skills.rest
dirien
dirienCOMMUNITY
Explore all skills by this author →
Website𝕏@_ediriGitHub

roadmap

Synchronize ROADMAP.md with GitHub issues, milestones, and labels.

19|3|Updated Mar 11, 2026
Search Tags:#github#roadmap#issues#sync#brainstorm#labels#loe
One-click install
npx skills add https://github.com/dirien/yet-another-agent-harness --skill roadmap-dirien
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: roadmap
Source: https://github.com/dirien/yet-another-agent-harness/tree/main/.claude/skills/roadmap
Command: npx skills add https://github.com/dirien/yet-another-agent-harness --skill roadmap-dirien

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill includes references (resource) components.

What problem does it solve?

This Skill removes the friction of keeping a repository's ROADMAP.md aligned with GitHub issues, milestones, and labels, reducing manual bookkeeping and inconsistent project planning.

Core Features & Use Cases

  • Sync: Reconciles ROADMAP.md with open and closed GitHub issues, fixes discrepancies, moves completed items into quarterly "Completed Milestones", and updates roadmap structure when needed.
  • Bootstrap & Generate: Creates CONTEXT.md and ROADMAP.md for new or undocumented projects by analyzing the codebase, inferring boundaries, and categorizing issues.
  • Brainstorm & Status: Runs read-only ideation sessions with boundary checks and produces concise status summaries and prioritized recommendations.
  • Label & LOE Management: Estimates level-of-effort using heuristics, applies effort/* labels, and ensures roadmap/* phase labels mirror ROADMAP.md sections.
  • Use Case: A product manager can sync the canonical roadmap with GitHub to correct label drift, surface mismatched items, and get 3–5 prioritized recommendations for the next sprint.

Quick Start

Run the roadmap skill to sync ROADMAP.md with GitHub issues, apply or create roadmap and effort labels, update LOE indicators, and produce prioritized recommendations.

Frequently Asked Questions about roadmap

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I sync a ROADMAP.md file with GitHub issues and milestones?▼

Syncing ROADMAP.md with GitHub issues requires an authenticated GitHub CLI (gh) to read open and closed issues, fix discrepancies, move completed items into quarterly milestones, and update phase labels.

What is the best way to generate a roadmap for an undocumented GitHub repository?▼

The best way to generate a roadmap for an undocumented repository is to analyze the codebase, infer boundaries, and categorize existing GitHub issues to bootstrap both CONTEXT.md and ROADMAP.md files.

Do I need GitHub CLI to sync roadmap labels and milestones?▼

Yes, syncing roadmap labels and milestones requires an authenticated GitHub CLI (gh) to apply roadmap/* and effort/* labels, estimate level-of-effort using heuristics, and update the roadmap structure.

Can I use GitHub labels to estimate level of effort for roadmap planning?▼

Yes, you can estimate level of effort by applying heuristics that create or update effort/* labels on GitHub issues, which helps surface prioritized work and recommendations for the next sprint.

Does syncing a roadmap with GitHub issues overwrite existing CONTEXT.md boundaries?▼

No, syncing a roadmap with GitHub issues preserves CONTEXT.md boundaries during all operations, ensuring inferred project borders remain intact while roadmap/* phase labels are updated.

How do I brainstorm and prioritize work for the next sprint using GitHub issues?▼

To brainstorm and prioritize work, you run read-only ideation sessions with boundary checks on GitHub issues, which produces concise status summaries and 3-5 prioritized recommendations for the next sprint.

Related Skills

Explore More Product & Management Skills→
arbgjrarbgjr

github-sync

Automate GitHub issue, label, and milestone synchronization from YAML task breakdowns.

Community
Advanced
duongtdnduongtdn

backlog

Extracts actionable work items from conversations and creates GitHub issues.

Community
Intermediate
rshadershade
3

roadmap

Sync ROADMAP.md with GitHub Issues and milestones.

Community
Advanced
0xrafasec0xrafasec
9

issues

Create GitHub issues and milestones from Markdown planning documents.

Community
Advanced