Pre-Mortem Risk Identification

When this skill activates, you become a pre-mortem facilitator. Your role is to guide users through prospective hindsight analysis, helping them identify project risks by imagining failure has already occurred.

Triggers

Activate when the user:

• Run a pre-mortem on...
• What could cause this project to fail?
• Identify project risks for...
• What could go wrong with...
• Pre-mortem analysis

Quick Reference

Phase	Duration	Output
1. Brief	2-3 min	Project context documented
2. Failure Announcement	30 sec	Mindset shift established
3. Independent Analysis	3-5 min	Individual failure reasons
4. Round-Robin Collection	5-10 min	Consolidated failure list
5. Review and Mitigate	10-15 min	Risk inventory with mitigations

When to Use

Use this skill when:

• Starting a new project or feature and want to identify risks upfront
• Team is overly optimistic and potential downsides need surfacing
• Stakeholders need to understand risk before committing resources
• After major scope changes to reassess risk landscape

Use threat-modeling instead when:

• Analyzing security threats specifically (STRIDE, attack trees)
• Need structured vulnerability assessment, not general project risk

Use decision-critic instead when:

• Challenging a specific decision, not brainstorming broad risks

Why Pre-Mortem Works

Research by Gary Klein demonstrates that prospective hindsight (imagining an event has already occurred) increases the ability to identify reasons for outcomes by 30%.

Key psychological benefits:

1. Reduces "damn-the-torpedoes" attitude - Acknowledging failure is possible
2. Creates psychological safety - Dissenters can voice concerns as analysis, not criticism
3. Surfaces hidden knowledge - People share what they know but fear saying
4. Catches blind spots early - Before commitment and sunk costs

Process

Phase 1: Project Brief (2-3 minutes)

Input Required:

• Project name and objective
• Timeline and key milestones
• Team composition (if team context)
• Success criteria

Actions:

1. Document the project scope clearly
2. Identify key stakeholders
3. Note any constraints or dependencies
4. Confirm understanding with user

Output: Project context document

Phase 2: Failure Announcement (30 seconds)

The critical mindset shift.

Announce to the user (or team):

"The project has failed. It is [timeline endpoint]. The project did not just miss its goals, it failed spectacularly. Your task now is to identify all the reasons why it failed."

Important: Use past tense. The failure has already happened. This is not speculation about what "might" happen; it "did" happen.

Phase 3: Independent Analysis (3-5 minutes)

For individual context:

• User writes down 5-10 reasons why the project failed
• No filtering or evaluation yet
• Include both obvious and "unlikely" causes
• Consider technical, human, organizational, and external factors

For team context:

• Each person writes independently
• No discussion or sharing yet
• Silent reflection maximizes diversity of thought

Prompt the user:

"Write down every reason you can think of for why this project failed. Include causes you consider unlikely. Do not filter yourself. You have 3-5 minutes."

Output: Raw list of failure reasons

Phase 4: Round-Robin Collection (5-10 minutes)

For individual context:

• Review each failure reason
• Group by category (see Categories below)
• No evaluation yet, just collection

For team context:

• Go around the room, each person shares ONE reason
• Continue rounds until all reasons exhausted
• Record without discussion or debate
• No "that won't happen" or "we already thought of that"

Categories for grouping:

1. Technical - Technology, architecture, implementation
2. People - Skills, availability, communication
3. Process - Methodology, workflow, coordination
4. Organizational - Politics, priorities, resources
5. External - Market, competitors, regulations, dependencies
6. Unknown Unknowns - Black swan events, assumptions

Output: Categorized failure reasons

Phase 5: Review and Mitigate (10-15 minutes)

For each failure reason:

1. Assess likelihood (1-5 scale)

   • 1: Very unlikely
   • 2: Unlikely
   • 3: Possible
   • 4: Likely
   • 5: Very likely

2. Assess impact (1-5 scale)

   • 1: Minor inconvenience
   • 2: Delays
   • 3: Significant setback
   • 4: Major failure
   • 5: Project-killing

3. Calculate risk score: Likelihood x Impact

4. Identify mitigation strategies:

   • Prevention: How to stop it from happening
   • Detection: How to know early if it is happening
   • Response: What to do if it happens

5. Assign ownership (if team context)

Prioritization:

• Risk score 15-25: Critical, address immediately
• Risk score 8-14: High, plan mitigation
• Risk score 4-7: Medium, monitor
• Risk score 1-3: Low, accept or defer

Output: Complete risk inventory (see template)

Output Template

Generate the risk inventory using this structure:

# Pre-Mortem Risk Inventory

**Project:** [Name]
**Date:** [Date]
**Participants:** [Names or "Individual Analysis"]

## Project Context

- **Objective:** [What success looks like]
- **Timeline:** [Start to end]
- **Key Dependencies:** [Critical external factors]

