5 Questions Every Mentee Should Ask in Their First Session

Your first session with a new mentor can feel daunting. What do you talk about? How formal should it be? Here are five research-backed questions that set the foundation for a productive mentorship relationship.

1. "What's one thing you wish you'd known at my stage of career?" — This opens an authentic dialogue and shows you value their experience. It also reveals your mentor's communication style.

2. "How do you prefer to structure our sessions?" — Understanding expectations early prevents awkwardness later. Some mentors prefer agendas; others prefer open conversation.

3. "What's the best way to follow up between sessions?" — Establishing communication norms early. Some mentors welcome Slack messages; others prefer email only during business hours.

4. "Can you share a professional failure and what you learned?" — Vulnerability builds trust. If your mentor can share setbacks, you'll feel safer discussing your own challenges honestly.

5. "What does success look like for this mentorship in 6 months?" — Aligning on outcomes ensures you're both working toward the same thing. It also gives you a milestone to celebrate.

Remember: the best mentorship relationships are built on honesty, structure, and mutual respect. Coming prepared to your first session signals that you value your mentor's time — and that sets the tone for everything that follows.