/ceos-annual
Use when conducting, reviewing, or planning the annual planning session
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/ceos-annual
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Use when conducting, reviewing, or planning the annual planning session
SKILL.md
ceos-annual.SKILL.mdname: ceos-annual
description: Use when conducting, reviewing, or planning the annual planning session
file-access: [data/annual/, templates/annual-planning.md, data/vision.md, data/rocks/, data/scorecard/, data/issues/, data/accountability.md, data/people/]
tools-used: [Read, Write, Glob]
ceos-annual
Facilitate the EOS Annual Planning session — the formal year-end process (typically a 2-day offsite) where the leadership team refreshes the V/TO, reviews the outgoing year, sets the new 1-Year Plan, and establishes Q1 Rocks. This is the most comprehensive EOS meeting of the year.
When to Use
- "Run annual planning" or "annual planning session"
- "Plan next year" or "let's plan for 2027"
- "Review 2026" or "year in review"
- "Refresh our vision" or "update the V/TO for the year"
- "Annual offsite" or "strategic planning session"
- Any end-of-year or start-of-year strategic planning discussion
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
| File | Purpose | |------|---------| | `data/annual/YYYY-planning.md` | Annual planning session notes (one per year) | | `data/vision.md` | V/TO document (read and update during V/TO Refresh) | | `data/rocks/YYYY-QN/` | Rock files by quarter (read for year-in-review scoring) | | `data/scorecard/weeks/` | Weekly scorecard data (read for trend analysis) | | `data/scorecard/metrics.md` | Scorecard metric definitions (reference for updates) | | `data/issues/open/` | Open issues (read for issues sweep) | | `data/issues/solved/` | Solved issues (count for year summary) | | `data/accountability.md` | Accountability Chart (read for org checkup) | | `data/people/` | People Analyzer evaluations (read for org checkup) | | `templates/annual-planning.md` | Template for new annual planning files |
Annual Planning Agenda
The full annual planning session follows a 7-section agenda:
| # | Section | Focus | |---|---------|-------| | 1 | Year in Review | Score Q4 Rocks, review annual Scorecard trends, celebrate wins | | 2 | V/TO Refresh | Update 3-Year Picture, set new 1-Year Plan with measurable goals | | 3 | Issues Sweep | Clear the long-term issues list via IDS | | 4 | Organizational Checkup | Review Accountability Chart, run People Analyzer | | 5 | Set Q1 Rocks | First quarter's Rocks aligned to the new 1-Year Plan | | 6 | Set Scorecard | Review and update weekly measurables for the new year | | 7 | Conclude | Key decisions, cascading messages, next steps |
Year Determination
When determining the planning year:
- If run in Q4 (Oct-Dec): "Next year" is current year + 1. The "outgoing year" is the current year.
- If run in Q1 (Jan-Mar): "Next year" is the current year. The "outgoing year" is current year - 1.
- If run mid-year (Q2-Q3): Warn that annual planning typically happens at Q4/Q1 boundary. Ask which year to plan for.
Key EOS Principles
- **Annual Planning reviews the FULL V/TO** — not just the 1-Year Plan. All 8 sections get reviewed.
- **10-Year Target and Core Focus rarely change** (if ever). Confirm they still resonate, but don't pressure updates.
- **3-Year Picture updates** to reflect progress and changing conditions.
- **1-Year Plan is entirely new** each year with 3-7 measurable goals.
- **Q1 Rocks are set during annual planning**, aligned to the new 1-Year Plan.
- **All leadership team members must attend.** If someone is missing, note it but proceed.
Process
Mode: Plan
Use when conducting the full annual planning session with the structured 7-section agenda.
Step 1: Setup
1. **Determine the planning year.** Ask if not clear from context. Follow the Year Determination rules above.
2. **Check for existing planning file.** Look for `data/annual/YYYY-planning.md`.
- **Exists:** Ask: "Annual planning for YYYY already exists. Open it to review, append notes, or start fresh?"
- **New:** Continue with Step 2.
3. **Gather session details:**
- Attendees (all leadership team members should be present)
- Location (office, offsite, etc.)
- Date (default to today)
4. **Gather context.** Read these files silently:
- `data/vision.md` — current V/TO state
- `data/rocks/` — all quarters for the outgoing year
- `data/scorecard/weeks/` — scorecard data for the year
- `data/issues/open/` — open issues list
- `data/accountability.md` — current org structure
- `data/people/` — People Analyzer evaluations
5. **Create the year directory** if it doesn't exist: `data/annual/`
Display a preparation summary:
Annual Planning — [Year]
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
Date: [Date]
Attendees: [Names]
Location: [Location]
Data loaded:
V/TO: [Last updated date]
Rocks: [Count] across [N] quarters
Scorecard: [N] weeks of data
Open issues: [Count]
People evaluations: [Count]
Let's walk through the 7-section agenda.
Step 2: Section 1 — Year in Review
1. **Score Q4 Rocks.** Read all Rocks from `data/rocks/YYYY-Q4/`. Display current status for each Rock. For any Rocks still `on_track` or `off_track`, ask: "Complete or incomplete?" Update status to `complete` or `dropped`.
Calculate Q4 completion rate: `(complete / total) * 100`.
If no Q4 Rock files exist: "No Q4 Rocks on file. Skip Q4 scoring, or enter scores manually?"
