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Stepping into a new mentorship relationship—whether you’re a mentor or a mentee—can feel both exciting and a bit daunting. The first meeting is your chance to set the tone, establish expectations, and build a shared foundation for success. Asking intentional, open-ended questions can help break the ice, clarify goals, and show that you’re committed to making the most of your time together. Here’s a guide to some of the most impactful questions to ask during your initial meeting.
1. What inspired you to participate in this mentorship?
For mentees, this is a chance to learn what drives your mentor to give back and share their knowledge. For mentors, it’s an opportunity to ask your mentee what led them to seek guidance. Understanding each other’s “why” can spark connection and reveal shared values that strengthen your partnership.
2. What do you hope to gain from this experience?
While the focus of mentorship is typically on the mentee’s growth, mentors often have their own reasons for participating. They might be looking for personal fulfillment, hoping to improve their own leadership skills, seeking fresh perspectives from mentees or simply wanting to give back. Exploring this question together sets the tone for a mutually rewarding relationship.
3. How can we make our time together most effective?
This question works both ways. Mentees can show initiative by asking how to best prepare, communicate, or follow up. Mentors can share preferences on structure or expectations, and ask their mentee how they learn or receive support best. For example, some of these preferences could be sending agenda items prior to meeting, bringing specific questions to each meeting, or coming prepared to discuss blockers and updates. Clarifying these details early helps ensure your meetings are productive and respectful of each other’s time.
4. How often would you like us to meet, and what’s the best way to communicate between sessions?
Establishing logistics early on is always wise and will help both individuals manage expectations from the get go. Align on meeting frequency, preferred formats (in-person, video, phone), and how to communicate between sessions. Mentors and mentees may have different work styles or availability, so this conversation helps prevent miscommunication and keeps momentum strong.
5. What advice would you offer—or are you seeking—at this stage of your career?
If you’re a mentee, this is your chance to receive guidance tailored to your goals. If you’re a mentor, ask what your mentee is navigating and offer insights based on where they are now. Swapping perspectives here leads to meaningful dialogue and more relevant advice on both sides.
6. What challenges have shaped your career?
Personal stories and lessons learned can open the door to honest, vulnerable conversation. Mentors can share roadblocks they’ve overcome, while mentees can talk about recent hurdles they’re facing. It helps normalize struggles, build empathy, and spark problem-solving as a team.
7. What expectations should we have of each other?
Rather than focusing solely on what a mentee should bring to the table, this question encourages both people to share expectations, from preparedness and honesty to punctuality and follow-through. A transparent conversation here sets the groundwork for trust and accountability.
8. What does success look like for this mentorship?
Take time to define your shared vision. Success might mean measurable outcomes, like landing a promotion or learning a new skill, or more intangible ones, like increased confidence or stronger communication. Whatever it may be, this shared vision of success will keep you motivated and give both of you a sense of direction.
9. How do you like to give and receive feedback?
Feedback is a powerful tool for growth, and discussing it upfront can make it more comfortable. Ask each other how you typically approach feedback and let them know how you prefer to receive it. Some people respond well to direct or constructive criticism, while others may prefer a more balanced approach. Understanding each other’s preferred feedback styles can make the mentorship more effective and enjoyable.
10. Is there anyone else you recommend I connect with, either individually or together with you?
Mentors, you often have valuable networks and can introduce your mentee to people who might help them reach their goals. Mentees can also help connect mentors to up-and-coming talent or resources they may not be aware of. Keep this question open and ongoing as it can lead to opportunities, collaborations, and community.
Wrapping It Up
The first meeting in a mentorship is an essential step in building a meaningful relationship. By asking thoughtful questions and actively listening to their responses, you can lay the groundwork for a mentorship that’s productive, respectful, and inspiring. Use these questions to get the conversation started and feel free to add your own too, but remember that mentorship is a two-way street. By being open, proactive, and receptive, you’ll create a successful partnership that brings value to both the mentee and mentor.