25 Great Questions to Ask Your Mentor

Georgia Pascoe
Georgia Pascoe
  • Updated

As a mentee, you are generally expected to drive the mentoring relationship. This can be daunting when your mentor has more experience than you, is more senior than you, or if you simply don't have much experience running 1-to-1 meetings.

Having prepared questions may feel a bit cheesy, but your mentor will appreciate the effort and you'll find the conversation flows when you start with purpose. These 25 questions cover four key areas: stories, situations, self-awareness, and skill-building.

Feel free to revisit these questions as your relationship develops. Some make great ice-breakers, while others help maintain momentum later in the program.

What questions should I ask my mentor?

The best questions to ask a mentor fall into four categories. Before each meeting, try preparing one question from each area. This simple structure ensures your conversations are varied, focused, and productive, covering your mentor's experience, your current challenges, how others perceive you, and the skills you want to build.

Stories - learn from your mentor's experience

Ask your mentor to share a story from their career. These questions help you learn from real-world experience and build rapport early in the relationship.

  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 manager? 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 role you applied for and got, but you weren't 100% qualified?
  8. How did you build the skill of speaking confidently in front of others?

Situations - use your mentor as a sounding board

Identify a challenging situation you're facing and share it with your mentor. These questions invite your mentor to help you think through real problems you're navigating right now.

  1. I'm considering a career transition. What do you see as the pros and cons?
  2. Who are the people I need to align with in this organisation to achieve success?
  3. What advice can you offer on how to progress in my career?
  4. How do you stay connected to key people who don't work in the same office or location?
  5. When trying to gain buy-in to implement a new program, what tactics have worked for you?

Self-awareness - understand how others see you

Ask a question that invites your mentor to contribute to your self-awareness. These can be confronting, so they work best once you've built some trust in the relationship.

  1. Where do you see my strengths, and what should I focus on to improve?
  2. What do you see as some of my blind spots?
  3. How do you think others perceive me?
  4. How am I viewed by leadership?
  5. Do I come across as poised and calm?
  6. What's my personal brand in our organisation, and is it working for me?
  7. Did everyone understand what I presented at the last meeting?
  8. How could I have communicated my idea more clearly?

Skill-building - develop the capabilities you need

Identify a skill you currently want to develop, and ask your mentor for advice or resources. These questions turn your mentoring sessions into practical development conversations.

  1. How do you approach risk-taking?
  2. What new skills do I need to move ahead?
  3. How can I become a more assertive negotiator?
  4. How can I become better at influencing people who don't report to me?

How should I prepare questions for my mentoring sessions?

Before each meeting, pick one question from each of the four categories above. You don't need to use all 25 in a single session, in fact, one well-chosen question per category is enough to fill a productive conversation. Write your questions down beforehand so you're not trying to remember them in the moment.

As your relationship deepens, you'll find that some categories become more useful than others. Early on, stories and situations help you build rapport and get to know your mentor. Later, self-awareness and skill-building questions drive deeper development conversations.

How to use these questions in Mentorloop

Mentorloop gives you several tools to make the most of these questions:

  • Meeting agendas: Use Mentorloop's meeting agenda templates to structure your session around your chosen questions. Share the agenda with your mentor beforehand so they come prepared too.
  • Notes: After your session, capture what you discussed and any actions you agreed on using the Notes feature. Shared notes mean both of you have a record to refer back to.
  • Goals: If a conversation surfaces a clear development area, turn it into a SMART goal with tasks and due dates so you can track your progress.
  • Scheduling: Book your next session from within your Loop before you finish the current one. Regular, scheduled meetings keep the momentum going.

Questions adapted from Jo Miller, Be Leaderly.

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