  • What are some things you might do to change the situation (in no particular order)?

How Wipfli can help

Wipfli’s leadership development programs help leaders at every level cultivate a leadership mindset that empowers others to thrive. Learn more about how we help clients with people, process and strategy on our organizational performance consulting web page or learn more in these articles:


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