Your First Session As A Mentor; A Guide

Topics: Mentor

Getting to know each other

The first session is the easy one but the most important. This is the place to start to get to know each other.

Before the first session

Prepare by reading the mentee's Linkedin profile.

It can be daunting to ask for somebody's help, so try to make the mentee feel as relaxed as possible in the first session . That approach starts before you meet. If they have not got in touch with you a few days before the online meeting, you can maybe send a friendly email. If the first contact comes from the mentor it can help break the ice.

The first session

This is a great opportunity to practice your active listening skills. Or as my Dad reminds me..

"2 ears one mouth".


Ask open questions

Good questions that will help you find out how you can support your mentee include: “Tell me about your relationships at work”; “How did you get to where you are?”; “What key challenges do you face in your role?”; and “What are your career goals over the next three years?”

Make it clear that you are here to help them. If they do not know what their goals are- this is a great time to say you are here to help them define those goals.

Ask about their careers so far. What are they working on at the moment? What do areas of work excite them the most etc.

Tell them about your career. The highlights the challenges and mistakes. They should also ask questions of you.

You both need to know each others background and motivations to develop a good productive relationship.

It is important to be as honest as possible.

Set boundaries & expectations

It’s important to mention confidentiality early on in your first meeting to help your mentee feel comfortable. Discussing what you both want out of the process, and your mentee’s expectations of what mentoring is, can help to establish your working relationship.

Personally define the mentor role as you see it. Give any boundaries. What are you happy to help them with. What won't you do? (For example no calls or emails on a weekend or after Xpm etc). Most of all emphasise you are there to listen and help them find their own way .

Bigger picture, the goal is to help the mentee maximise their sustainability impact, but the mentor’s role is to share experiences, suggestions, and provide support to assist mentee and help them gain more empowerment over their future.

Ask your mentee how they’d like to use your sessions together and what they’d like to achieve by the end of your agreed timeframe. Discuss their longer term goals and how you can support them to work towards these.

Discuss practicalities

Allow time to discuss things like how often you will meet, how long for, and put some dates in the diary. way ahead of schedule.  Have an open discussion about timescales so that you can agree a rough end date.

After the session

If the mentee does not have a clear intention vision and goals for the relationship this is what they will work on for the next sessions. This will be their home work. 

It is up to the mentors/mentees to set up follow up meetings. You can follow our programme. The expectation is to have a catch up every month. The mentee should be the one that pushes this relationship. 

Good luck with your first session and please feedback to us on any support you think you need. 


Daniel O'Connor

Daniel O'Connor

I use my time and experience to contribute to the transition to a regenerative sustainable society for all.