Claude-Skills scenario-war-room

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Scenario War Room

Tier: POWERFUL Category: C-Level Advisory Tags: scenario planning, war room, risk modeling, cascade effects, contingency planning, pre-mortem, crisis simulation

Overview

The Scenario War Room models cascading what-if scenarios across all business functions. Not single-assumption stress tests -- compound adversity that shows how one problem creates the next, and where the cascade can be interrupted. Every scenario produces concrete hedges with costs, owners, and deadlines.


When to Use

  • A major risk has probability above 15% and impact above 20% of ARR
  • Two or more threats could plausibly co-occur
  • A strategic decision has significant downside if wrong
  • Board or investors are asking "what's the worst case?"
  • Pre-mortem before a major commitment (fundraise, acquisition, market entry)
  • Quarterly risk review for leadership team

When NOT to Use

  • Single-variable financial sensitivity analysis (use CFO Advisor stress testing)
  • Routine project risk assessment (use project management risk frameworks)
  • Technical failure mode analysis (use engineering incident planning)

The 6-Step Cascade Model

Step 1: Define Scenario Variables (Maximum 3)

More than 3 variables creates analysis paralysis, not insight. Choose the 3 that actually keep leadership awake at night.

For each variable, specify:

FieldDescriptionExample
What changesSpecific, quantified"Top customer (28% of ARR) gives 60-day termination notice"
ProbabilityYour best estimate15%
TimelineWhen it could hitWithin 90 days
Detection signalHow you would know it is happeningSponsor goes dark, usage drops 25% MoM

Variable Template:

Variable A: [Specific change]
  Probability: [X]%  |  Timeline: [When]
  Detection: [Early warning signal]
  First-order impact: [Immediate consequence]

Variable B: [Specific change]
  Probability: [X]%  |  Timeline: [When]
  Detection: [Early warning signal]
  First-order impact: [Immediate consequence]

Variable C: [Specific change]
  Probability: [X]%  |  Timeline: [When]
  Detection: [Early warning signal]
  First-order impact: [Immediate consequence]

Step 2: Domain Impact Mapping

For each variable, assess impact across every business function:

DomainKey QuestionsTypical Impact Areas
Finance (CFO)Burn impact? Runway change? Bridge options?Cash, runway, covenant triggers
Revenue (CRO)ARR gap? Churn cascade? Pipeline affected?NRR, expansion, new logo risk
Product (CPO)Roadmap derailed? PMF at risk? Customer need shift?Delivery timeline, feature priority
Engineering (CTO)Velocity hit? Key person risk? Technical debt impact?Capacity, architecture, hiring
People (CHRO)Attrition cascade? Hiring freeze? Morale impact?Retention, culture, bench strength
Operations (COO)Capacity affected? Process breaks? OKR impact?SLAs, efficiency, scale
Market (CMO)CAC affected? Competitive exposure? Brand risk?Pipeline generation, positioning
Legal/ComplianceRegulatory timeline risk? Contract exposure?Obligations, deadlines, penalties

Step 3: Cascade Mapping (The Core)

This is the most valuable step. Map how Variable A triggers consequences that amplify Variable B.

Cascade Diagram:

TRIGGER: Customer churn ($560K ARR)
  │
  ├──▶ CFO: Runway drops 14 → 8 months
  │     │
  │     └──▶ CHRO: Hiring freeze imposed
  │           │
  │           └──▶ CTO: 3 open engineering reqs frozen, roadmap slips 2 months
  │                 │
  │                 └──▶ CPO: Q4 feature launch delayed → 2 more customers at risk
  │                       │
  │                       └──▶ CRO: NRR drops → additional churn risk (DEATH SPIRAL ENTRY)
  │
  └──▶ CRO: Revenue concentration increases (next largest = 22%)
        │
        └──▶ Investors: Concentration risk flagged → Series A terms worsen

Name the cascades explicitly. Common cascade patterns:

