How to Structure a Mentorship Program: Proven L&D Insights

In theory, mentorship makes perfect sense: You take a seasoned pro, pair them with a less experienced mentee, and give them room to cultivate their relationship and grow their skills. It all sounds so simple! But when it comes to how to structure a mentorship program, it turns out there are countless obstacles that come up—administrative and logistical hurdles as well as big, important questions, like how to prove your program is even working.

If you’ve ever felt frustrated or stuck dealing with all the little details, you’re not alone. That’s why we’ve collected insights and advice from mentorship program managers. Our goal is to help you anticipate common challenges and structure your program so it has the best chances of success.

👋 P.S. Want more insights on how to structure a mentorship program? Book a chat with one of our mentorship experts to learn best practices, insights from top companies, and how Together can help you build a thriving mentorship culture.

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How to structure a mentorship program: Experts share their mentorship program guidelines

What are the key components of a successful mentorship program? We turned to L&D and mentorship experts to uncover their best practices as well as their benchmarks for the types of results you can expect. Here’s what they told us.

1. Start with business goals to inform your mentoring program structure

Establishing clear and concise mentorship goals is a foundational pillar of a successful mentorship program. Ensure that the goals you set for your mentorship program align with your broader business objectives. 

“Consider the program’s target, whether it be career development, DEIB, onboarding or a global community,” says Meaghan Shepherd, Director of Customer Success at Together, who has helped hundreds of mentorship programs get up and running. “Customization is key; ensure the program caters specifically to its primary use case.” 

Here’s an example from Together customer Wellabe, an insurance company with around 400 employees: Wellabe already had a low voluntary turnover rate of 6.4%, but Senior Learning & Development Specialist Joey Spivey wanted to protect and reinforce it—especially during periods of transformation, including a CEO transition and product line restructuring. 

Joey emphasized that mentorship became a critical tool in ensuring employee “stickiness,” especially during their critical early months. Wellabe’s 90-day onboarding program, “Culture Colleagues,” paired new hires with seasoned employees to support integration and cultural alignment.

And it worked! Wellabe maintained their turnover rate, which Joey credits to structuring the mentorship program around retention outcomes. “We’ve had significant organizational change, and our turnover rate is still at 6.4%. Mentoring helps keep it there,” says Joey.

Joey’s also seen qualitative feedback that demonstrates the success of the revamped onboarding program. Onboarding surveys began to reflect deeper, more enthusiastic comments about new hires’ relationships and support systems. One new hire described the culture as “a breath of fresh air.”

The Culture Colleagues program has also led to renewed commitment from more established employees. Those who serve as Culture Colleagues report a deeper sense of fulfillment in their work and many have eagerly volunteered to re-enlist in future cohorts.

Hear more from Joey on how Wellabe created different goals for different mentoring programs:

💡Expert tip: The experts agree that it’s better to create separate programs with distinct goals than to create a single program that aims to be all things to everyone. 

2. Build your mentorship plan around intentional participant pairing

How do you approach pairing mentors and mentees? The decisions you make about pairing methodologies, data modeling, and architecture design are critical to your mentoring program’s success. Make sure you think through these topics early in your mentoring program design process. 

One L&D leader and Together customer, Andy Wade, who works as a Training Programs Manager at Fortive (a subsidiary of facility and asset lifecycle company Gordian), explains his two-pronged approach to pairing methodology. There are some rules where admins set the match strength and others where the users (AKA mentors and mentees) set the match strength.

Rules where admins set match strength

• Capacity: They want to make sure mentors don’t get bogged down by too many mentees, so they set capacity rules to limit the number of mentees a mentor can be paired with.
• OpCo: Fortive is a large company with many smaller operating companies (or “OpCos” as they call them) that roll up into it. They set a rule that both the mentor and mentee must identify that they want a match within the same OpCo, or they won’t be an eligible match.
• Time zone: They don’t want mentors feeling like they have to be awake in the middle of the night to have conversations with their mentees, so Fortive has set a maximum of a seven-hour time difference to avoid that situation.

