Worst Day on the Job: When Vancouver CEO Mike Chisholm was tasked with cutting a third of his workforce

Mike Chisholm is a Vancouver-based business leader who has spent his career guiding companies through growth, acquisitions and difficult transitions. He is the founder and CEO of Chisholm Consulting Group Inc., where he works with boards and executives on operational challenges, strategy and turnarounds. Before starting his firm, he held senior leadership roles—including CEO and COO positions—across several industries, helping organizations improve performance and adapt to change.

In 2009, I was working at one of North America’s largest customs brokerage and trade compliance firms. The CEO had tried to get other executives to take on an assignment, since I already had a full plate, but they all turned it down. I didn’t really want the job either, but I’ve never backed down from a challenge, and I knew this one would be big.

I was brought in to take over a group of five logistics divisions that had been consolidated under one management team. At the time, the group was losing $750,000 a month and trending in the wrong direction. My mandate was to stop the losses, return the business to profitability and prepare it for eventual sale.

I knew turning things around would require significant layoffs. And while we didn’t yet know exactly who would be impacted, I made the decision to be as honest and transparent as possible from the start.

The morning of the announcement, I felt sick to my stomach. How do you stand in front of nearly 300 people and tell them that one-third will lose their jobs—without being able to say who or when? That weight is something I’ll never forget. These are people with families, mortgages, responsibilities. And here I was, about to take food off their tables.

But I also knew that being upfront was the only path forward. We needed to move quickly and decisively to turn the business around, and we couldn’t do that without trust. I tried to rehearse my remarks, but nothing felt right. In the end, I spoke from the heart. No script. Just sincerity. I owed them that much.

There were four main locations: Toronto, Winnipeg, Vancouver and Chicago. All of them needed to be addressed, but I couldn’t be in four locations at once (this was before Zoom). I knew once we held the first meeting, word would spread quickly to the other locations. So I made it a priority to get to all four cities in person, within two days.

That first meeting was incredibly difficult. Standing in front of the team, delivering that kind of message—it’s not something you can ever prepare for. But as hard as it was for me, I knew it was even harder for the people hearing it. There was a quiet tension in the room. People were anxious. They knew something was coming. And while I could feel their fear, I also felt a sense of resolve, like they were bracing for the worst, but still hoping to be treated with honesty and respect.

The message I delivered in those meetings was straightforward. We were in serious trouble, and the only path forward was to reduce costs significantly. That meant letting go of about a third of the team over the coming months.

I was honest in saying that we didn’t have the full plan finalized yet, but I wanted them to be aware of what was coming. I committed to having clear answers within three weeks and promised to communicate them directly. That meant we would let people know if they were being let go.

It felt harsh to ask them to wait, but pretending everything was fine would have been worse. I believed they deserved transparency. Even if we couldn’t give them certainty that day, we could at least give them time to prepare and begin looking for other opportunities.

What surprised me most was how many people already saw it coming. Several told me they expected the cuts to happen much sooner. The business had been struggling for a long time, and for many, there was a sense of relief that someone was finally saying it out loud. At least now they could stop wondering.

Some people were understandably angry. They asked how leadership had allowed the situation to get that bad, and why no one acted sooner to try and save their jobs. It was a fair question. I told them the truth. We missed the signs, and we should have acted earlier. But we were where we were, and I could not change the past. My focus was on taking ownership and doing the right thing for the people who would stay.

There were two moments from that day that stayed with me. One person approached me in tears. She told me I had ruined her life. She asked how she was supposed to feed her family if she ended up being one of the ones let go. She looked me in the eye and asked how I could live with myself. It was one of the hardest things I’ve ever heard. And I couldn’t say it wasn’t my fault. At that point, I had accepted responsibility. Blaming others, even if I hadn’t created the situation, would have destroyed any credibility I had left.

A little while later, another person came up and thanked me. He appreciated the honesty. He said they had all seen this coming, but no one had been willing to say it out loud. He thanked me for taking ownership, even though the problems hadn’t started with me.

The hardest part for me personally was knowing the people I was looking in the eye had done nothing wrong, yet they were the ones who would bear the weight of the consequences. Standing in front of the team, and delivering the kind of news no one wants to hear, was one of the most difficult moments of my career. I knew how deeply it would impact their lives, and I carried the weight of that knowledge with me into every conversation.

I stayed after each meeting as long as it took, making sure that anyone who wanted to speak with me had the chance. I answered every question as honestly as I could. From there, I knew we had made a commitment to come back with a clear plan within a couple of weeks, so we got to work immediately. Later that day, I sat down with our HR leader to talk through next steps and also just to decompress. The stress of the day was heavy, and I felt a real sense of guilt for feeling that way because whatever weight I was carrying, I had just handed something much heavier to a lot of other people.

That day taught me a lasting lesson about the importance of transparency. When you’re honest with people, even when the news is hard to hear, they respect it. You give them something to work with. That experience shaped how I lead and how I support other leaders today. In uncertain times, clear communication builds trust and trust lays the foundation for everything else—execution, alignment and forward momentum.

Leaders today are dealing with constant change. Rising costs, geopolitical pressure, supply chain issues and workforce fatigue are creating a tough environment to navigate. Most executives are being asked to do more with less, make fast decisions, and still keep their teams engaged. These challenges aren’t abstract—they’re happening every day—and they require leaders to show up with clarity, consistency and credibility.

That’s where these lessons come into play. I work with leaders who are managing acquisitions, restructurings, growth pivots and tech transformation. What I bring isn’t just operational know-how—it’s real experience leading through difficult moments with integrity. When people understand where things stand, even if the road ahead is hard, they’re far more likely to lean in and help move things forward.

I’ve had a long, storied career, and there have been plenty of tough days that could compete for the title. But I still consider this the worst day of my career. What made it different was, it wasn’t about something happening to me—I was delivering news and implementing changes that would deeply affect people’s lives, their families, their sense of stability. It wasn’t personal in the traditional sense, but I understood the weight of what that moment meant for so many.

That kind of day stays with you. It forces you to confront what leadership really means—not when things are going well, but when you’re the one carrying out decisions that cause pain, even when they’re necessary. That’s what makes it stand out. Not just as a hard day, but as a defining one.