Your First Session As A Mentee; A Guide

Topics: Mentee

Getting to know each other

Even though it is online, it can be a daunting prospect"meeting" your mentor for the first time.

Anyone would feel nervous at the thought of talking about themselves to someone they don’t know.

It is also understandable to feel inferior to your mentor, as they have more experience than you.

By taking on a mentor you are making a big jump in trusting a stranger.  You believe in the idea of mentoring, but because they are still a stranger have very little understanding of what to expect!

So that's why the first session might be the hardest!

Do not worry use our guide below and everything will go great.

fortune cookie mentor

Before the first session

It should go without saying that the more you put into this the more you will get out. So make sure you book out a couple of hours in the diary just to prepare.

Check out your mentor’s digital footprint — are they on Twitter or just LinkedIn? Do they have a blog? By getting to understand their background you can start to relate to how they can help you.

Using their Linkedin profile, start to think about how you think your mentor could best assist you.

This exercise can also give you a few things to talk about in those opening few moments when it is a bit awkward. What city did they study in? Have you been? What have they been saying on Twitter or Linkedin. Do you agree or do you need a bit more clarity on a certain point?

Send through a quick intro/bio via the chat facility or via email — don’t go crazy with a cover letter and 6-page CV — just a couple of paragraphs about where you are right now and what you hope to get out of the experience.  In that intro just re confirm your meeting time and what form of communication- telephone/ skype etc. And make sure you get the mentors contact details 

Start to consider your goals for the mentoring relationship — why are you here, and where do you want to be in 6 / 12 months? It doesn't matter if you cannot think of anything because the mentor will help you but at least try to think about your intention for the relationship. 

Do not worry if you do not know! You will work in this in more depth in the next couple of session were you will define your intention and goals. 

Have a look at our reasons to get a mentor article for some ideas about what you want to learn or how you want to develop.  It is OK just to have a rough idea at the moment. 

If you do need to cancel make sure you call or send an email. 

Remember the do's and don'ts of mentoring!

life is too short do stuff that matters

The first session

This session is all about just getting to know your mentor. And letting them know who you are. 

This takes time. 

Breaking the ice

Your mentor will ask you questions about how they can help you and your career to date. 

It is important to be as honest as possible. The mentor is on your side. There is no need to exaggerate or over state your credibility. The mentor is trying to learn how best they can help you so be brutally honest.

The following questions can be used as inspiration, do not sound too wooden and get quiet deep. 

Yes you can ask them about their career and interests please do start off with that.

Then you might like to go a bit deeper...

  • What have been your career highlights?
  • When did you really feel stretched?
  • How do you cope with all the demands of your current role?
  • Why do you want to be a mentor?
  • What advice would you give to your 20 year old self?
  • What is your favourite book/ film/ play?
  • How has an apparent failure then set you up for success later in life?
  • If you could have a giant billboard across [insert busy motorway in your country] what message would you tell the people?
  • What is one of your favourite quotes?
  • What advice would you give to a smart student about to enter the real world. What advice would you tell them to ignore?

question mark neon ment

Remember that you need to build a relationship with the mentor in order to get the most out of mentoring and that takes time – be patient!

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

"2 ears one mouth".


Boundaries & expectations

You should both set boundaries together. Meetings frequency and length. Contact rules etc.

You should both discuss what the mentor mentee relationship means. 

Personally define the mentee role as you see it.  Bigger picture, the goal is to help the mentee maximise their sustainability impact.

Your mentor will ask you  how you’d like to use your sessions together (we provide you with a framework) and what you’d like to achieve by the end of your agreed timeframe. They will discuss their longer term goals and they can support you to work towards these.



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.


Take notes!!!!

I put that as a heading because it is very important. Take notes. It does not have to be war and peace. But especially take notes of any action points.  I am still amazed that some people listen and listen and do not take notes . This is why some people get stuff done and some don't. Be a doer!

After the session

You will have homework after the session. That is to define your vision and action plan for the relationship. There will be a guide on how to develop that vision  and action plan sent to you.  The action plan will be followed over the course of the relationship.

Clarify what you will do before the next session.  Send a copy of the meeting notes and action points. 

Say thank you. Give gratitude to this fellow human who is helping you. 

Send a follow up thank you email from the heart because someone has just given up their time to help you move forward for free. 

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. 

thank you  mnentora


Daniel O'Connor

Daniel O'Connor

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