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roadmap

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npx machina-cli add skill littlebearapps/pitchdocs/roadmap --openclaw
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SKILL.md
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Roadmap Generator

ROADMAP.md Structure

# Roadmap

> **Mission**: [One sentence describing the project's north star goal]

This roadmap reflects our current plans and priorities. It's a living document — priorities shift based on community feedback and real-world usage.

**Last updated**: [Date]

## Legend

| Status | Meaning |
|--------|---------|
| :white_check_mark: Done | Shipped and available |
| :construction: In Progress | Actively being worked on |
| :dart: Planned | Committed for this milestone |
| :thought_balloon: Exploring | Under consideration, feedback welcome |

---

## Current Milestone: v1.3 — [Milestone Title]

**Target**: Q1 2026 · **Progress**: 6/10 items complete

| Status | Feature | Issue | Notes |
|--------|---------|-------|-------|
| :white_check_mark: | Marketing-friendly README generation | #42 | Shipped in v1.2 |
| :white_check_mark: | Changelog from conventional commits | #38 | Shipped in v1.2 |
| :construction: | GitHub Projects integration | #45 | PR open |
| :construction: | User-benefit language in changelogs | #44 | In review |
| :dart: | Comparison table generator | #50 | Starting next sprint |
| :dart: | CONTRIBUTING.md generator | #48 | Blocked on #45 |

---

## Upcoming

### v1.4 — [Milestone Title] (Q2 2026)

| Status | Feature | Issue |
|--------|---------|-------|
| :dart: | Full docs suite audit command | #55 |
| :dart: | GitHub issue template generator | #56 |
| :thought_balloon: | Blog post generator from README | #60 |
| :thought_balloon: | Multi-language README support | #62 |

### v2.0 — [Milestone Title] (Q3 2026)

| Status | Feature | Issue |
|--------|---------|-------|
| :thought_balloon: | Interactive README builder | #70 |
| :thought_balloon: | Auto-update on CI | #72 |

---

## Completed Milestones

<details>
<summary>v1.2 — Documentation Foundation (January 2026)</summary>

- :white_check_mark: Basic README generation (#10)
- :white_check_mark: Badge detection and generation (#12)
- :white_check_mark: Package.json/pyproject.toml parsing (#15)
- :white_check_mark: Quick start section generator (#18)

</details>

---

## How to Get Involved

We'd love your input on what to build next:

- **Vote on features**: React with :+1: on issues you want prioritised
- **Propose ideas**: [Open a discussion](link)
- **Contribute**: See [CONTRIBUTING.md](CONTRIBUTING.md) for how to get started
- **Report issues**: [File a bug](link)

Items marked :thought_balloon: are especially open to community feedback.

Data Sources

GitHub Milestones (via github MCP)

mcp__github__list_issues with milestone filter

Use milestones to group features into releases. Each milestone becomes a section.

GitHub Projects (via github MCP)

If the repo uses GitHub Projects (v2), pull items from there:

  1. Get project board items
  2. Map columns/statuses to roadmap legend
  3. Extract issue numbers and titles

Git Tags

git tag --sort=-v:refname | head -20

Map tags to completed milestones. Include completion dates.

Open Issues with Labels

# Issues labelled as enhancements/features
gh issue list --label "enhancement" --state open --limit 50
gh issue list --label "feature" --state open --limit 50

# Issues in milestones
gh issue list --milestone "v1.3" --state all

Language Rules

  • Mission statement: One sentence, present tense, aspirational but concrete
  • Feature descriptions: Benefit-focused, not implementation-focused
  • Status updates: Factual, linked to issues/PRs
  • Timeline: Use quarters (Q1/Q2/Q3/Q4), not specific dates (they create pressure and disappointment)
  • Tone: Transparent, inviting, community-oriented

Anti-Patterns

  • Don't promise specific dates — use quarters or "upcoming"
  • Don't list every issue — curate to significant features
  • Don't include internal tasks — roadmaps are for users
  • Don't forget completed milestones — they show momentum
  • Don't make it static — include "last updated" date
  • Don't forget the "get involved" section — roadmaps are conversation starters

Source

git clone https://github.com/littlebearapps/pitchdocs/blob/main/.claude/skills/roadmap/SKILL.mdView on GitHub

Overview

Roadmap Generator creates ROADMAP.md by pulling data from GitHub Projects, milestones, and issues. It structures content with a mission statement, current milestone progress, upcoming milestones, and a community involvement section. This living document helps teams communicate plans clearly and adapt to feedback.

How This Skill Works

The tool pulls data from GitHub sources such as milestones, projects (v2), and issues to populate a Markdown Roadmap. It maps milestone statuses to a legend, formats sections like Mission, Current Milestone, Upcoming, and Community Involvement, and outputs ROADMAP.md for review and sharing. It follows language rules (present-tense mission, quarterly timelines) to keep content consistent and actionable.

When to Use It

  • Starting a project roadmap to share goals with the team and community.
  • Updating ROADMAP.md after milestone progress or changes in scope.
  • Communicating current and upcoming work to stakeholders and contributors.
  • Planning upcoming milestones (e.g., v1.4, v2.0) with quarterly timelines.
  • Encouraging community involvement by inviting feedback on features and priorities.

Quick Start

  1. Step 1: Point the generator at your GitHub repo to collect milestones, issues, and Projects.
  2. Step 2: Generate ROADMAP.md; review the Mission, Current Milestone, Upcoming, and Community sections.
  3. Step 3: Commit ROADMAP.md to the repository and push changes; repeat as milestones evolve.

Best Practices

  • Write the mission in one present-tense sentence that is aspirational yet concrete.
  • Use quarterly timelines (Q1/Q2) rather than exact dates to reduce pressure.
  • Link status cells to concrete issues or PRs (e.g., #42, PR #50).
  • Keep Roadmap.md updated with a clear Last updated timestamp on changes.
  • Invite broad community input via the How to Get Involved section and feedback markers.

Example Use Cases

  • Mission: Create a user-friendly README generator for developers.
  • Current Milestone: v1.3 — Progress 6/10, includes README generation and changelog from conventional commits.
  • Upcoming: v1.4 — 'Full docs suite audit command' (Q2 2026).
  • Status: :construction: In Progress for 'GitHub Projects integration' (#45).
  • Community Involvement: Vote on features via issues and discussions.

Frequently Asked Questions

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