Agent Skills: Scenario War Room

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)

Clarify First

Before generating, confirm these inputs. If any is unknown or vague, ASK — do not assume:

• [ ] The (maximum 3) variables that actually keep leadership awake — the entire model is built around these; the wrong variables produce a useless scenario
• [ ] Probability, timeline, and quantified impact for each variable — "revenue drops" is not actionable; "$420K ARR at risk over 60 days" is, and severity levels depend on it
• [ ] Current baseline (ARR, runway in months, headcount) — cascade and severity math (e.g., runway going 14→8 months) requires the starting numbers
• [ ] Company stage — common scenario patterns and what counts as existential differ by stage

Stop rule: ask only the 2-3 that most change the output. If the user says "just draft it," proceed and list your assumptions at the top of the artifact.

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

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

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

Python Tools

| Tool | Purpose | Usage | |------|---------|-------| | 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 |