My Greatest Strength Is My Greatest Weakness
Breakthroughs rarely look like they do in the movies. There are no ethereal choirs or beams of light shining down from the heavens. In reality, they’re usually much messier. They're raw. They strip away self-perceptions until you’re left face-to-face with the truth—uncomfortable, unfiltered, and impossible to ignore.
I want to tell you about one of those moments, and why I still think about it almost every day.
About ten years ago, I walked into “The Lounge Room”—a small, relaxed conference room at our office, complete with wingback chairs and a couch that we always used for performance reviews. I had been leading marketing and business development at the agency for about five years and had helped grow revenue by more than 50%. I was confident, prepared, and proud of the new work and new clients my team landed over the last year.
The partner conducting my review was known for his "shoot-you-straight" approach, so I suppose I should have anticipated a 100-mph fastball. But halfway through our conversation, he leaned in and said, “Colin, I have to tell you something you may or may not have realized about yourself.” I nodded, curious. He continued:
“Your greatest strength—and your greatest weakness—is that you care about people.”
I smirked. Grimaced. Probably said something as a witty deflection that I don’t remember. But I thought about it. For what felt like a long time.
Was that a compliment or a criticism? Was I being naive? Was this my Dunning-Kruger blind spot?
In business development, there’s a familiar archetype: cutthroat, hyper-competitive, slick, charming yet deceiving. I’ve met people who fit this mold—who gain success because of their edginess and beady-eyed focus on winning at all costs. I’ve seen them bulldoze clients into decisions on projects they didn’t need, ignore colleagues’ calls for help, and chew through teams without a second thought. And I’ve seen those same people rewarded for that behavior—praised, promoted, even handed trips to Aruba.
And while Aruba sounds nice, I’ve never been willing to trade my values for a plane ticket.
Ten years later, I’ve made peace with that moment. If my biggest flaw is that I care too much about people, I’ll take it. I actually think it’s what’s made me successful in my BD career. But yes, that openness can be exploited. And it has been by people I didn’t think would step on my neck to serve their own ends, yet they did. But I believe that business is personal, and the best relationships—whether with clients, teams, or partners—are built on trust, empathy, and integrity.
Caring isn’t a liability. It’s a responsibility. It’s the reason I do what I do: to help people grow businesses in ways that are both effective and human. That kind of growth creates something far more lasting than quarterly earnings: it creates real bonds that last for years – even decades.
Because at the end of the day, neither companies, dollar bills, nor Aruba will show up at your funeral (although Aruba is still invited to come). But the people you cared for—and who cared back—will. And you will have a career that created possibilities and opportunities for others. I sincerely hope my “weakness” becomes my legacy.