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25 Mentorship Questions to Ask Your Mentor or Mentee

stuck mentoring

Feeling stuck after your first few meetings with your mentor or mentee? Not sure what to talk about?

Luckily, we’ve crafted this list of engaging mentorship questions sure to spark conversation, help you go deeper, and add some extra structure to your meetings in order to ensure you get the most out of them.

First Steps

First, as a mentee, we want to make sure you’ve had a chance to look at and work through this first meeting checklist. It will help you better understand your mentor’s background, experience, and what s/he’s bringing to the table. It will also help you better articulate your goals for the mentorship and help you both give and receive feedback.

If you have completed this checklist, why not check out these four mentoring session guides. They can further help you construct your sessions to pack more of a punch. Whether you choose the Storyteller, Guru, Situation, or Skill-Builder session guide, you’ll get to know your mentoring partner in a new light with each one.

Have you already used those too? We’ve got your back. Without further ado, here are 25 mentorship questions to ask your mentor or mentee.


25 Mentorship Questions

We’ll first look at good questions to ask a mentor, then questions for mentors to ask mentees.

Good Questions to Ask a Mentor

Here are some fun, quirky questions to break the ice and get to know a different side of your mentor, one that might not be immediately apparent in his or her professional persona.

  1. If you could be an animal, what would you be and why?
  2. What would the title of your autobiography be?
  3. What was your favourite toy as a child?
  4. What’s an activity you did a lot when you were a child that you wish you could do more of now?
  5. Do you remember one of the first things (a pet, toy, etc.) you named? Why did you name it that?
  6. If you could curate a museum gallery, what would you put in it?
  7. What TV or movie character is most like you, and why?
  8. If you could combine any two animals, what would they be? What would you call this new animal?

Once you’ve had some fun with these questions (some responses can be quite telling!), it’s time to get a little more insight into your mentor’s professional past.

  1. What was your first-ever job? What did you love and hate about it?
  2. Did you think you’d find yourself in this industry? If so, when did you know this was the work you’d go into? If not, how did you get here?
  3. What would be your dream job?
  4. How do you make yourself happy in your current role/industry?
  5. What’s something you’d like to change about your current role/industry?
  6. Did you have a mentor at some point in your career? If so, how did s/he help you? If not, why did you never seek one out?

Questions for Mentors to Ask Mentees

Now it’s time to flip the script! Mentors, here are some questions you can ask your mentee on both the personal and professional to better understand him/her and why s/he’s interested in this mentoring partnership.

  1. What was your favourite gift you received from the Tooth Fairy?
  2. If you could learn to play any instrument, what would it be?
  3. Who’s your favourite person (friend, family member, etc.)?
  4. What’s something silly that made you angry as a kid?
  5. What superhero do you resonate with the most? Why?
  6. If you could have the life of any famous artist or musician (dead or living), whose would you choose?

Next, we’ll dig into the professional side of things a bit more.

  1. Who do you talk with about the struggles and successes of your job?
  2. In your current role, have you ever thought about quitting? Why?
  3. Do you feel you are a part of a community, either in or outside of work? Who makes up that community and how do you support one another?
  4. If you could learn any new professional skill (it doesn’t have to be related to your current role or industry), what would it be?
  5. Where do you ultimately want to end up in your career (role, title, income, etc.)?

Wrapping Up

It’s not uncommon for both mentors and mentees to be unsure if they’re a good match or not. That’s because it’s normal to get stuck getting to know a mentoring partner. 

We understand that building rapport is the best way to get the most out of your mentorship experience. Hopefully, these quirky and digging mentorship questions will help you get to know your mentor or mentee on a more personal level and provide more common ground.

Got a few more questions up your sleeve that we should add?
Tell us below!

Emily Ryan

Em is our Marketing Manager at Mentorloop. That's a lot of 'm's! | She is passionate about crafting messages, crafternoons and craft beer.

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