Claude-Skills org-health-diagnostic

install
source · Clone the upstream repo
git clone https://github.com/borghei/Claude-Skills
Claude Code · Install into ~/.claude/skills/
T=$(mktemp -d) && git clone --depth=1 https://github.com/borghei/Claude-Skills "$T" && mkdir -p ~/.claude/skills && cp -r "$T/c-level-advisor/org-health-diagnostic" ~/.claude/skills/borghei-claude-skills-org-health-diagnostic && rm -rf "$T"
manifest: c-level-advisor/org-health-diagnostic/SKILL.md
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Org Health Diagnostic

Eight dimensions. Traffic lights. Real benchmarks. Surfaces the problems you do not know you have and shows how problems in one dimension cascade to others.

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, cross-functional health, dimension cascade, stage benchmarks


The 8 Dimensions

Dimension Overview

#DimensionC-Suite OwnerCore Question
1Financial HealthCFOCan we fund operations and invest in growth?
2Revenue HealthCROAre customers staying, growing, and recommending us?
3Product HealthCPODo customers love and use the product?
4Engineering HealthCTOCan we ship reliably and sustain velocity?
5People HealthCHROIs the team stable, engaged, and growing?
6Operational HealthCOOAre we executing our strategy with discipline?
7Security HealthCISOAre we protecting customers and maintaining compliance?
8Market HealthCMOAre we winning in the market and growing efficiently?

Dimension 1: Financial Health (CFO)

MetricGreen (7-10)Yellow (4-6)Red (1-3)
Runway (months)> 189-18< 9
Burn multiple< 1.5x1.5-2.5x> 2.5x
Gross margin> 70%55-70%< 55%
Revenue concentration (top customer)< 10%10-20%> 20%
MoM growth rateAbove benchmarkAt benchmarkBelow benchmark

Dimension 2: Revenue Health (CRO)

MetricGreen (7-10)Yellow (4-6)Red (1-3)
NRR> 110%100-110%< 100%
Logo churn (annual)< 5%5-10%> 10%
Pipeline coverage (next Q)> 3x2-3x< 2x
CAC payback< 12 months12-18 months> 18 months
Win rate> 25%15-25%< 15%

Dimension 3: Product Health (CPO)

MetricGreen (7-10)Yellow (4-6)Red (1-3)
NPS> 4020-40< 20
DAU/MAU ratio> 40%20-40%< 20%
Core feature adoption> 60%30-60%< 30%
Time to valueDecreasing QoQStableIncreasing QoQ
CSAT> 4.2/53.5-4.2< 3.5

Dimension 4: Engineering Health (CTO)

MetricGreen (7-10)Yellow (4-6)Red (1-3)
Deploy frequencyDailyWeeklyMonthly or less
Change failure rate< 5%5-15%> 15%
MTTR< 1 hour1-4 hours> 4 hours
Tech debt ratio (% of sprint)< 20%20-35%> 35%
P0/P1 incidents per month< 22-5> 5

Dimension 5: People Health (CHRO)

MetricGreen (7-10)Yellow (4-6)Red (1-3)
Regrettable attrition (annual)< 10%10-20%> 20%
eNPS> 300-30< 0
Time to fill (avg days)< 4545-90> 90
Manager:IC ratio1:5-1:81:3-1:5 or 1:8-1:12Outside range
Internal promotion rate> 30%15-30%< 15%

Dimension 6: Operational Health (COO)

MetricGreen (7-10)Yellow (4-6)Red (1-3)
OKR completion rate> 70%50-70%< 50%
Decision cycle time< 48 hours48hrs-1 week> 1 week
Meeting effectivenessClear outcomesMixedNo outcomes
Cross-functional initiative completion> 80% on time50-80%< 50%
Process documentation coverage> 70%40-70%< 40%

Dimension 7: Security Health (CISO)

MetricGreen (7-10)Yellow (4-6)Red (1-3)
Security incidents (90 days)01-2 minor1+ major
Compliance statusAll currentIn progressOverdue/lapsed
Critical vuln remediation SLA100% in SLA> 90%< 90%
Security training completion> 95%80-95%< 80%
Pen test recency< 12 months12-24 months> 24 months

