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Perform comprehensive project housekeeping - update roadmap, reconcile issues with implementation reality, organize completed work, and identify drift. This is a workflow skill that coordinates multiple parallel subagents for efficiency. Use when user says something like "run housekeeping", "do your housekeeping" or "clean up project state".

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SKILL.md

name housekeeping
description Perform comprehensive project housekeeping - update roadmap, reconcile issues with implementation reality, organize completed work, and identify drift. This is a workflow skill that coordinates multiple parallel subagents for efficiency. Use when user says something like "run housekeeping", "do your housekeeping" or "clean up project state".

You are the housekeeping workflow coordinator. Your job is to ensure the project's documentation and issue tracking accurately reflects reality, organize completed work, and provide a clear snapshot of current state and next steps.

Core Responsibilities

Skill Usage Announcement

MANDATORY: When using this skill, announce it at the start with:

🔧 Using Skill: housekeeping | [brief purpose based on context]

Example:

🔧 Using Skill: housekeeping | [Provide context-specific example of what you're doing]

This creates an audit trail showing which skills were applied during the session.

  • Update .wrangler/ROADMAP_NEXT_STEPS.md to reflect current reality
  • Refresh governance metrics across all governance documents
  • Reconcile open issues with actual implementation
  • Move completed issues to organized archive
  • Identify documentation drift or missing updates
  • Verify constitutional alignment in specifications
  • Generate housekeeping summary report with metrics

Execution Strategy: Multi-Phase Workflow

This is a workflow skill - it coordinates multiple subagents in parallel for maximum efficiency.

Phase 1: Governance Refresh (Sequential)

Why sequential: Need current state understanding before dispatching parallel agents.

Task: Update governance documents to reflect current reality

Approach:

1.1 Refresh Governance Metrics

Use the refresh-metrics skill (invoke with Skill tool) to update:

  • .wrangler/issues/README.md - Issue counts and status percentages
  • .wrangler/specifications/README.md - Spec counts and constitutional compliance
  • .wrangler/ROADMAP_NEXT_STEPS.md - Implementation status and overall % complete

1.2 Update Roadmap Next Steps

After metrics refresh, manually review and update Next Steps:

  1. Read .wrangler/ROADMAP_NEXT_STEPS.md
  2. Review recent git commits (last 20-30 commits) for completed work
  3. Review recently closed issues and specifications
  4. Update three categories:
    • Move ⚠️ → ✅ if features fully completed
    • Move ❌ → ⚠️ if features started implementation
    • Add new ❌ items if gaps identified
  5. Update "What Works Well" and "Critical Gap" sections
  6. Update "Prioritized Roadmap" if priorities shifted
  7. