Fourty Questions to Ask a Mentor for Better Results


Not sure where to start? Lost on what to focus on? Need help prompting your mentor? If you find a mentor relationship becoming stale, don’t write it off immediately. Try asking some of the following questions to reinvigorate your relationship.

Questions are courtesy of Forbes.

A Printable Version is available from the IR2 Future Leaders Program, but is applicable to everyone.

1. Stories

Ask your mentor to share stories about their career. Stories allow your mentor to reflect on their career path, and you can gain some valuable lessons from their experiences.

  • Was there a time you messed up and felt like you’d failed? How did you bounce back?
  • How did you learn to embrace risk-taking?
  • Tell me about a recent operations setback. How did you recover?
  • Think back to five years ago. Did you envision your career as it is today?
  • Was there ever a role you applied for and landed, but weren’t 100% qualified to do? How did you proceed?
  • What do you wish you had known before taking your first management role?
  • Which leadership skills were the most difficult to develop?
  • Can you tell me about a time when you had a difficult boss? How did you handle the situation?
  • What’s the most important leadership lesson you’ve learned and how has it proven invaluable?
  • How did you develop the skill of speaking so engagingly in front of groups?

2. Situations

Now that you’ve spoken with your mentor about their experiences, begin sharing some of yours. Describe some work situations where you weren’t sure what to do, and ask for advice.

  • I tried to delegate a task last week and it did not go well. Can we work through what to do differently next time?
  • Who are the people I need to align with in this organization to achieve success?
  • My boss said I need to be more strategic. What does that mean?
  • How can I let my boss know that I don’t need to be micromanaged?
  • How can I stay connected to key influencers who do not work in the same office or geographical area?
  • When trying to gain buy-in to implement a new program, what tactics have worked for you?
  • My performance review is coming up. What type of preparation do you most appreciate seeing from your employees?
  • I have two very different career path options available to me. Can you weigh in to help me make a final decision?
  • I’m considering a career transition. What are some other areas of the business that might be a good fit for me?
  • I’ve heard that taking a stretch assignment could help my career trajectory. What are the pros and cons?

3. Self-Awareness

Understanding how others see you as an employee can help you make improvements when needed. A mentor can productively show you how to do so.

  • How am I viewed? In other words, what’s my personal brand in our organization?
  • Where do you see my strengths?
  • What do you see as some of my blind spots and how can I improve?
  • How am I viewed by leadership?
  • What do people say about me when I’m not in the room?
  • Could you offer feedback on ways to improve my executive presence?
  • Do I come across as strategic or tactical in my day-to-day communication?
  • Am I viewed as high-maintenance when I send my boss weekly status updates?
  • How could I have communicated my idea more clearly?
  • When I presented at the last meeting, how did I do? Did my communication style support the message I intended to deliver?

4. Skill-Building

Building skills is an excellent way to develop in your career. If you are trying to build a particular skill, ask your mentor about it.

  • How can I become a more assertive negotiator?
  • Can we role-play asking for a raise and a promotion?
  • How can I become better at managing people who do not report to me?
  • Do you have any quick tips for re-energizing an overworked team?
  • Can you recommend a book or resource for dealing with difficult conversations?
  • What practices can you recommend for dealing with nervousness when speaking to groups?
  • I have been asked to facilitate a team-building activity at a staff retreat. What are some keys to success?
  • What’s a good methodology or tool for project management and tracking team commitments?
  • Do you have a template that you use for long-range visioning and strategic planning?
  • What new skills do I need to move ahead?

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