25 Questions to Ask a Mentor

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A few years ago, around the time when I was launching this blog, I wrote an article called 4 Types of Questions to Ask A Mentor. To this day, it is the most-read article on Be Leaderly, and its popularity keeps growing.

In the article, I share a simple model for making the most out of every conversation with your mentor. To begin, come prepared with four questions. 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 then ask the participants to compile their own questions to ask a mentor. Here are some good ones they’ve come up with recently:

Stories

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?

Situations

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

9. I’m considering a career transition. What do you see as the pros and cons?

10. Who are the people I need to align with in this organization to achieve success?

11. What advice can you offer on how to progress in my career?

12. How do you successfully stay connected to key influencers who do not work in same office or geographical area?

13. When trying to gain buy-in to implement a new program, what tactics have worked for you?

Self-awareness

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

14. Where do you see my strengths and what should I focus on to improve?

15. What do you see as some of my blind spots?

16. How do you think others perceive me?

17. How I am viewed by leadership?

18. Do I come across as poised and calm?

19. How am I viewed (i.e., what’s my personal brand) in our organization?

20. Did everyone understand what I presented at the last meeting?

21. How could I have communicated my idea more clearly?

Skill-building

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

22. How do you approach risk-taking?

23. What new skills do I need to move ahead?

24. How can I become a more assertive negotiator?

25. How can I become better at managing people who do not report to me?

Which of these questions 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.

Recommended further reading: Four Types of Questions To Ask Your Mentor.

Jo Miller

A leading authority on women’s leadership, Jo Miller is a sought-after, dynamic, and engaging speaker, delivering more than 70 speaking presentations annually to audiences of up to 1,200 women. Her expertise lies in helping women lead, climb, and thrive in their corporate careers. Jo has traveled widely in Europe, North America, Asia Pacific, and the Middle East to deliver keynotes and teach workshops for women’s leadership conferences, women’s professional associations, and Fortune 1000 corporate women’s initiatives. Jo is founding editor of BeLeaderly.com. Learn more about her speaking engagements at www.JoMiller.net and follow @Jo_Miller on Twitter.

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