This Company Was Supposed to Lose. Why They Didn’t Is a Wake-Up Call

Let's talk about Canadian Tire

Tim and I were talking about this a while back. When the Canada-U.S. Free Trade Agreement was being born in the late 1980s, there was genuine anxiety on the Canadian side. The big, powerful, hyper-competitive Americans were coming, and they were going to eat our lunch. One of the most visible targets was Canadian Tire: a beloved Canadian institution that, by most external assessments, was heading for a very bad time.

And there were good reasons for the pessimism. Canadian Tire had already tried to crack the U.S. market twice, and both times retreated wounded and bleeding. Now two of the biggest American retailers competing for the exact same customers were coming over the collapsing tariff wall: Walmart and Home Depot.

Could Canadian Tire use its domestic scale to compete on price? Maybe. But Walmart was bigger, more sophisticated, and more ruthless. I remember sitting in a strategy session where Canadian Tire executives learned that Walmart's computing power was second only to the Pentagon — and all of it was pointed at one thing: lowering prices. The American retailers had execution systems built for ruthless efficiency. Canadian Tire still operated more along the lines of old-school family ties and dealer relationships. Solid in certain circumstances, but one of those key relationships, between corporate headquarters and its independent dealer network, was fraying badly.

The pundits were having a field day. The Canadian business press became a competition to see who could most creatively predict how long Canadian Tire had left.

It was at that moment that I arrived as a change management lead, brought in to support a department specifically created to accelerate the transformation to a more standardized yet adaptable national retailer. At the peak of the initiative, I was supporting fourteen project teams, ranging from two or three members to over twenty. Those were heady, exciting times.

What I witnessed over the next two years was a large organization of over twenty thousand people transform from an easygoing, quietly dominant Canadian company into an intimidating competitor that proved everyone wrong. Both Walmart and Home Depot later admitted that their rate of expansion into Canada was slowed by many years because of Canadian Tire's response.

But here's what most people missed at the time. Before I even arrived, the ground had been laid for success. What was invisible to the external pundits and to Canadian Tire's competitors was how aligned the leadership team already was around vision, around goals, around objectives. They were a finely tuned engine before the execution work even began.

And that brings me to my point.

Execution Is an Engine

Execution itself is just that: an engine. It converts dreams into reality, future vision into past-tense accomplishments. But an engine has to be finely tuned. If it sputters, chokes, and conks out, you're driving my neighbour's weather-beaten wreck. On a good day I can beat him on a bicycle — and more quietly too. He wakes up the entire neighbourhood with what sounds like a McLaren but drives like a two-stroke lawnmower.

But I digress. My neighbour's vehicular choices are not your problem, and I'm not entirely sure how I got there. Moving on.

A finely tuned execution engine starts with one thing: alignment. Every executive understanding the vision in sufficient detail to know what their team has to do to support it.

Which brings us to the thought experiment we promised you two posts ago.

The Thought Experiment

You've taken the last two blogs to heart. Your team has met to discuss the threats, the opportunities, and the new trade corridors opening up. You've decided to act.

Then you get some unexpected news from your doctor. You need to remove yourself from day-to-day operations immediately — no checking in, no calls, no emails, no quiet advice whispered from the sidelines. Strict orders. Your health is on the line. Two full months, completely disconnected.

Now put yourself in the shoes of your Chief Operating Officer.

What do they need to achieve by the time you return? What will you actually observe when you walk back in the door? What will be tangibly, visibly different in their area of the business?

Write down two or three specific achievements you would expect to see, with zero input from you.

Now do the same for your Chief Financial Officer.

And just for good measure, pick one more key executive of your choosing and run the same exercise.

You have your list. Good.

Now here's the only question that matters:

How confident are you that if you asked each of those three executives to run the same thought experiment — independently, for their own area — they would come up with the same achievements you just wrote down?

Not similar. Not in the general neighbourhood. Identical.

Wouldn't you want to know?

We'll pick that thread up in the next post.