Pruning for Growth: A Leader’s Toughest Decision

Recently, a fellow leader reached out to me to discuss one of the most challenging issues a leader can face—knowing when to let go of a team member. It’s never an easy decision, and it often involves tough conversations and difficult judgment calls. The question is: at what point does it become necessary, and how do you determine the best path forward?

This dilemma reminded me of an experience I had with a team member I hired from a prestigious overseas university. Given his impressive credentials, my supervisor and I were confident that he would be a great asset to the team. However, after bringing him onboard, we began to encounter issues. While he was an excellent independent worker, he struggled with collaboration, often miscommunicating with the rest of the team. This resulted in frequent misunderstandings and friction within the group.

As time passed, I found myself faced with three options:

1. Let it ride: Maybe the issue wasn’t him but the team dynamics. After all, he came from a top university. Perhaps with more time, the team could adjust, and everything would fall into place.

2. Coach him: Provide more guidance and structure, helping him adjust to the team environment. With the right support, maybe he could thrive and find his footing.

3. Press the eject button: Maybe it was time to cut our losses. Sometimes, even the most talented individuals don’t fit within a team, and it’s best to part ways before it affects everyone’s morale.

At that point, I was conflicted, not knowing which direction to take.

Much later, I listened to Jill Sherer Murray’s TEDx Talk, "The Unstoppable Power of Letting Go." In the talk, Murray reflected on her experience of staying in a long-term relationship that wasn’t working. She spoke about how the fear of the unknown kept her holding on, even though deep down she knew that the situation wasn’t right for her. By staying in that relationship, she felt stuck—unable to move forward or grow in other areas of her life.

Murray described how difficult it was to finally let go, but she emphasized that letting go wasn’t about giving up. Rather, it was an act of courage that allowed her to create space for new opportunities to enter her life. She spoke in past tense about how, once she had made that difficult decision, she experienced emotional freedom and personal growth that she hadn’t anticipated. Murray reflected on how that decision to let go had ultimately led her to thrive in ways she hadn’t imagined while she was still holding onto something that wasn’t serving her.

Her message resonated with the idea that many people—whether in relationships or professional settings—struggle to let go of situations or individuals that are no longer working. Murray emphasized that holding on too long can prevent both personal and professional growth. The process of letting go, though painful, opens the door for new opportunities and experiences that wouldn’t have been possible otherwise.

After much reflection, I returned to my team member's situation. I had tried to make things work by assigning him more independent, isolated tasks, which he handled brilliantly. But teamwork, the kind that requires close collaboration, was a critical part of our operations, and he struggled in that area. I knew I couldn’t continue to shield him from that reality. At some point, every team member must contribute to the group effort, and the fact was, he wasn’t thriving.

So, I sat down with him for what was a very difficult conversation. My heart was heavy because I could see he was struggling too. For reasons neither of us could fully pinpoint, the culture just didn’t fit. We talked through his challenges, and after a series of honest discussions, I think he also realized that he wasn’t thriving in the way he should. In the end, he made the decision to move on. It wasn’t an easy outcome, but it was the right one—for him and for the team.

Reflecting on that experience, here’s my take on the key factors leaders need to evaluate when considering whether to let a team member go:

1. Performance: Was the individual consistently meeting job expectations? Performance is a clear indicator of whether someone is a good fit for their role. Despite feedback and support, if performance hasn’t improved, it might signal that the current role isn’t the right match.

2. Potential: Does the individual show promise for future growth? Coaching and mentoring can often unlock hidden potential, but sometimes, despite your best efforts, the fit just isn’t right. Leaders need to assess whether the person’s strengths align with the team’s needs.

3. Team Fit: How well does the individual integrate with the team? A lack of collaboration and cohesion can undermine a team’s productivity. If the individual continually disrupts the team’s harmony, it might be time to consider whether they belong in a different environment.

4. Values and Behaviors: Does the individual’s behavior align with the organization’s culture and values? Consistently clashing with the company’s core principles can create ongoing friction within the team, which hinders progress for everyone.

Murray’s reflection on the power of letting go served as a timely reminder in my own leadership journey. It made me think about how I had held onto my team member for too long, out of a mix of hope and fear of making the wrong decision. By holding on, I had unintentionally prevented both him and the team from finding the growth and success they needed. The courage to let go, as Murray described, was a critical lesson that applied to leadership just as much as it did to personal relationships.

Letting go isn’t easy, but sometimes, it’s the most compassionate and effective decision a leader can make. Like pruning a tree to help it flourish, removing what no longer works allows space for new growth to take place. The real question for every leader is: How can we balance providing support and making tough decisions to ensure the team’s and the individual’s growth?