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
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

| Date       | Participants | Overall | Vision | People | Data | Issues | Process | Traction | Status |
|------------|-------------|---------|--------|--------|------|--------|---------|----------|--------|
| 2026-02-15 | 3           | 4.2     | 4.3    | 4.1    | 4.0  | 4.5    | 3.5     | 4.3      | ✓      |
| 2025-11-10 | 3           | 3.8     | 4.0    | 3.5    | 3.2  | 4.0    | 3.0     | 3.8      | ✓      |
| 2025-08-01 | 2           | 3.2     | 3.5    | 3.0    | 2.8  | 3.5    | 2.5     | 3.2      | ✓      |

Step 3: Trend Analysis

For each component, show direction vs. the previous checkup:

Trend Analysis (Latest vs Previous)
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

| Component | Previous | Current | Change | Trend |
|-----------|----------|---------|--------|-------|
| Vision    | 4.0      | 4.3     | +0.3   | ↑     |
| People    | 3.5      | 4.1     | +0.6   | ↑↑    |
| Data      | 3.2      | 4.0     | +0.8   | ↑↑    |
| Issues    | 4.0      | 4.5     | +0.5   | ↑     |
| Process   | 3.0      | 3.5     | +0.5   | ↑     |
| Traction  | 3.8      | 4.3     | +0.5   | ↑     |
| OVERALL   | 3.8      | 4.2     | +0.4   | ↑     |

Trend indicators:

• ↑↑ = improved by 0.5+
• ↑ = improved by 0.1-0.4
• → = unchanged (within 0.1)
• ↓ = declined by 0.1-0.4
• ↓↓ = declined by 0.5+

Step 4: Flag Stale Checkups

Calculate days since the most recent checkup. If > 120 days:

📅 Last checkup was [N] days ago (recommended: quarterly / every 90 days).
   Consider running a new checkup to track progress.

Step 5: Component Deep Dive

Ask: "Want to drill into a specific checkup or component?"

If the user selects a checkup, display the full file with all participant ratings and action items.

If the user selects a component, show that component's score history across all checkups as a progression.

Mode: Compare

Use when analyzing alignment gaps between team members' ratings on a specific checkup.

Step 1: Select Checkup

Default to the most recent checkup. If multiple exist, ask: "Which checkup? (Default: most recent — [date])"

Load the selected checkup file and parse participant ratings.

If the checkup has only one participant: "Alignment analysis requires 2+ participants. This checkup has only one. Run a new checkup with multiple team members, or select a different checkup."

Step 2: Calculate Per-Question Statistics

For each of the 20 questions, calculate across all participants:

• Mean: Average rating
• Min: Lowest rating
• Max: Highest rating
• Range: Max - Min
• Spread: Whether ratings are clustered or dispersed

Step 3: Identify Alignment Gaps

Flag questions where the team diverges significantly:

• High variance: Range >= 3 (e.g., one person rated 5, another rated 2)
• Moderate variance: Range = 2
• Aligned: Range <= 1

Sort by range (highest first) to surface the biggest gaps.

Step 4: Display Alignment Gap Table

Alignment Analysis — [Date] Checkup
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Participants: Brad, Sarah, Mike

HIGH VARIANCE (Range >= 3) — Discuss These
| # | Question (abbreviated)       | Brad | Sarah | Mike | Avg | Range | Flag |
|---|------------------------------|------|-------|------|-----|-------|------|
| 7 | Proven customer process      | 5    | 2     | 3    | 3.3 | 3     | 🔴   |
| 16| Core Processes documented    | 4    | 1     | 3    | 2.7 | 3     | 🔴   |

MODERATE VARIANCE (Range = 2)
| # | Question (abbreviated)       | Brad | Sarah | Mike | Avg | Range | Flag |
|---|------------------------------|------|-------|------|-----|-------|------|
| 3 | Core Focus clear             | 5    | 3     | 4    | 4.0 | 2     | ⚠️   |

ALIGNED (Range <= 1)
| # | Question (abbreviated)       | Brad | Sarah | Mike | Avg | Range |
|---|------------------------------|------|-------|------|-----|-------|
| 1 | Clear vision in writing      | 5    | 5     | 4    | 4.7 | 1     |
| 11| Leadership team trust        | 5    | 4     | 5    | 4.7 | 1     |
| ... (remaining aligned questions)

Step 5: Alignment Summary

Alignment Summary
━━━━━━━━━━━━━━━━
High variance (Range >= 3):  2 questions — need team discussion
Moderate variance (Range 2): 1 question — worth reviewing
Aligned (Range <= 1):        17 questions — team consensus

Top Discussion Topics:
1. Q7: "Proven customer process" — Range 3 (Brad: 5, Sarah: 2)
   → Team sees this very differently. Discuss what "proven process" means.
2. Q16: "Core Processes documented" — Range 3 (Sarah: 1, Brad: 4)
   → Consider running ceos-process to document core processes.

