Claude-skill-registry gsd-new-milestone

<objective>

Start a new milestone through unified flow: questioning → research (optional) → requirements → roadmap.

This is the brownfield equivalent of new-project. The project exists, PROJECT.md has history. This command gathers "what's next" and takes you through the full cycle.

Creates/Updates:

• .planning/PROJECT.md

  — updated with new milestone goals

• .planning/research/

  — domain research (optional)

• .planning/REQUIREMENTS.md

  — scoped requirements

• .planning/ROADMAP.md

  — phase structure

• .planning/STATE.md

  — updated project memory

After this command: Run

/gsd-plan-phase [N]

to start execution.

</objective>

<execution_context>

@.github/get-shit-done/references/questioning.md @.github/get-shit-done/references/ui-brand.md @.github/get-shit-done/templates/project.md @.github/get-shit-done/templates/requirements.md

</execution_context>

<context>

Milestone name: $ARGUMENTS (optional - will prompt if not provided)

Load project context: @.planning/PROJECT.md @.planning/STATE.md @.planning/MILESTONES.md @.planning/config.json

</context> <process>

Phase 1: Validate

MANDATORY FIRST STEP — Execute these checks before ANY user interaction:

1. Verify project exists:

   [ -f .planning/PROJECT.md ] || { echo "ERROR: No PROJECT.md. Run /gsd-new-project first."; exit 1; }
   

2. Check for active milestone (ROADMAP.md exists):

   [ -f .planning/ROADMAP.md ] && echo "ACTIVE_MILESTONE" || echo "READY_FOR_NEW"
   

   If ACTIVE_MILESTONE: Use AskUserQuestion:

   • header: "Active Milestone"
   • question: "A milestone is in progress. What would you like to do?"
   • options:
     • "Complete current first" — Run /gsd-complete-milestone
     • "Continue anyway" — Start new milestone (will archive current)

   If "Complete current first": Exit with routing to

   /gsd-complete-milestone

   If "Continue anyway": Continue to Phase 2

3. Load previous milestone context:

   cat .planning/MILESTONES.md 2>/dev/null || echo "NO_MILESTONES"
   cat .planning/STATE.md
   

Phase 2: Present Context

Display stage banner:

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 GSD ► NEW MILESTONE
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Present what shipped:

Last milestone: v[X.Y] [Name] (shipped [DATE])

Key accomplishments:
- [From MILESTONES.md]
- [From MILESTONES.md]
- [From MILESTONES.md]

Validated requirements:
- [From PROJECT.md Validated section]

Pending todos:
- [From STATE.md if any]

Phase 3: Deep Questioning

Display stage banner:

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 GSD ► QUESTIONING
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Open the conversation:

Ask inline (freeform, NOT AskUserQuestion):

"What do you want to build next?"

Wait for their response. This gives you the context needed to ask intelligent follow-up questions.

Follow the thread:

Based on what they said, ask follow-up questions that dig into their response. Use AskUserQuestion with options that probe what they mentioned — interpretations, clarifications, concrete examples.

Keep following threads. Each answer opens new threads to explore. Ask about:

• What excited them
• What problem sparked this
• What they mean by vague terms
• What it would actually look like
• What's already decided

Consult

questioning.md

for techniques:

• Challenge vagueness
• Make abstract concrete
• Surface assumptions
• Find edges
• Reveal motivation

Decision gate:

When you could update PROJECT.md with clear new goals, use AskUserQuestion:

• header: "Ready?"
• question: "I think I understand what you're after. Ready to update PROJECT.md?"
• options:
  • "Update PROJECT.md" — Let's move forward
  • "Keep exploring" — I want to share more / ask me more

If "Keep exploring" — ask what they want to add, or identify gaps and probe naturally.

Loop until "Update PROJECT.md" selected.

Phase 4: Determine Milestone Version

Parse last version from MILESTONES.md and suggest next:

Use AskUserQuestion:

• header: "Version"
• question: "What version is this milestone?"
• options:
  • "v[X.Y+0.1] (patch)" — Minor update: [suggested name]
  • "v[X+1].0 (major)" — Major release
  • "Custom" — I'll specify

Phase 5: Update PROJECT.md

Update

.planning/PROJECT.md

with new milestone section:

## Current Milestone: v[X.Y] [Name]

**Goal:** [One sentence describing milestone focus]

**Target features:**
- [Feature 1]
- [Feature 2]
- [Feature 3]

Update Active requirements section with new goals (keep Validated section intact).

