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Even the best mentoring relationships can fall into a rut over time, often falling back to the same conversation topics. However, by asking new or different questions of your mentor, you can unlock new insight and advice, which can help reinvigorate the mentoring relationship on both sides. As a mentee, you should prepare thoughtfully for each session with your mentor. Why not try some of these conversation prompts to suit your situation and needs?


Tell me about…

Ask your mentor to share a story from their professional experiences. For example:

  • ​When was a time when you messed up and felt like you’d failed? How did you bounce back?
  • How did you learn to embrace risk-taking?

  • Is your career today as you envisioned it five or ten years ago?

  • What do you wish you knew before taking your first management role?

  • Which leadership skills were the most difficult to develop?


Help me with…

Let your mentor support you in handling a specific work situation. For example:

  • ​I tried to delegate a task and it did not go well. Can we discuss what happened, and what I could do differently next time?
  • How can I be more connected with key influencers or strategic leaders who don’t work in my organisation? OR Who are the people I should align with in this organisation to support future success?

  • I need to introduce/implement a new initiative and need buy-in from my team/colleagues. What tactics have worked for you?

  • My performance review is coming up – what type of preparation do you appreciate seeing from your team?

  • I have an important choice to make about my career path – can you offer some perspectives to help me make a final decision?


Improving self-awareness and reflection

Ask your mentor to help you understand how others perceive you. For example:

  • How do you think others perceive me? What are my strengths, and my blind spots?
  • How can I help improve my professional presence or visibility? What do you think is important to my professional ‘brand’?

  • I think I learned this from [CPD], how can I apply it more effectively to my work?

  • How can I improve the communication of [this idea]


Transform your toolkit

Your mentor can help you practise and develop key skills and techniques. For example:

  • I’d like to be more assertive in my career negotiations. Can we role-play asking for a raise and promotion?
  • I have been asked to facilitate a team-building session – what might be key to its success?

  • How can I become better at managing or influencing people who don’t report to me?

  • Do you have any quick tips for re-energising a busy and stretched team?

  • What other skills and knowledge do you think it is critical that I develop for future success?


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How to cite

Royal Geographical Society (with IBG) (2021) Questions to reinvigorate a mentoring relationship. Available at Last accessed on: <date>


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