ADD Roadmap Command v0.9.10

ADD Roadmap Command v0.9.10

View, edit, and reorder project milestones across roadmap horizons (Now / Next / Later). This skill manages the strategic layer of ADD's work hierarchy — bridging the PRD roadmap table and individual milestone files.

Roadmap (Now / Next / Later)        ← this skill
  → Milestones (/add:milestone)     ← tactical operations
    → Cycles (/add:cycle)           ← execution
      → Features (/add:spec)        ← specification

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Pre-Flight

All subcommands begin here:

1. Read .add/config.json — extract maturity.level, planning.current_milestone
   • If not found: abort with "No ADD project found. Run /add:init first."
2. Read docs/prd.md — locate Section 6 ("Milestones & Roadmap"), parse the roadmap table and milestone detail blocks
   • If docs/prd.md missing: abort with "No PRD found. Run /add:init first."
3. Glob docs/milestones/M*.md — for each, parse: Status, Goal, feature count, feature positions (hill chart data), success criteria progress
4. Read .add/handoff.md if it exists — note any in-progress decisions relevant to roadmap changes
5. Build roadmap model — merge PRD table (source of truth for horizons) with milestone files (source of truth for status/content). Flag discrepancies.

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Command: /roadmap --view (default)

Display current roadmap. No file modifications.

Output

Show project context, then milestones grouped by horizon:

Project: {project_name} | Maturity: {level}
Active Milestone: {planning.current_milestone or "None"}

═══ NOW ═══
  M3 — Authentication Overhaul
    Goal: Stabilize auth and reduce session bugs by 90%
    Status: IN_PROGRESS | 2/5 success criteria met
    Features: 3 (1 downhill, 1 peak, 1 uphill) | ~55% complete

═══ NEXT ═══
  M4 — Payment Integration
    Goal: Accept payments via Stripe
    Status: NOT_STARTED | 0/4 success criteria met
    Features: 2 (all shaped) | 0%

  M5 — Analytics Dashboard
    Goal: Real-time usage analytics for admins
    Status: NOT_STARTED | 0/3 success criteria met
    Features: 4 (all shaped) | 0%

═══ LATER ═══
  M6 — Multi-tenant Support
    Goal: Isolate data per organization
    Status: NOT_STARTED | 0%

Discrepancy Warnings

If pre-flight detected mismatches:

Warnings:
  ⚠ M2 is COMPLETE in milestone file but still listed as NOW in PRD
  ⚠ M7 exists in docs/milestones/ but is not in PRD roadmap table

Maturity Scaling

Detail	POC	Alpha	Beta	GA
Goal	✓	✓	✓	✓
Status + criteria	—	✓	✓	✓
Feature positions	—	—	✓	✓
Risks + dependencies	—	—	—	✓

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Command: /roadmap --edit

Interactive menu for milestone management. Loop until user selects "Done."

Step 1: Show Current State

Display --view output first for context.

Step 2: Present Menu

Roadmap actions:

1. Move a milestone between horizons (Now/Next/Later)
2. Add a new milestone
3. Archive a milestone
4. Update a milestone's goal
5. Done — save and exit

Ask via AskUserQuestion. Loop back after each action.

Action 1: Move Between Horizons

Ask which milestone, then which horizon. Handle these cases:

Moving TO Now: If another milestone is already Now + IN_PROGRESS, warn: "M3 is the current Now milestone. Moving M4 to Now makes it the new active milestone. This updates planning.current_milestone in config. Continue?"

Moving FROM Now: Warn that planning.current_milestone will update to the next Now milestone, or null if none remain.

Action 2: Add New Milestone

Follow the same interview steps as documented in /add:milestone --create (3-8 questions scaled by maturity). Do not invoke the milestone skill directly — replicate the interview inline so changes can be batched with other roadmap edits.

Action 3: Archive Milestone

Show the milestone, then:

Options:
  1. Archive — mark COMPLETE in PRD, keep milestone file
  2. Cancel

If milestone is IN_PROGRESS with active features, warn: "This milestone has active work. Complete or rescope features first."

Action 4: Update Goal

Show current goal, ask for new text. Optionally update target maturity and appetite.

Step 3: Confirm All Changes

Before applying, show a summary:

Changes to apply:

1. MOVE M4 (Payment Integration): Next → Now
2. MOVE M3 (Auth Overhaul): Now → Next
3. ADD M7 (Notification System) to Later
4. CONFIG: planning.current_milestone → "M4-payment-integration"

Files to modify:
  - docs/prd.md (Section 6 + revision history)
  - docs/milestones/M4-payment-integration.md (goal update)
  - docs/milestones/M7-notification-system.md (NEW)
  - .add/config.json (planning.current_milestone)

Apply all changes? (y/n)

Step 4: Apply Changes

1. Update docs/prd.md Section 6:

   • Rewrite roadmap table with updated horizons/statuses, ordered: Now first, then Next, then Later
   • Update milestone detail blocks
   • Append to Section 10 (Revision History): | {DATE} | {VERSION} | roadmap | {summary} |

2. Update milestone files: Edit existing (goal, status), create new from ${CLAUDE_PLUGIN_ROOT}/templates/milestone.md.template

3. Update .add/config.json: Set planning.current_milestone to first non-COMPLETE Now milestone, or null

4. Update .add/handoff.md if it exists — append a note summarizing the roadmap changes for session continuity

Step 5: Present Result

Roadmap updated.

  M4 (Payment Integration) → Now (active milestone)
  M3 (Auth Overhaul) → Next
  M7 (Notification System) added to Later

Next: /add:cycle --plan to start work on M4

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Command: /roadmap --reorder

Quick reordering without the full edit menu.

Step 1: Show Current Order

Current Roadmap:

NOW:   1. M3 — Authentication Overhaul (IN_PROGRESS, ~55%)
NEXT:  2. M4 — Payment Integration (NOT_STARTED)
       3. M5 — Analytics Dashboard (NOT_STARTED)
LATER: 4. M6 — Multi-tenant Support (NOT_STARTED)

Step 2: Ask for New Order

Enter new order grouped by horizon. Use | to separate horizons.
Example: "2 | 1, 3 | 4" → M4 to Now, M3+M5 to Next, M6 to Later

Current: 1 | 2, 3 | 4
New order:

Validate:

• All milestone numbers accounted for
• POC/Alpha: warn if >1 milestone in Now
• Beta/GA: allow multiple Now (parallel work)

Step 3: Confirm and Apply

Show proposed layout. On confirmation, apply same logic as --edit Step 4.

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File Synchronization Rules

PRD is source of truth for horizon placement. Milestone files are source of truth for status and content.

Sync Protocol

1. Parse existing PRD Section 6 roadmap table
2. Rebuild table in horizon order (Now → Next → Later), preserving order within horizons unless reorder requested
3. Update milestone detail blocks to match
4. Update .add/config.json planning.current_milestone to first non-COMPLETE Now milestone

Conflict Resolution

Conflict	--view behavior	--edit behavior
Milestone COMPLETE but in Now	Show warning	Auto-suggest archive or move to Later
File exists but not in PRD	Show as orphaned	Offer to add to roadmap
PRD references missing file	Show as missing	Offer to create from template

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Integration

Skill	Relationship
/add:init	Creates initial milestones. Roadmap manages them afterward.
/add:milestone	Tactical ops (switch, split, rescope). Roadmap does strategic horizon planning.
/add:cycle	Reads planning.current_milestone set by roadmap changes.
/add:dashboard	Reads milestone data. Roadmap ensures consistency.