Most leaders can point to a mentor who shaped their career—or to a mentorship that never quite worked. In theory, mentorship holds the promise of growth for both participants. Mentees gain guidance and confidence, while mentors refine their own thinking and leadership. Yet in practice, many mentorship opportunities fall short of what they could achieve.
Why mentorships fail
The role of being a mentor is not always easy. It involves pouring time, effort, and often emotion into another person. It is much like being a good parent, where your primary concern is what’s best for your child. The mentor’s role is to guide, challenge, listen, and support the mentee. While parenting is natural, the workplace dynamic is different. The mentor must consciously choose to invest.
Sometimes, making that decision is easy because the mentor feels a genuine affinity for the mentee. Other times, the situation is more complicated. The mentor may not want to commit the time, the prospective mentee may lack interest, or personalities may clash. The mentor can still choose to engage, however. Doing so becomes a deliberate decision to invest effort for the mentee’s benefit. While challenging, this type of mentorship can also be extremely rewarding.
Failures can often give us the most insight into improvement and future success. I once mentored an underperformer and worked to identify ways to leverage her strengths. She showed promise in teaching and training others, so I encouraged her to shape her role around those skills. About a month later, she told me she would no longer do what I was asking. Her response was direct: she wanted to continue working exactly as she had been. The mentorship stalled, and she soon resigned.
In another case, I mentored a high performer. She learned quickly, produced strong work, and showed clear technical ability. I assigned increasingly complex tasks and eventually moved her into a role supporting several critical lab functions. Her career seemed to be progressing well—until she submitted her resignation. The feedback she gave me was that she simply did not like doing her job. She said she would have preferred to remain in production. She was capable of expanding her role, but did not want to.
These experiences highlighted a distinction I had overlooked: mentorship is not a fix for disengagement or underperformance. It is a tool for developing individuals who are already willing to grow. In the first case, she wanted to remain an underperformer. She was comfortable and allowed to operate that way for a long time. In this case, what I framed as mentorship should have started as a clear performance conversation. Without alignment on expectations, mentorship had no foundation.
In the second case, the issue was not capability but direction. She was engaged, just not in the path I had chosen for her.
The journey of mentorship
As I struggled to understand these outcomes, I began receiving mentorship through a program designed to support those seeking higher management roles. My mentor was from another part of the organization, and I did not know him. The man who mentored me approached the situation by intentionally asking questions to get to know me and build a relationship. He then developed a plan to help me grow. The key to making the process effective was the time he took to understand who I was. He listened and learned about me, then customized our focus within that context.
Through this relationship and my own introspection, I learned that I must continuously assess the mentee's buy-in. The failures arose because, once I saw the best path for them, I committed to leading them down it. Their vision of best, however, was different from mine. Now, I regularly incorporate the discipline of shelfing my thoughts and perceptions and instead inquire and listen. Asking questions like “How are you doing?” and “How are you liking the direction we’re going?” can help, but ultimately the mentee needs to believe their perspective matters, that they get a say.
Identifying the positives
Today, I am mentoring one of my direct reports, and it is very positive. When I started my current role, she was my sole employee. Initially, she was unhappy and actively pursuing other avenues of employment. I knew my success depended on her success as much as my own work. In our first meeting, I told her that I had a plan to improve the program and I would help her understand her role and how the program should work. She was open and tentatively hopeful.
Over the subsequent three years, she has grown into not only the strongest contributor in the program but also has begun leading and mentoring others. I scheduled weekly one-on-one meetings with her. I listened to her struggles and offered ways to overcome them. I took the time to explain the program and her role. She was always engaged, listening, and learning how to think. I made the process about helping her grow into who she wanted to be.
In return, I can trust her to make decisions and provide direction to the labs as an expert. I would never have realized the benefits for her and me if I had not actively taken key actions.
How to ensure a successful mentorship
Before investing in mentorship, I now look for a few signals of readiness:
- Openness to feedback
- Willingness to change how they work
- Interest in growth beyond current responsibilities
Once these signals are present, your work as a mentor can truly begin. First, be willing to do whatever it takes to help the mentee be successful. Second, give the mentee a voice. Let who they are and what drives them define the course. Letting go of personal bias as the mentor is key.
Mentorship is both highly rewarding and extremely challenging. The mentor must be willing to learn and grow, leaning into their strengths and filling the gaps created by their weaknesses. My primary weakness was believing I knew best and failing to actively pursue buy-in from my mentees. Being introspective and willing to listen and learn as a mentor is how one can achieve the greatest success. This means accepting that, while the mentor has something to offer, the process may be personally challenging. Leaning into the challenge is the path to the best outcome.
Prospective mentees should jump in with both feet, be flexible in their thinking, and be willing to listen. They should be honest and provide feedback, even if that feedback is a lack of desire to engage. Honesty will help avoid situations where the process fails. Mentees should also remember that the mentor is also learning and growing through the process and that they are providing value to them as well.














