Happy Monday Leaders,

Mentorship is often described as one of the most fulfilling aspects of leadership. The opportunity to invest in someone’s growth, to share the hard-earned lessons from your own journey, and to witness their transformation is deeply rewarding. In many ways, it is why I do what I do. Why I love to teach, coach and consult. But what happens when a mentorship fails? When the mentee doesn’t achieve the potential you saw in them, or worse, when the relationship falters? Today, I want to explore this uncomfortable yet invaluable experience.

Years ago, I mentored a promising young player—let’s call him Alex. Alex was bright, ambitious, and eager to learn. I saw in him a spark that reminded me of my younger self. I poured time and energy into guiding him, offering advice, connecting him with opportunities, and challenging him to think bigger. I held him accountable for his performance, and tried to empower him to think bigger, and to expect more of himself.

At first, things went well. But over time, Alex became increasingly disengaged. Performance lacked, feedback was ignored, and his enthusiasm seemed to dwindle. I reached out multiple times to understand what was going on, but my efforts were met with vague responses. Eventually, Alex left the organization, and our mentorship ended on a note of disappointment.

I’d be lying if I said it didn’t sting. I questioned my approach: Had I pushed too hard? Was I too hands-off? Was I the right mentor for him?

Over the years, I’ve come to realize a few key truths about failed mentorships:

1. You Can’t Control the Outcome. As mentors, we can guide, support, and inspire, but we can’t dictate someone’s path. People are ultimately responsible for their own growth.
2. Not Every Match Will Work. Mentorship is as much about chemistry as it is about skill and experience. Sometimes, the fit simply isn’t right—and that’s okay.
3. Failure Teaches, Too. Reflecting on a failed mentorship can provide insights that make you a better mentor. In my case, I learned the importance of setting clearer expectations and ensuring that I properly vet those I plan to surround my team with. "Trust over everything..."

Focus on the Wins

While it’s easy to dwell on the mentorships that didn’t work out, it’s just as important to celebrate the ones that did. For every Alex, there’s a Colton who went on to thrive because of your guidance. For every disappointment, there’s a success story that reminds you why you lead in the first place.

Take stock of the people you’ve helped shape. Reach out to those mentees who’ve grown under your direction and let them know you’re proud of them. Their achievements are a testament to your impact as a leader.

Closure

I recently ran into Alex at a speaking engagement. As I was getting on the elevator to go down to speak. He was attending the conference, but instead of attending the sessions, he got off the elevator with a no shirt, towel around his waist, coming back from the pool... at 7pm... as the evening lineup was beginning to speak... As the elevator shut, I couldn't help but think about the missed potential, and once again questioning my role in it. I couldn't help but smile and shake my head.

If you’ve experienced a failed mentorship, don’t let it discourage you. Instead, use it as an opportunity to refine your approach. And if you’ve been hesitant to continue on your path of leadership and mentorship, consider this your sign to keep going. There will always be an Alex or two... but there will always be a Colton as well. Someone who desperately needed you in that moment in time, and because of your guidance, redirected the trajectory of their life. The next person you invest in might just be the one who reinspires your faith in the power of leadership.

Keep empowering. Keep inspiring.

Strive for Excellence,

RB​​

The Leader’s Window​
​Empowering Leaders. Inspiring Excellence.