How to Make the Best Mentorship Matches: An Overview

A successful mentorship program is engaging, supportive, and ultimately has a lasting impact on the participants. One of the critical pieces of programming is making great matches. Whether you are matching employees, students to alumni, or community members, it’s important to remember that you are working with people. People and their lives are complex, so don’t be afraid to put time and energy into your matching. There are a number of methods and strategies you can use to make matches. Each has their own merit, and while your method may depend on the specifics of your program, the effort and intention behind your choice should always be present. 

To Automate or Not to Automate? 

Many options for mentorship software exist in the market today. So making the choice to use a software to help you automate your matching may depend on the size of your program, the cycle or duration of programming, and even the locations of mentors and mentees. Choosing to make your matches manually works well when you have a smaller group, have more intimate knowledge of participants or need to meet specific matching requirements for funders or employers.

Regardless of the method you choose you will use participant information and their responses to your intake to create your matches. Here are a couple key differences in both methods:

• If using automated matching, algorithms can curate lists of potential matches based on aligned responses and compatibility factors

• Automated systems typically rank potential pairings in order of compatibility, allowing you to review each pair's criteria responses before finalizing matches

• Manual matching can be time intensive, and laborious

• Manual matching is helpful when you have a smaller group or program that requires specific outcomes. Reviewing each person's responses manually can help to narrow down specific choices for matches, or even multiple matches for one mentor or mentee 

The Critical Role of Strategic Matching in Mentorship Success

A well-defined matching strategy is the foundation of any successful mentorship program. Research consistently shows that the quality of the mentor-mentee match is the single most important factor in determining program outcomes. Without a thoughtful approach to pairing participants, even the most well-intentioned mentorship initiatives can fail to deliver meaningful results.

Effective matching goes far beyond simply pairing available mentors with mentees. It requires a systematic approach that considers multiple dimensions of compatibility, including anything from professional goals, personality traits, communication styles, industry experience, and personal values to simple requests from either party. When matches are made strategically, mentees are more likely to remain engaged, achieve their development objectives, and maintain long-term relationships that extend beyond the formal program period. Here is an example of a simple matching strategy for a smaller reskilling focus mentorship program. 

Matching Plan and Timeline: 

1. First match participants who requested specific mentors or those you know well and believe would be a great fit.

2. Next, review mentors and mentees who’ve shared specific requests or preferences. Start with your smallest pool and prioritize matches based on those criteria—for example, mentors who might have requested to support 2SLGBTQ+ mentees.

3. Following those very specific matching requests, match mentee goals with mentor strengths or expertise. Review possible pairs. 

4. Then match mentees by interest with mentors who have relevant expertise.

5. When you have come to the end of the pool of candidates, begin to match based on skill sets that the mentors may have - a plumber with their own business could be a great match for someone who is interested in business management. 

The Program Managers Secret Ingredient? Encourage Feedback and Provide Resources. 

Once matches are created, participants will begin to meet with their matches— ideally your program includes options for participants to reflect on each meeting, and surveys to gather feedback through the program. Encourage participants to ask for support when needed. 

 Some helpful Tips to Keep in Mind: 

• Know Your Participants: Review the participant intakes to understand who’s in your program.

• Stay Goal-Focused: Keep your mentorship program’s objectives in mind with every match.

• Prioritize Inclusion: Be consistent and intentional about promoting diversity.

• Set Expectations Early: Remind participants to stay open-minded—through orientation, agreements, or program messaging.

• Don’t Hesitate to Ask: Reach out to participants if you need more info before matching—it can make all the difference.

Here are some examples of Career Development focused Mentorship programs that have targeted outcomes that help to support matching strategies. 

• Ascend Canada – Emerging Leaders Program

Ascend Canada’s Emerging Leaders Mentorship Program is designed to empower mid-career Pan-Asian professionals by pairing them with senior executives across various sectors, including finance, consulting, and technology. The program focuses on fostering leadership development, enhancing visibility, and building influence within corporate Canada. Through structured mentorship, participants gain insights into navigating corporate hierarchies, developing executive presence, and overcoming cultural barriers that may impede career progression. Mentors, in turn, refine their leadership and coaching skills, contributing to a more inclusive workplace culture. Notably, 92% of mentors reported enhancing their leadership skills through participation.

• TRIEC Mentoring Partnership—ACCES Employment

The TRIEC Mentoring Partnership, facilitated by ACCES Employment, connects skilled immigrants with established professionals in their field to support their integration into the Canadian workforce. This three-month program focuses on helping newcomers understand industry trends, develop effective job search strategies, and build professional networks. Participants in the program have reported significant improvements in their employment outcomes. An evaluation found that skilled newcomers who engaged in the mentorship were 2.45 times more likely to secure good-quality employment within three months compared to those who did not participate. Additionally, over 80% of mentees reported enhanced job search skills and a better understanding of the Canadian labour market.