Coding & DevelopmentšŸ¤–claude🌐universal

pre-mortem

skills/pre-mortem/SKILL.md

Imagine the project has already shipped and failed catastrophically — work backwards from the failure to identify the most likely causes BEFORE building. Forces concrete risk identification, not vague "what could go wrong" lists.

Quick Start

Install this SKILL.md

npx skills add https://github.com/avelikiy/great_cto/tree/main/skills/pre-mortem
---
name: pre-mortem
description: Imagine the project has already shipped and failed catastrophically — work backwards from the failure to identify the most likely causes BEFORE building. Forces concrete risk identification, not vague "what could go wrong" lists.
when_to_use: |
  Apply BEFORE implementation begins:
  - architect, after writing ARCH but before gate:plan
  - pm, while breaking work into tasks (Pre-mortem section in PLAN-*.md)
  - security-officer, when threat-modeling
  - any time the feature is irreversible or high-blast-radius
effort: medium
allowed-tools: Read, Write
paths:
  - "docs/plans/**"
  - "docs/architecture/**"
  - "docs/threat-models/**"
---

# Pre-mortem — fail-it-before-you-build-it

A retrospective for a project that hasn't happened yet. Surfaces real
risks that "list every risk" prompts miss.

Originated in Gary Klein's research at MIT Sloan, now standard at AWS
and other ops-mature orgs.

## The 5-step pre-mortem

### Step 1. Imagine you're 6 months in the future

The project shipped. It is a clear, public failure. There's a Reddit
thread about it. The CEO is asking what went wrong.

### Step 2. Write the post-mortem newspaper headline

One sentence. Concrete. Specific. Examples:

- āŒ Bad: "We had some quality issues."
- āœ… Good: "On 2026-09-12, the Stripe webhook handler deduplicated by raw body hash, so 30K customers were double-charged after Stripe retried delivery during a network blip."

The headline forces you to name the failure mode SPECIFICALLY.

### Step 3. List every individual reason this exact failure happened

Brainstorm 10-15 reasons. Be specific. Each item should reference:
- A real component / file
- A real failure mode (race condition, schema mismatch, expired credential)
- A real human factor (oncall didn't see alert, runbook was outdated)

Reject hand-waves like "testing was insufficient." Replace with "we
didn't write a property-based test for the dedup-key collision case."

### Step 4. Rank by likelihood Ɨ severity

For each cause, score:
- **Likelihood:** 1-5 (1=once-in-a-decade, 5=monthly)
- **Severity:** 1-5 (1=cosmetic, 5=data loss / regulatory breach)
- **Risk score:** likelihood Ɨ severity

Top 3 by risk score → these are your highest-priority mitigations.

### Step 4b. Classify risks — Tigers / Paper Tigers / Elephants

After scoring, classify each risk into one of three types:

**🐯 Tigers** — Real problems you personally believe could derail the project
- Based on evidence, past experience, or clear logic
- Should keep you awake at night
- Require concrete action
- Classify each Tiger by urgency:
  - **Launch-Blocking**: Must be resolved before shipping (broken core feature, regulatory blocker, data integrity risk)
  - **Fast-Follow**: Must be resolved within 30 days post-launch (performance issues, secondary features)
  - **Track**: Monitor post-launch, fix if it becomes an issue (edge cases, nice-to-haves)

**šŸ“„ Paper Tigers** — Concerns others might raise that you don't believe are real risks
- Valid-sounding on the surface but unlikely or overblown
- Not worth significant resource investment
- Worth documenting to align stakeholders and avoid repeated debates
- For each: explain WHY you don't believe it's a real risk

**🐘 Elephants** — Things the team knows about but isn't discussing openly
- Uncomfortable concerns: technical debt, team tension, unrealistic timeline, design that nobody likes
- Uncertain — you're not sure if it's a problem, but nobody is investigating
- Deserve explicit surfacing before launch — silent elephants become Tigers post-launch

### Step 5. For each top-3 cause, write a guardrail in the plan

Each guardrail is a concrete change to the plan:
- A test that would have caught it
- A circuit breaker / feature flag
- A runbook entry
- A monitoring alert with specific SLO

If a top-3 cause CANNOT be mitigated within the time/budget, escalate to
the user: "This plan accepts the risk of X with no mitigation."

## Template — add to PLAN-*.md

```markdown
## Pre-mortem

Six months from now, this project failed. Headline:

> <one-sentence failure headline>

### Top reasons (likelihood Ɨ severity)

| Cause | L | S | Risk | Mitigation in plan |
|---|---|---|---|---|
| <specific cause> | 4 | 5 | 20 | <Task #N: write idempotency test> |
| ... | | | | |

### 🐯 Tigers (real risks — require action)

| Tiger | Classification | Mitigation | Owner | Due |
|-------|---------------|-----------|-------|-----|
| <risk> | Launch-Blocking | <concrete action> | <team/person> | <date> |
| <risk> | Fast-Follow | <concrete action> | <team/person> | <date> |
| <risk> | Track | <monitoring approach> | <owner> | post-launch |

### šŸ“„ Paper Tigers (overblown — document to align stakeholders)

- **<concern>**: Not a real risk because <reason>. If <condition> changes, revisit.

### 🐘 Elephants (unspoken — needs open discussion)

- **<concern>**: Nobody is talking about this. Suggested conversation: "<how to raise it>".

### Accepted risks (no mitigation)

- <risk> — accepted because <budget/scope reason>. Owner: <name>.
```

## Common failure modes by archetype

Quick start — most-common pre-mortem causes per archetype:

| Archetype | Common failure |
|---|---|
| fintech / commerce | Idempotency-key collision; double-charge during retry storm |
| healthcare | PHI leak via debug log; BAA not signed with vendor |
| web3 | Oracle staleness; flash-loan exploit on bonding curve |
| mlops | Training/serving skew; model drift undetected |
| iot-embedded | OTA bricks devices in a region with no recovery path |
| data-platform | Late-arriving data overwrites correct values |
| ai-system / agent-product | Prompt injection exfiltrates other users' data |
| enterprise-saas | Cross-tenant data leak via RLS gap |
| cli-tool | Destructive flag with no confirmation (rm -rf equivalent) |
| library | Breaking change in minor version bump |

## Anti-patterns in pre-mortems

āŒ **Vague risks.** "Performance might be a problem." Be specific: which
operation, at what load, what's the SLO.

āŒ **Cosmic risks.** "AWS could go down." Yes, but that's not actionable.
Focus on what you can mitigate.

āŒ **Defensive list.** Listing risks you've already mitigated to look
thorough. Only list risks the current plan does NOT yet address.

āŒ **Skip the headline.** Without the headline, the team won't believe
the failure scenario is real.

## When to skip

- **nano project_size** — pre-mortem is overhead.
- **Pure refactor with full test coverage** — guardrails already exist.
- **Bug-fix with one-line repro** — risk is well-bounded.