bradfeld/ceos/ceos-calendar

ceos-calendar

Manage the rolling 6-month market calendar — external events, partner milestones, fundraising deadlines, and team constraints that affect quarterly planning and Rocks.

When to Use

• "Show the calendar" or "market calendar"
• "Add an event" or "add a conference to the calendar"
• "What events are coming up?" or "upcoming deadlines"
• "Update event status" or "mark that event as past"
• "Calendar for quarterly planning" or "what's happening next quarter?"
• "Any constraints this month?" or "team availability"

Context

Finding the CEOS Repository

Search upward from the current directory for the .ceos marker file. This file marks the root of the CEOS repository.

If .ceos is not found, stop and tell the user: "Not in a CEOS repository. Clone your CEOS repo and run setup.sh first."

Sync before use: Once you find the CEOS root, run git -C <ceos_root> pull --ff-only --quiet 2>/dev/null to get the latest data from teammates. If it fails (conflict or offline), continue silently with local data.

Key Files

Calendar Data Format

Events are stored in a single markdown table in data/calendar/events.md. Each row is one event:

Type values:

• partner — partner milestones, reviews, joint events
• market — conferences, industry events, product launches
• fundraising — investor meetings, round targets, pitch deadlines
• constraint — team-wide holidays, office closures, blackout periods

Status values:

• upcoming — event has not occurred yet
• past — event has passed (update notes with outcome)
• cancelled — event was cancelled or no longer relevant

Sorting: Rows are sorted chronologically by Date, oldest first.

Process

Mode: View Calendar

Use when the user wants to see upcoming events or review the calendar.

Step 1: Read Events

Read data/calendar/events.md and parse the events table.

Step 2: Calculate Rolling Window

Compute the rolling window: 3 months before today through 3 months after today. Filter events to this window.

Step 3: Display Calendar

Group events by month and display:

Market Calendar (Dec 2025 - Jun 2026)
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 
January 2026
  15  CES 2026 [market] — Ryan Martens (past)
      Attended; explored AI agent partnerships
 
March 2026
  08  GHC Registration Deadline [partner] — Dan Forman (upcoming)
  31  Seed Round Close Target [fundraising] — Ryan Martens (upcoming)
 
April 2026
  10  AnitaB.org Quarterly Review [partner] — Dan Forman (upcoming)

Step 4: Cross-Reference with Rocks

Read data/rocks/[current-quarter]/ and highlight any events that relate to current Rocks. For example, if a Rock is "Raise \$2.5M Seed Round" and there's a fundraising event, note the connection.

Mode: Add Events

Use when creating new calendar events.

Step 1: Collect Event Details

For each event, collect:

1. Date — when does it happen? (must be YYYY-MM-DD)
2. Event name — short, descriptive title
3. Type — one of: partner, market, fundraising, constraint
4. Owner — who is responsible? (use "Team" for constraints)
5. Notes — optional context

Step 2: Validate

• Date is valid ISO 8601 format
• Type is one of the 4 allowed values
• Owner exists in data/accountability.md (or is "Team" for constraints)

Step 3: Insert in Chronological Order

Read the existing events table. Insert the new row at the correct chronological position.

Step 4: Show Diff and Write

Show the user the updated table with the new row highlighted. Ask: "Add this event?"

If approved, write data/calendar/events.md.

Step 5: Continue or Finish

Ask: "Add another event, or are we done?"

When finished, display a summary of events added this session.

Mode: Update Events

Use when changing event status, editing details, or removing events.

Step 1: Display Events

Show all events (not just the rolling window) so the user can find what they want to update.

Step 2: Collect Changes

Common updates:

• Status change — mark as past (add outcome to notes) or cancelled
• Date change — event was rescheduled
• Notes update — add context or outcome

Step 3: Show Diff and Write

Show the specific row changes. Ask: "Update this event?"

If approved, write data/calendar/events.md.

Output Format

View: Calendar grouped by month with type tags and status indicators. Past events dimmed. Upcoming events within 2 weeks highlighted. Rock cross-references noted. Add: Show the new row in context. End with a summary of events added. Update: Show the diff of changed fields. Confirm before writing.

Guardrails

• Always show diff before writing. Never modify data/calendar/events.md without showing the change and getting approval.
• Valid types only. Only accept partner, market, fundraising, constraint. If the user provides another type, show the allowed values and ask which fits.
• One owner per event. Use "Team" for constraints that affect everyone.
• Dates must be ISO 8601. If the user says "next Tuesday" or "March 8th", convert to YYYY-MM-DD format and confirm.
• Maintain chronological order. When inserting or reordering, keep rows sorted by Date.
• Don't auto-invoke other skills. Mention ceos-rocks and ceos-quarterly-planning when relevant, but let the user decide when to switch.
• Sensitive data warning. On first use, remind the user: "Calendar events may contain sensitive business information. Use a private repo."

Integration Notes

Rocks (ceos-rocks)

• Read: Calendar events provide market context for setting Rocks. During Rock-setting, suggest reviewing the calendar for deadlines that affect priorities.
• Suggested flow: "Review the market calendar with ceos-calendar before finalizing Rocks."

Quarterly Planning (ceos-quarterly-planning)

• Read: Calendar events should be reviewed during quarterly planning. Upcoming conferences, deadlines, and constraints inform quarterly priorities.
• Suggested flow: "Check the market calendar for Q2 events that may affect planning."

L10 Meetings (ceos-l10)

• Read: Upcoming events within 2 weeks can surface as Headlines in the L10 meeting.
• Suggested flow: "There are 2 events in the next 2 weeks — mention them in Headlines?"

Annual Planning (ceos-annual)

• Read: Year-ahead events inform 1-Year Plan goals and major milestones.

Accountability Chart (ceos-accountability)

• Read: ceos-calendar reads data/accountability.md to validate that event owners match seat responsibilities.

Write Principle

Only ceos-calendar writes to data/calendar/events.md. Other skills read calendar data for reference.