The Same Movie, Different Technology

I started my career in 1997, just as the internet was beginning to change everything. In the years that followed I worked inside and alongside dozens of companies navigating that shift. What I watched play out wasn't really about technology. It was about leadership.

What I watched wasn't random. The same three responses played out across industries, across company sizes, across leadership teams. And where a company landed told you almost everything about where it was headed.

The first group simply didn't engage. Not because they couldn't see what was happening, but because it wasn't going to be their problem. They were close enough to the end of their tenure that the disruption would land on whoever came next. So they kept running the business the way they always had, collected their remaining years, and left. I call them the Clock-Watchers. You probably know a few. And if you watched them closely, you saw what came next — leaders who eventually recognized what they had missed, coming back to fight for relevance from a weakened position, with fewer resources and a shrinking runway.

"The fight to catch up is always harder than the fight to stay ahead."

The second group felt the pressure to do something, so they did just enough to check the box. They stood up a separate e-commerce operation, hired a VP to run it, gave it its own systems and its own P&L, and called it a digital strategy. They could point to the effort when asked. The Fence-Sitters were covered, and being covered felt like enough. It wasn't. The work sat beside the business rather than inside it, disconnected from stores, from supply chain, from customer data. The bill for all that disconnected activity came due later, when companies spent the better part of a decade and billions of dollars trying to unwind it under the banner of omnichannel.

"Being covered felt like enough. It wasn't."

The third group never stopped looking at their own business with fresh eyes. They weren't defensive about how things worked today because they were too focused on how things could work tomorrow. When new technology emerged they didn't ask whether it was a threat. They asked whether it could make them better. And when the answer was yes they moved. Not into a lab. Not into a pilot. Into the business itself. They were the Driven, and that drive compounded over time into a gap their competitors spent years trying to close.

The Clock-Watchers retired fine personally. Their companies, mostly, did not. The Fence-Sitters didn't collapse. They kept the lights on, made their announcements, and pointed to the effort when asked. But their shareholders experienced something worse. They experienced a decade of nothing, while companies that moved decisively compounded returns that made the gap nearly impossible to close. The Driven built something durable.

I'm watching the same movie right now.

The names are different. The technology is different. The pace is faster, significantly faster. But the three camps are identical. I can already place most of the CEOs and companies I encounter into one of the three categories, and the early signals of where each ends up are exactly what I saw in 2001, in 2005, in 2010.

The Clock-Watchers are easier to spot this time. The AI wave is moving fast enough that the math on outlasting it doesn't work the way it did with the internet. Fifteen years of runway is not what's on offer.

The Fence-Sitters are the most dangerous place to be, because it feels responsible. You have an AI task force. You're running pilots. You're being thoughtful. But if AI lives in a department rather than running through your operations, your customer experience, your decision-making, you're not being thoughtful. You're just covered.

The Driven are already separating. They're not talking about AI strategy. They're just using it, learning from it, cutting what doesn't work, and doubling down on what does. Every month that compounds.

So here is the only question that matters: which camp is your company in right now? Not which camp you intend to be in. Not which camp your strategy deck describes. Which camp does your business actually live in today?

The outperformers of the next decade are being decided right now. Same as they were in 1997.