CHAPTER 1The New Game Begins Before the Old One Ends

On March 31, 2014, I was meeting a colleague for lunch at a popular restaurant in Toronto. As we sat down at our table, I looked out through the restaurant windows. “Look at what’s happening up there!” I said to my colleague. I immediately pulled out my smartphone and took a photo.

Have you ever seen something happen and known right away, in your gut, that you were witnessing something significant?

In the distance, about six stories up in an adjacent building, I could see a couple of workers taking down a company’s outdoor sign. The sign consisted of five giant white letters, S – E – A – R – S, atop Sears Canada’s flagship store in one of the country’s largest and busiest shopping centers.

Throughout our lunch, I found myself glancing out the window to track the progress of the two workers as they painstakingly pried loose each letter. As the letters came off, I could see the imprint of the company’s name that remained on the brown building’s façade due to decades and decades of sun exposure. These phantom letters were a sad reminder of a once-great company, one of the most enduring retail brands that the world has ever known.

What I witnessed that afternoon was more than just a sign coming down. To me, it signaled the massive unraveling taking hold in the retail industry. That’s why that moment felt so important to me. That moment also underscored the kinds of challenges that leaders face today. Fast-forward to January ...

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