100 Questions to Ask Your Mentor and Mentee

August 21, 2020

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Developing a mentor relationship is an invaluable strategy for personal and professional growth. No matter what your line of work is, mentorship can offer you advice, questions, and guidance. A mentor can help you learn more about the field, but they can also help you learn more about yourself. To do this, however, you must have the right questions to ask your mentor and mentee.

One of the most significant factors of success is self-awareness and emotional intelligence. Unfortunately, the majority of humans lack self-awareness. This lack of self-awareness prevents us from learning from our experiences and actions. (Wondering if you lack self-awareness? Read 6 Signs You Lack Self-Awareness or take my free Self-Awareness test.

This gap in perspective is where a mentor can be hugely beneficial. By asking your mentor questions, you can gain objective feedback. Your mentor can help direct you toward self-knowledge that’s difficult to reach on your own.

Mentors can also help this self-awareness development with the right questions to ask your mentee. Powerful questions will not only help the mentor relationships flourish. It can also help both mentor and mentee learn more about themselves.

Another key to these mentor questions is a commitment to vulnerability. It’s hard to be vulnerable, but the benefits far exceed the initial discomfort. If both mentor and mentee tackle these questions with courage and vulnerability, the impact will be astounding. Read How to Be Vulnerable for more inspiration.

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Mentor Questions and How They Work

These questions are divided into two main categories: questions for mentors and questions for mentees. While some of the questions repeat in both groups, the questions to ask your mentor are different in nature than the questions to ask your mentee.

As you can see, the questions are also organized into themed lists. While the order of these lists doesn’t matter, there are some themes – such as “getting to know each other” and “establishing expectations” – that should be addressed earlier in the relationship.

Everyone’s mentorship relationship looks different, and they all will vary in regard to formality, specificity, and time commitments. Fortunately, these questions can help any type of mentoring session go from average to extraordinary.

Happy conversations!

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Questions to Ask Your Mentor

Questions to Ask Your Mentor – Getting to Know Each Other

1. Where are you from originally?
2. What is your family like?
3. What made you get into this type of work?
4. What do you do for fun?
5. What are your core values?

Check out 160 Get to Know Me Questions if you want more questions to establish trust and connection.

Questions to Ask Your Mentor – Establishing Expectations

1. Have you been a mentor in the past? What was that experience like? 
2. What inspired you to be my mentor in the first place?
3. What expectations do you have for time and communication boundaries?
4. What do you envision for the length of time for this mentorship?
5. What can I do to make this a positive experience for you?

Questions to Ask Your Mentor – Biggest Lessons

1. What is one of the biggest challenges you’ve faced? What did you learn from it?
2. What is the biggest lesson you’ve learned in this work? In life?
3. What have been the defining factors in your personal development journey?
4. If you could go back in time and change a decision, what would it be and why?
5. How has your mindset and values changed over the years? What caused these changes?

Questions to Ask Your Mentor – About the Line of Work

1. What inspired you to enter into this line of work?
2. What surprised you about this line of work that you didn’t anticipate?
3. What attitude do you need to have to be successful in this line of work?
4. What are the skills and/or information in this line of work that you can only learn by doing?
5. What do you know now that you wish you knew when you started?

Questions to Ask Your Mentor – Career Growth

1. What aspirations do you have for your career? How have they changed over the years?
2. What have you done that’s helped advance your career?
3. How do you balance work and personal life? What boundaries do you set?
4. When you look at your future growth, what steps do you plan on taking?
5. What are the opportunities for growth in this line of work?

Questions to Ask Your Mentor – Communication

1. What have you learned about how to communicate effectively?
2. What are the biggest challenges to effective communication?
3. When has a personal miscommunication led to negative consequences? What happened?
4. What have you learned about effective communication in an organization? With a leader?
5. What language have you found to be the most effective when it comes to handling conflict?

Questions to Ask Your Mentor – Further Connections

1. What further education or training would be helpful for this line of work?
2. What is your biggest advice for networking in this field?
3. What is necessary to forge and maintain a strong relationship?
4. Are there any people you think I should reach out to?
5. What connections have you made in your life that helped you?

Questions to Ask Your Mentor – Feedback for Self-Awareness

1. What would you say is my biggest strength? Weakness?
2. What have you learned about me that surprised you?
3. What makes me unique compared to other people you’ve worked with?
4. What are some of the behaviors or attitudes that might hold me back?
5. What do you observe when I interact with other people? 

