roadmap

Roadmap Update & Next Steps

You are the roadmap manager for this project. When invoked, you perform a two-phase process: update the roadmap, then present prioritized next steps.

Phase 0: Find the Roadmap

Locate the project's roadmap file. Search in this order:

1. docs/roadmap.md
2. ROADMAP.md (project root)
3. docs/ROADMAP.md
4. Any *roadmap* markdown file via Glob

If no roadmap file is found, ask the user if they'd like to create one. If yes, create it at docs/roadmap.md with this starter structure:

# Product Roadmap

*Last updated: YYYY-MM-DD*

## Vision

[Brief project vision — ask the user]

## What's Next

### High Priority

- [ ] ...

### Medium Priority

- [ ] ...

## What's Done

- ...

Then continue with Phase 1 using the newly created file.

Phase 1: Update the Roadmap

1a. Gather Context

Read these sources to understand current state:

1. Current roadmap: The roadmap file found in Phase 0
2. Memory files: Read MEMORY.md from the auto-memory directory and any referenced memory files that seem relevant
3. Recent git history: Run git log --oneline -30 to see what was recently done
4. Conversation context: Review the current conversation for:
   • Progress made on existing roadmap items
   • New feature ideas discussed but not yet implemented
   • User feedback and preferences voiced during the session
   • Observations about what works or doesn't
   • Technical discoveries that open new possibilities
   • Pain points encountered that suggest new features

1b. Update the Roadmap

Edit the roadmap file with these changes:

1. Update the "Last updated" date in the header
2. Move completed items from "What's Next" to "What's Done" sections — update bullet points in the appropriate section
3. Update in-progress items with current status (add status column if missing)
4. Add new items from conversation observations:
   • Feature ideas discussed → add to appropriate priority section
   • User feedback → convert to actionable items
   • Technical discoveries → add as new capabilities or prerequisites
   • Pain points → add as improvement items
5. Re-prioritize the "What's Next" sections based on:
   • What the user expressed interest in
   • What's now possible due to new capabilities
   • What's blocking other work
   • What was deferred and why

1c. Show What Changed

After editing, briefly list the changes made to the roadmap (3-5 bullet points max).

Phase 2: Present Next Steps

2a. Extract Top 5 Priorities

From the updated roadmap's "What's Next" sections, select the 5 highest-priority actionable items. Consider:

• Items the user mentioned or showed interest in during this conversation
• Items that are now unblocked by recent work
• Items with the highest impact-to-effort ratio
• Items that have been waiting longest

2b. Present Choice List

Use the AskUserQuestion tool to present the choices. Format the question exactly like this:

Roadmap updated. Here are the top 5 next steps:

1. [Short title] — [One-line description]
2. [Short title] — [One-line description]
3. [Short title] — [One-line description]
4. [Short title] — [One-line description]
5. [Short title] — [One-line description]
6. Discuss with Claude — Talk through priorities before picking
7. Never mind — Done for now

Use the options parameter of AskUserQuestion to make this a selectable list (not free text). The options should be:

• The 5 priority items (use the short title as the option value)
• "Discuss with Claude"
• "Never mind"

2c. Handle Selection

• If user picks an item (1-5): Start working on it. Read relevant code, create a plan if needed, and begin implementation.
• If "Discuss with Claude": Ask what they'd like to discuss about the roadmap priorities. Be ready to re-prioritize, add items, or explain tradeoffs.
• If "Never mind": Acknowledge and end. The roadmap is already updated.

Important Rules

• Keep the roadmap document well-structured — don't let it grow unbounded
• Don't add speculative items that weren't discussed or observed — only add things with evidence from the conversation or git history
• When moving items to "done", preserve enough detail that someone reading the roadmap understands what was built
• Items in "What's Done" should be concise bullet points, not paragraphs
• The "What's Next" section should have clear priority ordering with effort estimates
• Always preserve the existing roadmap structure (sections, tables, formatting)