25 Questions for Your Mentor

A simple model for getting the most of every mentoring conversation.

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Mentors are an amazing resource. To maximize the benefits of a mentoring relationship, it’s important to come prepared to every conversation. It’s a way to show appreciation for your mentor and their time and commitment to you. Ultimately, both of you should leave every conversation feeling like it was time well spent. All it takes is a few minutes of thoughtful preparation.

Here’s how it works: Before every meeting with your mentor, prepare one question from each of these categories: stories, situations, self-awareness, and skill building.

In my workshops and group coaching programs, I like to share those categories, and ask the participants to come up with a list of questions to ask their mentors. Here are some good ones they’ve come up with recently:


Ask your mentor to tell a story from his or her career. Some questions to consider:

  1. How did you land your current role?
  2. Think back to five years ago. Did you envision this is where you would be?
  3. Can you tell me about a time when you had a difficult boss? How did you handle it?
  4. How did you learn to embrace failure?
  5. What’s the most important leadership lesson you’ve learned and how is it valuable?
  6. Tell me about a recent setback and how you recovered?
  7. Was there ever a job position that you applied for and got, but you weren’t 100% qualified?
  8. How did you build the skill of always speaking so engagingly in front of others?


Identify a challenging situation and share it with the mentor. Ask your mentor to act as a sounding board. Some questions to consider:

  1. I’m considering a career transition. What do you see as the pros and cons?
  2. Who are the people I need to align with in this organization to achieve success?
  3. What advice can you offer on how to progress in my career?
  4. How do you successfully stay connected to key influencers who do not work in same office or geographical area?
  5. When trying to gain buy-in to implement a new program, what tactics have worked for you?


Ask a question that invites your mentor to contribute to your self-awareness. Some questions to consider:

  1. Where do you see my strengths and what should I focus on to improve?
  2. What do you see as some of my blind spots?
  3. How do you think others perceive me?
  4. How I am viewed by leadership?
  5. Do I come across as poised and calm?
  6. How am I viewed (i.e., what’s my personal brand) in our organization?
  7. Did everyone understand what I presented at the last meeting?
  8. How could I have communicated my idea more clearly?


Identify a skill you currently want to develop, and ask your mentor for advice or resources. Some questions to consider:

  1. How do you approach risk-taking?
  2. What new skills do I need to move ahead?
  3. How can I become a more assertive negotiator?
  4. How can I become better at managing people who do not report to me?

Which of these could you ask your mentor? Do you have any to add to this list?

By preparing thoughtfully for each mentoring session, you’ll avoid the awkwardness of feeling like you’re wasting your mentor’s time, and it guarantees that the mentoring relationship can continue to be gratifying for both of you for many years to come.

What are your favorite mentoring questions? Leave your reply in the comments.

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