Organizational Flow · Front matter · 2 min read · First Public Draft

A Digital Awakening

An honest question I couldn't answer, and where it sent me.

“Is our IT future-proof?”

Our CEO asked it in a company meeting, the way you ask something you already suspect the answer to. I didn’t have a good answer, and worse, I wasn’t sure what a good answer would even sound like.

So I went looking for people who might. This was around 2015 and 2016 — ten years ago now, which is worth saying, because a good deal of what sounded radical in those conversations is ordinary today and the part that mattered still isn’t. Through a fortunate chain of introductions I ended up talking to Adrian Cockcroft, then at Netflix and AWS, and Rodrigue Schaefer, Head of Engineering at Zalando. Both were generous with their time, and neither said anything I could have found in a book, though I had certainly looked. They arrived at much the same thing in different words: IT should not sit as a separate function. It should be the engine of innovation.

That rearranged something for me. I had spent two decades getting steadily better at running the engine, and almost no time asking why it had been built as a separate room from the rest of the business to begin with.

Once I started looking, the pattern turned up more or less everywhere, including in my own organization. Digital transformation as a rebrand rather than a rebuild — new tools, new vocabulary, the same operating model underneath. The organizations that genuinely changed were the ones where business and technology reinforced each other rather than negotiating a truce.

Years later, working across media, telecom and insurance, the tell has stayed much the same. The companies still struggling tend to be the ones treating architecture as a technical concern rather than an organizational one.

I still think about that meeting, though not because the question was clever. It was honest, which is rarer. Most transformation efforts start with the answer already decided; this one started with someone willing to say they didn’t have it.

That is where the argument in this paper came from. It wasn’t reasoned out from a theory so much as noticed slowly, in particular rooms, over a long time — worth knowing before reading the rest, because there is a difference between a model someone constructed and one someone kept running into.

Part I is where it stops being a story and starts being an argument.