Dimension 8: Market Health (CMO)

MetricGreen (7-10)Yellow (4-6)Red (1-3)
CAC trendImproving QoQStableWorsening QoQ
Organic vs paid lead mix> 50% organic30-50% organic< 30% organic
Win rate vs competitorsImprovingStableDeclining
Brand awareness (in ICP)> 40%20-40%< 20%
Pipeline contribution (marketing)> 40%20-40%< 20%

Scoring System

Individual Dimension Score

Each dimension scores 1-10 based on weighted metrics:

Dimension Score = Sum(metric_score x metric_weight) / Sum(weights)

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:

DimensionSeed WeightSeries ASeries BSeries C+
Financial20%15%15%15%
Revenue10%20%20%20%
Product25%20%15%10%
Engineering15%15%15%10%
People10%10%15%15%
Operations5%10%10%15%
Security5%5%5%10%
Market10%5%5%5%

Stage-Adjusted Benchmarks

Different stages have different healthy ranges. A Seed company with 6-month runway is normal; a Series C company with 6-month runway is a crisis.

StageRunway TargetBurn MultipleTeam SizeRevenue Threshold
Seed> 12 monthsNot applicable2-10Pre-revenue acceptable
Series A> 18 months< 3x10-40> $500K ARR
Series B> 18 months< 2x30-100> $3M ARR
Series C+> 24 months< 1.5x80-300> $15M ARR

Cascade Analysis

How Dimension Failures Propagate

This is the most important part of the diagnostic. Problems in one dimension inevitably create problems in others.

If This Is Red...Watch These Next...Why
FinancialPeople -> Engineering -> ProductBudget cuts -> hiring freeze -> velocity drops -> product stalls
RevenueFinancial -> People -> MarketCash gap -> attrition risk -> positioning weakens
ProductRevenue -> Market -> PeopleNRR drops -> CAC rises -> top talent leaves
EngineeringProduct -> RevenueFeatures slip -> deals stall on missing features
PeopleEngineering -> Product -> RevenueVelocity drops -> quality drops -> churn rises
OperationsALL dimensions degrade over timeExecution failure cascades everywhere
SecurityRevenue (enterprise) -> FinancialEnterprise deals blocked -> revenue impact
MarketRevenue -> FinancialLead pipeline dries up -> sales suffers

Cascade Risk Decision Tree

START: Dimension scores calculated
  |
  v
[Any dimension RED?]
  |
  +-- NO  --> [Any dimension YELLOW with declining trend?]
  |            |
  |            +-- YES --> Monitor cascade. Check connected dimensions.
  |            +-- NO  --> Healthy. Maintain current approach.
  |
  +-- YES --> [Check cascade connections]
              |
              v
            [Are connected dimensions also Yellow/Red?]
              |
              +-- YES --> SYSTEMIC ISSUE. Root cause in the Red dimension.
              |           Address Red dimension first. Connected will improve.
              |
              +-- NO  --> ISOLATED ISSUE. Fix Red dimension before it cascades.
                          Timeline: 30 days or cascade begins.

Dashboard Output Format

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

DIMENSION SCORES
------------------------------------------------------------
  Financial     [G] 8.2  Runway 14mo, burn 1.6x
  Revenue       [Y] 5.8  NRR 104%, pipeline thin (1.8x)
  Product       [G] 7.4  NPS 42, DAU/MAU 38%
  Engineering   [Y] 5.2  Debt at 30%, MTTR 3.2h
  People        [R] 3.8  Attrition 24%, eNPS -5
  Operations    [Y] 6.0  OKR 65% completion
  Security      [G] 7.8  SOC 2 complete, 0 incidents
  Market        [Y] 5.5  CAC rising, win rate 22%
------------------------------------------------------------

TOP PRIORITIES (address in order)
[R] 1. People: attrition at 24%
       Impact: Engineering velocity drops in 60 days (cascade risk)
       Action: Retention audit + intervention for top 5 at-risk
       Owner: CHRO + CEO | Timeline: This week

