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Although mentoring journeys are often insightful and exciting, there could be times where it needs a little push to keep going in the same purposeful direction, or a helping hand to get off the ground. has compiled a list of questions that can be asked in the mentor/mentee relationship to help each individual get to know their partner better and (re)evaluate what direction is best for both parties.

Below is an arrangement of questions that can be asked by both mentor and mentee relating to different areas of development.


  1. What was your first ever job? Is there anything you particularly liked/disliked about it?

  2. Who is your favourite person (friend, relative etc)?

  3. Have you ever thought about quitting the role you’re in now? If so, why?

  4. Did you think you would find yourself working in this industry? If so, when did you know? If not, what made you?

  5. What new skills do I need to develop to get to where I want to be?

  6. Could you offer me some feedback on how to improve ______?

  7.  What is your biggest achievement to date?

  8. If you could learn a new (professional/personal) skill, what would it be?

  9. Are there any books that you would suggest I read?

  10. How would you describe your idea of success and how has this changed over the course of your career?

Each of these questions allow for you to get to know your mentor/mentee better but can also help to refresh your relationship when it feels like it has run its course. They all serve different purposes whether they add insight, create points of focus for development or just simply allow you to grow your partnership so that you can get the most from it. 

Try a few of these questions in your next meeting and let us know how it went by tagging us on social media! 

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