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Diary of a Flawed Leader
December 4, 2025

Who Really Shapes the Way We Lead?

A reflection on the leaders we admire and the unexpected places our leadership lessons come from.

Tracey Maconachie
The Founder
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A reflection on the leaders we admire, the influences we carry, and the unexpected places our leadership lessons truly come from.

I’ve been thinking about leadership and the people who shape how we show up.

This article started as one of those classic questions about who you’d invite to dinner if you could choose any leadership hero.

My answer was Adam Grant, Brené Brown and Malcolm Gladwell. And of course Simon Sinek, but someone else at the table had already claimed him and I’d basically invited myself to their dinner. Which felt fair because if you’re talking leadership, Simon usually ends up on the guest list.

But as I sat with the anniversary of my father’s passing, I realized I would change that list. When I thought about who has actually shaped the way I lead, the answer became unmistakable. My father would be at that table. Not because he was famous, but because his example influenced my leadership more than any bestselling author ever could.

Last year at this time, while writing his obituary and eulogy, I saw it clearly. He leaned into uncomfortable moments. He looked out for the underdog. He took people under his wing because he believed they deserved a real chance. He mentored and hired people who were “underqualified” on paper because he saw potential where others only saw limits.

Looking back on my own career, I can see how much of that I absorbed. I’ve always gravitated toward supporting people who were overlooked or underestimated, often because leaders before me never bothered to look past a title.

He was also the one who sat with you when you had work to do. When I was young, he probably did too much of it. As I grew older, he shifted into being a sounding board instead of a problem-solver. That’s what real leadership looks like. Guidance without taking the wheel.

And he always had my back. Whether I was leaving home for a job in Toronto that made no sense on paper, or putting my name on a provincial ballot, he showed up every single day. Not just as a proud dad, but as someone who believed in supporting people fully.

So let me ask you. Who shaped your leadership? Is it someone you worked with? Someone you heard on a podcast or saw on a stage? What drew you to them? Has it changed over time?

For me, it took writing my dad’s eulogy to understand just how much his example shaped mine. I only wish I had realized it sooner so I could have thanked him.

If reflections like this resonate with you, you may be ready to step into your own next chapter as a leader.

My coaching and workshops focus on exactly that—helping leaders understand their patterns, shift their habits, and build a presence rooted in clarity and responsibility.
If your organization could benefit from deeper, more human leadership development, let’s connect.

Diary of a Flawed Leader

Honest stories from thirty-five years of leadership, what I got wrong and what it taught me.