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pre-mortem
skills/pre-mortem/SKILL.md
Imagine the project has already shipped and failed catastrophically ā work backwards from the failure to identify the most likely causes BEFORE building. Forces concrete risk identification, not vague "what could go wrong" lists.
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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 ā 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 ā 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 Bad: "We had some quality issues." - ā 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mode (race condition, schema mismatch, expired credential) - A real human factor (oncall didn't see alert, runbook was outdated) Reject hand-waves like "testing was insufficient."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 Ć 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 Ć severity Top 3 by risk score ā these are your highest-priority mitigations. ### Step 4b. Classify risks ā Tigers / Paper Tigers / Elephants After scoring, classify each risk into one of three types: **šÆ Tigers** ā 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) **š Paper Tigers** ā 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 **š Elephants** ā Things the team knows about but isn't discussing openly - Uncomfortable concerns: technical debt, team tension, unrealistic timeline, design that nobody likes - Uncertain ā you're not sure if it's a problem, but nobody is investigating - Deserve explicit surfacing before launch ā 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 ā add to PLAN-*.md ```markdown ## Pre-mortem Six months from now, this project failed. Headline: > <one-sentence failure headline> ### Top reasons (likelihood Ć severity) | Cause | L | S | Risk | Mitigation in plan | |---|---|---|---|---| | <specific cause> | 4 | 5 | 20 | <Task #N: write idempotency test> | | ... | | | | | ### šÆ Tigers (real risks ā 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 | ### š Paper Tigers (overblown ā document to align stakeholders) - **<concern>**: Not a real risk because <reason>. If <condition> changes, revisit. ### š Elephants (unspoken ā needs open discussion) - **<concern>**: Nobody is talking about this. Suggested conversation: "<how to raise it>". ### Accepted risks (no mitigation) - <risk> ā accepted because <budget/scope reason>. Owner: <name>. ``` ## Common failure modes by archetype Quick start ā 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 **Vague risks.** "Performance might be a problem." Be specific: which operation, at what load, what's the SLO. ā **Cosmic risks.** "AWS could go down." Yes, but that's not actionable. Focus on what you can mitigate. ā **Defensive list.** Listing risks you've already mitigated to look thorough. Only list risks the current plan does NOT yet address. ā **Skip the headline.** Without the headline, the team won't believe the failure scenario is real. ## When to skip - **nano project_size** ā pre-mortem is overhead. - **Pure refactor with full test coverage** ā guardrails already exist. - **Bug-fix with one-line repro** ā risk is well-bounded.
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