My first BIG win
One of the first wins I earned as a new leader was something I didn’t fully appreciate until years later. It wasn’t the type of victory most people think of when considering what it means to succeed as a manager or business leader. Often, we’re trained to focus on tangible results—like hitting sales targets or achieving key performance indicators (KPIs). These milestones are important, of course, but this particular win wasn’t something you could measure on a spreadsheet.
It came in the form of a person—let’s call him Ronald Wentworth, although that’s not his real name. His story is important because it illustrates that leadership isn’t just about numbers or goals; it’s about people.
Often, when you step into a new management role or receive a promotion, it’s because there has been some form of organizational change. This is a polite way of saying that someone before you probably wasn’t meeting expectations, or the performance of the group wasn’t up to par. In other words, you’re often walking into a situation with a history of underperformance, and that’s the challenge you’ve been hired to fix.
To be clear, this isn’t always the case. Sometimes, you’re stepping into a high-performing team, which presents its own unique set of challenges—like keeping momentum or pushing performance even higher. But in the case of Ronald, it was different. I had been asked to take over an underperforming team, one that was responsible for selling products across a large geographic area. Our territory covered four states, which added a layer of complexity to the role.
As a young leader, I found myself in a position where those who promoted me naturally felt the need to share their wisdom and insights, which, of course, made sense. When you’re stepping into a new role, especially one that carries significant responsibility, people want to guide you. And while their intentions are good, there’s an important balance to strike between receiving guidance and managing those expectations—a topic I’ll dive into further in a later post, as understanding how to manage your boss is crucial for any leader.
But in this particular instance, what I received from my manager was essentially a rundown of the personnel who would be reporting to me, along with a laundry list of their challenges. And I want to be very clear here—these weren’t just minor performance issues. The way these challenges were presented made it seem as though I was inheriting a team with fundamental and deep-rooted problems.
In the weeks leading up to my relocation and the transition into my new role, I was flooded with information about the failures that plagued the group. I was copied on emails from vendors, back-office team members, and essentially anyone who had a complaint or issue related to the team I was about to take over. It felt overwhelming, as though I had been selected to step into what, to put it politely, was a mess. Every interaction seemed to highlight the dysfunction within the team, and I hadn’t even officially started yet.
What made it even more chaotic was the narrative that accompanied all this information. I was repeatedly told that almost every major issue could be traced back to one person: Ronald. According to my manager and various others, Ronald was the root of most of the team’s problems. It was made abundantly clear to me that Ronald wasn’t considered a good employee—he was seen as a liability, someone who was dragging the team down. In fact, I was strongly encouraged to release him from the organization as soon as I took over.
This wasn’t just advice; it felt like a directive. Ronald had become the scapegoat for everything that was wrong with the team, and before I had even met him, I was being steered toward the idea that his departure was necessary for any hope of improvement. It’s interesting to look back now and reflect on how easy it would have been to simply follow that path—after all, when you’re new and trying to make your mark, it’s tempting to take the advice of those above you at face value. But what I would come to learn, through my own interactions and observations, was that the reality of the situation—and of Ronald’s potential—was far more nuanced than the story I had been told.
This experience highlighted an important lesson: leadership isn’t just about cleaning up after others or following the directives handed down from above. It’s about digging deeper, understanding the people and the dynamics at play, and recognizing that every challenge comes with a human element. In Ronald’s case, the ‘problem’ wasn’t nearly as clear-cut as I had been led to believe, and it would become one of my greatest opportunities as a leader to challenge those initial perceptions and discover the value in people that others may have overlooked.
When I transitioned into the role, I had some preconceived notions about how to handle Ronald, especially given what my manager had told me. The phrase “manage him out” echoed in my head, as I had been led to believe that Ronald was the root of many problems and was steering others in the wrong direction. As a result, I initially thought my main task would be to remove him from the team.
In my first days and weeks, it was incredibly difficult to sit with the discomfort of the existing team dynamic—the one I had been warned about. The inclination to make immediate changes was strong, but instead, I chose to pause and observe. What I didn’t realize at the time was that this period of discomfort was crucial for my growth as a leader.
