25 Questions to Ask a Mentor

Like this on Facebook

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.

Recommended

Ask Jo: Interviewing for a new job with a current employer.

Question: Jo, can I pick your brain about a quick question that I have? I am interviewing for a new role at the place where I ...

Leaderly Quote: Delivering a lofty goal

Want to make 2016 a breakthrough year for your career? "Have the confidence, courage and agility to go after lofty goals," says Colleen Flaherty of Kraft ...

Emerging Leader Spotlight: Risa Hunter

Every month we ask an emerging leader we admire to share what she is doing to take the lead in her career. We invite her ...

  • Tom Roberts

    I recently retired but retain a mentor relationship with one of my former employees. We spend about 1 hour a month talking on the phone and exchange e-mails regularly. Your list is very good and many of the ideas we have used without even realizing it!

    Thanks for your insight.

    • http://www.beleaderly.com BeLeaderly

      Thanks for mentoring and giving back, Tom.

Ready to lead?

We'll show you how!
Get email updates from Be Leaderly.

Our mission is to provide the career strategies that help you lead, climb and thrive as a rising woman of influence.

Four Types of Questions To Ask Your Mentor

Have conversations with your mentor gotten a bit repetitive lately? Perhaps you approached ...

5 Ways to be a Leader, Not a Manager

Have you ever wondered about the difference between a manager and a leader? ...

How to Shut Down a Colleague Who Takes Credit for Your Work

Has this ever happened to you? You’re in a meeting and the unthinkable ...

15 Songs for Your Leadership Playlist

It was one of those conference moments I’ll never forget: Carly Fiorina had ...

10 Killer Leadership Skills: The Great Differentiators?

Last week at Hallmark I hosted a couple gentlemen from a partner company. ...

Influencing Without Authority—Using Your Six Sources of Influence

I am in the difficult situation of being unofficial project lead, responsible for ...

11 Leadership Lessons Learned

Here are 11 lessons I’ve learned about leadership—mostly from much-admired colleagues, and just ...

6 Critical Missteps That Hurt Your Career Advancement

Let’s face it: it isn’t easy to break out and establish yourself as ...

Nine Qualities of Female Leaders Who Get Beyond the Glass Ceiling

I’m frequently asked to speak about women in law and specifically the issue ...

9 Traits of Exceptional Leaders

Truly great leaders are hard to come by, but it seems everyone thinks ...

5 Things Women Leaders Should Stop Doing. TODAY.

Over the last couple years, I’ve had a front row seat to career ...

4 Characteristics of Leaders Who Get Hired and Promoted

Imagine if you had the opportunity to sit down with a senior executive ...

8 Types of Courage for Aspiring Leaders

“The truth is that courage resides within you; you must simply decide to ...

25 Questions to Ask a Mentor

A few years ago, around the time when I was launching this blog, ...

Emerging Leader Spotlight: Erin Lo
Emerging Leader Spotlight: Erin Lo

Every month we ask an emerging leader we admire to share what she is doing

How to Go After Awards and Recognition (and Win)
How to Go After Awards and Recognition (and Win)

Just last week, a Director at a well-regarded business school explained to me that she

Leaderly Quote: Don’t let fear steal your dreams
Leaderly Quote: Don’t let fear steal your dreams

“Don’t let fear steal your dreams.” — Sabina Nawaz

Five Strengths of Vulnerable Leaders
Five Strengths of Vulnerable Leaders

The biggest misconception in corporate America is the thinking that vulnerability and weakness are synonymous.

How to Convince a Stranger to be Your Mentor
How to Convince a Stranger to be Your Mentor

When I arrived in the U.S. from India to attend college, I was excited and

Leaderly Quote: Take on things outside your comfort zone…
Leaderly Quote: Take on things outside your comfort zone…

“Take on the things outside your comfort zone that the world is pushing you toward.”

Top 10 Most-Read Articles of 2017
Top 10 Most-Read Articles of 2017

Grab a cup of cocoa, take a seat in your favorite comfy spot, and find

Our Best of 2017 – 33 Leadership Quotes (Slideshow)
Our Best of 2017 – 33 Leadership Quotes (Slideshow)

Every other Monday morning at BeLeaderly.com we post one of our favorite leadership quotes to help you

4 Ways to Execute a Stretch Assignment Like a Rock Star
4 Ways to Execute a Stretch Assignment Like a Rock Star

Want to uncover a bigger, bolder vision for your career than you can imagine today?

Lend Your Voice! Participate in Our Research Survey
Lend Your Voice! Participate in Our Research Survey

Help us change the game for working women by participating in our brief research survey

Cultivate Your Inner Voice of Courage (Video)
Cultivate Your Inner Voice of Courage (Video)

You’re not smart enough. You’re too new to this. You make bad choices. We all

Leaderly Quote: Someone sees the leader in you
Leaderly Quote: Someone sees the leader in you

Sometimes a thought or quote leaves an indelible mark on us. It was more than

What Does it Mean to Have a Sponsor? (Podcast)
What Does it Mean to Have a Sponsor? (Podcast)

What does it mean to have a sponsor? How is a mentor different? And how

The 5 Best Times to Negotiate on the Job
The 5 Best Times to Negotiate on the Job

When we negotiate and fail, the effects can set us back both personally and professionally. Perhaps

At Be Leaderly, our mission is a simple one: To provide proven career strategies that help you lead, climb, and thrive as a rising woman of influence. If you’re ready to lead, we’re here to support and inspire you.

Subscribe

captcha

PRIVACY

We will never share, rent, or sell your personal information or email address.
Copyright 2018, Be Leaderly