Years ago, a mentor asked me a simple question: “Do you have any of the wrong people in your company?”
I did. I’d known it for six months and hadn’t acted. He made me commit to a date, then a time, that same day, by noon. “You make sure you’re there for him,” he told me. “Six months ago is when you should have let him go. For the last six months, you’ve been stealing from him.”
We both cried when I did it. It remains one of the hardest, most important conversations of my career.
The Real Problem Isn’t the Conversation
For years, I treated confrontation as something to win. In my own journal, reflecting on my time as COO, I wrote it out plainly: my debates tended to be about arguing to be right instead of arguing to solve a problem.
I’d let things get to me personally. I countered my own insecurities by arguing back, and it never helped.
A friend once asked me a question that changed how I show up in hard conversations: “Are you arguing to be right, or are you trying to be understood?” That question is worth carrying into every difficult conversation you’ll ever have.
Listening Is the Skill Most Leaders Skip
I noticed something about myself: when someone brought me their problems one-on-one, I was a great listener. But in meetings, I kept cutting people off.
I’ve had to learn to catch myself, slow down, and remember: if I’m truly listening, I don’t need to talk as much.
Difficult conversations rarely fail because of what you say. They fail because both people are waiting to talk instead of trying to understand.
Delay Is Its Own Kind of Damage
The hardest lesson from that firing story wasn’t the conversation itself. It was the six months I waited to have it.
Waiting doesn’t protect anyone. It just steals time from someone who deserves a straight answer sooner.
Bottom line
Great leaders don’t have hard conversations because they enjoy conflict. They have them on time, with respect, and with the goal of understanding, not winning. Waiting doesn’t make it easier; it just makes it later.
For more real, unfiltered lessons on leadership, listen to Cameron’s podcast, The Second in Command.
