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12.02.21

Six expert tips to achieve the most successful mentoring matches

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Jo Gray
Jo Gray Director of Membership Services and Engagement Youth Business International

Matching participants is one of the most important steps in a mentoring programme and one of the first questions that participants will ask you  – so designing a clear approach and getting that right will make the biggest difference to your programme's success.

Our Director of Membership Services and Engagement, Jo Gray, shares six tips for successful mentoring matching.  

Mentor matching is an art, not a science, so the rules aren’t hard and fast. Relationship success in mentoring is directly linked to the level of rapport established, so it’s important to be confident that the people matched will get along and be able to work together. 

When you have a good match, a young entrepreneur will be supported to develop both personally and professionally. In a time where youth unemployment is growing, mentoring is key to help young business owners survive the COVID-19 financial crisis. It’s in this context that the YBI network stood up to the challenge and implemented the global SOS mentoring programme.  

For more than a decade, our network has been using mentoring as a tool for driving effective support for young entrepreneurs. Part of this work meant designing programmes with the best matching processes so that organisations ensure the best possible fit. But how can we nail the art of mentor matching?  

Matching tips for a successful mentoring relationship 

  1. Think differently. While it’s instinctive to pair those with the most in common, it’s also important to make sure there is enough differenced to enable opportunities for learning. Does a mentor have to do what the mentee does?  - the pool of mentors available might not have the exact skills to match. The key is really in the broader experience in the world of entrepreneurship or business that helps. 
  2. See people as individuals. Although matches are made via identified criteria, it is helpful to know something about the people behind the names. It will be important to know that the pair will be able to build rapport and having a common area of interest can support this.   Think about who people are as individuals as well as what type of support they are looking for. If they don’t get on - it will never work 
  3. The personal touch. Anyone who has ever been involved in matching will tell you that the personal touch or intuition is key. If you have time to explain matching choices to mentees (if they are not choosing themselves) or to get their feedback, the level of commitment to the match is much stronger. 
  4. Recognise the wrong match. Ensure you build in the option for pairs to go their separate ways if they feel the match is not right. Also don’t be afraid to re-match people. We are dealing with human beings and any mentoring programme will always have a small percentage of relationships that do not work. Intervene early and support pairs to move on 
  5. It’s two-way learning. Great matches, needs great participants. Make sure you recruit mentors who see mentoring as a two way learning experience and not solely about giving something back. You also need to work with mentees that understand how mentoring works – so preparing both to get the most out of the relationship is important.  
  6. Manage expectations. Don’t put expectations out of reach by having too many criteria when you match pairs. Designing a clear process and helping your participants to understand this is critical. If there is no opportunity to choose you need to explain why. 


Digital tools are constantly improving and are used more and more to support mentoring programmes to scale, and the wonder of AI supporting the matching process gets better every year. While this is helpful, practitioners who have been involved with mentoring for years (in my time alone I’ve matched hundreds of mentoring pairs) will tell you that while the science speeds things up, the art is in the deep understanding of people and what makes relationships work. If you manage to bring the best of digital and human together you might just crack it. 

Did you know that we have supported over 40 YBI members to design and launch their own mentoring programmes? Read our learnings and recommendations to organisations after more than a decade  designing and implementing mentoring programmes.  

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