Top Mentoring Challenges and How to Overcome Them

1 minutes

Despite mentoring being a highly successful learning and development strategy, it doesn’t come without its challenges. Whether it’s planning, communication, matching, time commitment or the sessions themselves, it’s good to be prepared for any potential mentoring challenges you might encounter. In this article, we’ll explore the top mentoring challenges faced by program managers, mentors & mentees, and talk you through how to overcome them.

Top Mentoring Challenges for Program Leads

Those managing mentoring within an organisation may face a number of challenges, from program design to low sign ups. Don’t worry, you’re not alone. Here are some of the top mentoring challenges you may be experiencing, and some tips for how to tackle them:

How Do I Generate Interest?

So you’ve got your mentoring program designed, your key objectives set, and you’re ready to get started – but you’re worried about potential sign up numbers. This is a very common mentoring challenge and one that needs to be tackled early on in your planning. There’s nothing worse than designing and launching an entire program, for it to simply be ignored by fellow employees. Building a base of eager mentors and mentees can take time and patience, but education is key! Here are some ways to overcome this mentoring challenge:

  • Share Social Proof

As humans, we like to see things to believe them. In order to build trust in your program, and the concept of mentoring as a whole, share messaging that will resonate best with your audience. Gather individual success stories of the positive impact of mentoring from people within the business from previous mentoring cohorts. For example, if it’s a graduate mentoring program, speak to past graduates about their experience and ask them to share their story over video or a blog.

If mentoring is a first for your organisation, try finding stories of famous mentors and mentees, or we have some examples from Guider customers.

  • Emphasise the Benefits of Mentoring

Some people may be unfamiliar with the benefits of mentoring, particularly the benefits for mentors. Mentoring is a learning and career development opportunity for everybody involved, and it’s important to articulate that value. Your most motivated employees will be eager to know that:

  • Mentees are promoted 5 times more often than employees without mentors.
  • Mentors are 6x more likely to be promoted.
  • 89% of mentees believe that their coworkers value their work vs 75% of non-mentees.
  • 87% of mentors and mentees report feeling empowered and having increased confidence (sources).

Mentoring is empowering and impactful, increasing skills and confidence for both the mentor and mentee. Use our guides on The Powerful Benefits of Mentoring and Mentoring Statistics to help you with your promotional plan.

  • Get Senior Leadership on Board

One of the biggest ways to generate interest is by encouraging senior leaders to sign up. Behaviour from the top filters down, and having leadership buy in gives the mentoring program more weight. This will naturally make people be more aware of the program, and inspire more people to get involved. It also reinforces a culture of learning and growth, as employees see colleagues at every level participate.

Run an internal campaign aimed at senior leaders and influential figures within the company prior to your campaign for participants.

Resource: Explaining how a Mentoring Software works

How Do I Find Mentors?

It may be difficult to find mentors, as many will worry about a lack of time or experience.

But mentoring is a two-way street, where mentors also learn a lot from mentoring. They develop communication skills, leadership skills and develop connections across teams and departments, building a stronger company culture.

You can combat their concerns by offering training and support. Offer them a library of resources, something you’ve compiled yourself or choose to use a mentoring platform like Guider which hosts a wide range of resources. It gives mentors something to refer to, and acts as a teaching guide to aid mentees.

Run educational events on mentoring, breaking down common misconceptions and reiterating the value for mentors. This will help more people understand what’s expected of them, and renew their confidence in their ability to be a mentor.

What Happens If There’s a Bad Match?

One of the mentoring challenges you might eventually face is a mentor and mentee that just don’t get along. A good way to prevent a bad match is by using a robust matching system like Guider’s. When you match manually, you risk not having enough time, and personal biases getting in the way, potentially obstructing any diversity goals. You can reduce the risk of having a bad match by considering matching them on both skill and common ground:

  • Their hobbies
  • Their skills
  • Their strengths and weaknesses
  • Their goals

Help mentors and mentees create a safe space that allows them to comfortably communicate. Encourage them to speak about their strengths, weaknesses, mistakes, fears and motivations in order to build trust.

But sometimes, two people just don’t get along. Avoid pushing a relationship where there isn’t one, as participants might end up fading away if they feel there is no out.

Create clear guidance on what to do if it’s not working, and make it visible and accessible to everyone at the onset of the program. Emphasise that it’s okay for them to contact the program manager to find a new mentor/mentee, and to be honest early on.