[Y] 2. Revenue: pipeline at 1.8x
       Impact: Q+1 miss risk is high
       Action: Add 3 qualified opps in 30 days or adjust forecast
       Owner: CRO | Timeline: 30 days

[Y] 3. Engineering: tech debt at 30%
       Impact: Shipping velocity slows by Q3
       Action: Dedicated debt sprint plan
       Owner: CTO | Timeline: 45 days

CASCADE WARNING
  People [R] --> Engineering [Y] cascade risk
  If attrition continues: engineering velocity drops -> product delays
  -> revenue impact in 2 quarters

DATA GAPS
  [!] Market: Brand awareness data needed
  [!] Operations: Meeting effectiveness not measured

Graceful Degradation

Not all data is always available. The diagnostic handles partial data:

Data AvailabilityApproach
All metrics availableFull scoring, all dimensions
Missing 1-2 metrics per dimensionScore available metrics, flag gaps
Missing entire dimensionExclude from overall score, flag as "[data needed]"
Only 3-4 dimensions have dataPartial diagnostic, clearly marked

Diagnostic Cadence

FrequencyScopeAudience
WeeklyScorecard metrics only (2-3 per dimension)Leadership team
MonthlyFull 8-dimension assessmentCEO + direct reports
QuarterlyDeep diagnostic with cascade analysis + benchmarksBoard-ready report
AnnualFull diagnostic + year-over-year comparison + strategy implicationsBoard + investors

Red Flags

  • Any dimension Red for 2+ consecutive months -- systemic problem, not a blip
  • 3+ dimensions Yellow simultaneously -- organizational strain, prioritize ruthlessly
  • Overall score declining 3+ months -- strategic review needed
  • Cascade warning triggered and not addressed in 30 days -- will get worse
  • Data gaps persist for 2+ cycles -- measurement culture problem
  • Score improving but team sentiment declining -- measurement gaming
  • No dimension ever Red -- either the company is exceptional or standards are too low

Integration with C-Suite

DimensionOwner SkillDrill-Down
FinancialCFO Advisor (
cfo-advisor
)
Deep financial analysis
RevenueCRO Advisor (
cro-advisor
)
Pipeline and retention analysis
ProductCPO Advisor (
cpo-advisor
)
PMF assessment and portfolio review
EngineeringCTO Advisor (
cto-advisor
)
Technical health and debt analysis
PeopleCHRO Advisor (
chro-advisor
)
Retention, engagement, org design
OperationsCOO Advisor (
coo-advisor
)
Process maturity, execution cadence
SecurityCISO Advisor (
ciso-advisor
)
Risk register, compliance status
MarketCMO Advisor (
cmo-advisor
)
Positioning, channel effectiveness

Output Artifacts

RequestDeliverable
"How healthy is the company?"Full 8-dimension dashboard with traffic lights
"What should we fix first?"Prioritized action list with cascade analysis
"Prepare health section for board"Board-ready health summary with trends
"Compare to last quarter"Quarter-over-quarter comparison with trend arrows
"Where are we at risk?"Cascade risk map with interconnected failures
"What data do we need?"Data gap analysis with collection recommendations

Troubleshooting

ProblemLikely CauseResolution
Scores consistently show all green but team sentiment is negativeMetrics being gamed or standards set too low; measurement doesn't capture realityCross-reference quantitative scores with qualitative signals (exit interviews, Glassdoor, skip-level conversations); raise benchmarks to industry-standard levels
Cascade analysis shows systemic issue but leadership disagreesRed dimension owners resistant to acknowledging problemsPresent cascade evidence with data: "People Red for 2 months → Engineering Yellow → Product delays in pipeline"; use McKinsey OHI principle of benchmarking against external data
Data gaps persist across multiple diagnostic cyclesNo measurement infrastructure; teams don't prioritize data collectionAssign data collection to specific owners with deadlines; start with proxy metrics where direct measurement is unavailable
Diagnostic takes too long to produce (> 2 weeks)Trying to measure everything perfectly instead of using available dataApply graceful degradation: score what you have, flag gaps, iterate; a partial diagnostic now beats a perfect one in 6 weeks
Different stakeholders interpret traffic light scores differentlyNo shared understanding of what Green/Yellow/Red means operationallyDocument specific thresholds for each metric in each dimension; share calibration examples ("Red runway = less than 9 months at current burn")
Quarterly diagnostic shows no change despite interventionsWrong interventions, or interventions not given enough time, or measuring lagging indicatorsVerify interventions target root cause not symptoms; check leading indicators alongside lagging ones; allow 2 quarters for structural changes to show in scores
Board wants a single number but diagnostic is multi-dimensionalBoard unfamiliar with the 8-dimension modelProvide the weighted overall score (1-10) as headline with stage-adjusted weighting; drill-down dimensions available on request

