My most valuable AI agent does absolutely no work, and I mean that as the highes
By Allie K. Miller · June 18, 2026 · Curated by George's Blog
My most valuable AI agent does absolutely no work, and I mean that as the highest compliment.
For a while it was just me and my Chief of Staff, Simon. Simon runs six direct reports (Monica, Chandler, Phoebe...), each with their own sub-agents. I'd hand him a goal or task, he'd orchestrate it, work came back. Good, but things slipped, or we'd drift from a goal, or the same problem would resurface three times.
No one was watching the work going "is this good?" or "what keeps breaking?" or "what did we learn?" and updating the system.
So I gave Simon an assistant named Toby. All Toby does is watch and fix.
I love Toby.
(Not that way.)
He flags when we drift from our goals, catches recurring issues, and manages our memory. The whole system gets smarter instead of just busier. More effective instead of just more powerful.
Most people building agents seem to stop at the doer (task completer) or the judge (task verifier).
✔️ AI doers might draft your invoice reminder emails, run competitive research for you, narrow down a big vendor group for you based on criteria, run a forecast on your Brazil market
✔️ AI judges might review your code before you push or check your PPT draft against brand guidelines. Useful, but it only looks when you ask it to or gets triggered after task completion.
A watchdog looks all the time, and tells you what you didn't think to check. It's a safety net, a second set of eyes, a bar raiser.
All of this came through iteration (and I walked my AI Agent Mastermind students through all four iterations of my AI agent workforce and what I learned), but a massive unlock was splitting the "project management" work in two - orchestration and deep reasoning with one agent + monitoring and memory with another.
I keep saying this but the boring bits of AI are some of the most important bits. I'm sure the AI labs will add this functionality into their systems, but for now, Toby is a huge leg up for my AI workforce.