Mentorship programs

Matching mentors and mentees: The process to get it right

The success of a workplace mentoring program hinges on a good, solid mentor-mentee match. Together's mentoring software can help streamline the matching process.

Nick Saraev

Published on 

May 18, 2022

Updated on 

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There's no doubt that mentorship is an incredibly powerful tool. Mentorship research points out that 9 out of 10 employees who have career mentors are happy in their jobs, and 89% of mentees will successfully go on to become mentors themselves.

But these stats only apply if mentorship is done properly. Without proper consideration for things like training and matching the right pairs, only 1 in 3 mentorships are actually successful.

With this in mind, how can you make sure your mentorship program results in benefits for both mentors and mentees? Let's take a look.

How important is the mentor-mentee match?

Easy – it's crucial. 

Just as not everyone will be compatible as friends, the same goes for mentors and mentees. The relationship between the two should be one of trust, respect, and communication in order for it to be successful – but there's no guarantee that this will happen just because someone is placed into a mentor role.

Remember, the mentee is looking for guidance and support, while the mentor should be providing advice, feedback, and direction. If these roles are not properly balanced or if there's a mismatch in personalities, it can lead to frustration and resentment.

A common misunderstanding about mentor-mentee relationships is that if you match them based on their industry, skills, or experience, it'll be fine. But this is not the case – there are several other things you need to take into account.

For example, Jodi Petersen and Mary Schlegel from MentorStrat, a mentoring consulting and training firm, spoke with our team to understand what first-time program managers need to know to run a successful mentoring program.

They emphasized that the goals of the program should dictate who's matched with whom:

In addition to the program's goals, here are a few other questions to ask when assessing mentor-mentee pairings:

  • Are they risk-averse or risk-tolerant?
  • Do they like to plan and organize, or are they more spontaneous?
  • Do they like to take charge and be in control, or are they happy to let someone else take the lead?
  • Are they analytical or more creative?

These questions will give you an idea of their distinct working styles. Of course, you don't need to match personalities and work styles exactly – but it's important that you're aware of them and that you do your best to avoid clashes.

The difference between 'okay' matching and 'great matching'
 A great mentor-mentee match shares more than just work experience. It includes the unique traits that make us individuals. Finding overlap there is what makes a great match.

The old way to match mentors and mentees

People have been aware of the mentor-mentee mismatch issue for a long time, but the technology hasn't always existed to do something about it.

Traditionally, mentors and mentees were matched based on their similarities – if they had the same skills, for example, or came from a similar background. But it was all worked out on pen and paper, which took a lot of time and effort (with plenty of room for error).

Even when HR professionals started using spreadsheets, how could one or two people accurately and efficiently capture all the information needed to make a successful mentorship match? Especially in companies with tens or hundreds of employees, making accurate matches was next to impossible.

Thankfully, technology has come to the rescue, and Together is part of the new solution.

The new way: automating the mentor-mentee matching questionnaire

Rather than poring over employee profiles for hours and matching them based on vague, half-absent details, it's far easier to have employees fill out a mentor-mentee matching questionnaire. That way, you can ask all the right questions and get a better understanding of their skills and personality traits.

But what questions are best asked? When organizations sign up with Together, we recommend asking questions across three main categories:

  • Profile questions are about the individual and their work history. They might include questions about an individual's specific experience with disciplines and functions.
  • Skill questions probe into an individual's strengths and weaknesses, soft skills, and goals.
  • Experience questions ask about what the employee is hoping to gain from the mentorship, and what they can bring to the table.

The goal is to create a well-rounded questionnaire that will help you find the best mentor for each mentee. By focusing on the individual, you can help pair them with the perfect mentor who will help them grow and develop in their career.

Here are the questions we recommend in our registration questions template:

Profile questions

  1. How many years have you spent in your professional career to date?
  2. How many years have you spent in your current role to date?
  3. What is your current professional discipline?
  4. What other professional disciplines are you interested in learning more about or prefer your mentor to be from?
  5. What other professional disciplines/functions do you have experience in, either here or at other employers?

Skill questions

  1. [Soft Skills] Which skills are you looking to grow and develop through this program?
  2. [Soft Skills] Which skills are your greatest strengths; which you can mentor on?
  3. [Goals] Which goals do you hope to achieve through this program?
  4. [Goals] Which goals or accomplishments have you achieved in the past, which you can mentor on?


  1. Describe any experiences or learnings you are hoping to get from this mentoring program.
  2. Describe any experiences or topics you can help with as part of this mentoring program.
Download the Registration questionnaire template
Click the image to access the the 11 different questions you should ask during registration to help pair mentors and mentees.

Automating the registration questionnaire with Together

We are fortunate to live in an age where technology makes it possible to automate menial tasks like this. By using a tool like Together, you can easily create and manage a questionnaire like the one described above.

Together’s mentorship platform automates the registration process and makes it easy to set up employees as mentors and mentees. Your employees are issued a questionnaire upon joining the program and their information is then used to automatically recommend ideal pairings.

But the platforms go even deeper than that. With Together, you can customize our algorithm to prioritize certain answers over others. For instance: what if you want to match pairs based on common goals more than common positions? With Together, you can easily make changes to suit the program you’re running.

