What should you talk about in a first mentoring session?

Three things, in this order: enough of each other's background to have context, the mentee's actual goal and what is in the way of it, and the working agreement covering cadence, confidentiality, and scope. Resist solving the problem in session one. The first meeting is for establishing what the problem is.

How long should the first mentoring meeting be?

Sixty minutes. Thirty is not enough to get through background, goal, and working agreement without rushing, and rushing the working agreement is what causes pairs to lapse later. Later sessions can drop to thirty or forty-five.

Who leads the first mentoring meeting?

The mentee should own the agenda from session two onward, but the mentor should carry the first one. A mentee who has never been mentored does not yet know what to ask for, and putting that burden on them in session one produces an awkward hour that neither person wants to repeat.

What questions should a mentor ask in the first meeting?

Ask what the mentee wants to be different, what they have already tried, what they think is in the way, and what they want from a mentor specifically as opposed to from a manager or a course. The fourth question is the one most mentors skip and the one that most often reveals a mismatch worth naming early.

First Mentor Meeting Agenda (Free, 2026)

Before the session

Mentor, 10 minutes: read the mentee's application answers, particularly their goal and their stated obstacle. Come with one question about each. Do not come with a plan.

Mentee, 5 minutes: re-read what you wrote on your application. You wrote it weeks ago and your view may have moved. Note anything that has changed.

Both: have the mentor and mentee agreement open. You will fill it in together in the last 15 minutes.

The agenda

0 to 10 minutes: Context, not life stories

The goal is enough background to have useful conversations, not a full career history. Ten minutes, roughly five each.

Mentor asks:

"Walk me through how you got to the role you are in now, in about three minutes."
"What does a normal week look like for you at the moment?"

Mentor offers, unprompted:

One thing they got wrong early in their career. Going first with something unflattering is the fastest way to make the rest of the hour honest. A mentor who spends the first ten minutes on their highlight reel has already set the relationship up as performance.

10 to 30 minutes: The goal

This is the core of the session. Do not rush it and do not solve it.

Ask, in order:

"You wrote that you want [QUOTE THEIR GOAL]. Is that still right?"
"What would actually be different if that happened? What would you be doing on a Tuesday that you are not doing now?"
"What have you already tried?"
"What do you think is in the way?"
"What do you want from a mentor specifically, as opposed to from your manager, a course, or a promotion?"

Question 5 is the one most mentors skip. It is also the one that surfaces a mismatch early, while it is still cheap to name. If the honest answer is "I want someone to advocate for me in the promotion round", that is worth knowing in week one, and it belongs in the out-of-scope section of the agreement rather than as an unspoken expectation.

Mentor: listen for the gap between stated goal and actual obstacle. A mentee who says they want to move into management but whose obstacle is that they have never been given a scope large enough to demonstrate it has a visibility problem, not a management-skills problem. Those need different conversations.

Write down the goal as you both now understand it. It will have moved from what was on the application. That is normal and is the first useful output of the relationship.

30 to 45 minutes: The working agreement

Open the mentor and mentee agreement and fill it in together, out loud. Fifteen minutes.

Cover, in this order:

Cadence and length. Be realistic rather than ambitious.
Who schedules. Name one person. This single line prevents more lapsed pairs than anything else on the form.
Between-session contact and response time. Mentors, promise what you will actually deliver.
Confidentiality, including the two exceptions.
Scope, including what is explicitly out.
How this ends, including the fixed end date and the agreement that ending early is normal.

Do not send this to be signed later. The conversation is the point.

45 to 55 minutes: The first concrete thing

End with something specific rather than "let's think about it".

Ask:

"Between now and next time, what is one thing you will do?"
"What is one thing you want me to do?"

The second question matters. A mentor who takes no action between sessions is teaching the mentee that the relationship only exists in the meeting.

Write both down. Both get reviewed first thing next session.

55 to 60 minutes: Book the next one

Book it now, in the room, in the calendar. Not "I will send something over".

A first session that ends without a second session in the diary has roughly even odds of being the only session. This is the single highest-return five minutes of the hour.

After the session

Mentee: write three sentences on what you took away. Not for anyone else, just for you. You will want it at the midpoint review.

Mentor: note the goal as you now understand it, and the one thing you committed to. Do it within the hour, while it is accurate.

Both: if the session revealed that this pairing is not going to work, say so to the program manager this week. Early is cheap. Month four is not, and by then both of you will have spent a lot of energy being polite about it.

If the session is only 30 minutes

Cut in this order:

Section 0 to 10 down to five minutes total
Section 45 to 55 down to one question, "what is one thing you will do"

Do not cut the working agreement. A pair that skips it saves fifteen minutes now and loses the relationship in month three.

First Mentor Meeting Agenda