When Your Worst Day Shows You A Best Boss

As many of you know, I’ve been hard at work on my second book and it’s brought up a lot of memories. It’s also made me take a hard look at what brought me to this place in my career, and why I’ve had such a strong focus on creating more “best bosses” as part of my executive coaching and my communication efforts.

All this thinking has led me to what I believe to be the foundation of the “Best Boss Ever” podcast and the “Best Boss Ever” coaching program.

It’s the idea that you see your leader’s true colors on the worst day of your life.

For me, the first time it happened was September 11, 2001. I was working as a design engineer at the Chrysler Technology Center in Auburn Hills, Michigan, and my best friend was working in Washington, D.C.

That morning is still a bit of a blur to me, but there are a few things that stand out: the initial confusion, the fear as we all realized what was happening, and finally, the absolute panic as we all tried to get in touch with family and friends in New York and D.C.

The other thing that stands out is how colleagues around me behaved–particularly my boss at the time. While the rest of us quietly panicked, he seemed unphased and uninterested in the news. He was a young engineer who had recently been promoted. I didn’t doubt his technical skills, but at that moment, it was clear that he lacked leadership.

Finally, after what seemed like an eternity, the building was evacuated as a precaution. I was a few steps into the parking lot when I got a message from my supervisor letting me know I’d forgotten my laptop. He reminded me we had a presentation in the morning and that we’d need updated graphs so it was imperative I brought my computer home to prepare what was needed. I did as I was asked, despite being glued to the news and feeling absolutely heartbroken like so many other Americans.

That night, I sat up with my then-boyfriend and watched the news for hours in disbelief. I called family and friends and we attempted to support each other as we tried to process this tragic event. At 2am, I finally drifted off to sleep but I set my alarm for 6am to ensure my work was done—my manager had made it clear that this tragedy was no excuse to delay a deliverable.

The next morning, in my 9am meeting, I was prepared to review the data, but not for the response. My colleagues and boss were shocked that I had finished the presentation. They looked at me as though I was unaware of the gravity of 9/11.

I felt embarrassed and betrayed.

I may not have known it then, but that was the beginning of my Best Boss Ever journey.

After coaching thousands of leaders and listening to hundreds of stories on the Best Boss Ever podcast, I’ve come to believe that many people, myself included, will forever remember their most emotional days at work. Whether that’s learning of a death in the family, suffering a health emergency, announcing a pregnancy and an impending maternity leave, or dealing with the worst terrorist attack in history on American soil.

It’s these moments that shape us as humans personally and shape us as leaders professionally.

And I’m not the only one who’s had a work experience like that one that has forever changed them.

On episode 30 of the Best Boss Ever podcast, Stephanie Wolfe joined me to talk about her time working with FOUR(!) leaders who she would classify as “Best Boss Ever” material. But one that she mentioned really resonated, as it’s a similar situation to what I dealt with in 2001—except it was 2008 and Stephanie was working in the financial sector.

She recounts a particular period when things had really imploded, and the entire team was wrapping up a rough week in the midst of the financial crisis. Her leader at the time, Matt Snair, took the time to talk to everyone on his team. He wanted to really sit down and check in with each person to make sure everyone was okay.

He was stabilizing at a time when everything felt unstable.

These are just a couple examples that showcase how great leaders can respond to our worst days—and how those small actions can have big impacts decades later.

Have you had a worst day at work when your boss really showed up for you?

The Whipp is a variety of things — it's the whipped cream on top of your hot chocolate. It's that delicious layer of foam on top of your latte. It’s also my Wednesday newsletter, where I'll share wisdom, humour, and insights for professional peeps. Get a little something extra to help you put wisdom into professional practice.