2. **Annual Rock Summary.** Read Rocks from all four quarters of the outgoing year. Display a summary table:
Annual Rock Summary — YYYY
━━━━━━━━━━━━━━━━━━━━━━━━━━
| Quarter | Total | Complete | Rate |
|---------|-------|----------|------|
| Q1 | 5 | 4
Read more
name: ceos-annual description: Use when conducting, reviewing, or planning the annual planning session file-access: [data/annual/, templates/annual-planning.md, data/vision.md, data/rocks/, data/scorecard/, data/issues/, data/accountability.md, data/people/] tools-used: [Read, Write, Glob]
ceos-annual
Facilitate the EOS Annual Planning session — the formal year-end process (typically a 2-day offsite) where the leadership team refreshes the V/TO, reviews the outgoing year, sets the new 1-Year Plan, and establishes Q1 Rocks. This is the most comprehensive EOS meeting of the year.
When to Use
- "Run annual planning" or "annual planning session"
- "Plan next year" or "let's plan for 2027"
- "Review 2026" or "year in review"
- "Refresh our vision" or "update the V/TO for the year"
- "Annual offsite" or "strategic planning session"
- Any end-of-year or start-of-year strategic planning discussion
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
| File | Purpose | |------|---------| | `data/annual/YYYY-planning.md` | Annual planning session notes (one per year) | | `data/vision.md` | V/TO document (read and update during V/TO Refresh) | | `data/rocks/YYYY-QN/` | Rock files by quarter (read for year-in-review scoring) | | `data/scorecard/weeks/` | Weekly scorecard data (read for trend analysis) | | `data/scorecard/metrics.md` | Scorecard metric definitions (reference for updates) | | `data/issues/open/` | Open issues (read for issues sweep) | | `data/issues/solved/` | Solved issues (count for year summary) | | `data/accountability.md` | Accountability Chart (read for org checkup) | | `data/people/` | People Analyzer evaluations (read for org checkup) | | `templates/annual-planning.md` | Template for new annual planning files |
Annual Planning Agenda
The full annual planning session follows a 7-section agenda:
| # | Section | Focus | |---|---------|-------| | 1 | Year in Review | Score Q4 Rocks, review annual Scorecard trends, celebrate wins | | 2 | V/TO Refresh | Update 3-Year Picture, set new 1-Year Plan with measurable goals | | 3 | Issues Sweep | Clear the long-term issues list via IDS | | 4 | Organizational Checkup | Review Accountability Chart, run People Analyzer | | 5 | Set Q1 Rocks | First quarter's Rocks aligned to the new 1-Year Plan | | 6 | Set Scorecard | Review and update weekly measurables for the new year | | 7 | Conclude | Key decisions, cascading messages, next steps |
Year Determination
When determining the planning year:
- If run in Q4 (Oct-Dec): "Next year" is current year + 1. The "outgoing year" is the current year.
- If run in Q1 (Jan-Mar): "Next year" is the current year. The "outgoing year" is current year - 1.
- If run mid-year (Q2-Q3): Warn that annual planning typically happens at Q4/Q1 boundary. Ask which year to plan for.
Key EOS Principles
- **Annual Planning reviews the FULL V/TO** — not just the 1-Year Plan. All 8 sections get reviewed.
- **10-Year Target and Core Focus rarely change** (if ever). Confirm they still resonate, but don't pressure updates.
- **3-Year Picture updates** to reflect progress and changing conditions.
- **1-Year Plan is entirely new** each year with 3-7 measurable goals.
- **Q1 Rocks are set during annual planning**, aligned to the new 1-Year Plan.
- **All leadership team members must attend.** If someone is missing, note it but proceed.
Process
Mode: Plan
Use when conducting the full annual planning session with the structured 7-section agenda.
Step 1: Setup
1. **Determine the planning year.** Ask if not clear from context. Follow the Year Determination rules above.
2. **Check for existing planning file.** Look for `data/annual/YYYY-planning.md`.
- **Exists:** Ask: "Annual planning for YYYY already exists. Open it to review, append notes, or start fresh?"
- **New:** Continue with Step 2.
3. **Gather session details:**
- Attendees (all leadership team members should be present)
- Location (office, offsite, etc.)
- Date (default to today)
4. **Gather context.** Read these files silently:
- `data/vision.md` — current V/TO state
- `data/rocks/` — all quarters for the outgoing year
- `data/scorecard/weeks/` — scorecard data for the year
- `data/issues/open/` — open issues list
- `data/accountability.md` — current org structure
- `data/people/` — People Analyzer evaluations
5. **Create the year directory** if it doesn't exist: `data/annual/`
Display a preparation summary:
Annual Planning — [Year] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Date: [Date] Attendees: [Names] Location: [Location] Data loaded: V/TO: [Last updated date] Rocks: [Count] across [N] quarters Scorecard: [N] weeks of data Open issues: [Count] People evaluations: [Count] Let's walk through the 7-section agenda.
Step 2: Section 1 — Year in Review
1. **Score Q4 Rocks.** Read all Rocks from `data/rocks/YYYY-Q4/`. Display current status for each Rock. For any Rocks still `on_track` or `off_track`, ask: "Complete or incomplete?" Update status to `complete` or `dropped`.
Calculate Q4 completion rate: `(complete / total) * 100`.
If no Q4 Rock files exist: "No Q4 Rocks on file. Skip Q4 scoring, or enter scores manually?"
2. **Annual Rock Summary.** Read Rocks from all four quarters of the outgoing year. Display a summary table:
Annual Rock Summary — YYYY ━━━━━━━━━━━━━━━━━━━━━━━━━━ | Quarter | Total | Complete | Rate | |---------|-------|----------|------| | Q1 | 5 | 4
Run EOS with AI. CEOS brings the Entrepreneurial Operating System to Claude Code, giving your leadership team 23 AI-powered skills for Vision, Accountability Chart, Rocks, Scorecard, L10 Meetings, IDS, To-Dos, Process, People Analyzer, Quarterly