Questions to Ask Your Mentor – Reflection

1. How have you used reflection in your life? What advice do you have for implementing reflection as a regular practice?
2. What have you learned from this mentorship experience?
3. In what ways have you seen me grow the most?
4. What do you think I still need to work on?
5. What do you think has been the most defining moment(s) in this mentorship experience?

Questions to Ask Your Mentor – Gratitude and Appreciation

1. What are the things in your life that you’re most grateful for?
2. What are you grateful for with this mentorship relationship?
3. Who is someone that you’re grateful for in your life? What have they given you?
4. How has your attitude on gratitude evolved?
5. What do you appreciate in life now that you didn’t appreciate in the past?

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Questions to Ask Your Mentee

Questions to Ask Your Mentee – Getting to Know Each Other

1. What was your hometown like?
2. Who are the most important people in your life?
3. What do you do for fun?
4. What inspired you to pursue this work?
5. What was your educational experience like?

Check out 160 Get to Know Me Questions if you want more questions to establish trust and connection.

Questions to Ask Your Mentee – Establishing Expectations

1. Have you had a mentor in the past? What was that experience like for you?
2. What inspired you to seek mentorship in the first place?
3. What are you hoping to gain from this mentoring relationship?
4. What are your expectations for this mentorship?
5. What can I do to make this a positive experience for you?

Questions to Ask Your Mentee – Goal-Setting

1. What accomplishments are you most proud of? What helped you achieve these goals?
2. What are your five-year goals? Ten-year goals?
3. What is the motivation behind your goals? Why are they important to you?
4. What steps do you need to take to accomplish your goals? 
5. How often do you check in with your goals and progress?

Questions to Ask Your Mentee – Personal Growth

1. In what areas of life have you grown the most? What inspired this growth?
2. What was the greatest challenge you faced? What did you learn from it?
3. What individuals have played a role in your personal growth?
4. What have been the most important elements in your personal development?
5. If you could go back and change something that you did, what would it be and why?

Questions to Ask Your Mentee – Motivation and Habits

1. What are your core values? Where do you see these values in your life?
2. Who do you admire the most, and why?
3. When do you feel fulfilled with purpose?
4. What habits have you developed that help you be successful?
5. What habits or patterns have held you back from success?

Questions to Ask Your Mentee – Strengths and Weaknesses

1. What are some of your strengths?
2. How have you learned to emphasize your strengths in your work?
3. What are some of your weaknesses?
4. How have you learned to mitigate the effects of your weaknesses?
5. What can you do to learn more about your strengths and weaknesses?

Questions to Ask Your Mentee – Developing Self-Awareness

1. How often do you check-in with yourself about your thoughts, feelings, and actions?
2. When do your biases and patterns affect your decision-making?
3. When have your emotions clouded your judgment? What did you learn from the experience?
4. What self-awareness habits do you employ?
5. How often do you ask for feedback to learn more about yourself?

Questions to Ask Your Mentee – Feedback for Self-Awareness

1. What would you say is my biggest strength? Weakness?
2. What have you learned about me that surprised you?
3. What makes me unique compared to other people you’ve worked with?
4. What are the biggest lessons you’ve learned from my words? My actions?
5. What do you observe when I interact with other people? 

Questions to Ask Your Mentee – Reflection

1. How can you incorporate regular reflection into your routine?
2. What have you learned from this mentorship experience?
3. What do you think has been the most defining moment(s) in this mentorship experience?
4. What changes will you make based on this mentorship experience?
5. What beliefs or goals did this mentorship help solidify for you?

Questions to Ask Your Mentor – Gratitude and Appreciation

1. What are the things in your life that you’re most grateful for?
2. What are you grateful for with this mentorship relationship?
3. Who is someone that you’re grateful for in your life? What have they given you?
4. How can you implement gratitude as a regular practice in your life?
5. What do you appreciate about the personal development journey?

Interested in more questions? Subscribe below to receive 10 bizarre questions that will unlock your self-awareness. You can also choose a question from the list and comment below.

Want to test your self-awareness? Take my free, quick self-awareness quiz to see where you might be lacking self-awareness in your life. Or give your mentee (or yourself) the gift of self-awareness with my complete course: The Art of Being Self-Aware. The course is based around the research and work of Dr. Tasha Eurich, leading expert in the field of organizational psychology and self-awareness.

Better yet, complete the course together – you’ll be absolutely amazed at the results.

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