Mentorship doesn't have to be an uphill battle – and Together makes it a walk in the park.

Principles for a great mentor match

Regardless of the pairing method you use, there are some key principles to keep in mind when making a mentor match. 

Principles for a great mentor match

Mentors should have some training

It's usually not sufficient to pair employees off and hope for the best. Work skills don't always translate into mentoring skills, and a great mentor match comes down to more than just sharing a common interest. 

That's why it's important for mentors to have some training in mentoring, so they know how to give feedback, navigate difficult conversations, and set boundaries.

Mentor training programs should ideally cover the following:

  • How to listen to mentees;
  • Communication strategies;
  • How to help mentees identify and work towards their goals;
  • What’s expected of the mentor in your mentoring program;
  • What mentors and mentees should discuss during their session;
  • What good mentoring looks like; and,
  • Tips for building an effective mentoring relationship. 

Even if you have full confidence in your mentors, it never hurts to give them a refresher on best practices, and a chance to share any challenges they may be experiencing.

Personality types may not matter that much – but don’t ignore them

It's a good idea to avoid personality clashes where possible. Beyond that, though, personality matches aren't the be-all and end-all. According to an article in the Mentoring & Tutoring: Partnership in Learning journal:

“Where learning is to occur, therefore, then dissimilarity may be an advantage. Earlier empirical evidence, which profiled 50 adult mentoring pairs, found that mentor–protégé pairs were no more alike or dissimilar than control pairs (Alleman & Newman, cited in Haines, 2003), suggesting that in traditional mentoring relationships similarity of personality is not a critical factor."

Still, it's worth giving personalities and work styles some thought before making a match. Our own surveys have found that 52 percent of employees believe shared interests are important to the success of their partnership.

Mentors should have the skills mentees want

This is likely a no-brainer, but is worth mentioning regardless; mentors should be proficient in the specific skill set or area of knowledge that the mentee desires to learn. If you’re a web developer seeking a mentor, it would be counterproductive to be paired with someone who specializes in mechanical engineering. 

Granted, there are likely transferable skillsets and principles that can be learned from one another; but the focus of the mentorship should be on what the mentee wants to learn, not what the mentor already knows.

Mentees want options

Our studies show that, unlike lifelong friendships or relationships, mentees fully desire and expect to move through 2-3 different mentors during their career.

Mentorship pairing is a unique opportunity to learn from someone with more experience in a specific area, and then to pass that learning on to the next mentor. This provides the mentee with continual growth and development opportunities, versus sticking with one mentor for an extended period of time.

Clear boundaries and responsibilities

Mentorship pairings cannot function optimally if boundaries aren't set from the get-go. Both mentors and mentees need to be clear on what is expected of one another, and what the time commitment looks like.

Some of the most crucial boundaries to set include: 

  • Communication. How often will you be in touch with each other? What is the best way to communicate (email, phone call, Slack, etc)?
  • Meeting. How often should you meet in person? 
  • Topics of discussion. What are the specific areas you want to focus on during your mentorship? Is there anything you'd rather not discuss? 
  • Roles. What is the mentee's role in the relationship? What is the mentor's role? 
  • Duration. How long do both parties anticipate the mentorship to last? 

With the right boundaries in place, it becomes far less likely that either the mentor or mentee will feel taken advantage of.

Goals and objectives are developed

In the same conversation that pairs discuss boundaries, they should also be exchanging goals and setting objectives. Are you looking to land your first job in the industry? Develop a portfolio? Learn a new coding language?

Both mentors and mentees should have attainable goals that they're working towards, and regular check-ins should be scheduled to ensure both are on track. This can also help to prevent either party from feeling lost or unsupported.

Regular assessment of the relationship’s success

Like a garden, mentorships should be maintained regularly, or they'll struggle to make it past germination. This means assessing the relationship's success on a consistent basis.

Some factors that could be looked at include: 

  • The objectives of the mentorship. Have these been achieved? 
  • The chemistry between the mentor and mentee. Is it positive? Negative? Do both parties feel they are getting something out of the relationship? 
  • The level of communication. Is it appropriate for the mentorship? 
  • The amount of time spent together. Is this what was agreed upon at the beginning of the pairing? 

If, after assessing these factors, it is decided that the mentorship is not working, it is better to end it sooner rather than later. This allows both parties to move on and find a more successful pairing.

Mentorship pairings are complex and unique relationships that can provide great value to both the mentor and mentee – and as such, should be treated with care. Your best chance at pairing all of your employees successfully is via a tool like Together, where pairings are tailored, automated, and designed to last.


If you are faced with the task of pairing your organization into mentorships that truly work, it's likely that you are feeling daunted – not just by the time and effort required, but by the prospect of getting it wrong. 

With a tool like Together, all of that stress is swept away with our powerful matching algorithm and automated questionnaires. You'll be able to find the right mentor for each mentee in your organization and create lasting and mutually valuable relationships.

Above all, remember that the right pairs can be found through careful consideration of both mentors and mentees. Don't just focus on their personality types or areas of expertise – also think about what the mentee wants to get out of the experience. With a little effort, you can create an amazing program that benefits everyone involved.

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