Rules where users can set match strength

• Leadership and management skills
• Interpersonal and communication skills
• Personal development and self-improvement skills
• Career management skills

“This combination of rules allows us to set everyone up for success while still having the flexibility to find the best match,” said Andy. 

In addition to thinking about what criteria you’ll use for pairing participants, it’s also important to consider who will need to be involved in the approval process for potential matches. 

Kelly Pope, Onboarding & Development Programs Manager at The Compass Group, explained her company’s approach: “The Connect program uses user-led matching, so it has a one-sided user approval. Users can pick from some recommended matches or they can browse in there from all the people who are registered for that program… The Grow program is more traditional—it’s that intentional, longer-term focus on career development, so this one has also user-led matching, but two-sided approval, meaning that the mentee submits their shortlist of preferred mentors, and then the mentor can approve that match.”

Another Together customer, Joan Skelton, the Global Director of Diversity and Inclusion at Avison Young, describes the impact of thoughtfully pairing participants on her company’s mentoring program outcomes: “Creating meaningful pairings was essential to the success of our program,” said Joan. “Together’s platform does all the work in matching people based upon what they want and need in a mentoring relationship allowing for a truly customized experience for each mentee.”

Here are a few of the outcomes Avison Young’s mentorship program achieved:

• They paired over 550 participants. 
• The average rating for each mentoring pair was 3.97 out of 4.
• 98% of participants rated the program as satisfactory or very satisfactory.
• The company saw a decrease in turnover and an increase in retention. “That’s attributable, at least in part, to the implementation of the Together Platform,” said Joan.

One final piece of advice from Together Solution Engineer Keagan McMahon: Some companies find it beneficial to leave more flexibility in pairing rather than being too rigid. “Aim for a less restrictive set of pairing rules and encourage users to pair outside of what they would assume their ideal mentor might be. You never know what you might learn from someone you didn’t expect to engage with at your organization,” says Keagan.

💡Expert tip: When setting up pairing criteria, the experts agree you should set simple rules (like preventing mentees from being paired with their direct manager), but also try to leave flexibility in the system. You never know what magic might take place when unexpected pairings occur!

3. Design a scalable mentorship structure that reduces admin burden 

One of the biggest roadblocks to successful mentoring programs is when program managers get caught up in administrative work, whether that’s pairing participants, sending reminders, or creating customized materials to guide mentoring sessions.

Here’s a real-life example from Together customer Cruise. When Cruise launched a pilot mentorship program for their 1000+ person engineering department, their program managers quickly realized that coordinating hundreds of pairings between junior and senior engineers was a huge administrative burden. 

Mentoring software gave them a scalable way to pair senior and junior engineers and provide them with resources that supported a strong mentoring relationship.

Mentoring software also automated the registration and pairing process, condensing a task that would have taken up several days of the program managers’ time into just a few minutes’ worth of work. 

But wait, there’s more! Their mentoring platform, Together, also provided templated mentoring agendas to guide the participants’ conversations. Each agenda included guiding questions, links to articles, TED Talks, and other resources that encouraged meaningful conversations around their skills and goals.

Having these agendas automatically available made it easier for Cruise to launch their program and reduced the administrative burden on the program managers. As a result, Cruise was able to enroll 50% more engineers in their pilot mentorship program than they’d anticipated (300 vs. the 200 they’d initially planned).

Plus, participants loved the experience! On a scale out of 4, the average rating mentors and mentees gave was 3.8.

Program participants also shared feedback that praised the program’s effectiveness, saying things like: 

• "The session was great. We were able to talk about a specific problem and come up with some actionable solutions.”
• “After a brief catch-up, we dove deep into [my mentee’s] top three priorities, and how to convert them to actions...I feel very positively about the future of mentorship sessions with [my mentee]. He is very aware of his gaps and able to articulate ways to improve. Looking forward to diving deeper and nailing down some concrete action items with him."

