bradfeld/ceos/ceos-checkup

ceos-checkup

Measure organizational health using the standard EOS Organizational Checkup — a 20-question assessment across the Six Key Components (Vision, People, Data, Issues, Process, Traction). Each leadership team member rates the organization 1-5 on each question, and scores are calculated per component and overall. Use quarterly or semi-annually to track progress and surface alignment gaps.

Not for: Individual team member evaluation (use ceos-people), V/TO refresh (use ceos-annual), or quarterly Rock setting (use ceos-quarterly-planning).

When to Use

• "Run the organizational checkup" or "let's do the EOS checkup"
• "How healthy is the organization?" or "team health assessment"
• "Score the six key components" or "rate our EOS components"
• "Show checkup history" or "review past checkups"
• "Compare team ratings" or "show alignment gaps"
• "Are we improving on Vision/People/Data/Issues/Process/Traction?"
• Any discussion about overall organizational health, EOS component scores, or team alignment

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

Checkup File Format

Each checkup is stored at data/checkups/YYYY-MM-DD.md with YAML frontmatter:

date: "2026-02-15"
participants:
  - name: "Brad Feld"
    ratings: [5, 4, 5, 4, 3, 4, 3, 4, 5, 4, 5, 4, 4, 5, 4, 3, 4, 5, 4, 3]
  - name: "Sarah Chen"
    ratings: [4, 5, 4, 5, 4, 3, 4, 5, 4, 5, 4, 5, 5, 4, 5, 4, 3, 4, 5, 4]
status: complete   # in_progress | complete
overall_score: 4.2
component_scores:
  vision: 4.3
  people: 4.1
  data: 4.0
  issues: 4.5
  process: 3.5
  traction: 4.3

Ratings array: 20 integers (1-5), indexed by question number (index 0 = Question 1, index 19 = Question 20). Use null for unanswered questions.

The 20 Standard Questions

The EOS Organizational Checkup uses these 20 canonical questions, grouped by the Six Key Components:

Vision (Questions 1-6)

People (Questions 7-10)

Issues (Questions 11-12)

Traction (Questions 13-15)

Process (Question 16)

Data (Questions 17-20)

Rating Scale

Component Scoring

Each component score is the average of its questions across all participants:

Overall score = average of all 20 questions across all participants.

Interpretation:

Process

Mode: Run

Use when conducting a new Organizational Checkup session with the leadership team.

Step 1: Setup

Ask for:

• Date: Default to today's date (YYYY-MM-DD).
• Participants: Read data/accountability.md to suggest team members. Ask: "Who is participating? (Default: everyone on the Accountability Chart)"

If data/accountability.md doesn't exist or is empty, ask the user to list participants manually.

Step 2: Check for Existing Checkup

Check if data/checkups/YYYY-MM-DD.md already exists for today's date.

• Exists with `status: complete`: "A checkup already exists for [date]. Open it to review, or create a new session?"
• Exists with `status: in_progress`: "An incomplete checkup exists for [date]. Resume where you left off, or start fresh?"
• Doesn't exist: Continue to Step 3.

Step 3: Cross-Reference Context (Optional)

Before starting questions, briefly review available CEOS data for context:

• Read data/vision.md for Core Values and 1-Year Plan (Vision context)
• Read recent data/rocks/ for current quarter's Rocks (Traction context)
• Read data/scorecard/metrics.md for active metrics (Data context)
• Read data/issues/open/ for open issues count (Issues context)

Display a brief context summary:

Context for Today's Checkup
━━━━━━━━━━━━━━━━━━━━━━━━━━
Core Values:  [list from vision.md]
Current Rocks: [count] for [quarter]
Active Metrics: [count] on Scorecard
Open Issues:   [count]

If any data source is missing, note it and continue. The checkup doesn't require these — they provide context.

Step 4: Collect Ratings

Present the 20 questions organized by component. For each component:

1. Display the component name and its questions
2. For each participant, collect a rating (1-5) for each question
3. Show running totals as you go

Collection approach: Present all questions for one component at a time. For each question, collect ratings from all participants before moving to the next question.

Example interaction:

VISION — Question 1 of 6
"We have a clear vision in writing that has been properly communicated
and is shared by everyone in the company."
 
Rate 1-5 (1=strongly disagree, 5=strongly agree):
  Brad:  [rating]
  Sarah: [rating]

After each component, display the component subtotal:

Vision Complete — Component Average: 4.2
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
  Brad avg:  4.3
  Sarah avg: 4.0

Progress tracking: Show progress after each component:

Progress: 2/6 components [████████░░░░░░░░░░░░] 33%
Vision: 4.2  |  People: 3.8  |  Data: —  |  Issues: —  |  Process: —  |  Traction: —

Step 5: Calculate Scores

After all 20 questions are rated:

1. Per-component scores: Average all ratings for that component's questions across all participants.
2. Per-participant scores: Average all 20 ratings for each individual.
3. Overall score: Average of all 20 questions across all participants.

Step 6: Identify Strengths and Opportunities

• Strengths: Components scoring 4.0+ — these are working well.
• Opportunities: Components scoring below 3.0 — these need immediate attention.
• Attention needed: Components scoring 3.0-3.9 — monitor and improve.

If overall score < 2.5: Display warning: "Overall score below 2.5/5. Consider a focused IDS session to identify root causes across multiple components."

Step 7: Prompt for Action Items

For each component scoring below 3.5, ask: "Any specific action items for [Component]?"

Suggest relevant CEOS skills for low-scoring components:

Step 8: Save the Checkup File

Build the file from templates/checkup.md:

• Replace {{date}} with the session date
• Replace {{participants}} with participant names
• Fill in the ratings arrays in the frontmatter
• Populate the component scores tables in the markdown body
• Fill in strengths, opportunities, and action items
• Set status: complete

Show the complete file before writing. Ask: "Save this checkup?"

Write to data/checkups/YYYY-MM-DD.md.

Mode: Review

Use when reviewing historical checkup results and tracking trends over time.

Step 1: Read All Checkups

Read all files from data/checkups/. Parse YAML frontmatter for each.

If no files exist: "No checkups found. Run your first Organizational Checkup to establish a baseline."

Sort by date (most recent first).

Step 2: Display Summary Table

Organizational Checkup History
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━