Cameron HeroldFounder of the COO Alliance & Invest In Your Leaders Training

The Hardest Part of Leadership: Managing People | Skye Blanks

7 May 2026 · 0 min

Watch on YouTube

0:03

In this interview excerpt, Speaker B identifies managing people as the toughest aspect of leadership across any industry, emphasizing the difficulty of maintaining relationships and confronting performance issues that may lead to termination. Speaker A recounts their first experience firing an employee, describing the anxiety of the conversation and how a brief Moneyball clip—showing a direct, no‑nonsense dismissal—served as a practical model for delivering the news succinctly. The dialogue highlights the emotional challenges of firing, the importance of clear communication, and how observing concise, direct approaches can improve one’s own method over time.

What have been some of the hardest parts of your role?
Managing people is not easy. I think that's the hardest job in any industry, any organization. It's how can we manage people, manage relationships. You're with someone for 6 years and then they just, you know, you just see the kind of the spark of their initiative or their enthusiasm window and you're like, okay, now we have to have a hard conversation. You're not doing what you're supposed to be doing. You're not gonna be able to stay with us. And so firing people, it's never fun.
I was thinking while you were sharing that about my my first time ever needing to fire someone, and I was freaking out. I mean, how do you have that conversation? I'm telling the owner of the company I'm with at the time, like, okay, I gotta do this. Like, what do you recommend I say? And, uh, have you seen the movie? I think it's called Moneyball. He just sends me a YouTube clip of him kicking this guy off the team. I don't do it the same way as I did back then, But it did really help me. I think what he knew to be true about me is that I can get so lost in the "I'm so sorry about this, like I really care about you" and make it some bigger thing. I remember watching this 3-minute Moneyball clip where he's like, "I gotta let you go." And he's just like so direct and to the point. That was my first experience firing someone, and I can say my method has definitely gotten better since then, but it was a place to start.