The Leadership Moments I Didn’t Get Right — And What They Taught

Wear more blazers and be a little prickly.

That was the advice I once gave someone on my team when they were put in an uncomfortable and inappropriate situation. I cringe when I think about it now, but that’s where this story starts.

When I began leading teams, I had no training, no coaching, and very few resources. Leadership development wasn’t showing up on any feed because those feeds didn’t exist, and most of us were left to figure things out on our own. That’s not an excuse, but it is the reality I was operating in.

The first situation happened at a social event where an out-of-country official made inappropriate comments to one of my staff and followed them with text messages. They tried to downplay it. I did too. I handed the weight back to them when it was never their responsibility to manage someone else’s misconduct.

A few years later, it happened again. Another colleague experienced sexualized jokes and unwanted touching from someone they interacted with in a professional setting. They told me it wasn’t a big deal. I sought guidance and was advised that they could tell him his behaviour was making them uncomfortable. I followed that direction because I was trying to be a better leader, even if I didn’t have the full picture.

When the behaviour continued and he asked her for a private meeting, I reached out myself and asked that he and I meet because she wasn’t comfortable and it was more appropriate that he and I meet. His conduct toward her stopped, but I later learned he continued the behaviour with others. I hadn’t fixed the problem. I had only redirected it.

The next situation brought me closer to better practice, but still not where I should have been. A board member behaved inappropriately toward another staff member. We brought in an external investigator, a full investigation was completed, and he was removed from any involvement with our organization. It was the right action and much closer to the standard that should have been applied all along. Still, I know I could have supported my colleague more directly and with more care.

Across all these situations, I didn’t fully step into the leader I needed to be. I hesitated. I hoped things would resolve on their own. I leaned on the employee’s comfort instead of leading from principle. That’s the truth, and it’s the reason Diary of a Flawed Leader exists.

Leadership isn’t about the courses you take or the speakers you hear. It’s about what you do in the moments that are messy, uncomfortable, and deeply human.

When someone’s safety, dignity, or trust is at risk, you don’t wait for the perfect answer. You go find it. And you act.

Your team can only do their best work when they know you will stand between them and behaviour that harms them.

That’s the job. And that’s why I tell these stories.

These are the kinds of situations leaders rarely talk about — but they’re the ones that matter most. In my Diary of a Flawed Leader workshop, we dig into how to recognize these moments sooner, respond with clarity, and build the kind of trust teams rely on.