Guest Post by Jo Miller

Have conversations with your mentor gotten a bit repetitive lately?

Perhaps you approached someone you admire, and bravely asked that person to become your mentor. And they said “yes!” But a year into the relationship, those monthly mentoring conversations don’t seem to invigorate you like they used to, and aren’t quite as energizing for them, either.

In short, you suspect the mentorship may have run its course. The fact is, sometimes it’s not the relationship that’s stale – you just need some fresh material to discuss. So why not re-invigorate those mentoring sessions by preparing a thoughtful, diverse slate of questions ahead of time.

Here are four types of questions to prepare ahead of every mentoring conversation that will keep things interesting – and valuable – for you and your mentor:

I     Stories

Hey, everybody likes to talk about themselves! Ask your mentor to tell a story from his or her own career. For example, you could ask, “How did you get to where you are today?” or “Was there a time you messed up and felt like you’d failed? What did you do to recover?” or “What do you wish you had known before your first management role?”

II   Situations

Bring a situation to your mentor. One that you’d like help navigating. For example, “I tried to delegate a task last week and it did not go as well as I’d expected. Can you help me think through what to do differently next time?” or “I have these two very different career path options and would like your help making a decision” or “How can I let my boss know that I don’t need to be micromanaged?”

III  Self-awareness

One of the greatest gifts you can give yourself is the gift of self-awareness, meaning the ability to see yourself as others perceive you. That way, if you like how you’re perceived, you can embrace it and take steps to strengthen that positive perception. If you don’t like how you are currently perceived, you can take steps to change that perception to a more positive one.

Your mentor can help by “holding up the mirror” and giving you feedback on how your actions and communication are impacting the way others see you. Ask a question, such as, “When I presented in that meeting last week, how did I do?” or “Could you give me feedback on ways to improve my leadership presence?” or “Am I coming across as high-maintenance when I send my boss weekly status updates?”

IV  Skill-building

Is there a skill you’re currently working to enhance, such as project management, long-term strategic planning, delegating, or public peaking? Ask your mentor for advice and resources that will help you polish that skill.

The Takeaway

By preparing a new variation of each one of these four questions before every mentoring conversation, you can all but guarantee that you’ll have interesting conversations for years to come.

Conversely, if you share this list with those that you mentor and encourage them to prep ahead of time, you need never sit through another mentoring conversation wondering if the other person is finding this useful!

1 page flyer-corr-2.cdrJo Miller is Founding Editor of Be Leaderly, CEO of Women’s Leadership Coaching, Inc., and creator of the Women’s Leadership Coaching® system, a roadmap for women who want to break into leadership. She has traveled in Europe, North America, Asia Pacific, and the Middle East to deliver keynotes and workshops, and counts being the only Aussie women’s leadership coach in Iowa among her unique “koalafications.” Learn more about Jo’s services at and follow @jo_miller on Twitter


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2 thoughts on “Four Types of Questions to Ask Your Mentor

  1. Paul Cheese says:

    Thanks Bob (and Jo). This is seriously helpful – not just for formal mentoring situations, but also for the situations you just want to get the most out of, when you’re with someone you highly value or respect.

    1. Bob Tiede says:

      Thanks Paul! Jo Miller’s “Guest Post” is a 10!

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