When Leadership Meets Heartbreak
There are moments in our lives that shape us forever. As leaders, we often speak of the highs—the times when we see our teams flourish, the times when we witness a person’s potential come to life, and when we watch goals being met, if not exceeded. But there are other moments—ones we rarely talk about, and sometimes, never fully recover from.
One of the worst experiences in my leadership journey happened recently, and it’s something I’ll carry with me for the rest of my life.
I had to tell multiple people that their roles were being eliminated.
If you’ve ever had to be in that position, you know how gut-wrenching it can be. As someone who prides themselves on being a “people first” leader, it’s not just about the process or the business decision. It’s about the human impact. It’s about the person sitting across from you—their life, their emotions, their dreams—and in that moment, it feels like you’re crushing them. No matter how justified the decision may be from a business standpoint, it never feels right on a human level.
When I got the news that this elimination had to happen, it hit me like a punch in the stomach. I spent sleepless nights thinking about it, rehearsing the conversation over and over in my head. What would I say? How could I soften the blow? Could I ever say it in a way that didn’t leave lasting scars?
But no matter how much you prepare, there’s no script for that kind of conversation. No perfect set of words that will make it okay.
On Monday I had to deliver the news, I sat down with those affected individually – people who had given their time, energy, and heart to the organisation. People who had friends here. People who had built a life around this role. And I had to tell them that it was being taken away. I could see the shock in their eyes, the devastation in their body language and voice. I could feel the weight of what this meant to them, and in that moment, I wanted to find a way to undo it all.
But I couldn’t.
The conversation was brutal. I could tell they were trying to process it, searching for reasons, for explanations that might make it easier to swallow. But the truth is, there are no good reasons when it comes to someone losing their livelihood. Even if I offered reassurance or spoke to their worth, it wouldn’t change the fact that the news I was delivering was life-altering.
As leaders, we talk a lot about “people first,” but this was one of those moments where it felt like the system had failed. That I had failed, even though I wasn’t the one making the ultimate decision. It didn’t matter that it was a business necessity; in that moment, all I could think about was the person across from me and what this meant for them.
When you’re a leader who truly cares about people, these kinds of moments don’t just stay with you—they change you. After that conversation, I sat alone in my office, feeling the weight of it all. I had done my best, but it didn’t feel like enough. I had delivered the message, but the guilt and sadness lingered. And I knew that I would carry this with me for the rest of my life.
This experience has taught me more about leadership than any book or seminar ever could. It’s easy to lead when times are good—when your team is thriving, when there’s growth, when the goals are being hit. But true leadership is tested in the hardest of times, when you have to make impossible decisions, when you have to sit with someone and tell them that their role, their security, is being taken away.
If I can take anything from this experience, it’s a deeper understanding of empathy, vulnerability, and responsibility. Leadership isn’t about always making the right decision, because sometimes there is no “right” decision. It’s about standing in the fire with your people, even when it hurts. It’s about acknowledging the humanity in every decision, and feeling the weight of those decisions with every fibre of your being.
The pain of that day will sit with me for a lifetime, but I choose to hold onto it as a reminder of what it means to lead with heart. People first is not just a philosophy—it’s a commitment. Even when it’s hard. Even when it’s painful. Even when you feel like you’re breaking someone’s world apart.
And in those moments, when leadership feels more like heartbreak, I’ll remember that the strength lies in showing up, in caring deeply, and in feeling every bit of that responsibility with the people who are most affected. Because if I ever lose that, I will have lost what makes me a true leader.
Photo by Nik Shuliahin 💛💙 on Unsplash