Org Health Diagnostic

What This Skill Does

• This skill provides a diagnostic tool for assessing organizational health across eight key dimensions.
• It uses a traffic light system and benchmarks to surface potential problems.
• It's designed for leaders who want to proactively identify and address issues impacting their company's performance.

When to Use

• Assess financial health.
• Evaluate revenue health.
• Measure product health.
• Diagnose engineering health.
• Check people health.
• Monitor operational health.

Key Features

• Covers eight dimensions of organizational health.
• Uses a traffic light system for easy visualization.
• Provides benchmarks for each metric.
• Offers a guided CLI for scoring.
• Outputs raw JSON for integration.
• Includes key metrics for each dimension.

Manual Installation

Keywords

org health, organizational health, health diagnostic, health dashboard, health check, company health, functional health, team health, startup health, health scorecard, health assessment, risk dashboard

Quick Start

python scripts/health_scorer.py # Guided CLI — enter metrics, get scored dashboard python scripts/health_scorer.py --json # Output raw JSON for integration

Or describe your metrics: /health [paste your key metrics or answer prompts] /health:dimension [financial|revenue|product|engineering|people|ops|security|market]

The 8 Dimensions

1. 💰 Financial Health (CFO)

What it measures: Can we fund operations and invest in growth?

Key metrics: Runway — months at current burn (Green: >12, Yellow: 6-12, Red: <6) Burn multiple — net burn / net new ARR (Green: <1.5x, Yellow: 1.5-2.5x, Red: >2.5x) Gross margin — SaaS target: >65% (Green: >70%, Yellow: 55-70%, Red: <55%) MoM growth rate — contextual by stage (see benchmarks) Revenue concentration — top customer % of ARR (Green: <15%, Yellow: 15-25%, Red: >25%)

2. 📈 Revenue Health (CRO)

What it measures: Are customers staying, growing, and recommending us?

Key metrics: NRR (Net Revenue Retention) — Green: >110%, Yellow: 100-110%, Red: <100% Logo churn rate (annualized) — Green: <5%, Yellow: 5-10%, Red: >10% Pipeline coverage (next quarter) — Green: >3x, Yellow: 2-3x, Red: <2x CAC payback period — Green: <12 months, Yellow: 12-18, Red: >18 months Average ACV trend — directional: growing, flat, declining

3. 🚀 Product Health (CPO)

What it measures: Do customers love and use the product?

Key metrics: NPS — Green: >40, Yellow: 20-40, Red: <20 DAU/MAU ratio — engagement proxy (Green: >40%, Yellow: 20-40%, Red: <20%) Core feature adoption — % of users using primary value feature (Green: >60%) Time-to-value — days from signup to first core action (lower is better) Customer satisfaction (CSAT) — Green: >4.2/5, Yellow: 3.5-4.2, Red: <3.5

4. ⚙️ Engineering Health (CTO)

What it measures: Can we ship reliably and sustain velocity?

Key metrics: Deployment frequency — Green: daily, Yellow: weekly, Red: monthly or less Change failure rate — % of deployments causing incidents (Green: <5%, Red: >15%) Mean time to recovery (MTTR) — Green: <1 hour, Yellow: 1-4 hours, Red: >4 hours Tech debt ratio — % of sprint capacity on debt (Green: <20%, Yellow: 20-35%, Red: >35%) Incident frequency — P0/P1 per month (Green: <2, Yellow: 2-5, Red: >5)

5. 👥 People Health (CHRO)

What it measures: Is the team stable, engaged, and growing?

Key metrics: Regrettable attrition (annualized) — Green: <10%, Yellow: 10-20%, Red: >20% Engagement score — (eNPS or similar; Green: >30, Yellow: 0-30, Red: <0) Time-to-fill (avg days) — Green: <45, Yellow: 45-90, Red: >90 Manager-to-IC ratio — Green: 1:5–1:8, Yellow: 1:3–1:5 or 1:8–1:12, Red: outside Internal promotion rate — at least 25-30% of senior roles filled internally

6. 🔄 Operational Health (COO)

What it measures: Are we executing our strategy with discipline?

Key metrics: OKR completion rate — % of key results hitting target (Green: >70%, Yellow: 50-70%, Red: <50%) Decision cycle time — days from decision needed to decision made (Green: <48h, Yellow: 48h-1w) Meeting effectiveness — % of meetings with clear outcome (qualitative) Process maturity — level 1-5 scale (see COO advisor) Cross-functional initiative completion — % on time, on scope

7. 🔒 Security Health (CISO)

What it measures: Are we protecting customers and maintaining compliance?

Key metrics: Security incidents (last 90 days) — Green: 0, Yellow: 1-2 minor, Red: 1+ major Compliance status — certifications current/in-progress vs. overdue Vulnerability remediation SLA — % of critical CVEs patched within SLA (Green: 100%) Security training completion — % of team current (Green: >95%) Pen test recency — Green: <12 months, Yellow: 12-24, Red: >24 months

8. 📣 Market Health (CMO)

What it measures: Are we winning in the market and growing efficiently?

Key metrics: CAC trend — improving, flat, or worsening QoQ Organic vs paid lead mix — more organic = healthier (less fragile) Win rate — % of qualified opportunities closed-won (Green: >25%, Yellow: 15-25%, Red: <15%) Competitive win rate — against primary competitors specifically Brand NPS — awareness + preference scores in ICP

Scoring & Traffic Lights

Each dimension is scored 1-10 with traffic light: 🟢 Green (7-10): Healthy — maintain and optimize 🟡 Yellow (4-6): Watch — trend matters; improving or declining? 🔴 Red (1-3): Action required — address within 30 days

Overall Health Score: Weighted average by company stage (see references/health-benchmarks.md for weights).

Dimension Interactions (Why One Problem Creates Another)

Dashboard Output Format

ORG HEALTH DIAGNOSTIC — [Company] — [Date] Stage: [Seed/A/B/C] Overall: [Score]/10 Trend: [↑ Improving / → Stable / ↓ Declining]

DIMENSION SCORES ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 💰 Financial 🟢 8.2 Runway 14mo, burn 1.6x — strong 📈 Revenue 🟡 5.8 NRR 104%, pipeline thin (1.8x coverage) 🚀 Product 🟢 7.4 NPS 42, DAU/MAU 38% ⚙️ Engineering 🟡 5.2 Debt at 30%, MTTR 3.2h 👥 People 🔴 3.8 Attrition 24%, eng morale low 🔄 Operations 🟡 6.0 OKR 65% completion 🔒 Security 🟢 7.8 SOC 2 Type II complete, 0 incidents 📣 Market 🟡 5.5 CAC rising, win rate dropped to 22% ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

TOP PRIORITIES 🔴 [1] People: attrition at 24% — engineering velocity will drop in 60 days Action: CHRO + CEO to run retention audit; target top 5 at-risk this week 🟡 [2] Revenue: pipeline coverage at 1.8x — Q+1 miss risk is high Action: CRO to add 3 qualified opps within 30 days or shift forecast down 🟡 [3] Engineering: tech debt at 30% of sprint — shipping will slow by Q3 Action: CTO to propose debt sprint plan; COO to protect capacity

WATCH → People → Engineering cascade risk if attrition continues (see dimension interactions)

Graceful Degradation

You don't need all metrics to run a diagnostic. The tool handles partial data: Missing metric → excluded from score, flagged as "[data needed]" Score still valid for available dimensions Report flags which gaps to fill for next cycle

References

references/health-benchmarks.md — benchmarks by stage