Getting prepared for your first meeting with your mentee


So you’ve been matched with a mentee and you’ve got your first session coming up. You haven’t been a mentor before and you’re a little nervous about how to manage this first session.

No worries, we’ve got you covered! We’ve put together a guide to how to manage your first session with your mentee.


Your OneUpOneDown mentor-mentee relationship lasts three months, with four sessions.

The purpose of these short, intensive relationships is to focus on one primary skill to develop, one primary decision to make or one hurdle to get over. You will have been matched with your mentee because you have experience which they don’t yet have and can help them move closer to their goals.

The purpose of your first meeting is to:

(a) figure out your mentors current situation

(b) figure out where they want to get to in three months and

(c) figure out how you can best help them to get there

Where they are now is point A and where they want to be in point B.

We’re strong advocates for asking questions. Most people generally have the answers to their own problems, they just need help to pull everything out everything they’ve got going on in their minds, to sort through it and view it objectively. 


Your aim here is to get an understanding of your mentors story – what has gotten them to where they’re at now? Stories are the best way to understand a person and the important experiences that have shaped them.

Getting your mentee to share their story and asking ‘why’ to understand their key decisions will help you to quickly get a clear picture of who they are and what’s important to them.

Below are a few questions you can ask to get the ball rolling. Remember, you want to keep it conversational and follow the interesting topics that naturally arise — it doesn’t need to be scripted or too formal!

  • “Tell me a little bit about your self, what’s your story, or how did you get to where you are now? You can start as far back as you think relevant.”

As your mentee tells their story, you can dig deeper into the parts that you think are important.

  • What was it like growing up in XX?
  • Why did/didn’t you decide to study XX? Why did you change from XX to XX?
  • Why did you decide to apply for this job? Why did you quit?
  • Why did you decide to move countries, or travel?
  • Why is this important to you?

Most stories have a similar structure. There is a main character who exists in a particular way until something happens (an experience) that changes them, then they exist in a new way. 


Once you have a good enough understanding of your mentees ‘current reality’, you then need to understand their ‘desired reality’, or where they want to get to. This is the outcome they are trying to create for themselves.

Your mentee may have a clear idea of what this is, or they may not. If they don’t, the point B that you work towards may just be gaining clarity around the direction they would like to go/take.

Here are a few questions you can ask to get an idea of what their goals are:

  • What would you like to be doing in 5 years time? Why is this important for you?
  • Where would you like to be in 3-6 months time?
  • What are you actively doing to get there?
  • What’s the next step that’s most important?
  • You mentioned that you want to develop capabilities in [XXX, XXX,XXX], why are learning these skills important as next steps?

You are trying to understand the ‘after’ in the story that your mentee is living. 


Now you are trying to understand the catalyst that will help them to move from Point A to Point B. This mentor-mentee relationship is the event that causes them to learn something new, about themselves or a skill that they didn’t posses before.

So what is it that you can focus on, based on your own experience,  to help them transition to a new level over the next three months? Don’t let this questions daunt you, even a small shared experience of an observation can make a big difference! If you listen to your mentee, and ask good questions then you will be able to help them with this transition.

Here are some questions you can ask to get a good idea of what your mentee’s roadblocks might be:

  • What’s stopping you from …… (getting to the position they described in the previous questions)? Why is this stopping you? What are you worried about? Why?
  • What are some easy steps that you can take now to move forward?
  • What made you decide to sign up for a mentor through OneUpOneDown?

At this point you can contribute your experiences and the processes that have helped you in a similar situation. This may help your mentee to work out what actions they can take over the next three months to move towards their goal.


By this point you’ll have a good understanding of your mentee’s current position, where they want to get to, what’s stopping them and an idea of what needs to be done to move forward. 

Your next job is to paint a picture of what your mentor is working towards over the three months and some actions they can take between now and your next meeting. Accountability is one of the most valuable things a mentor can provide their mentee.

We suggest asking your mentee to tell you what they feel the next best steps will be rather than giving them the answer from the get go.

Here’s a suggestion for how you can present this to your mentee:

Based on what you’ve explained, it seems like a good goal for us to work towards over the next three months is……… What do you think?

What are the next steps you can take between now and our next catch up to move a step closer to this? (as they answer, support them in finding the actions that will make a meaningful difference and the most progress)

What’s the priority? (this is to get them to focus on one primary task, so they don’t try to do too much)

Why is this the priority?

Lastly, work out a time to meet next, so it puts a timeframe on the actions they are going to take.


We hope this article gives you some guidance on how to run your first mentor meeting. We’ve provided this resource to help new mentors feel more confident getting started as a mentor and encourage you to find your own unique style of mentorship as well as test and try new things.

One of our core values at OneUpOneDown is sharing knowledge so we’d love it if you could let us know about the techniques and tools that work well for you.

We also know that mentorship takes practice, and if you’re new to it it’s probably going to feel a little daunting or awkward to begin with. Don’t worry! You are not expected to be perfect. You’ll get better with practice and we’re here to support each other along the way.

Keep us up to date with how you’re getting on, and let us know what we can do to help.


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