Use when planning high-stakes initiatives (migrations, launches, strategic changes) that require clear specifications, proactive risk identification (premortem/register), and measurable success criteria. Invoke when user mentions "plan this migration", "launch strategy", "implementation roadmap", "what could go wrong", "how do we measure success", or when high-impact decisions need comprehensive planning with risk mitigation and instrumentation.
Creates comprehensive plans for high-stakes initiatives by chaining specifications, proactive risk analysis (premortem/register), and measurable success metrics. Use when planning migrations, launches, or strategic changes where you need clear specs, "what could go wrong" analysis, and defined success criteria.
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resources/evaluators/rubric_chain_spec_risk_metrics.jsonresources/examples/microservices-migration.mdresources/methodology.mdresources/template.mdThis skill helps you create comprehensive plans for high-stakes initiatives by chaining together three critical components: clear specifications, proactive risk analysis, and measurable success metrics. It ensures initiatives are well-defined, risks are anticipated and mitigated, and progress can be objectively tracked.
Use this skill when you need to:
Trigger phrases:
Skip this skill when:
Chain Spec Risk Metrics is a meta-skill that combines three complementary techniques into a comprehensive planning artifact:
Quick example:
Initiative: Migrate monolith to microservices
Spec: Decompose into 5 services (auth, user, order, inventory, payment), API gateway, shared data patterns
Risks:
- Data consistency issues between services (High) → Implement saga pattern with compensation
- Performance degradation from network hops (Medium) → Load test with production traffic patterns
Metrics:
- Deployment frequency (target: 10+ per week, baseline: 2 per week)
- API p99 latency (target: < 200ms, baseline: 150ms)
- Mean time to recovery (target: < 30min, baseline: 2 hours)
Copy this checklist and track your progress:
Chain Spec Risk Metrics Progress:
- [ ] Step 1: Gather initiative context
- [ ] Step 2: Write comprehensive specification
- [ ] Step 3: Conduct premortem and build risk register
- [ ] Step 4: Define success metrics and instrumentation
- [ ] Step 5: Validate completeness and deliver
Step 1: Gather initiative context
Ask user for the initiative goal, constraints (time/budget/resources), stakeholders, current state (baseline), and desired outcomes. Clarify whether this is a greenfield build, migration, enhancement, or strategic change. See resources/template.md for full context questions.
Step 2: Write comprehensive specification
Create detailed specification covering scope (what's in/out), approach (architecture/methodology), requirements (functional/non-functional), dependencies, timeline, and success criteria. For standard initiatives use resources/template.md; for complex multi-phase programs see resources/methodology.md for decomposition techniques.
Step 3: Conduct premortem and build risk register
Run premortem exercise: "Imagine 12 months from now this initiative failed spectacularly. What went wrong?" Identify risks across technical, operational, organizational, and external dimensions. For each risk document likelihood, impact, mitigation strategy, and owner. See Premortem Technique and Risk Register Structure sections, or resources/methodology.md for advanced risk assessment methods.
Step 4: Define success metrics and instrumentation
Identify leading indicators (early signals), lagging indicators (outcome measures), and counter-metrics (what you're NOT willing to sacrifice). Specify current baseline, target values, measurement method, and tracking cadence for each metric. See Metrics Framework and use resources/template.md for standard structure.
Step 5: Validate completeness and deliver
Self-check the complete artifact using resources/evaluators/rubric_chain_spec_risk_metrics.json. Ensure specification is clear and actionable, risks are comprehensive with mitigations, metrics measure actual success, and all three components reinforce each other. Minimum standard: Average score ≥ 3.5 across all criteria.
For each identified risk, document:
Leading indicators (predict future success):
Lagging indicators (measure outcomes):
Counter-metrics (what you're NOT willing to sacrifice):
| Component | When to Use | Resource |
|---|---|---|
| Template | Standard initiatives with known patterns | resources/template.md |
| Methodology | Complex multi-phase programs, novel risks | resources/methodology.md |
| Examples | See what good looks like | resources/examples/ |
| Rubric | Validate before delivering | resources/evaluators/rubric_chain_spec_risk_metrics.json |
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