thinking-pre-mortem

name: thinking-pre-mortem description: Before committing to a plan or launch, assume it has already failed and reason backward through why — prospective hindsight surfaces risks that "what could go wrong?" misses.

Pre-Mortem Analysis

Overview

The pre-mortem, developed by psychologist Gary Klein, uses "prospective hindsight": instead of asking "What could go wrong?", assume the plan HAS failed and reason backward through why. Stating failure as already-happened surfaces concrete risks that forward-looking risk assessment glosses over.

Core Principle: It's easier to explain a failure that "already happened" than to predict one. Use that asymmetry productively in a single reasoning pass.

When to Use

• Project kickoff (before work begins)
• Before committing to a major technical decision
• Sprint planning for high-risk work
• Before launch or major release
• When team seems overconfident
• After a plan is formed but before execution

Decision flow:

Starting significant work? → yes → Plan looks solid / on track? → yes → PRE-MORTEM ESSENTIAL
                                                              ↘ no → Pre-mortem still valuable
                         ↘ no → Standard risk assessment may suffice

When NOT to Use

• The work is small, local, and reversible — failure is cheap to undo, so skip the ceremony.
• You're mid-incident under time pressure — act on the likely cause now (ooda/occams-razor); pre-mortem belongs before execution, not during firefighting.
• You'd only generate generic risks ("requirements unclear", "scope creep") that don't bind to this specific plan — stop if nothing concrete surfaces.
• The risks are already enforced by automated gates (CI, canary, rollback) — don't re-list what the system already catches.

Trigger Card

Before committing to a plan or launch where optimism may be hiding risks:

1. Assume it has already failed — "It's six months later. The project was a disaster. What happened?"
2. List concrete failure reasons — specific to THIS plan, not generic. Why did it actually fail?
3. Mitigate the top 3-5 — for each top failure reason, add a concrete safeguard or change the plan.

Skip if you'd only generate generic risks that don't bind to this specific plan. If risks are already enforced by automated gates (CI, canary, rollback), don't re-list what the system already catches. For a full launch risk review, run the full procedure.

The Process

Step 1: Set the Failure Frame

Adopt the stance that the plan has already failed, stated in past tense:

"It is [future date, post-deadline]. This plan didn't just slip — it failed. The launch was rolled back / the migration corrupted data / adoption never happened."

Past tense is what makes this work: you are explaining a failure, not predicting one.

Step 2: Generate Failure Reasons (one prospective-hindsight pass)

Reason through why it failed across every angle. Push for breadth, not comfort — aim for 15+ distinct reasons before filtering:

• Technical: wrong architecture, integration/contract breaks, scale limits, data loss
• Process: untested paths, no rollback, deploy timing, missing migration step
• Assumptions: which load-bearing assumption turned out false?
• Dependencies/external: upstream API, vendor, rate limits, config drift
• Force a second sweep: "What did I, the author of this plan, most want to be true that wasn't?"

Generate the full list first; do not prune or rank while generating (premature filtering anchors on the obvious risks).

Step 3: Categorize and Prioritize

Group by theme and assess:

Step 4: Develop Mitigations

For top risks, define:

Risk: API integration fails
Mitigation:
- Spike on integration first, before depending on it
- Identify fallback vendor / degrade path
- Build abstraction layer for swap-ability
Verification: integration smoke test passes before downstream work begins

Step 5: Update the Plan

Incorporate mitigations into the plan:

• Add spike/investigation tasks ahead of dependent work
• Build in contingency for the highest P×S risks
• Add a concrete verification/checkpoint for each top risk

Pre-Mortem Template

# Pre-Mortem: [Project Name]
Date: [Date]

## The Scenario
It is [Future Date]. [Project] has failed. 

## Failure Reasons Identified

### Technical
- [Reason 1]
- [Reason 2]

### Process  
- [Reason 1]
- [Reason 2]

### People/Team
- [Reason 1]
- [Reason 2]

### External/Dependencies
- [Reason 1]
- [Reason 2]

## Priority Risks and Mitigations

### P0: [Risk Name]
- **Description**: [What went wrong]
- **Mitigation**: [How to prevent]
- **Owner**: [Who]
- **Checkpoint**: [When to verify]

### P1: [Risk Name]
...

## Plan Updates
- [ ] [Action item from pre-mortem]
- [ ] [Action item from pre-mortem]

Why Pre-Mortems Work

1. Reframes prediction as explanation: Explaining an "already-happened" failure is concrete; predicting one stays vague.
2. Defeats first-plausible-answer lock-in: Generating the full failure list before ranking stops anchoring on the obvious risk.
3. Surfaces buried assumptions: Asking "what did the plan need to be true that wasn't?" exposes load-bearing assumptions the forward plan hid.
4. Counters optimism: The forced-failure stance overrides the natural bias toward "this will work."

Common Failure Categories to Prompt

Execution Tips

• Use past tense consistently ("failed" not "might fail") — it's what triggers the hindsight effect.
• Generate before filtering — collect the full list, then rank; don't prune mid-sweep.
• Interrogate the plan's own optimism — what did the author most want to be true?
• Convert to action — a pre-mortem with no plan change is wasted; each top risk needs a mitigation + verification.

Verification Checklist

• Run before significant work begins (not mid-incident)
• Failure frame stated in past tense
• 15+ distinct failure reasons generated before ranking
• Risks prioritized by likelihood × impact
• Top 3-5 risks have explicit mitigations
• Each mitigation has a concrete verification/checkpoint
• Plan updated to incorporate findings

Key Questions

• "The plan failed. Why?"
• "What was obvious in retrospect that the plan missed?"
• "What warning signs would have shown up first?"
• "Which load-bearing assumption turned out to be false?"
• "What did the plan most need to be true that wasn't?"