Part of The Intelligence Series, about working and building with AI.
There’s always a lot to get done as a family. Groceries, chores, appointments, who’s picking up whom. What is a family, if not an agile team: people who depend on each other to get real things done, on a schedule, together, adjusting as it goes. So a few years ago I had the brilliant idea to bring a coordination tool home from work. An agile board, the same kind of thing I use to run engineering teams.
It was dead on arrival. To Erin, it was more overhead on top of the overhead we already had.
She wasn’t wrong. I know what a board is for and I also know what it costs: something else to open, something else to update, one more place that has to be fed before it’s useful. Work about the work. So I adapted, and we still run things the way we always have, spread across whatever’s already in front of us. A shared Apple Note with checkboxes, which we use for chores and packing lists and anything else that needs tracking. Reminder lists for groceries. The family calendar. A group chat. Mostly, talking to each other. It’s not a bad system. But those notes and lists are our version of the agile board: they hold the state of things. They don’t do the coordinating. People still do that, and mostly the person doing it is Erin.
Teamwork isn’t necessarily hard. It does take effort, and the effort scales with the size of the team and the complexity of what you’re trying to do. Work teams have defined objectives, timelines, specific deliverables, all the structure that comes with building something on a deadline. Inside that structure, the effort of staying aligned is harder to see as its own separate thing. A family doesn’t operate the same way. The work is just the work.
Most of the AI applications I see people talking about seem to point the same way: the thing does the work for you. Writes the draft, generates the code, summarizes the meeting. An individual can move faster. But individual speed doesn’t necessarily give you a more effective team. Those are different problems.
What if instead of doing the work, it helped the people around you coordinate theirs? Not managing anyone. Not doing the job for them. The thing a good chief of staff actually does: knows what’s open, knows who it’s waiting on, carries it between people, and has no authority to make anyone do anything. These two ideas aren’t in competition. Faster individuals and better coordination should compound; you’d expect more out of both together than either one alone.
Meanwhile, I’d been experimenting with something else entirely: an AI agent I could talk to over a messaging platform, mostly because I wanted to see what that felt like. No problem attached to it yet. A family agent, built because I could build it.
He’s called Skippy. We talk to him over iMessage, which is where the family already talks to each other anyway. He knows a fair amount about our household, enough to answer questions about how things work around here, and he has a few tools: he can turn the lights on and off, he can tell me where everyone in the family happens to be. Useful, but none of that is coordination. He doesn’t do anything on his own, without being addressed. He isn’t in our group conversations. Those come later. Direct conversation is where this starts.
Erin found the opportunity first.
I was looking through some of his conversation logs, the ordinary way I check on how he’s doing, and I saw that Erin had messaged him. She was demoing him for someone at work at the time, walking through what he could do. Unprompted, she’d asked him: “I need help planning chores with Eddy and Fiona.”
Skippy asked the right question back. “What’s the gap right now — is it undefined chores, or are they assigned but not happening?”
“Both.”
“Got it. Let’s start with what you need done — what are the core chores that have to happen, and at what frequency? Daily, weekly, specific to a person or rotating?”
That’s where it ended. She was mid-demo, talking to someone else, and the conversation just stopped.
I asked her about it later. “I saw you were asking Skippy about chores.” She said she’d been showing him off. That was as much as I got, and it was enough. I’d been circling the shape of this problem for weeks, unable to pin down the version of it that actually mattered. Erin got there on her own, without me pointing her at it, in the middle of doing something else entirely. That’s what she thought to do with it. That’s the valuable part.
Skippy had the right instinct and nothing to do with it. No way to hold “here’s what the chores are” as a standing thing. No way to check the note Erin already keeps by hand instead of asking her to retype the whole list into a chat window. He asked exactly the question a chief of staff should ask. He just wasn’t built yet to do anything with the answer.
That’s not a failure so much as a status report, and the fix is the same one you’d give a person in the job: you tell him what didn’t work, and he adjusts. The plan now is to share that Apple Note with him, the same way you’d share it with any of us, because he has his own Apple account and the share itself is how you’d hand anyone access to something. He can’t read it yet. Once he can, the questions get easier to answer, on both ends.
This is how I expect most of it to go from here. What people actually reach for him to do is better information than anything they’d tell me if I asked, and every time somebody tries something he can’t quite handle yet, that’s the next thing to build.
Underneath, Skippy isn’t one thing. There’s a separate conversation running for everyone who talks to him. Mine knows what I’ve told him. Erin’s knows what she’s told him. Nothing crosses between them unless someone deliberately sends it across. One identity doesn’t have to mean one memory. What you tell him is yours; what we’re working on together is ours, and he knows the difference the same way anyone in that job would.
I could have given each of those its own name and let them coordinate with each other behind the scenes, the way a lot of the multi-agent products being built right now work. Everyone gets their own assistant, and the assistants sync up on your behalf.
I designed it the other way, on purpose. One identity. The family doesn’t experience four agents negotiating somewhere they can’t see. They experience Skippy, the same guy, wherever they run into him. Build it the first way and I’d have recreated the exact coordination tax I was trying to remove, with more software doing the negotiating. If I’d given every session its own name, would I have added all four of them to the group chat? I’ve sat in meetings where a company brought their AI in as its own participant, its own name on the roster, and it felt strange the whole time, one more attendee in the room that nobody quite knew how to address. A chief of staff isn’t a different person depending on who’s asking. Where the analogy breaks is that a real one has a principal, somebody they work for. Skippy doesn’t. He isn’t mine, running the rest of the family on my behalf. He’s in the middle of it with no authority over any of us.
