The Quality of Your Questions

The best mentor-mentee relationships thrive on curiosity and powerful questions. Mentors should resist the urge to “fix” problems and avoid prescribing specific actions. Mentees should focus less on being who they think their mentor wants and more on approaching interactions with a willingness to learn, grow, and discover how to think.

I am always seeking great questions to facilitate these interactions. Recently, I discovered three excellent questions while listening to the audiobook Clear Thinking* by Shane Parrish. Parrish suggests that when seeking advice, your goal should be to understand how the other person thinks, not just what they think. Although his book is not specifically about mentoring, the questions he proposes can be highly beneficial for both mentees and mentors.

Questions Mentees can ask their Mentors
Mentees might ask….

1. What variables would you consider if you were in my shoes?
How do these variables relate to one another?

2. What do you know about this problem that I don’t?
What can you see based on your experience that someone without it cannot?
What do you know that most people don’t?

3. What would your process be for making this decision if you were in my shoes?

Questions Mentors can ask their Mentees
These questions are also valuable for mentors. Instead of offering solutions or suggestions, mentors can prompt their mentees to reflect by asking:

1. What variables in this decision are important to you?
Who else or what else does this decision impact?

2. What are you most worried about in making this decision?
What possibility excites you the most?

3. What have you tried so far?
What do you think is the best process for this decision?

These questions encourage reflection and empower mentees to solve both the current problem they are facing and future problems. They also enable mentees to develop authentic solutions that fit their unique needs, values, and learning styles.

What questions have you used to encourage clear thinking in your mentoring relationships?

*Clear Thinking by Shane Parrish: (Farnam Street, 2023, ISBN: 0593086112)

The quality of your questions
33 Questions Every Mentor Should Ask

33 Questions Every Mentor Should Ask

One of the biggest parts of mentoring? Asking questions! But when should you ask questions? And when the time is right, what should you ask? Here’s a handy list of questions you should be asking your mentee over the course of your mentoring relationship:

For starting the mentoring relationship:

  1. How do we make this process work for you?
  2. What are your expectations?
  3. What would you recommend we do to make this work?
  4. What are you willing to commit to?

For goal setting:

  1. What is the most important thing you want to achieve?
  2. What can I do to help you with your leadership development?
  3. What is your strongest attribute?
  4. Where do you see your challenges?
  5. What would help raise your confidence level?

For pushing and challenging your mentee:

  1. Is this goal worthy of our time and effort together?
  2. What might be a challenging project for you to undertake?
  3. What would it be like to step out of your comfort zone?
  4. How is this goal going to contribute to your development?
  5. Did you think you are putting in sufficient effort to accomplish results?
  6. Why do you think there is only one solution? What else might you try?
  7. If you were grading your results, what grade would you give yourself?

For goal achievement:

  1. Did you get the results you hoped for?
  2. How would you approach this situation?
  3. Where else can you apply that?
  4. What is your team looking for from you?
  5. Is your supervisor seeing a difference?
  6. How else might you tackle that?

For checking in and feedback:

  1. What value has this provided for you thus far?
  2. What can we do differently to improve this relationship?
  3. Are we on the right path?
  4. What feedback have you received?
  5. How do you know you are making an impact?
  6. How can we make this work for both of us?
  7. How do you think you are doing?
  8. Are you satisfied with your results?
  9. Are you putting in the effort you feel you should?
  10. You’re quiet … what are you thinking?
  11. Whose feedback would be a benefit to you?

Ready to get started? Let us know how these questions help improve your mentoring relationships.

(Photo via Flickr CC: Colin_K)