Cascade PatternDescriptionInterruption Point
Revenue-to-Runway Death SpiralCustomer churn → lower runway → hiring freeze → slower product → more churnEmergency revenue diversification
Key Person CascadeStar leaves → team morale drops → followers leave → velocity collapsesRetention bonuses before departure
Market SqueezeCompetitor raises → price war → margins compress → can't invest in productDifferentiation, not price matching
Trust CascadeIncident → customer concern → churn → press → more churnSwift, transparent communication
Fundraise-Burn SpiralMiss target → raise delayed → bridge at bad terms → burn cuts → team lossParallel fundraise tracks

Step 4: Severity Matrix

Model three scenarios with increasing severity:

ScenarioVariables HitDefinitionRecovery Difficulty
Base1 of 3Single shock, others don't materializeManageable with prepared response
Stress2 of 3Compound shock, cascade beginsRequires significant pivot, board involvement
SevereAll 3Full cascade, existential territoryRequires emergency action, may need board intervention

For each severity level, quantify:

BASE SCENARIO (Variable A only):
  Runway impact: [X] months → [Y] months
  ARR impact: -$[X] ([Y]% of total)
  Headcount impact: [freeze / reduction / none]
  Timeline to critical: [X] months
  Recovery plan: [specific actions]

STRESS SCENARIO (Variables A + B):
  Runway impact: [X] months → [Y] months
  ARR impact: -$[X] ([Y]% of total)
  Headcount impact: [specifics]
  Timeline to critical: [X] months
  Recovery plan: [specific actions]

SEVERE SCENARIO (All three):
  Runway impact: [X] months → [Y] months
  ARR impact: -$[X] ([Y]% of total)
  Headcount impact: [specifics]
  Timeline to critical: [X] months
  Existential: [yes/no]
  Emergency plan: [specific actions requiring board approval]

Step 5: Early Warning Signals (Trigger Points)

Define measurable signals that tell you a scenario is unfolding BEFORE it is confirmed. The value of this exercise is acting early, not reacting late.

Signal Design Criteria:

  • Observable (you can actually measure it)
  • Leading (appears before the full impact)
  • Specific (not just "things feel off")
  • Actionable (triggers a specific response)
VariableSignalThresholdResponse
Customer churnSponsor stops responding> 3 weeks silenceExec escalation, QBR request
Customer churnUsage drops> 25% MoM declineCS outreach, value review
Fundraise delayTerm sheets< 3 after 60 days in processParallel bridge conversations
Fundraise delayInvestor requests> 30 day DD extensionReduce burn, extend runway
Key person departureMarket compensationCounter-offer required in last 90 daysRetention package, succession plan
Key person departureExternal engagementEngineer presenting at conferences for competitorsDirect conversation, role expansion

Step 6: Hedging Strategies

For each scenario: actions to take NOW (before the scenario materializes) that reduce impact if it does. Hedges have costs -- the goal is cheap insurance, not paranoia.

Hedge Evaluation Criteria:

CriterionQuestion
CostWhat does this hedge cost to implement?
ReversibilityCan we undo it if the scenario doesn't happen?
Lead timeHow long to implement? (Must be shorter than detection-to-impact window)
CoverageWhich scenarios does this hedge protect against?
Side effectsDoes this hedge cause other problems?

Hedge Table Template:

HedgeCostProtects AgainstOwnerDeadlineStatus
Establish $500K credit line$5K/yearRunway shortfall (Base + Stress)CFO60 daysNot started
12-month retention bonus for 3 key engineers$90KKey person departure (all scenarios)CHRO30 daysIn progress
Diversify to <20% revenue per customerSales effort (6 months)Single-customer dependencyCRO2 quartersPlanning
Start parallel fundraise trackCEO time (10 hrs/week)Fundraise delay (Stress + Severe)CEOImmediateNot started
Pre-negotiate bridge terms with existing investors2 board conversationsRunway crisis (Severe)CFO + CEO45 daysNot started
Document architecture for bus factor reduction2 engineering weeksKey person departureCTO30 daysNot started