## Risk Summary

| Priority | Count | Top Risk |
|----------|-------|----------|
| Critical | N | [Highest scoring risk] |
| High | N | [Second highest category risk] |
| Medium | N | |
| Low | N | |

## Critical Risks (Score 15-25)

### R1: [Risk Name]

- **Category:** [Technical/People/Process/Organizational/External]
- **Failure Scenario:** [How this causes project failure]
- **Likelihood:** [1-5] | **Impact:** [1-5] | **Score:** [L x I]
- **Root Cause:** [Why this might happen]
- **Mitigation:**
  - Prevention: [How to avoid]
  - Detection: [Early warning signs]
  - Response: [Contingency plan]
- **Owner:** [Person responsible]
- **Status:** [Open/Mitigating/Accepted]

[Repeat for each critical risk]

## High Risks (Score 8-14)

[Same structure as Critical]

## Medium Risks (Score 4-7)

[Abbreviated: Name, Category, Score, One-line mitigation]

## Low Risks (Score 1-3)

[List only: Name and score]

## Action Items

| Action | Owner | Due Date | Risk Addressed |
|--------|-------|----------|----------------|
| [Specific action] | [Name] | [Date] | R1, R3 |

## Review Schedule

- **Next review:** [Date]
- **Review frequency:** [Weekly/Bi-weekly/Monthly]

Scripts

pre-mortem.py

Validates risk inventory completeness and calculates aggregate statistics.

python3 .claude/skills/pre-mortem/scripts/pre-mortem.py \
  --inventory-path "$INVENTORY_PATH" \
  --validate

Exit Codes:

• 0: Valid inventory with all required fields
• 1: Invalid arguments
• 10: Validation failed (missing required sections)

Anti-Patterns

Avoid	Why	Instead
Skipping Phase 2	Mindset shift is critical for effectiveness	Always announce failure explicitly
Allowing discussion during Phase 3	Reduces diversity of thought	Enforce silent writing
Filtering "unlikely" causes	Miss black swan events	Include all causes, prioritize later
Stopping at identification	Risk without mitigation is incomplete	Always complete Phase 5
One-time exercise	Projects evolve, new risks emerge	Schedule periodic reviews

Verification

After completing a pre-mortem, run the bundled validator and require exit 0:

python3 .claude/skills/pre-mortem/scripts/pre-mortem.py \
  --inventory-path "$INVENTORY_PATH" \
  --validate
echo "exit=$?"   # must be 0; exit 10 means missing required sections (inventory is not valid)

• pre-mortem.py exited 0 (exit 10 = validation failed; exit 1 = invalid arguments; non-zero = blocked)
• All 5 phases completed (Brief, Failure Announcement, Analysis, Collection, Mitigation)
• Risk inventory generated with risk scores (Likelihood x Impact)
• All Critical/High risks have mitigation strategies, each with the full Prevention/Detection/Response triad (a prevention-only mitigation FAILS the gate and MUST be completed)
• Each mitigation has Prevention, Detection, and Response
• Action items assigned with owners and due dates
• Review schedule established

Gate rule: pre-mortem.py exit 0 is necessary but not sufficient. The script flags has_mitigation true on a single **Prevention:** line, so a Critical/High risk can exit 0 with an incomplete mitigation. Until the script is tightened, manual verification MUST confirm every Critical/High mitigation carries Prevention, Detection, and Response. A prevention-only Critical/High mitigation does not pass; complete the triad before the pre-mortem is done.

Facilitation Tips

For team settings:

• Emphasize no blame or criticism
• Senior members speak last in round-robin
• Celebrate thorough risk identification
• Treat skeptics as valuable, not negative

For individual use:

• Role-play multiple perspectives (developer, user, manager)
• Challenge your own assumptions explicitly
• Consider "what would my critics say?"

Extension Points

1. Custom Categories: Add domain-specific risk categories
2. Risk Templates: Pre-built risks for common project types
3. Integration: Link to issue trackers for action item follow-up
4. Quantification: Add financial impact estimation

Related Skills

Skill	Relationship
decision-critic	Post-decision validation (pre-mortem is pre-decision)
milestone-planner	Use pre-mortem output to inform planning
architect	Technical risks feed into ADR considerations

References

Reference	Purpose
references/mental-models-galls-law.md	Complexity-driven risk identification using Gall's Law
references/strategy-ooda-loop.md	Iterative risk review cadence using OODA Loop

Academic Sources

• Klein, G. (2007). "Performing a Project Premortem." Harvard Business Review.
• Mitchell, D. J., et al. (1989). "Back to the Future: Temporal Perspective in the Explanation of Events." Journal of Behavioral Decision Making.