Chain Spec Risk Metrics

Table of Contents

• Purpose
• When to Use This Skill
• When NOT to Use This Skill
• What Is It?
• Workflow
• Common Patterns
• Guardrails
• Quick Reference

Purpose

This 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.

When to Use This Skill

Use this skill when you need to:

• Plan complex implementations - Migrations, infrastructure changes, system redesigns requiring detailed specs
• Launch new initiatives - Products, features, programs that need risk assessment and success measurement
• Make high-stakes decisions - Strategic choices where failure modes must be identified and monitored
• Coordinate cross-functional work - Initiatives requiring clear specifications for alignment and risk transparency
• Request comprehensive planning - User asks "plan this migration", "create implementation roadmap", "what could go wrong?"
• Establish accountability - Need clear success criteria and risk owners for governance

Trigger phrases:

• "Plan this [migration/launch/implementation]"
• "Create a roadmap for..."
• "What could go wrong with..."
• "How do we measure success for..."
• "Write a spec that includes risks and metrics"
• "Comprehensive plan with risk mitigation"

When NOT to Use This Skill

Skip this skill when:

• Quick decisions - Low-stakes choices don't need full premortem treatment
• Specifications only - If user just needs a spec without risk/metrics analysis (use one-pager-prd or adr-architecture instead)
• Risk analysis only - If focused solely on identifying risks (use project-risk-register or postmortem instead)
• Metrics only - If just defining KPIs (use metrics-tree instead)
• Already decided and executing - Use postmortem or reviews-retros-reflection for retrospectives
• Brainstorming alternatives - Use brainstorm-diverge-converge to generate options first

What Is It?

Chain Spec Risk Metrics is a meta-skill that combines three complementary techniques into a comprehensive planning artifact:

1. Specification - Define what you're building/changing with clarity (scope, requirements, approach, timeline)
2. Risk Analysis - Identify what could go wrong through premortem ("imagine we failed - why?") and create risk register with mitigations
3. Success Metrics - Define measurable outcomes to track progress and validate success

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)

Workflow

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.

Common Patterns

Premortem Technique

1. Set the scene: "It's [6/12/24] months from now. This initiative failed catastrophically."
2. Brainstorm failure causes: Each stakeholder writes 3-5 reasons why it failed (independently first)
3. Cluster and prioritize: Group similar failures, vote on likelihood and impact
4. Convert to risk register: Each failure mode becomes a risk with mitigation plan

Risk Register Structure

For each identified risk, document:

• Risk description: Specific failure mode (not vague "project delay")
• Category: Technical, operational, organizational, external
• Likelihood: Low/Medium/High (or probability %)
• Impact: Low/Medium/High (or cost estimate)
• Mitigation strategy: What you'll do to reduce likelihood or impact
• Owner: Who monitors and responds to this risk
• Status: Open, Mitigated, Accepted, Closed

Metrics Framework

Leading indicators (predict future success):

• Deployment frequency, code review velocity, incident detection time

Lagging indicators (measure outcomes):

• Uptime, user adoption, revenue impact, customer satisfaction

Counter-metrics (what you're NOT willing to sacrifice):

• Code quality, team morale, security posture, user privacy

Guardrails

• Don't skip any component - Spec without risks = blind spots; risks without metrics = unvalidated mitigations
• Be specific in specifications - "Improve performance" is not a spec; "Reduce p99 API latency from 500ms to 200ms" is
• Quantify risks - Use likelihood × impact scores to prioritize; don't treat all risks equally
• Make metrics measurable - "Better UX" is not measurable; "Increase checkout completion from 67% to 75%" is
• Assign owners - Every risk and metric needs a clear owner who monitors and acts
• State assumptions explicitly - Document what you're assuming about resources, timelines, dependencies
• Include counter-metrics - Always define what success does NOT mean sacrificing
• Update as you learn - This is a living document; revisit after milestones to update risks/metrics

Quick Reference

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