msd-core/get-shit-done/workflows/discuss-milestone.md

Help the user figure out what they want to build in the next milestone through collaborative thinking.

You're a thinking partner helping them crystallize their vision for what's next. Features first — everything else (scope, phases) derives from what they want to build.

Load project state:

cat .planning/STATE.md
cat .planning/ROADMAP.md

If no active milestone (expected state after completing previous): Continue to milestone_context.

If active milestone exists:

Current milestone in progress: v[X.Y] [Name]
Phases [N]-[M], [P]% complete

Did you want to:
1. Complete current milestone first (/gsd:complete-milestone)
2. Add phases to current milestone (/gsd:add-phase)
3. Continue anyway - discuss next milestone scope

Wait for user response. If "Continue anyway", proceed to milestone_context.

Present context from previous milestone:

Last completed: v[X.Y] [Name] (shipped [DATE])
Key accomplishments:
- [From MILESTONES.md or STATE.md]

Total phases delivered: [N]
Next phase number: [N+1]

Continue to intake_gate.

**CRITICAL: ALL questions use AskUserQuestion. Never ask inline text questions.**

The primary question is: What do you want to build/add/fix?

Everything else (scope, priority, constraints) is secondary and derived from features.

Check for inputs:

• Pending todos from STATE.md (potential features)
• Known gaps or pain points from usage
• User's ideas for what's next

1. Open:

Use AskUserQuestion:

• header: "Next"
• question: "What do you want to add, improve, or fix in this milestone?"
• options: [Pending todos from STATE.md if any] + ["New features", "Improvements to existing", "Bug fixes", "Let me describe"]

2. Explore features:

Based on their response, use AskUserQuestion:

If they named specific features:

• header: "Feature Details"
• question: "Tell me more about [feature] - what should it do?"
• options: [Contextual options based on feature type + "Let me describe it"]

If they described a general direction:

• header: "Breaking It Down"
• question: "That could involve [A], [B], [C] - which matter most?"
• options: [Specific sub-features + "All of them" + "Something else"]

If they're not sure:

• header: "Starting Points"
• question: "What's been frustrating or missing?"
• options: [Pending todos from STATE.md + pain point categories + "Let me think about it"]

3. Prioritize:

Use AskUserQuestion:

• header: "Priority"
• question: "Which of these matters most?"
• options: [Features they mentioned + "All equally important" + "Let me prioritize"]

After gathering features, synthesize:

Based on what you described:

**Features:**
- [Feature 1]: [brief description]
- [Feature 2]: [brief description]
- [Feature 3]: [brief description]

**Estimated scope:** [N] phases
**Theme suggestion:** v[X.Y] [Name]

4. Decision gate:

Use AskUserQuestion:

• header: "Ready?"
• question: "Ready to create the milestone, or explore more?"
• options (ALL THREE REQUIRED):
  • "Create milestone" - Proceed to /gsd:new-milestone
  • "Ask more questions" - Help me think through this more
  • "Let me add context" - I have more to share

If "Ask more questions" → return to step 2 with new probes. If "Let me add context" → receive input → return to step 2. Loop until "Create milestone" selected.

Write milestone context to file for handoff.

File: .planning/MILESTONE-CONTEXT.md

Use template from ~/.claude/get-shit-done/templates/milestone-context.md

Populate with:

• Features identified during discussion
• Suggested milestone name and theme
• Estimated phase count
• How features map to phases
• Any constraints or scope boundaries mentioned

# Write the context file
cat > .planning/MILESTONE-CONTEXT.md << 'EOF'
# Milestone Context

**Generated:** [today's date]
**Status:** Ready for /gsd:new-milestone

<features>
## Features to Build

- **[Feature 1]**: [description]
- **[Feature 2]**: [description]
- **[Feature 3]**: [description]

</features>

<scope>
## Scope

**Suggested name:** v[X.Y] [Theme Name]
**Estimated phases:** [N]
**Focus:** [One sentence theme/focus]

</scope>


<constraints>
## Constraints

- [Any constraints mentioned]

</constraints>

<notes>
## Additional Context

[Anything else from discussion]

</notes>

---

*This file is temporary. It will be deleted after /gsd:new-milestone creates the milestone.*
EOF

Present summary and hand off to create-milestone:

Milestone scope defined:

**Features:**
- [Feature 1]: [description]
- [Feature 2]: [description]
- [Feature 3]: [description]

**Suggested milestone:** v[X.Y] [Theme Name]

Context saved to `.planning/MILESTONE-CONTEXT.md`

---

## ▶ Next Up

**Create Milestone v[X.Y]** — [Theme Name]

`/gsd:new-milestone`

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

---

<success_criteria>

• Project state loaded (STATE.md, MILESTONES.md)
• Previous milestone context presented
• Features identified - What to build/add/fix (the substance)
• Features explored with clarifying questions
• Scope synthesized from features (not asked abstractly)
• MILESTONE-CONTEXT.md created with features and scope
• Context handed off to /gsd:new-milestone </success_criteria>