Files
Ken Yasue 3274aa41e2 Restructure milestone plan into phase files; /execute-milestones now requires a phase file
- /plan-milestones groups milestones into phases and generates one file per phase (phase1-milestones.md, phase2-milestones.md, ...) plus roadmap.md; milestone numbering stays global across phases
- /execute-milestones takes a required phase file argument (phase1-milestones.md | full path | phase1 | 1) and executes only that file's milestones one by one; with no argument it lists available phase files and stops; closes the phase in the roadmap when done
- milestone-planning skill/template rewritten around the Phase > Milestone > Feature hierarchy; milestone-execution skill scoped to one phase file per run
- /add-feature, AGENTS.md, README, and docs/milestones/README.md updated to phase-file references

Co-Authored-By: Claude Fable 5 <noreply@anthropic.com>
2026-07-02 12:18:32 +02:00

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milestone-planning Guide for planning development milestones grouped into phases and generating one phase file (phaseN-milestones.md) with the milestones and feature breakdown for each phase. Use when planning milestones, a release roadmap, or deciding implementation order under docs/milestones/.

Milestone Planning Skill

This skill explains how to break a product into ordered phases and milestones, and produce one phase file per phase under docs/milestones/. The documents are the bridge between the specification (docs/) and implementation: every feature in every milestone is sized to be implemented with one /add-feature run, and every phase file is sized to be executed with one /execute-milestones run.

Hierarchy

Roadmap (roadmap.md)
└── Phase (phase[N]-milestones.md — the /execute-milestones unit)
    └── Milestone (numbered globally: 01, 02, …)
        └── Feature (the /add-feature unit)

Core Principles

  1. MVP first: Phase 1 delivers the MVP; milestone 1 is its core — the smallest coherent, end-to-end usable product. Not a layer (e.g. "all the models"), but a vertical slice a user could actually use.
  2. Vertical slices: Each feature cuts through UI → logic → data. Avoid horizontal milestones like "backend milestone" / "frontend milestone".
  3. One feature = one /add-feature run: If a feature needs more than one steering directory to implement, split it. If it is a one-line change, merge it into a neighbor.
  4. One phase file = one /execute-milestones run: A phase groups 13 milestones that together form a meaningful release.
  5. Dependency order: A feature never lands in an earlier milestone than something it depends on, and a milestone never lands in an earlier phase than its dependencies.
  6. Exactly-once assignment: Every feature belongs to exactly one milestone; every milestone to exactly one phase file. Deliberately deferred items go to the roadmap's "Later / Icebox" — nothing silently disappears.
  7. Living documents: Phase files track status. /add-feature and /execute-milestones check off features ([ ][x]) as they complete, and milestone/phase statuses are updated in both the phase file and roadmap.md.

Inputs

Before planning, read:

  • docs/product-requirements.md — user stories, priorities (P0/P1/P2), success metrics
  • docs/functional-design.md — functional modules and data flows
  • docs/architecture.md — technical constraints and dependencies
  • docs/design/ui-blueprint.json (if present) — screens and user actions
  • docs/ideas/* (if present)

Outputs

docs/milestones/
├── roadmap.md               # Overview: phase/milestone table, ordering rationale, icebox
├── phase1-milestones.md     # Phase 1 (MVP): its milestones and their features
├── phase2-milestones.md
└── phaseN-milestones.md

File naming: phase[N]-milestones.md with N starting at 1 (e.g. phase1-milestones.md). Milestones are numbered globally and consecutively across all phase files (01, 02, …) — numbering never restarts per phase.

Use the structure in template.md for each phase file and for the roadmap.

How to Slice Features

A well-sized feature:

  • Delivers observable user value (or unblocks one that does)
  • Touches one primary screen/flow (may touch shared components)
  • Has 37 acceptance criteria
  • Can be described in one sentence starting with a verb ("Edit user profile", "Filter tasks by tag")
  • Works verbatim as a command argument: /add-feature Edit user profile

Too big (split it): "User management" → "Register account", "Log in / log out", "Edit user profile", "Reset password". Too small (merge it): "Change button color" → fold into the feature that owns that screen.

How to Group Milestones and Phases

  1. Tag every feature with its PRD priority and its dependencies.
  2. Milestone 1 (MVP core): the minimal dependency-closed set of P0 features that forms a usable product walk-through (a user can start, do the core job, and finish).
  3. Following milestones: group remaining features by theme and priority, keeping each milestone a meaningful step on its own ("after milestone N, the user can additionally …"). Prefer 38 features per milestone.
  4. Phase 1 contains milestone 1 plus any milestone required to make the MVP releasable. Following phases group the remaining milestones into meaningful releases — prefer 23 phases with 13 milestones each.
  5. A phase should be independently valuable: after /execute-milestones phase[N]-milestones.md finishes, the product is in a releasable state.

Status Tracking Rules

  • Feature status lives only in the feature checkbox inside its phase file.
  • Milestone status (Not started / In progress / Completed) lives in the milestone's section of the phase file and in the roadmap table — keep them in sync.
  • Phase status lives in the phase file header and in the roadmap table.
  • /add-feature Step 8 updates the feature checkbox; /execute-milestones additionally updates milestone and phase statuses and the roadmap pointers.
  • Re-planning (adding/moving/removing features or milestones) must update both the affected phase file(s) and roadmap.md in the same change.

Consistency Checklist

Before finishing:

  • Every P0/P1 PRD requirement maps to a feature in some milestone (or is explicitly in the icebox).
  • Every feature appears in exactly one milestone; every milestone in exactly one phase file.
  • Milestone numbering is global and consecutive across phase files.
  • No feature or milestone precedes one of its dependencies.
  • Phase 1 delivers a usable end-to-end MVP on its own.
  • Every feature has acceptance criteria and a ready-to-run /add-feature command line.
  • Every phase file header has its ready-to-run /execute-milestones command line.
  • roadmap.md table matches the phase files (names, counts, statuses).