ReachShout - What Matters in a Match?

Creating impactful mentoring relationships.

In the latest in a series of blogs sharing some of the key conversations we’re having at ReachOut, Head of Delivery Joy Upchurch shares her thoughts on what’s important when it comes to matching mentors and mentees.

“My mentor is absolutely amazing.  She reminds me that there’s a reason to put in the hard work because the end result is always worth it.”

We hear something like this every day at ReachOut. Our mentees are always so excited to tell us how much they value the relationship with their mentor; how much they support them; how much they’ve learned. 

This year we’re aiming to support almost 1,200 young people, each of whom we’re aiming to match with an adult mentor. That’s a lot of mentors and mentees who are going to be working together over the course of the year.

We know that when a mentoring relationship flourishes, it can have an enormous impact on both parties, helping everyone involved to grow in character and confidence, develop new skills, break down preconceptions, and expand horizons and outlooks.

Matching is both an art and a science – it requires a mixture of instinct and research. Setting up a relationship that will work consistently over the long term can be a complicated undertaking, but it’s worth putting in the effort upfront to get it right.

Here are some of the key steps we take, and things we look out for, when matching our mentors and mentees:

1) Gather as much insight as possible about mentees and mentors.

A mentee’s goals and background, likes and dislikes, as well as a mentor’s life experiences, motivations and interests are all key things we seek to learn about in detail before making a match.   

After our mentors have been through their training and safeguarding courses, we hold sessions on Zoom to get to know them better. Through ice-breaker activities as well as relaxed group discussions, we can get the insight we need into what they can offer their mentee.

For our young people, our initial insight comes from their teachers who can give us a good idea of the support they need from a mentor. We’ve found that the more information we can get from schools at this point about who the young people are as individuals, the easier it is to find them the right mentor.

2) Don’t rush into a match- give everyone the chance to get to know each other.

We don’t match our mentees and mentors until at least two weeks into our projects. In these initial stages, we facilitate a variety of discussions between mentors and mentees – including “speed mentoring” – so everyone gets to know each other.

We make sure to provide guidance for these discussions to facilitate meaningful learning and support everyone involved to identify shared interests, goals and experiences that could make for a brilliant partnership. 

It’s so important to gather as much information as possible to ensure that mentees can relate to their mentors whilst also being exposed to new points of view and experiences. If their mentor is someone they can see as an additional role model, someone they can feel comfortable being themselves with, it can break down barriers and spark the connection needed to build that strong relationship.

3) Be led by a mentee’s preference – but consider wider factors when making the final decision.

Understanding, and giving real weight to a mentee’s preference, is an important part of our process. We want every young person to feel comfortable and confident with their new mentor.

After everyone has got to know each other, we ask our mentees to pick two-three mentors they would like to work with – and we ask our mentors to do the same.

Whilst mentee preference is so important, and very often indicative of which matches will lead to excellent mentoring relationships, this needs to be balanced with a holistic view of what we’ve learned about that young person and there are times when other factors may equip another mentor to be a more suitable match.

In the end, it’s our responsibility to take all the different factors into account, looking holistically at what we think will be best for our mentees and their mentors.

Our team have a lot of experience matching mentors and mentees and we’re confident that our matching strategies are successful and lead to positive outcomes.

However, we’re always learning and looking to improve the way we do things.

For example, whilst we know that the ability for a mentee to relate to their mentor goes far beyond demographics like ethnicity and gender, we’re working hard to recruit more mentors that are representative of the areas that they’re working in and the young people they’re working with.

We’re also thinking about how long our mentors and mentees spend as a group before matching – potentially extending this period beyond the first two weeks to gain a deeper understanding of who our mentees are and the support they need. 

These learnings are a vital part of our continued development as an organisation – and we’ll share them with you as we adapt and improve the way we work. 

Our mentoring programmes can only be successful with the incredible support of our dedicated volunteers. If you think you could spend 1-2 hours a week supporting a young person as a volunteer mentor, head to to find out more.

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“At first, I was really hesitant to take on the Project Leader role, despite having mentored with ReachOut. However, with the support of the team I’ve really developed my skills. For example, at the Mentee Graduation, I stood up in front of 200 people and presented an award which is something I would never ever have been able to have done before, and isn’t an opportunity I could gain in my other situations.”

Amy McCutcheon, Project Leader at ReachOut Academy, Dean Trust Ardwick, Manchester.


“Being able to spend the summer working at Rede Partners, was an amazing experience. Whether it was working in HR or Finance, I learned so much about the world of private equity, made great connections with fantastic people and I got to learn first-hand what it would be like to work there! I really believe that I can go onto build the career I want now I’ve been a part for a workplace for real”

Victor Adekunle, 18 years old, ReachOut Ambassador, London


“When I first my mentee, she was very reluctant to participate in the sessions. Now, I see a completely different person! Her confidence has grown and she is happy to join in! She still has some self-doubt when it comes to academic work, but that’s what I hope to help her overcome, because she is a very bright person!

Through mentoring, I’ve learnt I’m a lot more patient than I realised. There will be days where she refuses to participate and those are the days that I really see the importance of the character strengths, for both the mentees and the mentors. It also makes it easier for the mentee to understand the character strengths, when I use them myself”

Myrtle, ReachOut Club mentor at Tufnell Primary School, London


“There are more distractions than ever outside of school, and the commitment of our students to attend ReachOut sessions is testament to the value they place on the relationships they foster there, and the challenge and enjoyment they provide.

ReachOut’s focus on communication skills and character development has become an important aspect of our provision of support for these students. The opportunity to relate to a positive role- model other than their usual teachers is key to the programme’s impact, and the evidence of this has been seen in the students’ attendance, resilience and to their overall progress across all the subjects in the school.”

Thomas Janvrin, Assistant Vice Principal at the Petchey Academy London