How to prepare for your first mentorship session

One of the biggest reasons mentorship sessions under-deliver is lack of preparation - on both sides.

Here’s a simple framework that works whether you’re the mentee or the mentor.

Key Takeaways

For mentees

Have one primary goal for the session.
Not “help me with my career.” Something specific like:
- “Review my approach to a recent incident and tell me what I missed.”
- “Help me decide between two job offers and what to negotiate.”
- “Walk me through how you would tackle this type of red team assessment.”
Bring concrete artifacts.
A short writeup of the problem, a redacted log snippet, your current resume, a decision matrix, etc. Context is everything.
Do 15 minutes of homework first.
Search for the mentor’s public writing or talks. You’ll waste less time on basics and show respect for their time.
End with a clear next step.
“In the next two weeks I will X. Can I follow up with you on Y?”

Ask the mentee to send context 24 hours in advance when possible.
Start by confirming the goal of the session out loud.
Be generous with specific resources and introductions, not just general advice.
If something should be a writeup, encourage them to publish it (even privately at first).

Most great sessions happen in 45-60 minutes if both people come prepared. Longer sessions often just mean the preparation work wasn’t done upfront.

The best mentees we’ve seen treat the session like a high-leverage meeting, not an open-ended chat.

Go prepared. You’ll get dramatically more out of it.