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Mentoring questions are designed to open up the possibilities, increase the options, reach deeper levels, stimulate creativity, and enhance thoughtfulness or reflection. Powerful questions can be challenging, but not necessarily adversarial. Powerful questions can be seeking factual or objective information or they can be seeking emotional and spiritual connections.

Powerful questions are almost always open-ended. Such questions cannot be answered typically by a one-word answer. The questions below were developed by Rey Carr (2004) as part of an exercise to create one hundred questions that could not be answered with yes or no. We encourage you to develop your own list of great questions that work well for you or add to this one as you move through your mentoring relationship. The following are some questions that might help you along the way.

  • What do you hope to accomplish through a mentoring relationship? How do you think your expertise and experience will affect this mentoring relationship?
  • What characteristics are you seeking in a mentor?
  • What do you need to know to ensure that this mentoring relationship will be beneficial to you?
  • What do you know about or have heard about the boundaries or role limits to this mentoring relationship?
  • What should we do in case we are not compatible?
  • How might we come to closure or terminate our relationship?
  • What are your goals (at work)?
  • To what degree are these goals capable of being measured?
  • What concrete things will you be able to do as a result of achieving these goals?
  • What other resources are needed to help you achieve your goals?
  • What kind of time line needs to be established to help with your goals?
  • Why are these goals important to you?
  • What do you hope to achieve within the next 5-10 years of your life?
  • When you think about yourself 5-10 years ago and compare yourself with who you are today, how would you describe the differences and similarities?
  • What important goal in your life never seems to get the attention it needs?
  • What is holding you back from achieving your life goals? What is the most difficult goal for you to accomplish at work?
  • When you think about yourself ten years ago and compare yourself with who you are today, how would you describe the differences and similarities?
  • How does your vision match the vision or mission of your organization?
  • What would you say are the limits beyond which you will not go?
  • When you are trying to learn something new, how do you typically go about it and how does that work for you?
  • To what degree do you believe you are living up to your potential?
  • What would you describe as your greatest accomplishment?
  • If you wanted to become more creative or innovative in your work, what would you to do accomplish this?
  • What would you attempt to do if you knew you could not fail?
  • What is one thing you could stop doing, or start doing, or do differently, starting today that would most improve the quality of your life? What decisions have you made that when looking back, you would like to make differently?
  • In what ways are your learning needs being met? Not met?
  • What has been your greatest success in your progress so far?
  • What have you learned that might contribute to your own development as a mentor?
  • What have you learned about being a partner in a mentoring relationship?

Adapted with permission from Rey Carr