eddowding/onboard

Onboard

Populate Cockpit/Chief-of-Staff.md through a guided conversation. This makes every other skill work better — the briefing, email triage, meeting prep, and task management all read Chief-of-Staff.md for context.

[GOAL]

Interview the user and write a rich, populated Chief-of-Staff.md that matches the quality and density of the example file. The output should feel like a knowledgeable assistant wrote it after working with you for months.

[CONTEXT]

• The template is at Cockpit/Chief-of-Staff.md (already has profile basics from setup.sh)
• The example of a fully populated file is at examples/chief-of-staff.example.md
• Read BOTH files before starting the interview

[PROCESS]

Step 1: Read Current State

1. Read Cockpit/Chief-of-Staff.md — note what's already filled in from setup
2. Read examples/chief-of-staff.example.md — this is the target density
3. Identify which sections are empty or have only placeholder comments

Step 2: Welcome

Greet the user and explain what you're doing:

Welcome to {SYSTEM_NAME}! I'm going to ask you a few questions to set up
your command center. This takes about 5 minutes and makes everything else
work better — briefings, email triage, meeting prep, and task management
all draw from this context.

I'll ask 1-2 questions at a time. You can be as brief or detailed as you like.

Step 3: Interview

Ask questions in this order, 1-2 at a time. Wait for answers before proceeding. Skip sections that are already populated from setup.

Round 1 — What you're working on:

• What are you working on right now? Any businesses, side projects, or main job?
• For each one: what's the current status and what are you focused on?

Round 2 — Clients or collaborators (if relevant):

• Do you work with any clients, teams, or key collaborators?
• For each: who's the contact, what's the scope, what's the current status?

(If they say "no clients" or "just personal stuff", skip this — not everyone has clients.)

Round 3 — Priorities:

• What are your top 3-5 priorities right now, in order?
• What's your general priority framework? (e.g., family first, then main job, then side projects)

Round 4 — Working preferences:

• How do you prefer to communicate? (concise vs detailed, bullet points vs prose)
• Any meeting preferences? (batch days, no-meeting days, time blocks)
• How do you handle email? (frequency, urgency rules)
• What tone should I use with you? (formal, casual, direct)

Round 5 — Key dates and personal context:

• Any important dates coming up in the next few weeks?
• Any personal context that's useful to know? (family, health goals, routines, constraints)

Round 6 — Code and tools (Tech tier only):

• Where does your code live? (e.g., ~/Sites/project-name)
• What's your stack? (frameworks, hosting, databases)
• Any deployment workflows I should know about?

Step 4: Write Chief-of-Staff.md

Using the answers, write a complete Chief-of-Staff.md that:

1. Keeps the existing structure from the template (sections, headings, watch folders, project standards)
2. Replaces all placeholder comments (<!-- Add your... -->) with real content
3. Matches the density of the example file — concrete details, not vague summaries
4. Preserves system sections unchanged (Watch Folders, Project Standards, Pending Decisions)
5. Adds sections only if the user provided content for them — don't add empty Financial Snapshot or MCP tables if they didn't mention those topics

Present the draft to the user before writing.

Step 5: Confirm and Write

Show the user the populated file and ask:

Here's your Chief-of-Staff.md. This is what I'll read at the start of every
conversation to understand your context.

Does this look right? Anything to add, change, or remove?

Make any requested changes, then write the file to Cockpit/Chief-of-Staff.md.

Step 6: Create Project Folders

For each project or venture mentioned, create Projects/{Name}/README.md with:

• Current status
• Next actions (from the interview)
• Key dates if mentioned

For each client mentioned, create Clients/{Name}/README.md with:

• Contact details
• Scope
• Current status

Ask before creating these: "Want me to set up project folders for {list}?"

Step 7: Clean Up First Run

If the file FIRST_RUN exists in the vault root, delete it — the user has completed onboarding and shouldn't see the welcome message again:

rm -f "$VAULT_PATH/FIRST_RUN"  # or vault/FIRST_RUN relative to project root

Step 8: Next Steps

You're all set! Your command center is populated. Here's what to try:

  /briefing     — Daily focus update (start here each day)
  /email        — Triage your inbox
  /status       — Quick check on any project
  /do <task>    — Hand off a task for autonomous execution

Your Chief-of-Staff.md will evolve as you use the system — I'll update it
as priorities shift. You can always edit it directly in Obsidian too.

[IMPORTANT]

• Ask 1-2 questions at a time, never more
• Don't assume everyone has clients, ventures, or a tech stack — adapt to what they share
• Match the example file's density, but only for sections the user actually has content for
• Preserve all system sections (Watch Folders, Project Standards) exactly as they are in the template
• The user's answers are the source of truth — don't embellish or invent details
• If the user gives brief answers, write brief sections. Don't pad.
• Always show the draft before writing to disk