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, CLAUDE.md, README, and docs/milestones/README.md updated to phase-file references

Co-Authored-By: Claude Fable 5 <noreply@anthropic.com>
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2026-07-02 12:18:25 +02:00
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---
description: Plan development milestones and generate milestone documents with the features for each milestone
description: Plan development milestones grouped into phases and generate one phase file (phaseN-milestones.md) with the milestones and features for each phase
---
# Plan Milestones (Milestone Planning Phase)
This command breaks the product down into an ordered set of **milestones** and generates milestone documents under `docs/milestones/`. Each milestone document lists the features it contains, sized so that each feature can be implemented with one `/add-feature` run.
This command breaks the product down into **phases**, each containing one or more **milestones**, and generates one file per phase under `docs/milestones/` (`phase1-milestones.md`, `phase2-milestones.md`, …). Each milestone lists the features it contains, sized so that each feature can be implemented with one `/add-feature` run. Each phase file is the execution unit for `/execute-milestones`.
**Planning preferences (optional)**: `$ARGUMENTS` (e.g. `/plan-milestones 3 milestones, MVP in 2 weeks, auth first`)
**Planning preferences (optional)**: `$ARGUMENTS` (e.g. `/plan-milestones 2 phases, MVP in phase 1, auth first`)
## How to Run
```bash
claude
> /plan-milestones
> /plan-milestones 3 milestones, MVP first, payments last
> /plan-milestones 2 phases, MVP first, payments last
```
## Position in the Workflow
@ -27,7 +27,7 @@ claude
/plan-milestones ← you are here
/add-feature (once per feature, milestone by milestone)
/execute-milestones phase1-milestones.md (one phase file at a time)
```
## Pre-Run Check
@ -59,8 +59,8 @@ Read all of the following:
If `$ARGUMENTS` does not already answer these, ask the user about the following. If the user does not provide detailed preferences, **propose a sensible default** derived from the PRD priorities and confirm it before proceeding.
- **Number of milestones** (default: 24 depending on scope)
- **MVP definition** — what is the smallest product worth releasing?
- **Number of phases** (default: 23) and **milestones per phase** (default: 13)
- **MVP definition** — what is the smallest product worth releasing? (phase 1 must deliver it)
- **Priorities** — features that must come first or last
- **Constraints** — deadlines, dependencies on external systems, team capacity
@ -68,7 +68,7 @@ Collect the answers in a single round; do not pause again until generation is co
### Step 2: Load the Milestone Planning Skill
Load the **milestone-planning skill** (`Skill('milestone-planning')`) for the planning rules and the milestone document template.
Load the **milestone-planning skill** (`Skill('milestone-planning')`) for the planning rules and the phase file template.
### Step 3: Build the Feature Inventory
@ -80,49 +80,55 @@ Derive the complete list of features from the documents:
Size each feature so it can be implemented with **one `/add-feature` run**. Split anything larger; merge trivial fragments.
### Step 4: Group Features into Milestones
### Step 4: Group Features into Milestones, and Milestones into Phases
- **Milestone 1 is the MVP**: the smallest set of features that forms a coherent, end-to-end usable product.
- Number milestones globally and consecutively across all phases (`01`, `02`, …).
- **Milestone 1 is the MVP core**: the smallest set of features that forms a coherent, end-to-end usable product.
- Later milestones build on earlier ones, ordered by priority and dependency (a feature never lands before something it depends on).
- Every feature belongs to **exactly one** milestone. Explicitly park out-of-scope items in a final "Later / Icebox" section of the roadmap.
- **Phase 1 delivers the MVP**: it contains milestone 1 (plus any milestone needed to make the MVP releasable). Later phases group the remaining milestones by theme and priority — each phase should be a meaningful release on its own.
- Every feature belongs to **exactly one** milestone, and every milestone to **exactly one** phase. Explicitly park out-of-scope items in a final "Later / Icebox" section of the roadmap.
### Step 5: Create the Roadmap Overview
Create `docs/milestones/roadmap.md` containing:
- A table of all milestones: number, name, goal, feature count, status (`Not started` / `In progress` / `Completed`)
- A table of all phases and their milestones: phase, file, milestone number, name, goal, feature count, status (`Not started` / `In progress` / `Completed`)
- The ordering rationale (why this sequence)
- A pointer to the current milestone
- A pointer to the current phase file and current milestone
- The "Later / Icebox" list of consciously deferred items
### Step 6: Create One Document per Milestone
### Step 6: Create One File per Phase
For each milestone, create `docs/milestones/milestone-[NN]-[kebab-case-name].md` (e.g. `milestone-01-mvp.md`) following the milestone-planning skill's template. Each document lists the milestone's features, and each feature includes:
For each phase, create `docs/milestones/phase[N]-milestones.md` (e.g. `phase1-milestones.md`, `phase2-milestones.md`) following the milestone-planning skill's template. Each phase file contains:
- A checkbox for status tracking (`- [ ]`)
- Description and user value
- Related PRD requirements / user stories
- Affected screens from `ui-blueprint.json` (if a design spec exists)
- Acceptance criteria
- The ready-to-run command: `/add-feature [feature name]`
- The phase header: goal, status, and its ready-to-run command: `/execute-milestones phase[N]-milestones.md`
- One section per milestone in the phase (goal, scope, dependencies, definition of done)
- Under each milestone, its features — and each feature includes:
- A checkbox for status tracking (`- [ ]`)
- Description and user value
- Related PRD requirements / user stories
- Affected screens from `ui-blueprint.json` (if a design spec exists)
- Acceptance criteria
- The ready-to-run command: `/add-feature [feature name]`
### Step 7: Consistency Check
Re-read all generated files and confirm:
- Every P0/P1 requirement in the PRD is covered by a milestone (or explicitly parked in the icebox).
- Every feature appears in exactly one milestone.
- Dependencies are ordered correctly across milestones.
- Milestone 1 is a coherent, usable MVP on its own.
- Each feature name works as a `/add-feature` argument.
- Every feature appears in exactly one milestone, and every milestone in exactly one phase file.
- Milestone numbering is global and consecutive across the phase files.
- Dependencies are ordered correctly across milestones and phases.
- Phase 1 delivers a coherent, usable MVP on its own.
- Each feature name works as a `/add-feature` argument, and each phase file name works as an `/execute-milestones` argument.
Fix any inconsistencies found before finishing.
## Completion Criteria
- `docs/milestones/roadmap.md` exists
- One `milestone-[NN]-[name].md` per milestone exists
- Every feature is assigned to exactly one milestone with acceptance criteria
- One `phase[N]-milestones.md` per phase exists
- Every feature is assigned to exactly one milestone (in exactly one phase file) with acceptance criteria
Completion message:
```
@ -130,13 +136,13 @@ Completion message:
Milestone documents created:
✅ docs/milestones/roadmap.md (overview + status)
✅ docs/milestones/milestone-01-....md (MVP)
✅ docs/milestones/milestone-NN-....md
✅ docs/milestones/phase1-milestones.md (MVP phase: milestones 01NN)
✅ docs/milestones/phase2-milestones.md (milestones NNNN)
Next steps:
- Review docs/milestones/ and adjust priorities if needed
- Run /execute-milestones to implement all milestones one by one autonomously (a separate steering directory is created per milestone)
- Run /execute-milestones phase1-milestones.md to implement phase 1 (a separate steering directory is created per milestone)
- Or go feature by feature: run /add-feature [first feature of milestone 1]
- Either way, each feature is marked complete in its milestone document as it finishes
- Either way, each feature is marked complete in its phase file as it finishes
"
```