Claude-Skills scenario-war-room
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T=$(mktemp -d) && git clone --depth=1 https://github.com/borghei/Claude-Skills "$T" && mkdir -p ~/.claude/skills && cp -r "$T/c-level-advisor/scenario-war-room" ~/.claude/skills/borghei-claude-skills-scenario-war-room && rm -rf "$T"
c-level-advisor/scenario-war-room/SKILL.mdScenario 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:
| Field | Description | Example |
|---|---|---|
| What changes | Specific, quantified | "Top customer (28% of ARR) gives 60-day termination notice" |
| Probability | Your best estimate | 15% |
| Timeline | When it could hit | Within 90 days |
| Detection signal | How you would know it is happening | Sponsor 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:
| Domain | Key Questions | Typical 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/Compliance | Regulatory 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 ($560K ARR) │ ├──▶ CFO: Runway drops 14 → 8 months │ │ │ └──▶ CHRO: Hiring freeze imposed │ │ │ └──▶ CTO: 3 open engineering reqs frozen, roadmap slips 2 months │ │ │ └──▶ CPO: Q4 feature launch delayed → 2 more customers at risk │ │ │ └──▶ CRO: NRR drops → additional churn risk (DEATH SPIRAL ENTRY) │ └──▶ CRO: Revenue concentration increases (next largest = 22%) │ └──▶ Investors: Concentration risk flagged → Series A terms worsen
Name the cascades explicitly. Common cascade patterns:
| Cascade Pattern | Description | Interruption Point |
|---|---|---|
| Revenue-to-Runway Death Spiral | Customer churn → lower runway → hiring freeze → slower product → more churn | Emergency revenue diversification |
| Key Person Cascade | Star leaves → team morale drops → followers leave → velocity collapses | Retention bonuses before departure |
| Market Squeeze | Competitor raises → price war → margins compress → can't invest in product | Differentiation, not price matching |
| Trust Cascade | Incident → customer concern → churn → press → more churn | Swift, transparent communication |
| Fundraise-Burn Spiral | Miss target → raise delayed → bridge at bad terms → burn cuts → team loss | Parallel fundraise tracks |
Step 4: Severity Matrix
Model three scenarios with increasing severity:
| Scenario | Variables Hit | Definition | Recovery Difficulty |
|---|---|---|---|
| Base | 1 of 3 | Single shock, others don't materialize | Manageable with prepared response |
| Stress | 2 of 3 | Compound shock, cascade begins | Requires significant pivot, board involvement |
| Severe | All 3 | Full cascade, existential territory | Requires emergency action, may need board intervention |
For each severity level, quantify:
BASE SCENARIO (Variable A only): Runway impact: [X] months → [Y] months ARR impact: -$[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)
| Variable | Signal | Threshold | Response |
|---|---|---|---|
| Customer churn | Sponsor stops responding | > 3 weeks silence | Exec escalation, QBR request |
| Customer churn | Usage drops | > 25% MoM decline | CS outreach, value review |
| Fundraise delay | Term sheets | < 3 after 60 days in process | Parallel bridge conversations |
| Fundraise delay | Investor requests | > 30 day DD extension | Reduce burn, extend runway |
| Key person departure | Market compensation | Counter-offer required in last 90 days | Retention package, succession plan |
| Key person departure | External engagement | Engineer presenting at conferences for competitors | Direct 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:
| Criterion | Question |
|---|---|
| Cost | What does this hedge cost to implement? |
| Reversibility | Can we undo it if the scenario doesn't happen? |
| Lead time | How long to implement? (Must be shorter than detection-to-impact window) |
| Coverage | Which scenarios does this hedge protect against? |
| Side effects | Does this hedge cause other problems? |
Hedge Table Template:
| Hedge | Cost | Protects Against | Owner | Deadline | Status |
|---|---|---|---|---|---|
| Establish $500K credit line | $5K/year | Runway shortfall (Base + Stress) | CFO | 60 days | Not started |
| 12-month retention bonus for 3 key engineers | $90K | Key person departure (all scenarios) | CHRO | 30 days | In progress |
| Diversify to <20% revenue per customer | Sales effort (6 months) | Single-customer dependency | CRO | 2 quarters | Planning |
| Start parallel fundraise track | CEO time (10 hrs/week) | Fundraise delay (Stress + Severe) | CEO | Immediate | Not started |
| Pre-negotiate bridge terms with existing investors | 2 board conversations | Runway crisis (Severe) | CFO + CEO | 45 days | Not started |
| Document architecture for bus factor reduction | 2 engineering weeks | Key person departure | CTO | 30 days | Not started |
Output Format
Every war room session produces this structured output:
SCENARIO: [Name] DATE: [Date of analysis] PARTICIPANTS: [Who was involved] VARIABLES: A: [Description] — Probability: [X]%, Timeline: [When] B: [Description] — Probability: [X]%, Timeline: [When] C: [Description] — Probability: [X]%, Timeline: [When] MOST LIKELY PATH: [Which combination actually plays out, with reasoning] SEVERITY LEVELS: Base (A only): Runway [X]→[Y]mo, ARR impact -$[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
- Maximum 3 variables per scenario. More is noise. Model the ones that actually matter.