Update "Last updated" footer.

Commit PROJECT.md:

git add .planning/PROJECT.md
git commit -m "$(cat <<'EOF'
docs: start milestone v[X.Y] [Name]

[One-liner describing milestone focus]
EOF
)"

Phase 6: Research Decision

Use AskUserQuestion:

• header: "Research"
• question: "Research the domain ecosystem before defining requirements?"
• options:
  • "Research first (Recommended)" — Discover patterns, expected features, architecture
  • "Skip research" — I know this domain well, go straight to requirements

If "Research first":

Display stage banner:

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 GSD ► RESEARCHING
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Researching [domain] ecosystem...

Create research directory:

mkdir -p .planning/research

Milestone context is "subsequent" — Research focuses on new features, not re-researching validated requirements.

Display spawning indicator:

◆ Spawning 4 researchers in parallel...
  → Stack research
  → Features research
  → Architecture research
  → Pitfalls research

Spawn 4 parallel gsd-project-researcher agents with context:

Task(prompt="
<research_type>
Project Research — Stack dimension for [domain].
</research_type>

<milestone_context>
Subsequent milestone (v[X.Y]).

Research what's needed to add [target features] to an existing [domain] app. Don't re-research the existing system.
</milestone_context>

<question>
What's needed to add [target features] to [domain]?
</question>

<project_context>
[PROJECT.md summary - core value, validated requirements, new goals]
</project_context>

<downstream_consumer>
Your STACK.md feeds into roadmap creation. Be prescriptive:
- Specific libraries with versions
- Clear rationale for each choice
- What NOT to use and why
</downstream_consumer>

<output>
Write to: .planning/research/STACK.md
Use template: .github/get-shit-done/templates/research-project/STACK.md
</output>
", subagent_type="gsd-project-researcher", description="Stack research")

Task(prompt="
<research_type>
Project Research — Features dimension for [domain].
</research_type>

<milestone_context>
Subsequent milestone (v[X.Y]).

How do [target features] typically work? What's expected behavior?
</milestone_context>

<question>
What features are expected for [target features]?
</question>

<project_context>
[PROJECT.md summary]
</project_context>

<downstream_consumer>
Your FEATURES.md feeds into requirements definition. Categorize clearly:
- Table stakes (must have)
- Differentiators (competitive advantage)
- Anti-features (things to deliberately NOT build)
</downstream_consumer>

<output>
Write to: .planning/research/FEATURES.md
Use template: .github/get-shit-done/templates/research-project/FEATURES.md
</output>
", subagent_type="gsd-project-researcher", description="Features research")

Task(prompt="
<research_type>
Project Research — Architecture dimension for [domain].
</research_type>

<milestone_context>
Subsequent milestone (v[X.Y]).

How do [target features] integrate with existing [domain] architecture?
</milestone_context>

<question>
How should [target features] integrate with the existing system?
</question>

<project_context>
[PROJECT.md summary]
</project_context>

<downstream_consumer>
Your ARCHITECTURE.md informs phase structure in roadmap. Include:
- Component boundaries (what talks to what)
- Data flow (how information moves)
- Suggested build order (dependencies between components)
</downstream_consumer>

<output>
Write to: .planning/research/ARCHITECTURE.md
Use template: .github/get-shit-done/templates/research-project/ARCHITECTURE.md
</output>
", subagent_type="gsd-project-researcher", description="Architecture research")

Task(prompt="
<research_type>
Project Research — Pitfalls dimension for [domain].
</research_type>

<milestone_context>
Subsequent milestone (v[X.Y]).

