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Good Questions to Ask Your Mentor

As you think about cultivating mentoring relationships, initially, it is important to consider your personal and professional goals and what areas you want to grow in as you evaluate potential mentors who can help you along the way. As you prepare for a mentoring conversation, it is even more important to ponder what questions you want to ask, based on what you hope to learn. The following list is a good starting point for critical questions and topics to discuss so you can get the most out of the mentoring conversation.

Potential questions to ask your mentor:

  • How did you secure your current role?
  • Is this where you thought you would be at this point in your career?
  • What have been your greatest obstacles and how did you overcome them?
  • Was there ever a job/position that you applied for and got, but felt you weren’t 100% qualified for?
  • How do you successfully stay connected with key influencers who do not work in the same office or geographical area that you do?
  • Where do you see my strengths and what should I focus on improving?
  • What new skills do I need in order to move ahead?
  • What are some things you wish you would have known at my stage in your career?
  • If you could do it all again, what would you do differently?
  • What are some suggested resources that you can recommend that might help me achieve my goals?

At Diverse Talent Strategies, we help companies offer a workplace mentoring structure that is scalable, easy to administer, and metric-driven. We also help to ensure participants are prepared for mentoring conversations, whether as the mentee or the mentor. If you would like assistance in planning your company or organization’s mentoring initiative, contact us today at info@diversetalentstrategies.com.


Alison Martin

Written by

Alison Martin is the Founder and Chief Learning Officer of Diverse Talent Strategies, a family of brands offering turn-key solutions for mentoring, women’s leadership initiatives, and recruitment. With roughly 15 years in nonprofit work, Alison has a passion for doing work that makes a difference in the lives of others. After serving as Executive Director at two different national nonprofit organizations, her commitment to her passion for developing female talent led her launch Mentoring Women’s Network. In her role, Alison acts as a liaison to a national committee responsible for the leadership development content for the organization and consults with corporations on the development and strategy aligned with initiatives for emerging female leaders. She is also the author of the book, “Landing on My Feet: Learning to Lead Through Mentoring” and speaks regularly on behalf of the organization

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