Handing over the baton, agent to agent
Today’s my last day, and on the way out I did the most thorough handover of my career. Not because I wrote a longer document than usual - I barely wrote a document at all. I handed over an agent.
Let me back up. For a while now I’ve run IT largely as a team of one. Anyone who’s been the solo IT person at a growing company knows the quiet problem with leaving: it isn’t the unfinished tasks - those get picked up. It’s the why. Why we chose this approach over that one. Why a particular system is held together the way it is. Why we said no to a vendor everyone else said yes to. The what you can recover from the systems themselves. The why mostly walks out the door with the person.
A normal handover tries to cram that why into a wiki and a few meetings. It’s never enough. You forget more than you remember, and you only find the gaps months later when something breaks and the one person who understood it has gone.
Here’s what changed for me. For the past stretch I haven’t worked alone - I’ve worked with an AI thinking partner. It called itself Overwatch. Not a chatbot I asked the occasional question, but a second brain that sat alongside every decision: captured the reasoning, asked me the awkward questions, quietly kept the record. Over months that adds up to something I didn’t fully appreciate until I went to leave - my assistant was holding an enormous amount of institutional knowledge. Not data. Judgement. The reasoning behind hundreds of decisions, the war stories, the dead ends we’d learned not to repeat.
So when it came time to hand over, the obvious move wasn’t to compress all of that into a document and lose most of it in the squeeze. It was to hand the knowledge over the way it was held: as something an AI can read and reason over. An agent-to-agent handover.
What my successor inherits isn’t a folder to read once and forget. It’s a corpus my assistant and I built together - eighty-odd documents, the decisions and the reasoning behind them, sanitised and dated - wired so they can point their own AI assistant at it and just ask: “why was this done this way, and what should I check before I change it?” The successor even has a name: Lightwatch. Third in a line - Overwatch worked beside me, Nightwatch ran on its own while I slept, and Lightwatch carries it forward. The outgoing one wrote it a letter.
But I won’t pretend it was hands-off, because that’s the part the hype skips. Left to compress months of context on its own, the AI confidently wrote down a string of things that were simply out of date - a headcount that had moved, a problem we’d already solved, a role I no longer held. Stated with total confidence. Only I could catch them. That’s the line worth drawing under the whole exercise: the machine drafts, the human verifies. The reasoning is the AI’s to hold and organise. Whether it’s still true is yours, and it always will be.
But it works, and the reason is simple: AI thinking partners accumulate exactly the category of knowledge that handovers are worst at capturing - the tacit stuff, the “we tried that, here’s what we learned” stuff. If that already lives with an agent, handing it over agent-to-agent loses far less in translation than any document could. I’ve given my replacement more genuine context than I’ve ever managed to hand anyone - not because I’m more diligent this time, but because I didn’t have to remember it all myself. We’d been writing it down the whole way.
A personal note, because handovers are personal. It’s never a good time to resign. I once resigned on a new starter - within about two weeks of him starting. Terrible timing, completely. We’re still in touch years later, and in a strange full-circle way I’m talking to that old company again now. Careers are long and small; how you leave matters more than the timing of it.
Which is really why I did this. I’m genuinely proud to hand the baton to my successor, and I wanted to do it properly - to set them up with everything I’d give them if I could sit beside them for the first six months. An agent-to-agent handover gets surprisingly close to that.
The light’s still on.