What are common mistakes when adding [target features] to [domain]?
</milestone_context>

<question>
What pitfalls should we avoid when adding [target features]?
</question>

<project_context>
[PROJECT.md summary]
</project_context>

<downstream_consumer>
Your PITFALLS.md prevents mistakes in roadmap/planning. For each pitfall:
- Warning signs (how to detect early)
- Prevention strategy (how to avoid)
- Which phase should address it
</downstream_consumer>

<output>
Write to: .planning/research/PITFALLS.md
Use template: .github/get-shit-done/templates/research-project/PITFALLS.md
</output>
", subagent_type="gsd-project-researcher", description="Pitfalls research")

After all 4 agents complete, spawn synthesizer:

Task(prompt="
<task>
Synthesize research outputs into SUMMARY.md.
</task>

<research_files>
Read these files:
- .planning/research/STACK.md
- .planning/research/FEATURES.md
- .planning/research/ARCHITECTURE.md
- .planning/research/PITFALLS.md
</research_files>

<output>
Write to: .planning/research/SUMMARY.md
Use template: .github/get-shit-done/templates/research-project/SUMMARY.md
Commit after writing.
</output>
", subagent_type="gsd-research-synthesizer", description="Synthesize research")

Display research complete:

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 GSD ► RESEARCH COMPLETE ✓
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

## Key Findings

**Stack:** [from SUMMARY.md]
**Table Stakes:** [from SUMMARY.md]
**Watch Out For:** [from SUMMARY.md]

Files: `.planning/research/`

If "Skip research": Continue to Phase 7.

Phase 7: Define Requirements

Display stage banner:

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 GSD ► DEFINING REQUIREMENTS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Load context:

Read PROJECT.md and extract:

• Core value (the ONE thing that must work)
• New milestone goals
• Validated requirements (what already works)
• Stated constraints

If research exists: Read research/FEATURES.md and extract feature categories.

Present features by category:

Here are the features for [milestone focus]:

## [Category 1]
**Table stakes:**
- [Feature]
- [Feature]

**Differentiators:**
- [Feature]

**Research notes:** [any relevant notes]

---

## [Next Category]
...

If no research: Gather requirements through conversation instead.

Ask: "What are the main things users need to be able to do in this milestone?"

For each capability mentioned:

• Ask clarifying questions to make it specific
• Probe for related capabilities
• Group into categories

Scope each category:

For each category, use AskUserQuestion:

• header: "[Category name]"
• question: "Which [category] features are in this milestone?"
• multiSelect: true
• options:
  • "[Feature 1]" — [brief description]
  • "[Feature 2]" — [brief description]
  • "None for this milestone" — Defer

Track responses:

• Selected features → v1 requirements
• Unselected table stakes → v2 (users expect these)
• Unselected differentiators → out of scope

Identify gaps:

Use AskUserQuestion:

• header: "Additions"
• question: "Any requirements research missed? (Features specific to your vision)"
• options:
  • "No, research covered it" — Proceed
  • "Yes, let me add some" — Capture additions

Validate core value:

Cross-check requirements against Core Value from PROJECT.md. If gaps detected, surface them.

Generate REQUIREMENTS.md:

Create

.planning/REQUIREMENTS.md

with:

• v1 Requirements grouped by category (checkboxes, REQ-IDs)
• v2 Requirements (deferred)
• Out of Scope (explicit exclusions with reasoning)
• Traceability section (empty, filled by roadmap)

REQ-ID format:

[CATEGORY]-[NUMBER]

(AUTH-01, CONTENT-02)

Requirement quality criteria:

Good requirements are:

• Specific and testable: "User can reset password via email link" (not "Handle password reset")
• User-centric: "User can X" (not "System does Y")
• Atomic: One capability per requirement
• Independent: Minimal dependencies on other requirements

Present full requirements list for confirmation:

Show every requirement (not counts) for user confirmation:

## v1 Requirements

### [Category]
- [ ] **[CAT]-01**: [Requirement description]
- [ ] **[CAT]-02**: [Requirement description]

[... full list ...]

---

Does this capture what you're building? (yes / adjust)

If "adjust": Return to scoping.

Commit requirements:

git add .planning/REQUIREMENTS.md
git commit -m "$(cat <<'EOF'
docs: define v[X.Y] requirements

[X] requirements across [N] categories
[Y] requirements deferred to v2
EOF
)"

Phase 8: Create Roadmap

Display stage banner:

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 GSD ► CREATING ROADMAP
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

◆ Spawning roadmapper...