Discomfort, in many ways, is a double-edged sword. On one hand, it can make you want to turn back, give up, or stop what you’re doing—just like pulling your hand away from a hot pan. In certain situations, like avoiding physical harm, that instinct is necessary. But in the realm of leadership, business, or personal performance, discomfort is often an opportunity for growth. By delaying any immediate action regarding Ronald or the team, I gave myself the space to learn and develop as a leader. The most valuable lesson I learned during this time was the importance of context.
What I discovered was that the situation I had walked into wasn’t the disaster I had been led to believe. Ronald wasn’t the enemy of the company, nor was he actively causing harm. In fact, the real issue was that the “team” wasn’t functioning as a cohesive unit at all. Over the course of those first few weeks, I realized the importance of observing with my own eyes and forming my own perspective rather than relying solely on the narratives I had been handed.
The irony of the situation was that my manager, who had urged me to “manage out” Ronald, hadn’t spent any meaningful time with him. His views were based on secondhand accounts of customer interactions, without any real investigation into the matter. Ronald’s previous manager fell into the same trap, once telling me, “I don’t have time to go up there; it’s too far.”
This lack of direct leadership was eye-opening. The people in positions of authority, those expected to lead, had essentially failed to do so. Instead of engaging with the situation or the people involved, they had opted to pass judgment from a distance. To his credit, my supervisor did recognize my potential and put me in the role for a reason. While his guidance regarding Ronald was off the mark, he allowed me the space to make my own decisions when I pushed back. He did caution me not to take too long, but ultimately, he gave me the freedom to make the changes I saw fit.
It’s clear by now that Ronald wasn’t “managed out” as I had initially been advised. Not only did he retain his position, but he went on to be celebrated as one of the top contributors on the team. Eventually, he even led that very team, continuing to drive success within the market. But this story isn’t just about rethinking decisions or taking a closer look at the situation—it’s about something much deeper. It’s about the importance of taking the time to truly understand the individual.
You see, it wasn’t until I got into the car and worked alongside Ronald that I began to see the full picture. I started to understand the history, not just from Ronald’s perspective, but also for the entire team. In our conversations, Ronald was able to openly and honestly share where he felt previous leadership had failed. He clarified many of the incidents that I had been warned about before I even took over the team. In those moments, I was grateful that I chose to listen instead of rushing to judgment or offering solutions right away. That decision to listen earned me Ronald’s respect, and ultimately, his trust.
Ronald had been labeled as “negative,” but the truth was, he was confident enough to speak up about his experiences with the company, vendors, and clients. Although his approach wasn’t always perfectly on target, by listening to him, I realized I could help guide him—show him where to focus and how to channel his energy more productively. This became my strategy not just for Ronald but for the entire team. It became evident that no one had really spent time with them on the frontlines, so they had formed their own opinions, set their own goals, and made decisions that suited their individual needs.
Ronald wasn’t necessarily speaking on behalf of the entire team. Each member had been missing the mark in their own way, but Ronald was simply the most vocal about it. Leaning into that discomfort—taking the time to truly understand both Ronald and the rest of the team—made all the difference in my success as a leader. In fact, Ronald became one of my most important life lessons.
The title of this insight is “My First BIG Win,” and Ronald was that win. When people ask me what my biggest achievement in my career has been, I don’t think about the awards, bonuses, or record-setting years. I always come back to Ronald. Not because he was the only person I’ve helped develop, or because he was the most successful, but because Ronald unlocked something within me that fundamentally changed the way I lead.
Kaleel Jamison wrote about this concept in The Nibble Theory and the Kernel of Power. The idea is that we all have something we draw power from (I’m paraphrasing here, as it’s been years since I read the book). For me, Ronald became that power source. The lessons of embracing discomfort, trusting myself in the face of outside opinions, and truly understanding context—all stemmed from my experience with Ronald. The man who was supposed to be “managed out” became a top contributor and has now led that same team for many years.
This power center is something I tap into often. It’s become an integral part of my leadership style. Whenever I find myself unsure of what to do, I think of Ronald—not just how I impacted his life, but more importantly, how he profoundly impacted mine. It was a true honor to work alongside him and to have had him guide me in what it really means to be a leader.