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Top Questions to Take Your Mentoring Relationship to a Deeper Level

Mentoring relationships evolve over time, in a process Woman to Woman Mentoring likes to describe as the “know you – like you – trust you” process. As mentors and mentees continue to get to know one another, you may be wondering how to take your relationship to a deeper level. How can you unlock even more authenticity? What are some of the foundational life adaptations I may need to understand to take my next steps? What haven’t I learned from this relationship that I know my mentor can teach me?  We asked some of our board members what questions have helped them develop a more significant bond with their mentors and make more progress on their goals. Here are their top question tips!


What is one piece of advice you would give your younger self? – Rachel Koontz

Thinking about an accomplishment that has been your most satisfying, what do you think was the key to that success? – Karen Justice

In your experience, how can you help meet me where I am, but still hold me accountable for the goals I want to achieve? -Laura Clarke

If you could do something over or do it differently in your 20s or 30s, what would it be? – Melissa Curtis-Cherry

We all have to have uncomfortable conversations sometimes. Have do you prepare and practice responding when faced with a difficult issue or topic? – Stacey Collins

How do you incorporate self-care into your daily life? – Jill Browning

What was a self-limiting belief you had and how did you remove it? -Theresa Harrison

Tell me the pathway you took to be where you are today with all the straightaways, switchbacks, curves, hills, and valleys. – Andi Overton


These questions can open up greater discussions and opportunities for learning and a-ha moments – for both mentees and mentors. YES! Who is ready to dive into these questions?


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