Picking up where we left off (See the last post), I had just learned a hard truth: technical knowledge alone doesn’t cut it. So, what did I do? I opened my eyes, shut my mouth, and started asking questions.
In those days, I was supporting five operations and interacting with dozens of leaders every month. This gave me an incredible vantage point to observe leadership in action—the good, the bad, and the downright confusing. My main responsibility was to train and support new CSRs, which offered me a low-pressure environment to test and refine my style repeatedly. And since I was on the road three weeks a month, I dove headfirst into emotional intelligence content during my downtime.
Looking back, I’m amazed I had the presence of mind to recognize the opportunity in front of me. I was failing, yes, but failure wasn’t an option. I’ve since learned that as an Enneagram 3, success is what drives me. At that moment, I realized I couldn’t let failure define me. So, I powered through. I asked anyone who would answer what they needed in a trainer, mentor, and leader. And then I put that knowledge to the test.
The crazy thing was, I didn't do all of this with the idea of being a CEO one day. I was just working to better myself and get to the next level (supervisor). Throughout my whole career (and life) I've always kept my eye, drive and attention on the next step. Turns out one step at a time can get you quite far.
By spring 2006, I was promoted to Client Service Supervisor in Baltimore, managing a group of eight CSRs. That’s when everything I’d learned had to come together. Not only was I new to leadership, but I was also new to Baltimore. And if you’ve ever been to Baltimore, you know, it’s got a style all its own.
I quickly realized that connecting with my team was the most important thing I could do. Football was huge for this group, and I found myself awkwardly standing in Monday morning huddles as they dissected every game from the weekend. I had no idea what they were talking about, but I knew I had to figure it out if I wanted to lead them effectively.
So, every Monday morning, as I got ready for work, I watched ESPN highlights. When the huddle started, I’d kick things off with, “Did you see that play in the ... game? Crazy!” To this day, I’m not sure if they bought it, but it helped me connect. And of course, I had to pick a team, so I became a Seahawks fan.
Building those connections paid off. Over my three years in Baltimore, I worked hard to understand and support everyone on my team. The result? I ended up promoting more people out of my teams than any other supervisor. Success was the driving force, and it wasn’t just mine—it was theirs too.
If any of my original team members are out there reading this, I’d love for you to chime in with stories you remember from our time together. Those years were some of the most formative of my career, and they taught me one critical lesson: Keep your eyes open, always. Observing and connecting with others is what transforms good leaders into great ones.
See you in the next post!
Gratefully,