name: roadmap-tracker
description: "Maintain and evolve project roadmaps based on execution history, learnings, and re-prioritization signals."
phase: COMPLETE
category: meta
version: "1.0.0"
depends_on: ["retrospective"]
tags: [meta, planning, roadmap, milestones, prioritization]

Roadmap Tracker

Maintain project roadmaps that evolve from execution learnings.

When to Use

• After loop completion — Update roadmap with what was learned
• Planning sessions — Review and re-prioritize the roadmap
• Milestone tracking — Check progress against planned milestones
• When you say: "update roadmap", "what's next", "milestone status"

Required Deliverables

Core Concept

Roadmap tracking answers: "What's planned, what's done, and what should change based on what we learned?"

Retrospective Insights → Roadmap Update → Re-prioritization → Next Loop Planning

Roadmaps are living documents that evolve with every loop iteration.

Roadmap Structure

# Project Roadmap

## Current Milestone: v1.0 Launch
- [x] Authentication system
- [x] Core API endpoints
- [ ] Admin dashboard
- [ ] Email notifications

## Next: v1.1 Polish
- [ ] Performance optimization
- [ ] Accessibility audit
- [ ] Documentation site

## Backlog
- Rate limiting
- Webhook system
- Multi-tenancy

Milestone Schema

{
  "id": "v1.0",
  "title": "v1.0 Launch",
  "status": "in-progress",
  "items": [
    { "id": "auth", "title": "Authentication", "status": "done", "loopId": "exec-001" },
    { "id": "api", "title": "Core API", "status": "done", "loopId": "exec-002" },
    { "id": "admin", "title": "Admin dashboard", "status": "planned" }
  ],
  "confidence": 0.8,
  "updatedAt": "2026-01-26"
}

Re-prioritization Triggers

Checklist

• [ ] Roadmap exists and is current
• [ ] Completed items linked to execution IDs
• [ ] Next milestone clearly defined
• [ ] Backlog prioritized
• [ ] Confidence score reflects reality
• [ ] Updated after every loop completion

Relationship to Other Skills

Key Principles

Living document. Roadmaps change with every iteration — that's a feature, not a bug.

Link to executions. Every completed item should reference the loop that delivered it.

Confidence over dates. Express milestone likelihood, not fixed deadlines.

Backlog is a queue. Items move forward based on priority, not wishful planning.