/preflight

Overview

This is the first command to run after installing the chief-of-staff plugin. It performs a full system readiness check — MCP connections, config file validation, and directory structure — then reports a pass/fail checklist with actionable fix instructions for every failure. Re-run it after any configuration change to confirm everything is wired up correctly.

What This Command Does

Execute these steps in order:

1. Invoke the orbitant-graceful-degradation skill to probe all MCP servers and detect config file presence. This gives the baseline availability map.
2. Go deeper on config files — parse each file and validate its internal structure, not just its existence:
   • rocks.yaml — YAML must parse cleanly; rocks array must exist; weights across all rocks must sum to approximately 1.0 (tolerance: 0.99-1.01).
   • voice.md — Must contain these required sections as H2 headings: "General Tone", "Formality Levels", "Length Preferences".
   • constraints.yaml — YAML must parse cleanly; must contain required top-level fields: timezone, work_hours, hard_stops, meetings.
   • contacts/ — Directory must exist and contain at least one .md file.
3. Compile the preflight checklist using the output format below.

MCP Connection Tests

For each server, attempt a lightweight API call. Report one of three states: connected, authentication error, or not configured.

Gmail

• Call mcp__gmail__search_emails with query: "newer_than:1d", max_results: 1.
• On success: report "connected (inbox accessible)".
• On failure: report the error category and provide the setup command.
• Fix: claude mcp add gmail -s user -- npx @anthropic/gmail

Google Calendar

• Call mcp__calendar__list_events for today's date range.
• On success: report "connected (N events today)".
• On failure: report the error category and provide the setup command.
• Fix: claude mcp add calendar -s user -- npx @anthropic/google-calendar

Slack

• Call mcp__claude_ai_Slack__slack_search_channels with query "general".
• On success: report "connected".
• On failure: report the error category and provide the setup command.
• Fix: claude mcp add slack -s user -- npx @anthropic/slack

Asana

• Call mcp__asana__asana_list_workspaces.
• On success: report "connected (N workspaces)".
• On failure: mark as optional and provide the setup command.
• Fix: claude mcp add asana -s user -- npx @anthropic/asana

Config File Validation

For each config, check two locations in order (./path then ~/.claude/path). Use the first match.

rocks.yaml

• Exists? Read and attempt YAML parse.
• Validate: rocks array present, each rock has name, weight, status, and key_results. Weights sum to ~1.0.
• On failure: cp plugins/orbitant-chief-of-staff/references/rocks.example.yaml ./rocks.yaml

voice.md

• Exists? Read and check for required H2 headings.
• Validate: "General Tone", "Formality Levels", and "Length Preferences" sections present.
• On failure: cp plugins/orbitant-chief-of-staff/references/voice.example.md ./voice.md

constraints.yaml

• Exists? Read and attempt YAML parse.
• Validate: top-level keys timezone, work_hours, hard_stops, meetings all present.
• On failure: cp plugins/orbitant-chief-of-staff/references/constraints.example.yaml ./constraints.yaml

contacts/

• Directory exists? Contains at least one .md file?
• On failure: mkdir -p ./contacts && cp plugins/orbitant-chief-of-staff/crm/contact.example.md ./contacts/example.md

Output Format

Print the checklist using this structure. Adjust icons and details based on actual results.

# Chief of Staff — Preflight Check

## MCP Servers
- Gmail — connected (inbox accessible)
- Google Calendar — connected (3 events today)
- Slack — not configured
   -> Run: claude mcp add slack -s user -- npx @anthropic/slack
- Asana — not configured (optional)
   -> Run: claude mcp add asana -s user -- npx @anthropic/asana

## Config Files
- rocks.yaml — valid (4 rocks, weights sum to 1.0)
- voice.md — not found
   -> Run: cp plugins/orbitant-chief-of-staff/references/voice.example.md ./voice.md
- constraints.yaml — valid (timezone: America/New_York)
- contacts/ — empty (0 contact files)
   -> Run: mkdir -p ./contacts && cp plugins/orbitant-chief-of-staff/crm/contact.example.md ./contacts/example.md

## Summary
Ready: N/8 checks passed
Action needed: N items require attention (see above)

Run /orbitant-chief-of-staff:status to see your operational dashboard.

Use status icons in actual output: checkmark for pass, cross for required-but-failing, warning for optional-but-missing. For every failing item, include the fix command indented below it.

Cowork Adaptation

When running inside a Cowork session (no local filesystem access):

• Skip all filesystem checks for config files. MCP connection tests work identically.
• Instead of checking files on disk, check whether rocks, voice, constraints, or contact data has been pasted into the conversation context.
• Mark filesystem configs as "not checked (Cowork mode)" with a warning icon rather than a cross.
• Print this notice at the top of the checklist: "Running in Cowork mode — config file checks skipped. Ensure your rocks, voice, and constraints are available in your project context."

After Preflight

Once the checklist is printed, suggest these next steps:

1. Fix any failing items using the provided commands.
2. Re-run /orbitant-chief-of-staff:preflight to confirm fixes.
3. Run /orbitant-chief-of-staff:status for the operational health dashboard.
4. Start using /orbitant-chief-of-staff:today for daily briefings.