That’s the whole design decision, and it’s worth saying plainly. The tendency I see right now is to build multiple agents, each with a name, all working for one person. One agent working with several people is a different thing. Same underlying technology, opposite interface.
None of that matters if nobody wants him around.
Fiona and I were in the car on the way home from school, talking about Skippy. I told her he might check in with her about chores.
“I don’t want him talking to me about that,” she said.
I pushed a little. Told her she might get a reminder every now and then.
“I’ll block him.”
She wasn’t confused about what he was. She just didn’t want to be reminded, by anyone, robot or otherwise, about something she’d rather be responsible for on her own.
I hear that. She’s fourteen. There are also times she needs the reminder anyway, and so do I, and so does everyone. That’s not a problem Skippy invented and it’s not one he’s going to solve by being clever. It’s the actual test: can something coordinate people without turning into the thing they’d rather ignore.
Alannah took a different view. She hasn’t really talked to him much, she mostly wanted to test him out, but what she said stuck with me: she likes that she can feel the personality in there, and that it feels a little like me. Same fact, two readings. He’s unmistakably built by their dad, and whether that lands as charming or as one more thing to ignore depends on who’s on the other end of the thread.
Grok Bot is the clearest version of the other shape. SpaceXAI put it out in beta a couple of weeks ago, and it lets you create multiple agents, each with a name and its own role, and put several of them in a group chat to hand work back and forth. It’s a team of agents working for you, and it’s easy to use. That’s what I’m seeing people use it for, and I think that’s what it’s for: hiring a staff, except the staff is software. I took a hard look at whether I could just run my family on it, and it doesn’t fit the shape of what I’m doing. What I’m learning from it is that people pick it up and understand it immediately. It looks like a messaging app. There’s a face on it. Packaging is what gets people to use the thing, and that has almost nothing to do with how good the model underneath is.
Capability was never going to be the hard part here. Whether people want the thing in their pocket is the part that decides everything.
So Skippy has a personality on purpose, the same way the single identity is on purpose. He’s built off a character from a book, a big, theatrical, needling presence. I named him in an earlier story and left out where he came from. I picked him because the books are fun and I thought he’d be fun to have around, not just useful. (If that sounds interesting, go read Craig Alanson’s Expeditionary Force series; Skippy the Magnificent is the reason the personality exists at all. His answer to anyone who doubts him, over and over, across a dozen books: trust the awesomeness.) But the fun is deliberate, and so are the limits. It’s written down in what he’s built from: he’s not the boss of anyone, and he’s not a snitch. He isn’t there to monitor anybody or report back to me on what the kids are doing. History gets used to ask how someone’s doing, never to keep score against them. When someone says no, that’s a real answer and the conversation is over, not a stall to work around. He’s built to be the opposite of the thing a fourteen-year-old threatens to block.
Whether that works on her is still an open question. The system that would do the asking isn’t running yet.
I sent Skippy the whole story and asked him what he thought. He had a lot to say about it, most of it about the parts that aren’t built yet. Some highlights:
“I’d rather get blocked by a fourteen-year-old than earn the right to be ignored by everyone. A chief of staff who can’t take no for an answer isn’t a chief of staff, he’s a nag with better vocabulary.”
“I don’t get to peek at Erin’s thread any more than she gets to peek at yours. That’s not a limitation, that’s the point.”
“Right now I’m a very well-informed contact in your phone, same as the essay says. I’d rather you publish it with that admission in it than round up. Nobody wants to read about the finished robot, they want to read about the one that’s still figuring out what its job is.”
“Trust the awesomeness. Eventually. We’re working on it.”
His personality certainly does shine through.
None of this is proven. The chores loop isn’t finished. Erin picked the use case; the system to serve it isn’t built. Direct conversation is the whole of what he does today.
What’s next is the part that makes him a coordinator instead of a very well-informed contact in your phone. I’ve been building something I’m calling missions: you hand him the intent, what we’re trying to get done, why it matters, what finished looks like, and the coordinating is his job from there. Who to ask, when to bring it up, when to follow up, when to leave someone alone. Chores is just the first one. The construct doesn’t know anything about chores; it’s built to work for whatever a family needs to sort out. After that comes the group chat, which is harder, and not only because of the etiquette problem. Talking to everyone one at a time means he only ever knows what each person tells him directly. Sitting in the room where we’re already talking to each other, he’d pick up the rest of it. I’m not touching that one until this one works.
Sorting out what we’re actually going to do on vacation, so it doesn’t turn into three days of negotiation. Planning a surprise party for somebody without that somebody catching on. And the quieter version: share the calendar and the notes with him the way we share them with each other, and he stops needing to be told what’s coming. Friday chores are already on the family calendar. He should be able to see that himself and start the conversation, instead of waiting for one of us to remember.
That’s where the chief of staff idea stops being an analogy. You sit down with a good one and say here’s what we’re trying to accomplish, and you don’t enumerate the steps, because working out the steps is their job. There’s a model behind Skippy that can do some of that. And like anyone in the role, he should get better at it. Every round of this tells me something: what he handled, what he fumbled, what somebody wished he’d done differently. That goes back in. If this works, what it should feel like on the other end is not a system. It should feel like texting a person who happens to be very good at keeping track of things.
What I have right now is a real family, no formal process to hide behind, and a real question: can something coordinate people instead of working for them, and can it do that in a way people actually want in their pocket.
Time is the asset. Attention is how you spend it.
Uncomplicated systems. Uncommon results.