Brian HoppeBoard-Level Advisor to MSP CEOs, Brian Hoppe Coaching · Board-Level Advisor to MSP CEOs at Brian Hoppe Coaching

The Hardest Part of Leadership

1 Jul 2026 · 1 min

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In this personal reflection, the speaker recounts the emotional difficulty of his first experience letting an employee go. He describes a series of conversations leading to the final dismissal, noting his natural aversion to conflict and how the event left him feeling wrecked for weeks. While acknowledging that such moments never become easy, he emphasizes that leaders must sometimes make painful decisions for the greater good of the company, and that repeated exposure has built his resilience, though the challenge remains.

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For me, that was one of the hardest pieces of my journey as a leader. I still vividly remember the first time I had to let somebody go. And it was really like, it was a multiple conversation thing. This was the last conversation. They knew it was going to happen. I knew it was going to happen. And I was just like, I was wrecked. And I was, at the time, I would say naturally averse to conflict and all of that. So it really rattled me for like weeks. And I've had more experience of that since then. It's not that it ever necessarily gets easy, but it's a lot of times you just, well, you have to do that for the greater good of the company.