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Training (For Humans) · 8 pieces

Training (For Humans)

The system is only half of it. These are for you — what you are taking on, when to hand something over, and what to do when it gets something wrong. Read the first three before you install anything; the rest once it is running.

Feeding one of these to your chief of staff? Every piece has a plain-Markdown twin — the piece's URL with .md on the end — and the whole site is indexed at /llms.txt.

Before you have one

What you are actually taking on, and the two decisions worth making before you install anything.

A quiet corridor in morning light: an open door with a lamp glowing inside, its brass nameplate reading Chief of Staff, and a closed door beyond it labelled Counsel.

What You're Actually Hiring

Chief of staff is a real human role, and borrowing the title means borrowing the shape of the job — including the part where you end up managing a manager rather than operating a tool.

4 min read
An office seen from the doorway: an empty desk in the foreground with a brass plate reading Leave a Note and a stack of papers on it, and beyond it a lit workbench with hand tools laid out in a row.

When You Talk To It, And When You Don't

The most-asked question about the whole system, answered — you do not stand in the assistant's doorway asking them to tell the engineer something, and the handoff is what keeps the two apart without letting them drift.

3 min read
An iron strongbox open on a desk by a window, folded papers inside and a key in its lock, a luggage tag on the key lettered Your Data; rooftops and aerials beyond the glass.

Where Your Data Lives

Inference and custody are two separate decisions wearing one coat, and conflating them is why the hosting conversation always stalls on the wrong axis.

3 min read

Once it is running

The practice. How authority widens, who is accountable when it goes wrong, and what separates people who get value from this from people who get annoyed by it.

An open notebook on a sunlit desk, one line of handwriting struck through with a red pencil stroke and the words here's my feedback written neatly beneath it, the pencil resting across the page.

Correct It, Don't Complain About It

The single habit that separates people who get value from a chief of staff from people who get annoyed by one — they treat a bad output as an input.

3 min read
A single sheet of paper on a desk stamped Approved in red above a signature, the rubber stamp and a fountain pen beside it, and a panelled door standing slightly ajar behind.

You Are The Security Boundary

A permission granted in passing does not expire when your attention does. The decision record that makes the system auditable is the same thing that makes a careless "yes" permanent.

3 min read
Three brass keys of increasing size laid in a row on linen, each tied with a paper tag; the three tags read Read, Draft and Send.

Hire Narrow, Then Widen

Give a new curator less than it needs and let the gaps prove themselves. A refusal you did not anticipate is the strongest evidence you have that the boundary is real.

3 min read
A desk at dawn with an open folder and a closed laptop, beside three stacked archive boxes whose spine labels read Today and Last Week.

Manage The Context Yourself

Turning memory off is not asceticism. It is the difference between a session that knows what you gave it and a session that knows something you cannot inspect.

3 min read
A drafting table beneath a window with a hand-drawn dashboard sketch pinned to it — bar charts, boxes and arrows in pencil — and a small card propped above it reading Built to Order.

Ask It To Build You The View

Most people accept whatever interface their tools shipped with. The system can build the one you actually wanted, in an afternoon, and rebuild it when your work changes.

3 min read