Calculate starting phase number:

# Find highest existing phase number
ls -d .planning/phases/[0-9]*-* 2>/dev/null | sort -V | tail -1 | grep -oE '[0-9]+' | head -1

If phases exist: New phases start at last + 1 If no phases: Start at Phase 1

Spawn gsd-roadmapper agent with context:

Task(prompt="
<planning_context>

**Project:**
@.planning/PROJECT.md

**Requirements:**
@.planning/REQUIREMENTS.md

**Research (if exists):**
@.planning/research/SUMMARY.md

**Config:**
@.planning/config.json

**Starting phase number:** [N]

</planning_context>

<instructions>
Create roadmap:
1. Derive phases from requirements (don't impose structure)
2. Map every v1 requirement to exactly one phase
3. Derive 2-5 success criteria per phase (observable user behaviors)
4. Validate 100% coverage
5. Write files immediately (ROADMAP.md, STATE.md, update REQUIREMENTS.md traceability)
6. Return ROADMAP CREATED with summary

Write files first, then return.
</instructions>
", subagent_type="gsd-roadmapper", description="Create roadmap")

Handle roadmapper return:

If

## ROADMAP BLOCKED

:

• Present blocker information
• Work with user to resolve
• Re-spawn when resolved

If

## ROADMAP CREATED

:

Read the created ROADMAP.md and present it inline.

Ask for approval:

Use AskUserQuestion:

• header: "Roadmap"
• question: "Does this roadmap structure work for you?"
• options:
  • "Approve" — Commit and continue
  • "Adjust phases" — Tell me what to change
  • "Review full file" — Show raw ROADMAP.md

If "Approve": Continue to commit.

If "Adjust phases":

• Get user's adjustment notes
• Re-spawn roadmapper with revision context
• Loop until approved

Commit roadmap:

git add .planning/ROADMAP.md .planning/STATE.md .planning/REQUIREMENTS.md
git commit -m "$(cat <<'EOF'
docs: create v[X.Y] roadmap ([N] phases)

Phases:
1. [phase-name]: [requirements covered]
2. [phase-name]: [requirements covered]
...

All v1 requirements mapped to phases.
EOF
)"

Phase 9: Done

Present completion with next steps:

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 GSD ► MILESTONE INITIALIZED ✓
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

**v[X.Y] [Name]**

| Artifact       | Location                    |
|----------------|-----------------------------
| Project        | `.planning/PROJECT.md`      |
| Research       | `.planning/research/`       |
| Requirements   | `.planning/REQUIREMENTS.md` |
| Roadmap        | `.planning/ROADMAP.md`      |

**[N] phases** | **[X] requirements** | Ready to build ✓

───────────────────────────────────────────────────────────────

## ▶ Next Up

**Phase [N]: [Phase Name]** — [Goal from ROADMAP.md]

`/gsd-discuss-phase [N]` — gather context and clarify approach

<sub>`/clear` first → fresh context window</sub>

---

**Also available:**
- `/gsd-plan-phase [N]` — skip discussion, plan directly

───────────────────────────────────────────────────────────────

</process> <output>

• .planning/PROJECT.md

  (updated)

• .planning/research/

  (if research selected)

  • STACK.md

  • FEATURES.md

  • ARCHITECTURE.md

  • PITFALLS.md

  • SUMMARY.md

• .planning/REQUIREMENTS.md

• .planning/ROADMAP.md

• .planning/STATE.md

</output>

<success_criteria>

• Project validated (PROJECT.md exists)
• Previous milestone context presented
• Deep questioning completed (threads followed)
• Milestone version determined
• PROJECT.md updated with new milestone goals → committed
• Research completed (if selected) → committed
• Requirements gathered and scoped
• REQUIREMENTS.md created with REQ-IDs → committed
• gsd-roadmapper spawned with context
• Roadmap files written immediately
• User feedback incorporated (if any)
• ROADMAP.md, STATE.md → committed
• User knows next step is

  /gsd-plan-phase [N]

</success_criteria>