Useful Questions for Mentors in a Mentorship Program


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Have conversations with your mentor gotten repetitive? Don’t write off the relationship too quickly, even if it seems like it may have run its course. Often, it’s not the relationship that’s stale–you just need some fresh material to discuss. To re-invigorate mentoring discussions, prepare a thoughtful, diverse slate of questions ahead of time.

Below are four types of questions to ask your mentor, along with related examples for each type. Implement these at your next meeting to keep things interesting–and valuable–for you and your mentor.

4 Types Of Questions To Ask A Mento

1. Stories

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To break the ice, have your mentor tell a story from his or her own career. Hey, everybody likes to talk about themselves! For example, you could inquire: “How did you get to where you are today?” or “How did you land your current role?” But you could also ask more specific questions that address your career objectives and concerns. Some questions to consider:

• 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 business setback. How did you recover?

2. Situations

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Now that the conversation is flowing, get more granular in your requests and bring a specific situation to your mentor–one that you’d like help navigating. For example

• 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?

3. Self-Awareness

One of the greatest gifts you can give yourself is the gift of self-awareness, meaning the ability to see yourself as others view you. That way, if you like how you’re perceived, you can embrace it and take steps to strengthen that positive perception. If you don’t like how you are currently perceived, you can take steps to shift that perception to a more positive one that supports, rather than undermines, your career and leadership goals.

After starting with the obvious question: “How do you think others perceive me?” become more specific, so your mentor can assist by “holding up the mirror” and providing detailed feedback on how your actions and communication are impacting the way others see you. Ask questions such as:

• 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?

4. Skill-Building

Is there a skill you’re currently working to enhance, such as project management, long-term strategic planning, delegating, or public speaking? Use questions like these to ask your mentor for advice and resources to help you polish that skill:

• 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?

With these four types of questions and their accompanying examples, you’ll never sit through another mentoring conversation wondering if the other person is finding the discussion useful. 

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