3 Questions to Ask Your Mentor in the First Meeting — To Know You Have Chemistry

Starting a mentoring relationship can feel both exciting and uncertain. You’re looking not just for guidance but for connection — that intangible sense of chemistry that allows mutual trust, curiosity, and growth to thrive. The first conversation with your mentor is your chance to sense that alignment.

Here are three questions to ask in your first meeting, drawn from insights in The Mentoring Manual by Julie Starr, I’m OK – You’re OK by Thomas A. Harris, and Coaching Supervision Groups by Jo Birch. These questions help you identify whether the relationship has the right energy, openness, and potential for authentic development.

1. “How do you like to create trust and openness in your mentoring relationships?”

Mentoring begins and ends with trust. Being a big fan of Julie Starr’s work this article was inspired by one of her talks. In her book The Mentoring Manual she reminds us that “mentoring isn’t about changing someone, or getting someone to do something differently, it’s about waking someone up to who they really are” 

Asking this question allows you to see whether your mentor values that kind of awakening — whether they create a space where you can unfold rather than be molded. Notice if their answer includes empathy, curiosity, or vulnerability — the hallmarks of relational safety. The way you want them to show up for you. While they respond, really be connected with their answer and see what spark in you. 

If your potential mentor describes mentoring as a two-way dialogue or a “shared journey,” you’re likely in good hands. Chemistry often shows up when both people feel safe enough to be curious, honest, and imperfect.

2. “What does self-awareness mean to you in a mentoring relationship?”

Jo Birch notes, “everything we are; our experiences with groups and the beliefs we hold about ourselves, others and groups, have the potential to affect the process that unfolds between us”. Authentic chemistry depends not just on liking each other but on shared self-awareness. 

When a mentor is aware of their own biases and emotions, they can hold space without overshadowing you. This question invites them to talk about reflection, learning, and boundaries — essential to healthy chemistry.

If the mentor describes regularly checking in with their inner responses or “holding power without harm” that’s a good sign. It shows emotional intelligence and the ability to maintain a balanced dynamic, that is so needed in a mentoring relationship.

3. “How do you see growth happening in a mentoring partnership?”

This question reveals whether your mentor approaches growth from a position of equality — or hierarchy. In supervision we like to invite the awareness of the deference threshold - and how at any point the relational partnering disappears or gets disrupted there is a shift in the energetic field. Thomas A. Harris’s I’m OK – You’re OK highlights how relationships are shaped by our internal “life positions.” The healthiest stance is when both parties operate from the belief “I’m OK – You’re OK” — a mindset where “being OK with yourself and with others is the way to happiness, personal satisfaction, and good relationships”. It is also about the fact that a mentor can always learn from their mentees in a reverse mentoring process that happens when both approach the relationship with curiosity and openness.

If your mentor’s philosophy sounds like mutual growth rather than top-down teaching, you’re likely aligned. Chemistry thrives when both people see each other as capable and worthy — not when one is “fixing” the other.

Based on my experience - the best mentor-mentee chemistry comes from shared presence, not just shared goals. It’s that mutual I’m OK – You’re OK energy — grounded in openness, self-awareness, and equality that creates powerful mentoring conversations and spaces. Ask these questions early, ideally in the first meeting, listen deeply, and pay attention not just to the answers — but to how the conversation feels. True chemistry in mentoring is felt as much as it is understood. 

References

• Starr, J. (2014). The Mentoring Manual: Your Step-by-Step Guide to Being a Better Mentor. Pearson Business.

• Birch, J. (2021). Coaching Supervision Groups: Resourcing Practitioners. Routledge.

• Harris, T. A. (1969). I’m OK – You’re OK. Harper & Row.