Mentor Matching: How to Make Career-Changing Pairings

The mentor-mentee match is critical to a mentorship program's success and benefits your entire organization. Here’s how to create the ideal pairings for more meaningful matches.

Matthew Reeves

CEO of Together

Published on 

January 11, 2022

Updated on 

October 27, 2023

Time to Read

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In its Workplace Learning Report, LinkedIn cited mentorship as the primary L&D focus area for 2023. But research from Gallup reveals that just 40% of workers have a mentor (and less than a quarter have sponsors).

It’s an odd disconnect when you consider that workers with mentors have more success in the workplace, are more likely to stick with your company, and experience higher employee satisfaction. 

But you can’t just randomly pair up coworkers and hope for the best. Mentees want a mentor who has faced the same challenges as them. And left to their own devices, the majority of mentors will choose mentees who look like them

Successful mentor-mentee pairings require a clear plan of action within your mentorship program. 

Which employees should be matched with a mentor?

Ideally, all employees will have a mentor at some point in their career, but certain employees benefit more from being paired with mentors:

  • New hires can be paired with a mentor during onboarding to learn the ropes and create social connections with other employees. 
  • Junior employees learn leadership skills, set goals, and expand their network. 
  • Employees from underrepresented backgrounds benefit from greater visibility within the company and more face time with leadership.  
  • Remote employees can develop skills, cultivate connections, and stay in the loop about possible advancement opportunities — areas where remote employees often miss out. 

What are the criteria for matching mentors?

Mentors need certain qualifications or traits for successful mentoring relationships. These characteristics set the tone for the mentoring experience

Potential mentors should be: 

Committed to mentoring

A mentor should value and believe in mentoring. As your mentoring program grows, ask former mentees to return as mentors. Employees who have experienced the advantages of mentoring themselves will be more committed to the process. 

Invested in others’ success

Successful mentors have a genuine interest in seeing others advance and grow. Look for someone who has demonstrated a passion for helping others or shown interest in a teammate's career development. They have a coaching-type personality and will inspire others with their positivity and leadership. 

Experienced communicators

Mentors who understand how to communicate in a way that will be most effective for the learning process are pros at helping others to grow. For example, mentors may be called upon to critique a report or presentation of their mentee. Constructive criticism works best when it’s tailored to each individual, and a mentor with solid communication skills will know how to do this.

Focused on guiding mentees

Mentorship is a learning experience, and mentees will learn more if they can discover the solution themselves. Using variations of the Socratic Method, mentors can help mentees find their own answers rather than tell them what to do. 

Curious about the world

The best mentors are well-read and enjoy staying up-to-date on a variety of topics. They love learning and will encourage and inspire others to become lifelong learners, which will help your organization build a culture of learning.

How do you choose mentors for your mentorship program?

There is no one right mentor for all mentoring programs. Any leaders or seasoned employees in your organization who have these qualities should be encouraged to be mentors but how you choose mentors will depend on the goals of your program

In a discussion with the mentoring consults at MentorStrat, L&D Lead Mary Schlegel said it’s best to recruit mentors differently for each program. 

For instance, in their reverse mentoring program, MentorStrat paired up junior employees and executives for skillsharing. The junior employees would serve as the mentors, so Mary wanted participation across a diverse set of candidates. With that in mind, the L&D team established broad criteria: any employees without performance issues were eligible to sign up and share their skills as mentors.

“Before you go about just setting criteria and saying well, this is what I think an ideal mentor looks like, take a look at what your goals are and then partner with the people that make sense depending on the objectives you're trying to accomplish and get their input.” – Mary Schlegel, Learning and Development Lead at MentorStrat
🧠 Learn More: What First-Time Mentorship Program Managers Need to Know to be Successful

How do you match someone with a mentor?

Mentor-mentee matches can make or break a mentorship program. An effective mentoring program includes a repeatable process for successful matches. Most programs handle this in one of two ways: manually or with mentor-matching software

Manually matching mentors

If your mentoring program is relatively small, you can get by with manually matching mentors. However, this strategy requires that you know your employees really well. If not, you’ll need to set up a method for collecting info on your participants. 