4. Think like a marketer when promoting your mentorship program

It’s not enough to simply launch your mentorship program and hope that employees will automatically sign up in droves. L&D leaders agree that you need to think like a marketer when promoting your mentorship program. This means you clearly communicate details like when the mentorship program is starting, what participants can expect (along with the benefits of participating), and how to register. 

Let’s hear from Kelly Pope, Onboarding Program Manager at The Compass Group. Kelly shares several best practices that worked well for promoting her company’s mentorship program.

Think beyond the basics

“We knew we needed more than an announcement email. We needed energy. We needed visibility. And most of all, we needed to make mentorship feel approachable and even… fun,” says Kelly.

Design timely and multi-stage campaigns 

Kelly timed the campaign to coincide with the beginning of the new year and called it “New Year, New Mentor.” This campaign ran during the first quarter of the year and came with a clear message: “Make mentorship part of your New Year’s resolution.” 

And it went beyond a simple announcement email. Here are a few of the other elements of the campaign:

• Kelly created a video where she explained how the programs worked, who they were for, and what participants could expect.
• They ran targeted communications across town halls, district calls, and regional team meetings so the message stayed top of mind. 

Consider offering an incentive

At The Compass Group, everyone who joined and completed at least one mentorship session during the campaign period was entered into a prize drawing. Kelly described this tactic as, “Simple, fun, and effective.”

And the results? The Compass Group saw a 39% increase in scheduled sessions compared to the previous period. “Better yet, people kept booking sessions after the campaign ended, with over 60 hours of future meetings already scheduled,” says Kelly. “The momentum was real—and lasting.”

💡Expert tip: Remember that while the benefits of mentoring might be obvious to you, potential participants might need a little extra nudge to see this. Look for ways you can play up the fun factor and show them why participating can have a positive impact on their lives and careers.

5. Build measurement into your mentoring plan from day one

We mentioned earlier that it’s essential to define program goals (and connect them to your business goals). But the best-performing mentorship programs don’t stop there: They’re designed with measurement frameworks and feedback loops so they can continue to be refined and improved over time.

For example, when you design your program, think about when and how you’ll collect feedback from program participants. Waiting until the very end of the program means you’re potentially missing the opportunity to identify issues and correct them.  

Robert Kaskel, VP of People at ezCater, encourages creating clear mentorship timelines so you can ensure regular check-ins and goal-setting happen for every pair: “You should also include program evaluations for the mentor and mentee along the timeline so you can see how well you're measuring up to expectations and effectively fostering professional relationships.” 

You might recall Together customer Wellabe defined their goal as keeping the company’s turnover rate low. In order to monitor how the mentorship program was impacting this metric, the company conducted engagement surveys to monitor employees’ favorability scores as well as onboarding surveys to assess how new hires felt about their relationships and support systems.

💡Expert tip: Feedback is a gift! Experts agree that regular feedback from program participants is what separates the best-performing mentorship programs from the rest.

What is a mentorship program? Your essential mentorship program outline 

Now that we’ve covered the best practices that will help you structure your mentorship program, let’s look at a more fundamental question. What exactly is a mentorship program and how does it differ from other L&D programs?

• At its core, mentorship involves an experienced individual or “mentor” who dedicates time to guiding, advising, and supporting a coworker or “mentee.”
• Mentorship is a form of social learning, which means that employees work together to find solutions to their challenges, work through problems, and make plans to develop skill sets they’ll need to excel in their current roles and in the future. 
• Unlike typical learning or training, mentoring involves highly personalized discussions where mentors share their lived experiences, mistakes, triumphs, and the wisdom they’ve gained along the way. The mentee brings fresh perspectives, new challenges, and the willingness to learn and grow. 
• While mentorship can happen naturally, structured mentorship programs in the workplace bring more intentionality to the process. To build this type of structured mentorship program, you’ll need to define clear objectives, consider how you’ll find compatible participants, and set the tone and pace so everyone gets maximum value from the program.
• Mentorship discussions don’t necessarily need to be confined to professional development. In addition to topics like industry insights and career strategies, mentorship discussions can cover work-life balance, managing stress, and navigating personal challenges. 

