Let's talk about Margaret

I've spent twenty-five years walking into industries I didn't know. Luxury fashion, refugee operations, global sports, insurance, beer. Figuring out what actually makes them work. I spent some of my career making wooden automata and some as a brand strategist and creative director. But the thinking was always the same underneath: understand how things work, find the signals. Make the invisible visible.

The thing I kept noticing, in every sector, was that the most important knowledge in any organisation was never in the system. It was in somebody's head. The person who'd been there long enough to know not just what happened, but why it mattered.

That observation is what led me to AI, not the other way around. I didn't start with the technology and go looking for a problem. I started seeing patterns and realised that's what AI could do too.

This newsletter is called The Contour because that's what we do. We map the contours of what an organisation actually knows, the terrain that doesn't show up on the org chart, and turn it into something durable.

If we know each other well, this will make sense. If we're just networkers, thanks for reading this far. Either way, let's start with someone you probably already know.

Every business has one.

That person who just knows. Knows where everything is. Knows why you made that decision three years ago. Knows not just what happened, but why it matters now.

She's not on the org chart as Chief Knowledge Officer. She's just Margaret.

Auditors ask difficult questions? Margaret. New starter needs to understand how things actually work around here? Margaret. Something feels off about a big decision? Check with Margaret first.

Here's what makes Margaret genuinely irreplaceable: anyone can give you the numbers. Margaret knows what they mean.

That's not memory. That's not data you can put in a spreadsheet. That's context. The relationships between things. The history that gives meaning to the present. The why behind the what.

Most conversations about AI in business skip straight to the technology. Which model. Which platform. Which vendor. How much it costs.

None of that is the hard part.

The hard part is that the AI has no idea who Margaret is.

It doesn't know that this client gets nervous when you lead with risk. It doesn't know why you stopped working with that supplier in 2019. It doesn't know that the document everyone cites as policy was actually written during a crisis and was never meant to be permanent.

Margaret knows all of this. And when Margaret's not there, on holiday, ill, or eventually somewhere else, that knowledge disappears with her.

This is the problem that sits underneath almost every struggling AI implementation we encounter. Not the technology. The context.

There's a term for what Margaret holds: institutional knowledge. Every firm has it. Almost none of them have found a way to make it durable.

The ones that figure this out first will have an advantage that compounds. Not because their AI is better. Because their context is deeper.

That's what we're here to think about.

Read the full piece: The Irreplaceable Expert

The Contour is published by Context is Everything. If this landed, forward it to whoever your Margaret is.