A registration survey will give you an idea about each participant’s mentorship goals. To keep your matching system manageable, we recommend separate surveys for mentors and mentees that only use limited or multiple choice responses. That way, once everyone is registered, you can use that info to make mentoring matches right away.

To make your pairs, keep track of names and details in a spreadsheet or project management tool. That way you can easily sort them by goals so you can find every mentee their ideal mentor.

Of course, matching mentors with mentees this way takes a lot of time. It can also be difficult to scale. In other words, it can limit you. 

Using mentor matching software

As your mentoring program grows, effective mentor-mentee matching can be overwhelming, especially if you’re also managing your workplace mentoring programs. That’s why many L&D teams use mentor matching software. These tools make pairing quick, informed, and scalable.

Together’s mentor matching engine creates pairings based on a questionnaire participants fill out during the registration process.

Catherine Marchand from the People and Culture Team at moved her mentoring program from Excel to Together’s mentoring platform. In our Mentorship Round-Table, Catherine said, “As we grew in size and expanded across different functional units in our program, nothing was really that simple anymore. So having the tools to manage that complexity is very, very valuable. With Together, we’re able to funnel everyone through a consistent, structured, and supportive [pairing] process.”

Together’s intuitive algorithm makes the matching process easy and scalable by tailoring matches to your specifications. You identify your program type, set up a questionnaire for participants, and decide on a pairing process — and you have full control of which criteria matter most. 

The result? A matching process with a 98% satisfaction rate that scales with your mentoring program. 

🧠 Learn more about intelligent matching with Together

What is the best way to match mentees and mentors?

Once you decide how you will manage mentor-mentee matches, you’ll need to decide the type of match. You can do this manually or with software. Broadly speaking, there are two ways to make matches:

  1. Mentee-led
  2. Admin-led

Here’s what you need to know about each matching type.


Mentee-led matching means that mentees choose their own mentors from a pool of possible matches. With Together's pairing algorithm, mentees can shortlist their top five mentors. If their first choice already has a match or they deny the request, Together automatically moves to  the next mentor on their list. This goes on until a match is made.

Mentees often prefer this strategy because they have the power to decide who is the best match for them. One downside is that mentees may all run for a select few mentors. 

For example, all of your junior executives may want to be mentored by the CEO. Or sales reps may all want to be paired with the top performer or an experienced mentor. 

For this reason, many HR teams managing the program may opt for admin matching.


Admin-led matches allow program managers to choose the mentoring pairs. Using employment data or survey responses, the team identifies potential successful pairings. Matches can be based on several criteria, including skills, backgrounds, shared interests, career goals, etc. 

Although this puts more control in the hands of professionals, it can add additional layers and time to the pairing process. With mentor matching software like Together, there is an option for auto-matching, where suggestions are automatically given to the program admin, and they just need to 'approve' the match. 

😎 Having trouble recruiting busy executives to your mentoring program? Read our guide

How to fix a poor mentor match

Not all matches work out, and that’s alright. The important thing is to address bad matches quickly. You don't want a negative experience to sour your participants' experience with mentorship. It will limit their opportunities for growth and learning. 

If you need to end a mentorship prematurely, ask both parties for feedback. Dig into what went wrong so you can improve the matching process in the future. 

Then get to work making a new match. You’ve got even more info about their preferences now. You’ll either put that info into your mentor-matching software or scour your spreadsheets for an ideal match. Either way it will take a bit of work to help them have a positive mentorship experience. 

Together’s algorithm makes the mentor matching process easy

Getting a good mentor-mentee match can seem difficult, but it doesn’t have to be. If you’re not interested in spending hours manually matching mentors and mentees, consider trying out Together’s mentoring software

Curious how Together can help you match up your employees with the ideal mentor? Book a demo with our team.

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