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/ceos-annual

Use when conducting, reviewing, or planning the annual planning session

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ceos
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Install
$ npx -y skills add bradfeld/ceos --skill ceos-annual --agent claude-code

How it fires

How this skill gets triggered: by you, by Claude, or both.

  • Fires itselfAuto-invocation. Claude auto-loads it when your prompt matches the work.Auto-invocation is when the right skill fires by itself at the right moment, driven by a FLOW.md router and a hook, instead of you invoking it by name. It is the difference between a skill being installed and a skill actually getting used.Read the full definition →
  • You can call itInvoke it directly when you want it.
  • Slash command/ceos-annual

Context preview

The summary Claude sees to decide when to auto-load this skill.

Use when conducting, reviewing, or planning the annual planning session

SKILL.md

ceos-annual.SKILL.md
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
Read more
Ships withceos

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

Get the whole plugin

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