feat: add value-based milestone planning capability
Add capability for organizing backlog into shippable business capabilities using value-based milestones (not time-based phases). Components: - milestone-planning skill: Value-based framework, vertical slice test, one active milestone - create-milestones skill: Orchestrator (Haiku) for analyzing and grouping issues - milestone-planner agent: Groups issues into capabilities autonomously (Haiku) Core Principles: - Milestone = shippable business capability (not phase) - One active milestone at a time (preserves focus) - 5-25 issues per milestone (right-sized) - Value labels: value/high, value/medium, value/low - Risk labels: risk/high (optional) - Vertical slice test (can be demoed independently) - No dates (capability-based, not time-based) Workflow: /create-milestones reads existing Gitea issues → analyzes capability boundaries → groups into milestones → creates in Gitea → assigns issues → applies labels → user manually activates ONE milestone Co-Authored-By: Claude Code <noreply@anthropic.com>
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skills/milestone-planning/SKILL.md
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skills/milestone-planning/SKILL.md
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---
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name: milestone-planning
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description: >
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Value-based milestone planning: milestones as shippable capabilities, not phases.
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One active milestone, vertical slices, value/risk labels. Use when planning
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milestones or organizing backlog by capability.
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user-invocable: false
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---
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# Milestone Planning
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Value-driven milestone framework: milestones represent shippable business capabilities, not time-based phases.
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## Core Principle
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**If you don't deliver by date, milestones must represent value slices, not time.**
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**Milestone = A shippable business capability**
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Not a phase. Not "MVP". Not "Auth".
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## What Makes a Good Milestone
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Each milestone should answer one business question:
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**"What new capability exists for the user once this is done?"**
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### Good Examples
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✓ Customer can register and authenticate
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✓ Order can be placed and paid
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✓ Admin can manage products
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✓ Audit trail exists for all state changes
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### Bad Examples
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✗ MVP (what capability?)
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✗ Backend (technical layer, not user value)
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✗ Auth improvements (vague, no completion criteria)
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✗ Phase 1 (time-based, not value-based)
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**Test:** If it can't be demoed independently, it's too vague.
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## Mapping DDD Issues to Milestones
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**DDD building blocks → issues**
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- Aggregates
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- Commands
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- Events
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- Read models
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- Policies
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**End-to-end capability → milestone**
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- Spans multiple aggregates
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- Commands + invariants + events
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- Read models for visibility
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- Maybe UI/API glue
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**Value is cross-cutting by nature.**
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A milestone usually includes:
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- Multiple aggregates working together
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- Commands that achieve user goal
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- Events connecting aggregates
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- Read models for user feedback
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- UI/API to trigger capability
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## One Active Milestone at a Time
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**Rule:** Exactly one open milestone = current value focus
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**Why:**
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- Preserves focus
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- Avoids parallel half-value
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- Forces completion
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- Makes priority explicit
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**Practice:**
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- Everything else stays unassigned
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- When done → close it → pick next highest-value milestone
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- Multiple open milestones = accidental roadmap
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## Priority Without Dates
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Since Gitea milestones have no ordering, use labels:
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**Minimal label set:**
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- `value/high` - Highest business value
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- `value/medium` - Moderate business value
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- `value/low` - Nice to have
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- `risk/high` - Technical risk or uncertainty
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**Issues have:**
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- Always: value label
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- Sometimes: risk label
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**You now have:**
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- **Milestone** → what capability
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- **Label** → why now
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## Sizing Guidelines
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A value milestone should:
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- Be completable in days to a few weeks
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- Deliver observable user value
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- Contain 5-25 issues
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**If it keeps growing:**
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- You discovered multiple capabilities
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- Split into separate milestones
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## Vertical Slice Test
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Before creating a milestone, verify:
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**Can this be demoed independently?**
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Test questions:
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- Can a user interact with this capability end-to-end?
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- Does it produce observable results?
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- Is it useful on its own (not just foundation)?
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- Can we ship this and get feedback?
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If NO to any → not a value slice yet.
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## Label Strategy
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**Value labels (always):**
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- Reflect business priority
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- Based on user impact, revenue, strategic alignment
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- Applied to every issue in milestone
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**Risk labels (optional):**
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- Flag technical uncertainty
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- Flag new patterns/technologies
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- Flag complex integrations
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- Helps sequence work (derisk early)
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## Anti-Patterns
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**"We just deliver highest value first"**
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Only works if:
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- Value is explicit (labels)
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- Scope is bounded (milestones)
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- Work is finishable (vertical slices)
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Without milestones, "value-first" quietly becomes "interesting-first".
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**Multiple open milestones:**
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- Splits focus
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- Encourages context switching
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- Hides incomplete work
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- Prevents shipping
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**Technical milestones:**
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- "Backend" is not a capability
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- "API layer" is not demoable
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- "Database migration" might be necessary but not a milestone
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**Phase-based milestones:**
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- "MVP" → what can user do?
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- "Phase 1" → what capability?
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- "Q1 goals" → what ships?
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## When NOT to Use Milestones
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**Don't use milestones when:**
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- Single capability with <5 issues (just label it)
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- Exploratory work (use spike label instead)
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- Refactoring without user-visible change (use technical debt label)
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- Everything ships together (waterfall project)
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**Milestones enforce discipline around value slices.**
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## Workflow Summary
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1. **Issues exist** (from DDD analysis or backlog)
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2. **Group by capability** (milestone-planner agent)
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3. **One milestone open** (current value slice)
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4. **Label for priority** (value/risk)
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5. **No dates** (capability-based, not time-based)
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6. **Close ruthlessly** (finish before starting next)
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## Tips
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- Start with 3-5 milestones defined, 1 active
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- Keep unassigned issues in backlog
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- Move issues between milestones if capability boundaries change
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- Split milestones that grow beyond 25 issues
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- Close milestone when capability is demoable
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- Review value/risk labels regularly
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- Active milestone = team's current focus
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