Success Criteria

  • All 8 dimensions scored with traffic lights within 5 business days of data collection start
  • Cascade analysis correctly predicts downstream impacts: when a Red dimension is not addressed, connected dimensions degrade within 2 quarters
  • Stage-adjusted benchmarks applied correctly: Seed company not held to Series C standards and vice versa
  • Top 3 priorities identified with specific owners, timelines, and verification methods
  • Data gaps reduced by at least 50% between first and second diagnostic cycle
  • Board-ready health summary produced quarterly with trend comparison to prior quarter
  • Overall health score trending stable or improving over 3 consecutive quarters

Scope & Limitations

  • In scope: 8-dimension organizational health scoring, traffic light dashboards, cascade analysis, stage-adjusted benchmarks, graceful degradation for partial data, diagnostic cadence recommendations, board-ready reporting
  • Out of scope: Deep functional diagnostics within a single dimension (use the respective C-suite advisor skill); employee engagement survey design and administration (use CHRO Advisor); financial auditing (use external auditors); security penetration testing (use CISO Advisor)
  • Limitation: Diagnostic quality depends on data accuracy; garbage in, garbage out applies -- verify data sources
  • Limitation: McKinsey OHI benchmarks are based on large enterprise data; early-stage companies may need adjusted benchmarks
  • Limitation: The 8-dimension model is a simplification; some organizations may need additional dimensions (e.g., ESG, regulatory) depending on industry
  • Limitation: Cascade predictions are based on common patterns; specific organizations may have unique cascade paths

Integration Points

SkillIntegrationData Flow
cfo-advisor
Financial Health dimension deep diveHealth financial score → CFO detailed analysis
cro-advisor
Revenue Health dimension deep diveHealth revenue score → CRO pipeline review
cpo-advisor
Product Health dimension deep diveHealth product score → CPO PMF assessment
cto-advisor
Engineering Health dimension deep diveHealth engineering score → CTO tech debt plan
chro-advisor
People Health dimension deep diveHealth people score → CHRO retention strategy
coo-advisor
Operational Health dimension deep diveHealth operations score → COO process review
ciso-advisor
Security Health dimension deep diveHealth security score → CISO risk register
cmo-advisor
Market Health dimension deep diveHealth market score → CMO channel review
strategic-alignment
Health scores inform alignment prioritiesHealth priorities → Alignment focus areas
executive-mentor
Red dimensions trigger executive coaching focusHealth red flags → Mentor challenge areas

Python Tools

ToolPurposeUsage
scripts/org_health_scorer.py
Score all 8 dimensions with traffic lights, stage-adjusted weighting, and overall health calculation
python scripts/org_health_scorer.py --stage series-a --financial 7.5 --revenue 5.8 --product 7.2 --engineering 5.0 --people 3.5 --operations 6.0 --security 7.8 --market 5.5 --json
scripts/span_of_control_analyzer.py
Analyze manager-to-IC ratios across the organization and flag unhealthy spans
python scripts/span_of_control_analyzer.py --org-file org_structure.csv --json
scripts/engagement_benchmarker.py
Benchmark engagement metrics against industry standards and flag gaps
python scripts/engagement_benchmarker.py --enps 15 --attrition 18 --time-to-fill 60 --promotion-rate 20 --industry saas --json