Mentoring plan overview

Once you’re ready to begin building your mentoring program, you’ll want to consider how to build out your mentoring plan. A well-designed mentoring plan serves as the foundation for a successful program, ensuring that both mentors and mentees have a clear understanding of the journey ahead. This plan should outline: 

• Your program’s goals 
• The steps participants will follow
• The key milestones along the way
• Expectations around roles and communication frequency
• What type of resources you’ll provide to participants 

By mapping out the process in advance, you can create a consistent experience that aligns with broader learning and development objectives. 

But having a mentoring plan doesn’t mean you dictate everything that happens in the mentorship program. Kaelan MacNeill, Director of Learning and Development at FYihealth group, believes there has to be space for flexibility: “There should be a really clear structure for mentors/mentees on how the mentoring relationship will work, but there should also be adequate flexibility for them to make it their own. Part of the magic of a mentorship pairing is the authentic relationship that emerges—make sure there’s space for that relationship to flourish.”

Get expert mentoring program structure support with Together

When we asked employee development experts what the biggest barriers to mentorship today are, this is what we heard:

• A lack of HR budget
• A lack of sufficient number of mentors to support mentee-base
• Not enough buy-in from leadership into HR initiatives or programs like mentorship
• Admins feeling “too busy” to run a program or like it will be a “heavy lift” 
• Difficulty capturing the impact of mentorship

Mentorship platforms like Together make it easy for people leaders to not only run mentorship programs you can monitor and track but also make it easier for program managers with a user-friendly system that does all the heavy lifting for them.

With Together, you can pair mentors and mentees via the customizable pairing algorithm at scale, calculate the real ROI of mentorship programs, and integrate it with apps you use on the go to make your programs more impactful. 

Want to easily implement mentorship programs? Book a demo to see what Together can do for you!

FAQs

What makes a good mentorship program?

 A good mentorship program starts with clear goals tied to business objectives, pairs participants intentionally, and includes built-in measurement frameworks to track progress and improve over time. But beyond the structural elements, the best programs also prioritize participant experience—providing resources like mentoring agendas, setting a regular meeting cadence, and equipping mentors and mentees with clear guidelines so they know what to expect.

What should a mentoring plan include?

 A strong mentoring plan should outline your program's goals, the participant pairing process, recommended meeting cadence, session structure, and how you'll measure success. It should also set expectations around roles, communication frequency, and the resources you’ll make available to support participants.  

How do you effectively pair mentors and mentees?

Effective pairing involves balancing being intentional about your criteria without being overly restrictive. Most experts agree that you can't just pair people and hope for the best—you need a structured approach with clear logic behind each match.

A good starting point is to set a few non-negotiable rules (like preventing mentees from being matched with their direct manager or capping the number of mentees per mentor) while leaving room for flexibility on other criteria like skills, interests, and career goals.  

How long should a mentorship program last?

There's no one-size-fits-all answer, but most structured mentorship programs run between 3 and 12 months. Shorter programs (around 90 days) work well for onboarding-focused mentorship, like Wellabe's "Culture Colleagues" program, which pairs new hires with seasoned employees during their critical first months. Longer programs (6 to 12 months) are better suited for career development or leadership-focused mentorship, where participants need more time to build trust and work toward deeper goals. 

How do you measure the success of a mentorship program?

Start by tying your measurement framework back to the goals you defined when you designed the program. If your goal is retention, track turnover rates and engagement survey scores. If it's skill development, you might look at manager feedback or participants’ self-assessments to see whether mentees are progressing toward their development goals.

Quantitative metrics like session completion rates, participant satisfaction scores, and ROI calculations are valuable, but don't overlook qualitative feedback, too. Prompt participants to share stories or insights they’ve gained through the program.