Output Format

Every war room session produces this structured output:

SCENARIO: [Name]
DATE: [Date of analysis]
PARTICIPANTS: [Who was involved]

VARIABLES:
  A: [Description] — Probability: [X]%, Timeline: [When]
  B: [Description] — Probability: [X]%, Timeline: [When]
  C: [Description] — Probability: [X]%, Timeline: [When]

MOST LIKELY PATH: [Which combination actually plays out, with reasoning]

SEVERITY LEVELS:
  Base (A only):  Runway [X]→[Y]mo, ARR impact -$[X]
    Recovery: [2-3 specific actions]
  Stress (A+B):   Runway [X]→[Y]mo, ARR impact -$[X]
    Recovery: [3-4 specific actions]
  Severe (A+B+C): Runway [X]→[Y]mo, ARR impact -$[X]
    Existential: [yes/no]
    Emergency: [actions requiring board approval]

CASCADE MAP:
  [A] → [domain impact] → [triggers B amplification] → [domain impact] → [end state]
  Interruption points: [where cascade can be broken]

EARLY WARNING SIGNALS:
  1. [Signal] → indicates [scenario], threshold: [specific]
  2. [Signal] → indicates [scenario], threshold: [specific]
  3. [Signal] → indicates [scenario], threshold: [specific]

HEDGES (implement now):
  1. [Action] — cost: $[X] — protects: [scenarios] — owner: [role] — deadline: [date]
  2. [Action] — cost: $[X] — protects: [scenarios] — owner: [role] — deadline: [date]
  3. [Action] — cost: $[X] — protects: [scenarios] — owner: [role] — deadline: [date]

RECOMMENDED DECISION:
  [One paragraph: what to do, in what order, and why]

REVIEW DATE: [When to re-run this analysis — typically 90 days or after any variable shifts]

Common Scenarios by Company Stage

Seed Stage

  • Co-founder departure + product misses launch deadline
  • Runway runs out + bridge terms are predatory
  • Key technical hire falls through + competitor ships first

Series A

  • Miss ARR target + fundraise delayed
  • Top customer churns + competitor raises large round
  • Key engineer leaves + critical feature deadline

Series B+

  • Market contraction + burn multiple spikes above 3x
  • Lead investor wants strategic pivot + team resists
  • Regulatory change + product requires rearchitecture

War Room Ground Rules

  1. Maximum 3 variables per scenario. More is noise. Model the ones that actually matter.
  2. Quantify or estimate. "Revenue drops" is not useful. "$420K ARR at risk over 60 days" is. Use ranges if uncertain.
  3. Don't stop at first-order effects. The real damage is always in the cascade.
  4. Model recovery, not just impact. Every scenario must have a "what we do" path.
  5. Separate base case from sensitivity. Don't conflate "what probably happens" with "what could happen."
  6. 3-4 scenarios per planning cycle. More creates analysis paralysis.
  7. Review every 90 days. Probabilities and variables change. Stale scenarios give false comfort.
  8. No judgment-free zone. People must feel safe naming ugly scenarios.

Related Skills

SkillUse When
ceo-advisorStrategic decisions that scenarios inform
cfo-advisorFinancial modeling for scenario impacts
coo-advisorOperational contingency planning
internal-narrativeCommunicating scenario outcomes to stakeholders
cs-onboardCompany context that feeds scenario variables

