Roadmap Planning

Project Roadmap Design & Maintenance Guide

This skill owns the writing and periodic maintenance of the project's top-level roadmap document. It focuses on mid/long-term direction across phases — phase boundaries, priorities, status tracking, links to related design docs — not single-feature design.

Write the roadmap and all user-facing output in the user's conversation language (or the project's documented language policy). The bundled template is in English; keep its structure.

Allowed: read-only investigation (Read / Grep / Glob / git log), and creating/updating the roadmap document (.md) after user approval. Prohibited: creating/modifying/deleting source code files; running build or execution commands.

When to Use

Enter this skill

• Establishing a new project's mid/long-term direction for the first time
• Large-scale roadmap restructuring — adding/splitting/merging/removing phases
• Officially updating phase completion / transfer / hold status
• Producing a document that shares overall direction with a team or stakeholders

Route to a different skill when

• Kicking off a single feature / single phase → mak:dev-kickoff
• Direction itself is vague and divergence is needed first → mak:brainstorming
• Writing the detailed design doc for a specific phase → mak:design-doc-template

Pre-Investigation Checklist

Before drafting the roadmap, confirm:

• Scan README, CLAUDE.md, docs/, and the project's design-doc path — grasp vision and constraints
• Check for an existing roadmap document — the roadmap path in the project CLAUDE.md, then docs/*roadmap*.md, then ROADMAP.md
• Recent commit trend (git log --oneline -20) — what has been completed
• Completed features, in-progress branches, unfinished work
• Project vision and constraints — team size, deadlines, business priorities

Procedure (in order)

1. Confirm vision, goals, constraints

Limit questions to 1–2. No open-ended questions that widen scope.

Example questions:

• "Is there a critical deadline or business priority right now?"
• "Any hard constraints this roadmap must include?"
  • If direction is too vague to draw phase boundaries, pause this skill, diverge with mak:brainstorming, and return once candidates narrow.

2. Draft the current-state summary

Write two blocks:

Strengths — structure, patterns, and completed features already in place Watch when extending — areas needing extension/improvement, still-incomplete parts

3. Set phase boundaries

Split phases by dependency, risk, and scope. Present 2–3 options in a comparison table with a recommendation. If hard constraints (fixed dependency order, a single viable phase boundary, etc.) leave only one real split, state the constraint and proceed with a single option. Do not fabricate alternative splits.

Recommendation: A. {{reason}}

4. Phase ordering logic

For each phase, write one sentence on "why this order". An order without a reason collapses under change pressure.

5. Each phase's "why" and sub-item draft

• Phase title: what it does
• First paragraph of the phase body: why this stage is needed
• Sub-items: Phase-Index naming (e.g. 3-7) for easy reference.

6. Decide the status scheme

Choose per team agreement. Icons are 1–2 characters, optimized for visual scanning.

Recommended default (changeable):

Put the legend as a blockquote (>) right under the phase summary table.

7. Transfer / hold rules

Decide in advance how phase moves are handled:

• Transfer: add a "moved to Phase N" note under the sub-item, update the summary table
• Hold: mark 🔵, record a one-line reason
• Done: add (✅ done) to the phase title; keep the body for maintenance reference

8. Draft and user approval

Present the draft in chat first, based on ${CLAUDE_PLUGIN_ROOT}/skills/roadmap-planning/assets/roadmap.template.md. Fill {{...}} placeholders with real content, but record only each phase's purpose, scope, status, next entry skill, and related doc links — no detailed implementation decisions.

Ask for explicit confirmation:

"I've drafted the roadmap. Please review the phase boundaries and priorities. If it looks good, reply 'save' or 'approve'. I'll write it to the roadmap document after explicit confirmation."

9. Save after approval

Save-path priority:

1. Roadmap path specified in the project CLAUDE.md → that path
2. An existing roadmap document → that file (docs/*roadmap*.md, ROADMAP.md, etc.)
3. A docs/ directory exists → docs/<index>.roadmap.md or docs/roadmap.md per the project's doc numbering
4. None of the above → ROADMAP.md (root)

10. Handoff

• Kicking off a single feature within a phase → mak:dev-kickoff
• A phase's direction is unclear and needs divergence → mak:brainstorming first

Core Principles

• Every phase needs a clear "why." Orders without reasons collapse when requirements change.
• Never delete completed items from the body. Keep them for maintenance reference.
• Mark transfers/holds as official states. Make deferral itself transparent.
• 3–9 phases recommended. Too many dilutes direction.
• Status icons: 1–2 characters. Keep tables scannable.
• Sub-items use Phase-Index naming (e.g. 3-7) — easy to reference from design docs and commits.

Maintenance Rules

On phase completion

1. Add (✅ done) to the phase title
2. Update the summary table status column
3. Keep the body text

On phase transfer

1. Add > moved to Phase N under the sub-item
2. Update the summary table row
3. Add the sub-item to the destination phase

After processing a phase completion or transfer, hand off to mak:doc-audit to check whether other documents referencing that phase still hold.

Recording status changes

State status changes as a change-log unit. Run git commit only when the user explicitly requests it. Example: <roadmap-file> > Phase 3 marked done / added sub-item 3-8

Output Format

See ${CLAUDE_PLUGIN_ROOT}/skills/roadmap-planning/assets/roadmap.template.md.

Excerpt (phase summary table):

| Phase | Content | Status |
| :--- | :--- | :--- |
| **Phase 0** | {{one-line description}} | ✅ **done** |
| **Phase 1** | {{one-line description}} | 🟡 **in progress** |
| **Phase 2** | {{one-line description}} | ⬜ planned |