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Common mentoring challenges 

We've had the opportunity to see a lot of mentoring relationships develop. Here are common pitfalls we've seen and how to avoid them.

Matthew Reeves

April 6, 2020

Workplace mentoring programs can be a great way for an organization to invest in their employees. Unfortunately, there are bound to be some challenges along the way.

But, if you are prepared for them, these issues will not become stumbling blocks to starting an effective mentorship program. Here are some of the most common mentoring challenges and ways that you can overcome them. 

Mentoring challenges

While every workplace mentoring program is unique, there are some common problems that organizations can face throughout the process. These include motivation, goal-setting, matching, feedback and more. Although these issues can dampen the mentoring process, there are ways to tackle them to create a successful mentoring program. 


One of the main problems that workplace mentoring programs encounter is motivating mentors. It can be difficult to convince qualified and dedicated mentors to participate in your program. But it doesn’t have to be impossible. Start by focusing on the benefits of the program for mentors such as enhanced skills, the ability to help someone else and the opportunity to learn and grow themselves. Often mentoring is seen as a one-way street where the mentor gives and the mentee receives. However, that is not reality. A mentorship can benefit the mentor in many ways and turn into a learning experience for the senior employee as well as the mentee. They can become stronger communicators, leaders, listeners and employees from the experience. Moreover, when paired with a younger mentee, mentors have the opportunity to learn new approaches and technologies that can benefit them in their careers. 


An essential element in any mentorship, setting goals can become a challenge for both the mentor and mentee.  When a mentee is unclear about what they want to accomplish within the mentorship, it can be a struggle to help them focus. There are some ways that this challenge can be overcome. Start by encouraging mentees to use the SMART goal setting technique. That is, set a goal that is specific, measurable, attainable, realistic and timely. Mentoring software can help track the goals so mentees can see how far they have come during the mentorship. 


The strength of a mentoring program can be tied to its ability to create good matches between a mentor and mentee. However, if you are trying to do the matching manually, it can be a big hurdle to jump. One of the biggest benefits of using mentoring software is its capability to create matches in just minutes. By using information obtained from participants as well as the mentor program manager, mentoring software has algorithms that identify good matches. Once you have identified a good pairing, give the mentorship every opportunity to excel by training both the mentor and mentee about their expectations and how to get the most from the mentorship. This can include having participants attend workshops or training sessions on communication techniques and leadership skills. 


Every good mentoring program should solicit feedback from its participants. This helps you understand what parts of the program are working well and what parts may need to be tweaked. Feedback can come in many forms including an interview when the mentee completes the mentorship, it could also simply be a form that participants fill out following the experience. Well, it doesn’t matter how you get the feedback, what does matter is what you do with it. 

Ongoing support

A successful workplace mentoring program should provide ongoing support to participants regardless of where they are in the mentoring journey. It is key that an admin checks in regularly with both mentors and mentees to gauge how their match and process is going. There will be times that one of the participants does not feel that it is working. At this point, an admin can help define and solve the problem, which may involve dissolving the match and creating a new one. Although tracking communication can seem like a time-consuming task, if you are using a mentoring software program it will be easier. Through mentoring software, program admins can track emails and meetings. It can also make staying in contact with participants simpler.


At the beginning of any mentoring program, an organization will set outcomes that they anticipate will be the result of the workplace mentorship. It is key that these be written down and that there is a way to measure these outcomes.  For example, if an organization is starting a mentorship program to improve diversity in its workforce, it could keep track of how many leadership positions are held by minorities. If the number increases following the implementation of the mentoring program, the mentorship experience can be seen as successful. Regardless of your organization’s outcomes for the workplace mentoring program are, it is important that the results be measured regularly. This can help you identify the level of success the program is having. If the program is not having the desired outcome, you may need to make some adjustments to the mentorship experience. 

Creating a successful mentoring program

Mentoring programs in the workplace can be one of the best experiences that an organization can offer an employee. There are a number of benefits for both the mentor and mentee who participate. However, creating a mentorship program that is successful will come with some challenges. These can include motivating participants, creating a good pairing and getting feedback. While these can be hurdles that your organization might face, there are ways to overcome them. It begins with being prepared for the possible problems and equipping your mentoring program administrator with the skills and resources to meet the challenges. Those organizations that opt to use mentoring software often have more resources at their fingertips to avoid the common mentoring challenges that arise. To find out more about how Together can benefit your mentoring program, contact us for a free demo. 

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We draw from the first-hand experience of managers at various companies leading mentoring programs and our own expertise to outline the best practices for running a mentorship program. This white paper is a comprehensive guide to help you build a world-class mentoring program.