Troubleshooting

ProblemLikely CauseResolution
Scenarios feel too abstract to act onVariables not specific or quantified enoughRequire dollar amounts, percentages, and timelines for every variable; "revenue drops" is not actionable, "$420K ARR at risk over 60 days" is
Team generates only obvious, low-probability scenariosConformity bias; not applying Shell scenario planning method of challenging mental modelsUse inversion technique: "What would guarantee our failure?"; bring in external perspective; reference industry-specific historical precedents
Cascade mapping stops at first-order effectsFacilitator not pushing past immediate consequencesRequire minimum 3 levels of cascade for each variable; use "and then what?" prompting for each domain impact
Hedges identified but never implementedNo ownership, deadline, or cost attachedEvery hedge must have: cost estimate, owner name, deadline, and status tracking; review in weekly leadership meeting
War room sessions take too long (> 4 hours)Too many variables or trying to model every scenarioEnforce maximum 3 variables and 3-4 scenarios per session; use severity matrix to focus on highest-impact combinations
Early warning signals not being monitoredSignals assigned but not integrated into existing reportingAdd signals to existing dashboards and weekly scorecards; assign specific person to monitor each signal
Participants reluctant to name worst-case scenariosFear of being seen as negative or alarmistEstablish ground rules explicitly; cite Shell's experience: "the value is in surfacing what others won't say"; reward naming hard truths

Success Criteria

  • Each scenario session produces exactly 3 variables, 3 severity levels, and a cascade map with interruption points identified
  • Early warning signals are specific enough to be monitored: observable, leading, and actionable with defined thresholds
  • Hedges are costed, owned, and have deadlines within 7 days of the war room session
  • At least one hedge per scenario is implemented (not just planned) within 30 days
  • Scenario review conducted every 90 days with probability updates based on new information
  • When an early warning signal fires, the pre-planned response is executed within the defined timeline
  • War room output is concise enough for board consumption: one-page summary per scenario

Scope & Limitations

  • In scope: Multi-variable scenario construction, cascade modeling across all business functions, severity matrix analysis, early warning signal design, hedge strategy with cost-benefit analysis, scenario review cadence
  • Out of scope: Single-variable financial sensitivity analysis (use CFO Advisor stress testing); technical failure mode analysis (use engineering incident planning); routine project risk assessment (use project management frameworks); insurance and risk transfer (use specialized broker)
  • Limitation: Scenario probabilities are subjective estimates, not actuarial calculations; value is in preparedness, not prediction accuracy
  • Limitation: Framework assumes scenarios are independent or correlated; black swan events by definition are not modelable
  • Limitation: Cascade mapping is based on common organizational patterns; unique company structures may have different cascade paths
  • Limitation: Maximum 3 variables per scenario is a deliberate constraint; more variables create analysis paralysis, not better insight

Integration Points

SkillIntegrationData Flow
ceo-advisor
Strategic decisions informed by scenario analysisWar room scenarios → CEO decision inputs
cfo-advisor
Financial modeling for scenario impacts and hedge costsWar room financial impacts → CFO stress test models
coo-advisor
Operational contingency planning and cascade interruptionWar room cascade map → COO contingency plans
executive-mentor
Pre-mortem failure modes feed into scenario variablesMentor failure modes → War room variables
internal-narrative
Crisis scenarios require pre-built communication plansWar room crisis scenarios → Narrative crisis templates
org-health-diagnostic
Health dimension scores surface scenario variablesHealth red flags → War room variable candidates
strategic-alignment
Scenario outcomes may require strategic realignmentWar room outcomes → Alignment reassessment

Python Tools

ToolPurposeUsage
scripts/scenario_builder.py
Build structured scenarios with variables, probabilities, detection signals, and severity levels
python scripts/scenario_builder.py --name "Customer Concentration Risk" --variable "Top customer churns" --probability 20 --impact 500000 --timeline 90 --json
scripts/impact_matrix_calculator.py
Calculate compound impact across multiple variables with severity matrix and cascade risk scoring
python scripts/impact_matrix_calculator.py --variables "churn:500000:0.2" "fundraise_delay:0:0.3" "key_departure:0:0.15" --arr 2000000 --runway-months 14 --json
scripts/decision_tree_analyzer.py
Build and evaluate decision trees with expected value calculations for strategic options
python scripts/decision_tree_analyzer.py --decision "Enter Japan market" --option "Direct:0.6:2000000:-500000" --option "Partnership:0.75:1000000:-200000" --option "Wait:1.0:0:0" --json