Step 6: Drill Down

Ask: "Want to discuss any specific question or create issues from these gaps?"

If the user wants to create issues, suggest using ceos-ids with the specific gap as the issue topic.

Output Format

Run Mode

1. Progressive display: Show questions component-by-component with running scores
2. Component completion: Show subtotal after each component
3. Final summary: Overall score, component scores table, strengths, opportunities
4. Action items: Table with owner, due date, related component

Review Mode

1. History table: Date, participants, overall score, per-component scores, status
2. Trend analysis: Previous vs. current with direction arrows
3. Stale checkup warning: If > 120 days since last

Compare Mode

1. Alignment gap table: Questions sorted by variance (highest first)
2. Per-participant ratings: Side-by-side columns
3. Summary statistics: Count of high/moderate/aligned questions
4. Discussion topics: Top gaps with context for team conversation

Guardrails

• Always show the complete file before writing. Never save a checkup file without displaying it to the user for review and approval.
• Validate ratings are 1-5 integers. If a participant gives a rating outside 1-5, re-prompt: "Ratings must be 1-5 (1=strongly disagree, 5=strongly agree)." Do not accept decimals.
• Present questions in component order. Always group questions by component (Vision, People, Issues, Traction, Process, Data) rather than randomizing or reordering.
• Don't skip questions. All 20 questions should be asked. If a participant cannot answer, store null and note it. Don't silently omit questions.
• Don't auto-invoke other skills. When low scores suggest using another skill (e.g., "Process is weak, run ceos-process"), mention the option but let the user decide. Say "Would you like to run ceos-process?" rather than invoking it automatically.
• Sensitive data warning. On first use in a session, remind the user: "Organizational Checkup ratings contain sensitive assessments of company health. Ensure this repository is private, not public."
• Use alignment gaps as conversation starters. Compare mode surfaces disagreements. Frame these constructively: "The team sees this differently — worth discussing" rather than "These people are wrong."
• Don't interpret scores prescriptively. The skill calculates and displays scores, but the meaning and action belong to the leadership team. Suggest relevant skills, don't mandate actions.
• Flag stale checkups. In Review mode, flag if the most recent checkup is > 120 days old. This is informational, not blocking.
• Questions are canonical. Do not modify, reword, or add custom questions. This skill implements the standard EOS Organizational Checkup.

Integration Notes

V/TO (ceos-vto)

• Direction: Read
• What data: data/vision.md — Core Values, Core Focus, 10-Year Target, 1-Year Plan
• Purpose: Provides context for Vision component questions (Q1-6). Core Values referenced in Run mode setup. V/TO changes may shift how the team rates Vision questions.

Accountability Chart (ceos-accountability)

• Direction: Read
• What data: data/accountability.md — seats and owners
• Purpose: Suggests participants for checkup sessions. The Accountability Chart defines who the "leadership team" is. Also provides context for People component questions (Q7-10).

Rocks (ceos-rocks)

• Direction: Read
• What data: data/rocks/ — current quarter's Rocks
• Purpose: Provides context for Traction component questions (Q13-15). Current Rock status shows whether the team is executing with discipline.

Scorecard (ceos-scorecard)

• Direction: Read
• What data: data/scorecard/ — metrics and weekly entries
• Purpose: Provides context for Data component questions (Q17-20). Active metrics count and Scorecard health inform the Data component discussion.

People Analyzer (ceos-people)

• Direction: Read
• What data: data/people/ — person evaluations
• Purpose: Provides context for People component questions (Q8-10). Current "right people, right seats" percentage gives context for how the team rates People health.

IDS (ceos-ids)

• Direction: Read
• What data: data/issues/open/ and data/issues/resolved/
• Purpose: Provides context for Issues component questions (Q11-12). Open issues count and resolution patterns inform the Issues component discussion. Low-scoring components may generate new issues via ceos-ids.

Annual Planning (ceos-annual)

• Direction: Related
• What data: data/annual/ — annual planning records
• Purpose: Annual planning includes an organizational checkup as Section 4. Checkup results from ceos-checkup can be referenced during annual planning to track year-over-year progress.

Quarterly Planning (ceos-quarterly-planning)

• Direction: Related
• What data: data/quarterly/ — quarterly planning records
• Purpose: Quarterly planning may reference checkup trends to inform Rock priorities. Low-scoring components suggest where to focus next quarter's Rocks.

Write Principle

Only ceos-checkup writes to data/checkups/. Other skills (particularly ceos-annual and ceos-quarterly-planning) may read checkup data for trend analysis and planning context, but they do not create or modify checkup files.