Questions to Ask a Mentor

by | Jan 29, 2024

questions to ask a mentor

How to Choose the Right Mentor: Key Questions to Ensure Values and Goals Alignment

As we close out National Mentoring Month, I find myself reflecting on the transformative impact of mentorship not only in professional endeavors but, more importantly, in the grand tapestry of our lives with questions to ask a mentor.

Research shows that…

  • 67% of businesses reported an increase in productivity due to mentoring
  • 55% of businesses felt that mentoring had a positive impact on their profits
  • 87% of mentors and mentees feel empowered by their mentoring relationship and develop greater confidence
  • Mentees are 5x more likely to be promoted
  • 84% of CEOs said mentors had helped them avoid costly mistakes

But let’s get real – these relationships can be profound life-changers or disappointing duds. 

Mentoring Maribeth Monroe GIF by CBS questions to ask a mentor

I have been fortunate to have many life-changing mentors and mentees in my life. I’ve also had mentors who thought nothing of being on their phones our entire time together. And I had mentees who seemed to just use me as an ATM.

Hands down, the most impactful mentor in my life was my graduate school supervisor, John Green. He taught me how important relationship building was in order to have organic and strategic success. It was something I always knew deep down, but he showed me step-by-step how to make it a part of standard expectations for how I led and the culture we created together.

All it took was slowing down, getting curious, and connecting authentically.

His embodiment of those values stuck with me in a major way for the rest of my life. 


(Me and John on his rooftop in NYC during my graduation party he generously hosted.)

My mentors have ranged from executives who saw my potential and wanted to help me soar to friends who are achieving success in ways I hope to one day. As I grew older and started my own business, I became more intentional about who I invested my time with and took advice from.

And lemme tell ya, it became suuuuper challenging to take advice from someone who I’d once admired only to realize they didn’t share my core values. Most of the time, they were giving me directions straight to burnout.

It was like my mentor criteria simply entailed: public image, wealth and reputation. I never considered how they went about achieving. Never pondered, “Are they happy?”, “Do they have a sense of well-being?” or “What’s the quality of their relationships?”

I hadn’t reflected on questions to ask a mentor…

Essentially, I made a whole bunch of assumptions based on values that were never mine.

What I know for sure today is that life is most impactful when your goals and values are in alignment. So why not find a mentor who is doing that, too?



So before you dive into investing in your next mentoring relationship, stop and reflect on why you want it and what you’re willing to do to invest in that outcome. 

  • Define Your Aspirations: Clearly articulate what you seek to gain and give from the mentorship. Understand your values, goals, and the areas in which you desire guidance. And get clear on how you’re going to nurture that relationship with intention.

Then filter your mentoring relationships by understanding where you’re in alignment and where you differ. While embracing differences is enriching – be sure that you’re asking someone for directions who has traveled the path in a way that you want to travel it.

Consider these three questions to ask a mentor and yourself:

  1. Do their core values match mine?? AKA Values Alignment! Explore whether your values align with those of your mentor. A shared foundation in core values ensures that the guidance you receive resonates with your authentic beliefs. Values mentors focus on shared values rather than formal credentials. This paradigm shift recognizes that mentorship is not about status but about embodying specific values that align with your aspirations. With John, he embodied the values of connection, authenticity, curiosity and well-being. So, I learned by simply being in his presence. Use our free core values quiz as a fun guide.
  2. Does their lifestyle emulate the type of lifestyle I desire??‍♀️  Assess whether your mentor’s lifestyle reflects the kind of life you aspire to lead. Do you wish you live a life of simplicity, prioritizing time with loved ones? If so, does your mentor live that type of life? Or are they working 24/7 and missing out on milestones outside of the office? Their experiences often shape their advice, making it crucial that their journey aligns with your vision.
  3. Do they have wisdom in an area I want to grow in?? Look for mentors who possess skills or experiences that align with your values and goals. Long-term success in mentorship is often grounded in the mentor’s expertise in an area you wish to explore. And if you want to get really deep in it together, establish clear expectations. How often will you meet and what area of growth do you want to focus on? Values-driven mentors ensure that both parties agree on the objectives, ensuring a mutually beneficial journey toward personal and professional growth.

As we venture into 2024, let’s not only seek success in our professional endeavors but also enrich our lives through authentic connections and mentorship that transcend the boundaries of the workplace. Life mentorship, rooted in shared values and genuine connections, has the power to transform not only your career but your entire existence.

Wishing you a season of purposeful connections, transformative mentorship, and holistic growth!

Have fun with these questions to ask a mentor!

When you are ready, here are three ways we can help you.

Alignment Coaching: Want to start the new year as your most authentic self?  Work with me 1×1 to align with your core values and ignite more well-being without compromising your impact. Fill out this inquiry form to see if we’re a good fit for one another.

Knowing and Living Your Values: During my 10-day course, you’ll identify your unique values, see where you’re currently activating them, and make small tweaks where you’re not so that every day is filled with purpose. Join 7,000+ Students Here.

Hire MaryBeth as a Speaker: Have an all-staff event, annual meeting or conference coming up? I will inspire your audience to give themselves and others, permission to be human, unleashing higher productivity, profit, and purpose through shared values. Learn more here.

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