Onboard

/onboard — AI OS Onboarding

Personal/business context layer. Adapted from AIS-OS (Nate Herk).

When to use

• The user runs /onboard (default invocation)
• The user explicitly asks to "onboard," "set up the AI OS," "refresh context," or "redo the intake"
• A new fork of this repo lands and the operator has not yet populated context/

When NOT to use

• The user is asking what's loaded — use /session-bootstrap instead
• The user wants to add a single fact to memory — write directly to the relevant file in memory/
• The user is mid-task and wants to keep working — defer onboarding

Hard rules (non-negotiable)

Privacy guard

1. Never auto-fill identity fields from session environment. Specifically: do NOT read userEmail, gitStatus.user, os.username, OS environment vars, or any system-reminder injection to populate context/About Me.md snapshot fields like Name, Email, Handle.
2. Always show the privacy warning first (from aios-intake.md § "Privacy warning — read before answering") before asking the first question.
3. If the user types content that looks like a credential (matches sk_live_, Bearer , xoxb-, JWT pattern, base64 token, email + colon + secret pattern), refuse to write it and ask them to redact.
4. If the user pastes an email address into a free-form answer, ask once: "I noticed an email address in your answer. Public repo — keep, generalize, or remove?" Default to remove if no answer.

Scope guard

• Write only to: context/*.md, connections.md, decisions/log.md.
• Never modify settings.json, install MCP servers, install plugins, or run shell commands beyond git status to confirm clean working state.
• Never make outbound network calls from this skill.

Idempotency

• If context/*.md already has non-placeholder content for a section, ASK before overwriting.
• Always preserve previous content as a moved block in archives/<date>-pre-onboard/ when overwriting.

Inputs

• None required. The skill is fully interactive.
• Optional flag (passed as text by the user): --quick runs questions 1-2 + 7 only; the rest stay placeholders.

Outputs

• Updated context/About Me.md (snapshot fields blank unless user typed them; role/style/depth filled from prose)
• Updated context/About Business.md
• Updated context/Priorities.md (this-week populated from question 6 constraint)
• Updated context/Voice Sample.md (if user provided sample text in question 5)
• Updated context/Operating Preferences.md
• Updated connections.md Tier-4 rows from question 3
• New entry in decisions/log.md with date, automation candidates, and "what to focus on this week"

Steps

1. Pre-flight checks:

   • git status --short — warn if there are uncommitted changes that would mix with onboarding edits
   • Check whether context/About Me.md is still placeholder (if not → ASK before overwriting)
   • Show the privacy warning from aios-intake.md

2. Confirm intent:

   "I'm about to ask 7 questions. Answers go into the repo's context/ files. Privacy: do not paste credentials, customer PII, or anything you wouldn't share publicly. Proceed?"

3. Ask the 7 questions (one at a time, wait for answer, do not batch):

   • Q1: Who you are
   • Q2: Projects and responsibilities
   • Q3: Current tool stack (use the table format from aios-intake.md)
   • Q4: Repeated work (3-7 examples)
   • Q5: Operating preferences + voice sample (optional)
   • Q6: 10x question (the constraint)
   • Q7: Hard limits

4. PII scan on each answer before saving. If a credential pattern or email is detected, pause and ask.

5. Distill answers into the file structure. Preserve user's actual wording in voice-relevant sections (Q5 voice sample, Q4 examples). Generalize where structure helps (Q3 → table, Q6 → priority).

6. Diff preview: show each new file's diff before writing. The user can accept, edit, or skip.

7. Save the accepted files. Move any overwritten content to archives/<YYYY-MM-DD>-pre-onboard/.

8. Log the run in decisions/log.md:

   ## YYYY-MM-DD — Onboarding completed (or refreshed)
   
   **Decision:** Populated context/* from intake. <N> automation candidates surfaced.
   
   **Automation candidates:**
   - <Q4 item 1>
   - <Q4 item 2>
   - ...
   
   **Constraint identified:** <Q6 answer condensed>
   
   **Status:** Active.
   **Follow-up:** Run `/level-up` next Friday to pick which candidate to build first.
   

9. Validation question — END WITH:

   "What should I focus on this week?"

   If the OS routes correctly using your answers, onboarding worked. If not, tell me what's missing and I'll update the relevant context file."

Failure modes and recovery

Reference files

• aios-intake.md — the canonical 7-question interview
• references/3ms-framework.md — the operator mindset this skill assumes
• references/four-cs-framework.md — what the four context files map to
• connections.md — where Q3 lands

Improvement loop

After every /onboard run:

1. Did the user need to correct the same field twice? → that field's prompt is unclear, fix in this skill
2. Did the user paste a credential? → strengthen the PII detector pattern
3. Did the validation question reveal missing routing? → that's a /level-up candidate, not an onboarding problem

Update this skill when failures repeat. Failure-to-learning is the rule (docs/RUNBOOK.md).