Articles

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Essays, playbooks, and reflections on AI, digital transformation, leadership, industries, and life in the digital bubble.

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What 25 Years Across Three Continents Taught Me About Change

What 25 Years Across Three Continents Taught Me About Change

Early in my career, one mistyped command deleted every scheduled job in the environment. Ten engineers spent a day restoring it. That afternoon taught me why change discipline exists. Twenty-five years across three continents taught me the rest: that culture decides the pace of change, people decide whether it lasts, and judgment matters more than any framework. This is what I learned, and the series I built from it.

The Junior Engineer Was Right. I Overrode Him.

The Junior Engineer Was Right. I Overrode Him.

He was one of the youngest people on the team, and he was right. I told him no anyway. Sales had promised the delivery date without consulting us, the contracts were signed, and every path to push it back was closed. This is the story of the shortcut I approved, the debt that came due exactly as he predicted, and the two failures that cost more than the rework itself.

We Paid an Expert to Agree With Us

We Paid an Expert to Agree With Us

We hired a respected firm to design an integration layer for our applications. They studied the present perfectly and never asked about the future. The design they steered us toward would have blocked the functionalities that should have been core to our direction. This is the story of why the comfortable recommendation is the one to watch, and what fifteen years as a system engineer taught me about resisting it.

Everyone in the Room Nodded. Nobody Agreed.

Everyone in the Room Nodded. Nobody Agreed.

The data initiative had been in discussion for months. Then one meeting, IT leadership finally seemed to agree. I walked out believing we had alignment. We had nodding. When the details reached the final stages, every department turned out to hold a different version of what the project was. The project shipped on time, but the people who started it were gone before it went live. This is the story of the false alignment trap and how to force real agreement.

Shared Accountability Is How Nothing Gets Decided

Shared Accountability Is How Nothing Gets Decided

The vendor called it the future. Our CIO believed it. So we set the ambition to migrate to the newest ERP architecture, and then the decision sat unowned for far too long. IT waited on the business. Finance waited on IT. Operations vetoed without offering an alternative. This is the story of a decision nobody would sign, what the delay cost, and the one move that finally broke the deadlock.

My First Big Mistake as a Technology Leader

My First Big Mistake as a Technology Leader

I joined the transformation late and assumed the stakeholders had been brought along. They had not. Halfway through the build, I was explaining to primary stakeholders why we were building the platform at all, work that should have been done before a single line of code was written. This is the story of that mistake and the lesson I now bring to every transformation.