Design thinking for growth

The Real Work of Leadership

Another chapter in my Diary of a Flawed Leader — lessons I’m still learning every day.

As a leader, I’ve never been shy about firing people. That might sound harsh. But I’ve also never been shy about taking a risk and hiring someone others might not.

Hiring and firing aren’t the parts of leadership most people want to focus on. They’re uncomfortable, emotionally charged, and rarely discussed in leadership programs.

Yet they’re two of the most critical skills that determine whether you can actually deliver on your objectives — whether you report to a board, a manager, or a VP.

Both decisions test your values.
Both reveal your courage.
And both leave a mark.

I learned that lesson firsthand.

During my first executive interview, the board kept asking how I handled personnel challenges — so often, in fact, that I finally asked if there was a real issue or if this was a theoretical question. They smiled and said it was theoretical.

It wasn’t.

But that’s a story for another day.

What I can tell you is this: that experience shaped the way I lead. It reminded me that leadership isn’t just about strategy or vision. It’s about people — the ones who make the work possible, and the ones who can derail it.

Hiring for Potential, Not Perfection

When I think back to my own start, I remember someone telling me I wasn’t the right fit for that type of job. Fortunately, another organization decided to take a chance on me — and I stayed there for 20 years, achieving outcomes I could never have imagined. That experience stayed with me.

So when I’ve been in the position to hire, I’ve tried to do the same: to see beyond the résumé, the accent, or the lack of direct experience building with compassionate leadership.

One of my favourite hires was a woman who had just completed her master’s degree in bioscience. She was relatively new to Canada and had a background in research. On paper, she wasn’t the obvious choice for a communications role — but I saw something else: curiosity, discipline, and a genuine passion for the work.

We spent time coaching, training, and building her confidence in a style of communication that was more conversational and less formal than she was used to. It wasn’t easy for either of us, but it was absolutely worth it. Our goal was to chase progress not perfection.

A few weeks ago, while I was in Vancouver, I reached out to her on a whim. Within hours, we were sitting together — laughing, reflecting, and talking about how we could support each other in our next chapters.

That’s what I love about leadership — when the people you once hired become colleagues, collaborators, and friends.

The Harder Lesson: When It’s Not Working

Of course, not every story ends that way.

There was another person I hired to work with clients. From early on, something felt off — not bad, just… misaligned. They were capable, kind, and professional, but never quite at ease in the role.

We invested in coaching, development, and clear expectations. Eventually, it became clear it wasn’t a fit. But when a colleague urged me to give them another chance, I did.

For six more weeks, I tried to make it work. We set measurable goals, met weekly, and discussed progress.
When it still didn’t work out, I had to make the call I’d delayed.

They were surprised.

I wasn’t.

And in truth, I’d failed them — not because I fired them, but because I waited too long to act. In trying to be kind, I had prolonged their discomfort and mine.

That’s one of the hardest lessons I’ve learned as a leader: compassion doesn’t mean avoidance.

Finding the Hidden Gems

But there’s another kind of story that keeps me in leadership — the joy of finding hidden gems.

Every organization has them: the quiet team member a few levels down who just gets the work done, the one nobody asks for input from, or the person whose first language isn’t English but whose insights are brilliant once they find the right words.

Spotting that potential — and giving it a chance to shine — is one of the most rewarding parts of leadership.

When people realize they’ve been seen and trusted, everything changes. Confidence builds. Energy shifts. The whole team starts to rise.

The Real Work of Leadership

Hiring and firing aren’t the glamorous parts of leadership. They don’t make for inspiring quotes or polished conference keynotes. But they are where integrity, courage, and empathy collide.

The truth is, leadership isn’t a science. It’s a series of imperfect decisions made with the best intentions at the time.

The key is to keep learning from them — to take risks on people, to make the tough calls when needed, and to trust your instincts even when it’s uncomfortable.

Because at the end of the day, the measure of a leader isn’t how many perfect hires they make — it’s how they handle the imperfect ones.

Hiring and firing will test every leader’s instincts. ‍

Coaching will prepare you for these challenges.