Roadmap

Skill rshade/agent-skills/skills/roadmap

Picks and Shovels for digging AI

Install

npx -y skills add rshade/agent-skills --skill roadmap

Assembled from the repository path, not quoted from the project. Check it against their README if it does not work.

One thing to look at

3 stars3 stars. Stars are a popularity signal and not a quality one, but at this level it is likely that nobody has read this closely except its author, and you would be relying on your own review.

What its author says it does

Copied from the file, not written here

Strategic roadmap management for GitHub repositories. Syncs ROADMAP.md with GitHub Issues and labels, bootstraps roadmap files from scratch, runs brainstorming sessions with boundary checking, and provides quick status summaries. Use when managing project planning, syncing roadmap state, or exploring feature ideas.

SKILL.md

6.8 KB, as published. Nobody here has run it

Strategic Roadmap Management

Manage project roadmaps through five modes: sync ROADMAP.md with GitHub reality, bootstrap planning files from scratch, brainstorm new features collaboratively, get a quick status summary, or show help.

Prerequisite check

gh --version 2>/dev/null && gh auth status 2>/dev/null

If gh is not installed, direct the user to https://cli.github.com. If not authenticated, direct them to run gh auth login. Do not proceed without a working, authenticated GitHub CLI.

Constitutional principle

CONTEXT.md is the project constitution. All modes must read and respect the boundaries defined in CONTEXT.md. If CONTEXT.md exists, read it first and constrain all analysis and recommendations.

When any recommendation would violate CONTEXT.md boundaries:

Explicitly flag the violation
Explain which boundary would be crossed
Suggest an alternative that respects the boundaries

Mode dispatch

Determine the mode from the user's input. If no mode is specified, default to sync.

Argument	Mode	Purpose
(none)	sync	Sync ROADMAP.md with GitHub, recommend priorities
`sync`	sync	Same as default
`generate`	generate	Bootstrap CONTEXT.md + ROADMAP.md from scratch
`brainstorm`	brainstorm	Creative ideation session (read-only)
`status`	status	Quick read-only summary
`help`	help	Show available modes

Mode: sync

Synchronize ROADMAP.md with GitHub and provide prioritized recommendations. This is the primary mode.

Fetch open issues, recently closed issues, and milestones via gh CLI
Read ROADMAP.md and CONTEXT.md
Check for legacy section layout — if found, ask the user whether to migrate to canonical structure (Vision → Immediate Focus → Near-Term → Future → Completed → Boundaries)
Detect discrepancies between ROADMAP.md and GitHub (issues marked done but still open, open but closed, missing entirely)
Update ROADMAP.md — fix discrepancies, move closed issues to "Completed Milestones" under quarterly sub-headings
Estimate LOE for open issues without effort/* labels using the heuristics in references/label-config.md
Sync GitHub labels — create missing labels, add/remove roadmap/* labels to match ROADMAP.md sections
Append LOE indicators ([S], [M], [L]) to issue lines in ROADMAP.md
Generate 3-5 prioritized recommendations based on dependencies, impact vs effort, theme coherence, and LOE balance
Present summary of all changes and recommendations

For detailed workflow steps, see references/sync.md. For label definitions and LOE heuristics, see references/label-config.md.

Mode: generate

Bootstrap CONTEXT.md and ROADMAP.md for a new or undocumented project.

If either file exists, ask the user: regenerate, merge, or abort
Investigate the codebase — structure, dependencies, entry points, capabilities
Infer project boundaries ("hard no's") — what the project does NOT do
Research externally for similar tools and industry context
Draft CONTEXT.md with: core identity, technical boundaries, data source of truth, interaction model, verification criteria
Fetch all GitHub issues and milestones
Categorize issues into Immediate Focus, Near-Term, Future, and Completed (grouped by quarter)
Estimate LOE per open issue and apply effort/* labels
Draft ROADMAP.md with canonical structure and LOE indicators
Write CONTEXT.md first, then ROADMAP.md. Run markdownlint on both.

For detailed workflow steps and templates, see references/generate.md. For LOE heuristics, see references/label-config.md.

Mode: brainstorm

Explore new possibilities through collaborative ideation. This mode is read-only by default — do not create issues or modify ROADMAP.md until the user explicitly approves.

Read CONTEXT.md and ROADMAP.md for current state and boundaries
Investigate the codebase for extension points, underutilized capabilities, and seams for new features
Research externally for similar tools, user requests, and trends
Use ideation techniques with the user: "What if...", "Who else...", "Why not...", "What's missing...", "What annoys..."
Evaluate each idea: boundary check against CONTEXT.md, effort, impact, dependencies
Present ideas in structured format (description, rationale, boundary check, effort, impact, next step)
Ask the user which ideas to formalize — only then create issues or update ROADMAP.md

For detailed workflow steps and idea template, see references/brainstorm.md.

Mode: status

Quick read-only summary of current roadmap state. No modifications.

Fetch issue counts and milestone progress via gh CLI
Read ROADMAP.md
Present summary tables: overall metrics, by category (enhancement/bug/docs), by LOE (small/medium/large)
Flag obvious discrepancies without deep analysis

For detailed workflow steps and table templates, see references/status.md.

Mode: help

Display available modes and usage:

roadmap — Strategic Roadmap Management

MODES:
  (default)    Sync ROADMAP.md + labels with GitHub, recommend priorities
  sync         Same as default
  generate     Bootstrap CONTEXT.md + ROADMAP.md from scratch
  brainstorm   Creative ideation session (collaborative, read-only)
  status       Quick read-only summary of current state
  help         Show this help message

LABELS (synced automatically):
  roadmap/current  → "Immediate Focus" section
  roadmap/next     → "Near-Term Vision" section
  roadmap/future   → "Future Vision" section
  effort/small     → 1-2 hours
  effort/medium    → half day to 1 day
  effort/large     → multi-day

KEY PRINCIPLES:
  CONTEXT.md is the project constitution (all modes respect it)
  Brainstorm mode is read-only until user approves ideas
  Generate mode asks before overwriting existing files
  Labels are synced to match ROADMAP.md sections
  LOE is auto-estimated for issues missing effort/* labels

Output guidelines

Use tables for structured comparisons
Use emoji sparingly and only for status indicators
Always include issue numbers when referencing GitHub issues
Run markdownlint after any file modifications