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70+ Questions a Mentor Should Ask a Mentee

We have already shared with you the importance of why you should have a mentor. We have also already shared with you the qualities that make a good mentor and the specific skills they might have.

Rather than stressing the importance of mentors again, we want to focus now on what makes a good dynamic between a mentor and a mentee, and a lot of that comes from the type of questions that a mentor asks their mentee.

Asking good questions is the best way to get to know each other, no matter what type of relationship you are embarking on.

A successful mentoring relationship between a mentor and a mentee is no different.

The mentor should ask the right questions to get to know the mentee as a person but also to get to know what their goals and aspirations are for career development.

At the end of the day, a mentor is meant to guide and coach their mentee to help them reach their goals or discover new goals.

In order to best do this, a mentor should know their mentee very well, both on a professional level and a personal level.

This makes the types of questions that a mentor should ask their mentee even more important to foster new ideas and understanding. So what should you ask? Here is a great list of questions.

Photo by Desola Lanre-Ologun on Unsplash

70+ Questions a Mentor Should Ask a Mentee

The biggest challenge mentorship programs and new potential mentors can face are not knowing where to start when establishing a trusting relationship. A prospective mentor can ask these great questions, and share their own experience, to help their mentee with any stage of their career journey – from job interview to year-end-review to a career change and more.

These mentor questions are not just about professional development. While knowing their line of work is important, knowing who your mentee is beneficial too. You’ll come to more innovative ideas and get through the hard work together if you can meet each other on deeper level.

Questions About Their Career Journey

  • Have you had a mentor in the past? What was that experience like for you?
  • What inspired you to seek mentorship in the first place?
  • What was your first job?
  • What led you to your current career path?
  • What made you take your current role?
  • Did you plan to have this career path, or did it happen organically?
  • What is it that you really want to be and do?
  • What are you doing really well that is helping you get there?
  • What are you not doing well that is preventing you from getting there?
  • What next steps would you like to make in your career? Are there any target positions you want to achieve?
  • Are there any topics of urgent interest? Are any topics off-limits?
  • What recent successes do you feel you’ve had in your career? Why do you consider them as successes?
  • Have you had a recent situation at work that required you to manage conflict? How did you handle it?

Questions about them as a person

  • Where are you from originally?
  • What is your family like?
  • Who are the most important people in your life?
  • What are your core values?
  • Where did you learn your current values?
  • What was your educational experience like?
  • Do you have any role models you look up to or people you admire?
  • What do you love to do outside of work?
  • What inspires you?
  • If you could go back and change something that you did, what would it be and why?
  • What individuals have played a role in your personal growth?
  • Are there any ground rules you would like to set (i.e. confidentiality, openness, candor)?

Questions to get to know their goals

  • What interested you about having a mentor?
  • What are your expectations for this mentorship?
  • What are your short-term goals?
  • What are your long-term goals?
  • What is the motivation behind your goals? Why are they important to you?
  • How often do you check in with your goals and progress?
  • What areas of your life do you want to grow in?
  • What skills do you want to develop?
  • What can I do to make this a positive experience for you?
Photo by Prateek Katyal on Unsplash

Questions to figure out what motivates them

  • What are your core values? Where do you see these values in your life?
  • Who do you admire the most, and why?
  • When do you feel fulfilled with purpose?
  • What habits have you developed that help you be successful?
  • What habits or patterns have held you back from success?
  • In what areas of life have you grown the most? What inspired this growth?
  • What was the greatest challenge you faced? What did you learn from it?
  • What individuals/books/events left the most impact on you?

Questions to figure out their strengths and weaknesses

  • What do you consider to be your strengths?
  • In what areas do you think you need to improve?
  • How have you learned to emphasize your strengths in your work?
  • Does your current role help you leverage your strengths?
  • What parts of your job do your weaknesses hinder you?
  • How do you mitigate your weaknesses?
  • Which decisions are easiest for you to make, and which ones do you struggle with the most? Why?
  • What can you do to learn more about your strengths and weaknesses?
  • What are areas that you think still needs to be developed?

Questions to help them reflect and express gratitude

  • How often do you check-in with yourself about your thoughts, feelings, and actions?
  • What are you most grateful for?
  • What are you grateful for with this mentorship relationship?
  • Who is someone that you’re grateful for in your life? What have they given you?
  • What self-awareness habits do you employ?
  • What was a period in your life or career where you felt like you had the most growth?
  • How often do you check-in with yourself about your thoughts, feelings, and actions?
  • When have your emotions clouded your judgement? What did you learn from the experience?
  • How can you implement gratitude as a regular practice in your life?
  • What do you appreciate about the personal development journey?
  • How often do you ask for feedback to learn more about yourself?
  • How can you incorporate regular reflection into your routine?

Questions to help evaluate the relationship

  • Where do you think I can help you the most?
  • Are you following up on the action items from every meeting?
  • What should I do differently to help you achieve more out of this relationship?
  • Am I doing a good job following up on my action items?
  • Are we meeting with the correct frequency and for the proper amount of time?
  • What do you expect from me in this relationship?
  • What do you like most about our mentor-mentee relationship?
  • What do you like the least about our mentoring relationship?

Asking these questions are a great way to find common ground when establishing a new mentor relationship. With each mentoring session you’ll learn more important insights that you can expand upon at your next meeting. Specific questions that are still open-ended are so beneficial for the mentorship experience.

So the next time you are working on your mentee’s goals, it’s a good idea to ask these thought-provoking questions.

Which of these powerful questions will you ask first? Tell us in the comments below.

About the Author

Michelle Ioannou

Michelle graduated from Fordham University with a Bachelors of Arts '13 and a Master of Arts '14. She's currently working in corporate America with a side of freelance writing. She wants you to learn from her experiences and mistakes so your 20s can be your best decade. When she's not working, she's likely planning her escape to a tropical island.


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