The gap between "we tried an AI agent" and "we have an AI teammate" is almost never the model. It's the setup: whether the agent has standing work, real access, and a first job whose value shows up without anyone remembering to ask. Here are the five setups we'd do in week one, in order. None takes longer than a coffee.
1. The morning brief
The simplest standing routine, and the one that changes how the day starts: every morning before you sit down, a brief: today's calendar with context attached, what moved since yesterday, what's waiting on you. Your Chief of Staff arrives with this reflex built in; your job is just to read it for three mornings and correct what's noise. By Thursday it's briefing you like someone who knows you, because corrections stick.
The setup: hire the teammate, tell it what a useful morning looks like, done. It schedules itself.
2. Wire the tools, then ask for one cross-tool job
Connect your tools (if your Claude account already has them, this step is already done), and then immediately give the teammate one job that crosses two of them. Read this morning's Sentry errors and open an issue for the real one. Pull the week's merged PRs into a change summary. The cross-tool job matters because it's the thing no single product you own can do, which is the fastest way to feel the difference between a connected teammate and another tab.
3. Put a triage pass on your inbox
Not full delegation on day one. A pass. The teammate reads what lands, sorts it into needs you / needs anyone / needs nothing, drafts replies for the middle bucket, and sends nothing without your approval. You keep doing the deciding; you stop doing the reading. A week of this teaches it how you decide, and teaches you which approvals you're ready to hand over. This is the executive assistant pattern starting from its thinnest safe slice.
4. The weekly report that writes itself
Pick the recurring document everyone values and nobody enjoys (the investor-update draft, the Friday team summary, the metrics recap) and make it a routine: the teammate assembles it from the tools it's now connected to, on schedule, into a shared doc where you edit rather than author. The first one will be mostly right, not perfect. Correct it once; the corrections are permanent staff.
5. A standing brief on the thing you're deciding about
Whatever decision looms this quarter (a market, a competitor set, a technology bet), give it to a research teammate as a living brief rather than a someday-weekend. It reads continuously, keeps the document current, and flags changes that matter. The payoff usually arrives the first time someone asks "what's the latest on X" and the answer is a link instead of a scramble.
Why these five
Each one runs unattended after setup. That's the filter. A teammate you have to remember to use is a tool with better manners; these five give it standing work, so the value compounds while you're doing something else. And they're deliberately spread across lanes: by Friday you'll know which one pulled hardest, and that answer, not a roadmap, is how small teams end up staffing whole functions this way. The second week's setup will be obvious by then.
