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 correctly. Without proper consideration for things like training and mentorship matching, 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 mentor mentee matching?
Simply put: 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 this type of relationship 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 matching is that if you match them based on their industry, skills, or experience, it'll be fine. But this isn’t always the case—there are several other factors that you need to be aware of and plan for.
How to match mentors and mentees
When figuring out how to pair mentors and mentees, sticking employees together and hoping for the best is not a sound strategy.
In the initial planning stages of all mentorship programs, defining the organizational goals is a crucial step since every move you make needs to have that guiding hand. Whether it’s leadership development goals, upskilling and reskilling, and/or strengthening your company culture, these objectives will help you determine how to match mentors and mentees in your program.
Your program’s goals absolutely influence how you approach mentorship matching, but where ‘okay’ pairings turn into ‘great’ pairings is at the individual level. In addition to your 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 old way of mentorship matching
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, mentor mentee matching was 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? Making accurate matches was particularly challenging in companies with hundreds of employees.
Technology has come a long way from spreadsheets. Now, mentor matching software, like Together’s, exists to make mentorship matching far easier.
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 in their own words.
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 individuals, matching mentors and mentees into a well-balanced partnership is far more intuitive, making for mutually valuable pairing.
Here are the questions we recommend in our registration questions template:
Profile questions
- How many years have you spent in your professional career to date?
- How many years have you spent in your current role to date?
- What is your current professional discipline?
- What other professional disciplines are you interested in learning more about or prefer your mentor to be from?
- What other professional disciplines/functions do you have experience in, either here or at other employers?
Skill questions
- [Soft Skills] Which skills are you looking to grow and develop through this program?
- [Soft Skills] Which skills are your greatest strengths; which you can mentor on?
- [Goals] Which goals do you hope to achieve through this program?
- [Goals] Which goals or accomplishments have you achieved in the past, which you can mentor on?
Experiences
- Describe any experiences or learnings you are hoping to get from this mentoring program.
- Describe any experiences or topics you can help with as part of this mentoring program.

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 mentor matching app like Together’s, 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 answer mentorship survey questions upon joining the program and the information they include will be used to automatically recommend ideal pairings.
But the platforms go even deeper than that. You can customize Together’s matching algorithm to prioritize certain answers over others. For instance: what if you want to match pairs based on common goals more than common positions?
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:
- Mentor training
- Complementary personalities
- Skill alignment
- Mentees have a say in the match
- Established boundaries
- Mentorship goals
- Consistent meeting cadence

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 or background.
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:
- Active listening
- 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 sessions
- What good mentoring looks like
- 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 work through new challenges they may experience in the mentoring relationship.
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 a web developer is seeking a mentor, it would be counterproductive to pair them 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 matching 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 set objectives. Is the mentee looking to land their first job in the industry? Develop a portfolio? Learn a new coding language? Both mentor and mentee should talk through their long term career goals.
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, one or both parties decide the mentorship relationship isn’t working, it’s better to end it sooner than later. This allows both parties to move on and find a more successful pairing.
Learn how to match mentors and mentees with Together
Mentorship pairings are complex and unique relationships that can be extremely valuable for both mentor and mentee. Because of this, learning how to match mentors and mentees with care and consideration is your best bet. Plus, leveraging the tools available to you such as Together’s automated mentor mentee matching gives you more time back to focus on running a successful program.
The task of pairing your employees into mentorships that truly work can seem daunting—not just because of the time and effort required, but the chance of getting it wrong. But, with what we explored in this article and new tools at your disposal, you’re ready to take on the challenge.
With a tool like Together, our powerful matching algorithm and automated questionnaires take a lot of the burden of matching mentors and mentees off your shoulders. You'll be able to find the right mentor for each mentee in your organization and create lasting, mutually beneficial 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—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.
Start improving your mentor mentee matching today—book a demo with Together!