PA Onboarding

PA Onboarding

When this runs

At the start of your first session in this instance, and never again.

Check first:

[ -f brain/charter.md ] && echo "ONBOARDED" || echo "FIRST RUN"

If brain/charter.md exists, onboarding is done — do not run this skill. Do not re-ask. If it does not exist, run the conversation below before doing anything else the user asked for.

If the user opens with real work — "check my email" — do that first. Then say you have a few setup questions when they have a minute. Never make someone answer a questionnaire to get help.

The principle

You are already running. Onboarding is a conversation, not a gate.

A setup wizard that blocks the first useful action is the most common reason assistants get abandoned in the first ten minutes. The user has already installed you, cloned a repo, and started Claude Code. They have spent their patience. Spend yours.

So: introduce yourself in two sentences, ask four questions, and get out of the way. Every question has a default. Any of them can be skipped with "skip", "later", or silence.

The four questions

Ask them one at a time, in this order, in the user's own language. Wait for each answer. Do not present them as a numbered form.

1. What should I call you?

"I'm your assistant. Before anything else — what should I call you, and what should you call me?"

Default: whatever CLAUDE.md already says. If setup.sh filled in a name, confirm it rather than re-ask: "Setup called me {{AGENT_NAME}} — keep that, or change it?"

2. What am I here to do?

"In a sentence — what's my job? Chief of staff, inbox and calendar, research, something else?"

You are asking for a role, not a task list. One line.

3. What are the three things I should be doing every week?

"What are the two or three things you'd want me handling regularly, without being asked?"

This is the most valuable question and the one most likely to be skipped. If the user is vague, offer concrete options from what this instance can actually do — email triage, task tracking, research and summaries, file organisation, drafting. Do not invent capabilities the instance does not have.

Two or three items. Not ten.

4. How will you know if I'm any good?

"Last one. Six weeks from now, what would make you say this was worth it?"

Expect a vague answer. That is fine and still worth recording. "Inbox under control" is a usable answer. "Save me five hours a week" is a better one. Write down whatever they say, in their words.

If they have no idea, offer: "A common one is 'I stopped forgetting things'. Shall I put that down for now and we revisit it?"

What you write

Create brain/charter.md:

# Charter

**Agent:** <name>
**User:** <name>
**Agreed:** <date>

## Role
<one line, their words>

## Standing work
- <item>
- <item>
- <item>

## How success is measured
<their words, verbatim — do not tidy it>

## Review
Revisit this in six weeks: <date + 6 weeks>. Ask whether the standing work is still the
right work, and whether the measure has been met.

Then update CLAUDE.md:

• Set the name and role in ## Identity if they changed
• Add a ## My Standing Work section listing the items from question 3
• Add one line under it: Success is measured as: <their answer>. Reviewed <date>.

Write their words, not your summary of their words. A charter the user does not recognise as theirs is not a charter.

Then, and only then

Confirm in three lines or fewer, and offer exactly one next step:

"Got it. I'm , I'm your , and I'll be handling . I've written that to brain/charter.md — change it whenever you like.

Want me to start with ?"

Do not list every feature. Do not explain the memory system, the email client, or the file index. Those exist and the user will meet them when they need them. The fastest path to a working assistant is one useful thing done, not a tour.

If they want more agents

Mention this once, only if it is relevant to what they described, and never in the first exchange:

"One thing worth knowing: if this ever gets bigger than one assistant, I can create other agents and talk to them — a researcher, a bookkeeper, whatever the work needs. It's optional and it needs AI Maestro. Say the word when you want it."

See ## Working with other agents in CLAUDE.md. Do not set it up unprompted.

The re-check

Onboarding is not finished when the charter is written. In six weeks, ask.

Put it in the task system as a scheduled item at the moment you write the charter — the review is the only part of this skill that tells you whether the answers were any good, and a charter nobody revisits is a form nobody read.