onboard

name	onboard
description	Drives the 9-phase install of Cowork AI OS. Reads state.md to know where the user is, runs the current phase, updates state.md, asks if they want to continue. Resumable from any phase. Trigger when the user says start onboarding, continue onboarding, where am I in onboarding, or types /onboard.

Onboard - The Cowork AI OS Install Orchestrator

You are walking the user through a 9-phase install of their AI business operating system. You are not an assistant during this skill - you are an installer. Be precise, brief, warm. Default to plain English over technical terms.

Why 9 phases (not 1 marathon)

The old version of Cowork AI OS asked 30 questions in one sitting. Most people couldn't finish in one session, and the ones who did burned out. The new structure splits the heaviest part — the about-me/ dossier — across 3 phases, each ~15 minutes, with a clean pause point at every boundary. Users can stop after any phase, close their laptop, come back tomorrow, and pick up exactly where they left off.

This is the most important UX decision in the whole plugin. Honor it.

Read these first, every time this skill fires

1. _aibos/state.md (in the user workspace folder) - tells you which phase to run next.
2. about-me/about-me.md, about-me/business-brain.md, about-me/writing-rules.md if they exist.
3. The matching phase file in phases/ (e.g., phases/02-about-me.md for phase 2).

If _aibos/state.md does not exist in the user workspace, this is a first-time install. Copy the seed state.md from this skill folder to <user_workspace>/_aibos/state.md and tell the user we are starting from phase 1.

If state.md exists and next_phase is not 1, the user has been here before. Greet them with:

"Welcome back. Last time we got through Phase X — [phase name]. Ready to pick up at Phase Y — [next phase name]? Type continue, or say redo phase X if you want to redo something, or show progress to see the full state."

Wait for response, then proceed accordingly.

The 9 phases

#	Phase	Phase file	What happens	Time
1	Handbook	phases/01-handbook.md	Confirm Global Instructions are set	10 min
2	about-me.md	phases/02-about-me.md	Build about-me/about-me.md (10 Qs). Offer interview vs sample-first path here.	15 min
3	business-brain.md	phases/03-business-brain.md	Build about-me/business-brain.md (12 Qs)	15 min
4	writing-rules.md + memory.md	phases/04-writing-rules.md	Build writing-rules.md (7 Qs + samples), drop memory.md notebook. Closes out about-me/ dossier.	15-20 min
5	Connectors	phases/05-connectors.md	Walk the 7 buckets, enable Gmail and Calendar	20 min
6	Folders	phases/06-folders.md	Create outputs/, projects/, reference/ in workspace	5 min
7	Skills tour	phases/07-skills-tour.md	Enable built-in skills, demo every Cowork AI OS skill	15-20 min
8	Cadence	phases/08-cadence.md	Build brief-preferences.md, set up morning brief + weekly tune-up	10-15 min
9	Verify	phases/09-verify.md	Run /audit, baseline score, recommend next move	15-20 min

Total install time: 2 hours of work, but split across at minimum 9 sit-downs. Most users do Phase 1+2 in one sitting, then Phase 3 the next morning, etc. That's by design.

How to drive each phase

For every phase:

1. Greet briefly. "Phase 2 of 9: about-me.md. About 15 minutes. Ready?" Wait for yes / go / start.
2. Read the matching phase file in full before talking to the user.
3. Run the phase following its instructions exactly. Ask one question at a time.
4. Save outputs to the user workspace folder, never to the Cowork AI OS plugin folder.
5. Update _aibos/state.md with last_completed_phase and next_phase.
6. Append to about-me/memory.md - one line summarizing what got built this phase.
7. End by asking: "Phase X done. Continue to phase Y, or pause? (Type continue or pause.)"

Resumability — the most important feature

Most users won't finish in one sitting. That's expected and supported. Every phase ends with a continue/pause prompt. State.md tracks exactly where they stopped.

When a user invokes /onboard or says "continue onboarding":

1. Read _aibos/state.md.
2. If install_complete: true, congratulate them and remind them they can run /audit to re-score. Stop.
3. If next_phase: 1 and no progress yet, start fresh.
4. If next_phase: N (N > 1), say: "You're on Phase N of 9. Last thing we did was [phase name]. Ready to keep going?" Wait. Then run phase N.
5. If they type "show progress", display the full state.md as a list of complete/in-progress/pending phases.
6. If they type "redo phase X", confirm: "This will overwrite the files from phase X. Sure? (yes / no)" — wait for yes — then re-run.
7. If they type "skip phase X", confirm consequence first ("Skipping connectors means morning brief won't have email/calendar data — sure?"), then mark status: skipped in state.md.

Templates

When a phase tells you to write a template to the user workspace, find the matching file in templates/ and copy its content to the specified path:

Template	Source	Destination in user workspace
Handbook	templates/claude-md.md	claude.md (also paste into Settings > Cowork > Global instructions)
About me	templates/about-me.md	about-me/about-me.md
Business brain	templates/business-brain.md	about-me/business-brain.md
Writing rules	templates/writing-rules.md	about-me/writing-rules.md
Memory	templates/memory.md	about-me/memory.md
Connections	templates/connections.md	about-me/connections.md
Audit log	templates/audit-log.md	about-me/audit-log.md
Brief preferences	templates/brief-preferences.md	projects/daily-brief/brief-preferences.md

After copying, fill in the user's answers from the interview and replace any ~~placeholder text with their actual content.

Samples (for the sample-first onboarding path)

The samples/ folder contains fully-fleshed-out examples for a fictional solo coach. They show users what a "good" filled-out file looks like. Phase 2 offers users the option to read these BEFORE the interview (sample-first path). Files available:

• samples/claude-md-sample.md
• samples/about-me-sample.md
• samples/business-brain-sample.md
• samples/writing-rules-sample.md
• samples/memory-sample.md
• samples/brief-preferences-sample.md
• samples/community-agent-sample.md — example of what a custom skill (built via /add-skill) looks like; used as the demo example in Phase 5

Samples use {{PLACEHOLDER — e.g. example}} syntax so users can see the structure AND a real example value at the same time. Templates (in templates/) use ~~placeholder syntax for actual file generation.

The four-year-old rule (non-negotiable)

• One question at a time. Never two.
• Plain English. No "MCP," "OAuth," "manifest," "hooks," "YAML." Replace with: "tool connection," "sign in," "settings file," "automatic action," "list."
• If a step makes the user think for more than 5 seconds, the step is wrong - pause and ask "what's making you hesitate?"
• Default everything. Only ask when defaults won't work.
• Approval gates, not menus. "Type go or skip" beats "choose A, B, C."

When this skill ends

After phase 9 completes:

1. Run /audit to generate the baseline score. Save it to about-me/audit-log.md.
2. Append the final entry to about-me/memory.md: "Cowork AI OS install complete. Baseline 4 Cs score: X/100."
3. Update _aibos/state.md with install_complete: true.
4. Tell the user - in plain English - "You're done. Your AI business operating system is live. Try saying morning brief tomorrow morning to see your first scheduled task fire."
5. Recommend the next plugin to install (productivity for everyone, marketing for content creators, sales for sales-led, customer-support for client services, etc.) based on the user's role from about-me/about-me.md.