The Mentoring Relationship

Everything you need to know about the mentoring relationship.

October 7, 2019

History’s first mentor was a transitional figure that helped a young boy grow into a man. 

The origins of the word mentor come from a piece of historical literature namely Homer’s Odyssey. In the story, Odysseus leaves his infant son in the care of his good friend, Mentor. Under Mentor’s watch and care, the son grows and matures.  

“Mentor was viewed as the transitional figure in Telemachus’s life during his journey from youth to manhood,” researchers with the Mayo Clinic note.

Since ancient times, the word mentor has come to mean a very special relationship that is different from other connections in a person’s life. While they may play a similar role as a teacher, role model or supervisor a mentor is distinct. 

Mentoring programs revolve around the relationship between the mentor and mentee. Unfortunately, there is no way to guarantee success in this area. It takes time and effort on both sides. For a mentorship to really work, the participants need to be committed to the process. This means they are ready to dedicate the extra time and effort needed that makes mentorship successful. 

Here are some ways that a mentor and mentee can create a successful relationship. 

Cultivating a successful mentoring relationship

Getting the most out of a workplace mentoring program really means getting the best from participants. Mentorship is essentially a unique relationship developed between the mentor and the mentee. 

Whether you are a mentor or mentee, there are some things that you can do to help cultivate a good relationship. These include being committed, developing trust, setting guidelines, productive communication and knowing when to say goodbye. 

Be active. Mentees and mentors need to be actively involved in the relationship. Mentees need to define goals, seek out advice, attend meetings and ask questions. Mentors are responsible for offering advice, guiding goal achievement and encouraging a mentee to develop their skills and networks. 

Get a good match. Finding a good mentor-mentee match doesn’t mean you should connect two people who are similar. Sometimes the best mentorship is between participants who are opposite of each other. This can challenge each individual in new ways and help them understand different perspectives.  Mentoring software can help create a good match using algorithms that feed off information obtained during the application and questionnaire process. It can also be customized to fit an organization’s desires when it comes to matching mentors and mentees. 

Develop trust. Trust is crucial to a mentoring relationship. Yet, it can also take some time to build trust between a mentor and mentee. Start your mentorship with a getting-to-know-you style meeting.  In this first session, both the mentor and mentee should exchange information about their backgrounds and interests. Slowly, as the relationship progresses, more and more information can be shared as each individual gets to know the other. This is how to build trust. 

Have guidelines. Every relationship has a set of “rules” that govern it. A mentorship should have some clear guidelines regarding behavior and responsibility of the participants. Early on in your relationship both the mentor and mentee need to set some rules about what their roles will entail. Share what you both expect from the other person. Also, consider what you bring to the relationship.   How can you help cultivate a successful connection?

Set goals. A big part of the job for mentees is to define the goals they want to accomplish during the mentorship. While this includes the career development steps they want to achieve,  it is also important to understand what you want from the mentorship as a whole. By identifying these goals early, it can help clarify the type of mentor you need. For example, are you looking to network, to gain new skills or to help advise you on major career decisions?

Communication. A good relationship will be built around good communication. In the context of mentorship, this means that the mentor needs to provide constructive criticism rather than harsh judgment. They should be effective speakers that are sensitive to the mentee’s feelings. A mentee also needs to be able to express themselves clearly. If they feel that a mentor is not understanding something or offering advice that they are not comfortable with, a mentee should say so in a diplomatic way. 

Know when to say goodbye. Mentorships are generally short-term connections that individuals make throughout their life and career. Traditionally, they last for 12 to 18 months. It is important to know when to move on and say goodbye. For some mentorships, this might be sooner than expected. If you are having a negative mentoring experience it is better to leave the relationship than to stay in it.  


Mentorship has always been about a relationship. From the very first time it was mentioned in ancient literature to the modern workplace, the connection between a mentor and mentee has been central to the success of mentoring programs. A mentor plays a special role in a person’s life and career. It is a mixture of advisor, role model and friend. 

Workplace mentoring programs that focus on the importance of the mentor-mentee match are ones that are most likely to meet its outcomes. Moreover, the commitment level of the participants also plays a big role in the mentoring relationship. If a mentor or mentee are not dedicated to the process, or not willing to put in the extra time and effort, the mentorship will likely fail. 

Mentoring software can help cultivate the mentoring relationship from getting a good mentor-mentee match to scheduling meetings to reporting and reviewing the process. Programs like Together help organizations and mentoring program managers optimize their workplace mentoring program for success. If you want to see Together in action, book a demo now

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