There are the top challenges for the people managing the mentoring, now for those actually doing it…

It is vital to discuss any mentoring challenges

Top Challenges for Mentors & Mentees

Mentoring relationships themselves can be challenging, particularly when you’re being a mentor or a mentee for the first time. Here are some of the top challenges you may face in your mentoring relationship or sessions:

Lack of Commitment

As mentors and mentees, it’s important to remember that mentoring is for your personal development, rather than another work task.

If you feel your commitment waning, firstly try to get to the route of why. Are you stressed from work and having trouble keeping up with the sessions or goals? Are you struggling to contribute in the sessions? Are there feelings of worry or embarrassment? Are you not getting what you expected from the relationship?

Just like any relationship, these feelings can be alleviated by communication. Once you’ve identified the cause of your lack of commitment, raise this in your next session with your mentor or mentee.

If you’re a mentee who struggles to commit because you feel that there’s too much pressure, discuss this with your mentor, programme manager or your company’s mental health champion.

Poor Communication

Following on from this, another common mentoring challenge you might run into is poor communication.

This could be about expectations, goals, intentions, issues, or simply a busy schedule. Clear communication helps to keep the mentoring relationship flowing, and creates a stronger bond between mentor and mentee. It’s hard to develop a proper mentoring relationship when communication isn’t there.

If you find the sessions quite daunting, remember that not all communications needs to be formal – create micro-moments where the two of you can speak casually about work, life and how your plans are moving along.

  • Mentoring communication isn’t just limited to face to face
  • Video communication allows you to talk from anywhere and still perceive each other’s expressions
  • Telephone communication works well for shorter conversations or where there’s a weak internet connection

Everybody communicates differently, so make sure you learn about your mentor or mentee in your early sessions so you can communicate in a mutually beneficial way for the rest of the program.

Communicate Stressors

Similarly, different things stress us out. Accepting our differences and working around them is a critical life and work skill, and so this is another thing to discuss early on in your relationship.

I.e Voice that last minute changes to schedules stress you out, so that your mentor / mentee is aware of it from the onset of your sessions. They can then work to avoid doing that.

If at any point in your ongoing relationship you feel:

  • That the check-ins are too frequent or not frequent enough
  • That your SMART goals are too unrealistic
  • Something is harder than you anticipated
  • That you’re not being as helpful as you could be

Don’t be afraid to voice them.

Mentoring is meant to be beneficial, not an additional stress to your busy working life.

Communicate Wins

On the other hand, make sure you’re communicating successes and celebrating progress! Let your mentor / mentee know if:

  • They’ve said something that has inspired you
  • They’ve taught you something that you plan to take on
  • They’ve helped you achieve your goal
  • They’re opened your eyes to a new perspective
  • You are proud of them
  • You are thankful for their support

While open and honest conversation is crucial for issues, it’s also important for the good stuff! It can be reassuring, particularly for first time mentors, to hear the sessions are genuinely benefiting their mentee. Similarly, mentors should praise mentees on their progress to further strengthen the relationship.


A potential challenge in a mentoring relationship is the mentee becoming overly dependent on their mentor. Messaging for every question they have, and taking up time beyond the agreed session or time commitment. This can lead to disgruntled mentors and may prevent the mentoring program’s success.

While resources ought to be available to participants, it’s important to take initiative as a mentee in any way you can. For example, is there an article or video that can answer your question? Are you going out of your way to advance your learning and act on something your mentor suggested?

An important aspect of mentoring is to develop skills, and independence in those skills. If, for example, your goal is to improve self-confidence, you’ll need to do things that take you out of your comfort zone. Sometimes that begins with being the first one to contact your mentor, arranging meetings, or eventually leading a project.

Unrealistic and Mismatched Expectations

Everyone from program managers, leadership teams, mentors and mentees might have big hopes for the results of mentoring. Some people will put pressure on others and themselves to achieve these results as soon as possible.

Individuals work at different speeds. Sometimes people are building on what they’ve previously learnt, others are starting from scratch, and others are working on moving past bad advice. Work with each other to set realistic goals through setting  goals. They act as realistic, motivational goals but also serve as a reminder that learning takes time.

If a mentor or a mentee expects too much or too little of the other, it can cause problems down the line in the relationship. Have an open and frank discussion at the beginning of your mentoring program about what you are expecting from the sessions and the relationship as a whole. You can then come up with a set of mutual expectation which can form the foundation of your relationship – maybe even write these down!


We’ve explored some of the mentoring challenges mentors, mentees and program managers might face during their mentoring programs.

Open communication between mentors, mentees and program managers is one of the most important aspects of a successful mentoring program. When we understand each other’s aspirations and motivations, it helps to create a more successful program with fewer roadblocks.

Want to find out how Guider can help? Get in touch with our team!

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