- Quantify or estimate. "Revenue drops" is not useful. "$420K ARR at risk over 60 days" is. Use ranges if uncertain.
- Don't stop at first-order effects. The real damage is always in the cascade.
- Model recovery, not just impact. Every scenario must have a "what we do" path.
- Separate base case from sensitivity. Don't conflate "what probably happens" with "what could happen."
- 3-4 scenarios per planning cycle. More creates analysis paralysis.
- Review every 90 days. Probabilities and variables change. Stale scenarios give false comfort.
- No judgment-free zone. People must feel safe naming ugly scenarios.
Related Skills
| Skill | Use When |
|---|---|
| ceo-advisor | Strategic decisions that scenarios inform |
| cfo-advisor | Financial modeling for scenario impacts |
| coo-advisor | Operational contingency planning |
| internal-narrative | Communicating scenario outcomes to stakeholders |
| cs-onboard | Company context that feeds scenario variables |
Troubleshooting
| Problem | Likely Cause | Resolution |
|---|---|---|
| Scenarios feel too abstract to act on | Variables not specific or quantified enough | Require 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 scenarios | Conformity bias; not applying Shell scenario planning method of challenging mental models | Use inversion technique: "What would guarantee our failure?"; bring in external perspective; reference industry-specific historical precedents |
| Cascade mapping stops at first-order effects | Facilitator not pushing past immediate consequences | Require minimum 3 levels of cascade for each variable; use "and then what?" prompting for each domain impact |
| Hedges identified but never implemented | No ownership, deadline, or cost attached | Every 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 scenario | Enforce maximum 3 variables and 3-4 scenarios per session; use severity matrix to focus on highest-impact combinations |
| Early warning signals not being monitored | Signals assigned but not integrated into existing reporting | Add signals to existing dashboards and weekly scorecards; assign specific person to monitor each signal |
| Participants reluctant to name worst-case scenarios | Fear of being seen as negative or alarmist | Establish 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
| Skill | Integration | Data Flow |
|---|---|---|
| Strategic decisions informed by scenario analysis | War room scenarios → CEO decision inputs |
| Financial modeling for scenario impacts and hedge costs | War room financial impacts → CFO stress test models |
| Operational contingency planning and cascade interruption | War room cascade map → COO contingency plans |
| Pre-mortem failure modes feed into scenario variables | Mentor failure modes → War room variables |
| Crisis scenarios require pre-built communication plans | War room crisis scenarios → Narrative crisis templates |
| Health dimension scores surface scenario variables | Health red flags → War room variable candidates |
| Scenario outcomes may require strategic realignment | War room outcomes → Alignment reassessment |
Python Tools
| Tool | Purpose | Usage |
|---|---|---|
| Build structured scenarios with variables, probabilities, detection signals, and severity levels | |
| Calculate compound impact across multiple variables with severity matrix and cascade risk scoring | |
| Build and evaluate decision trees with expected value calculations for strategic options | |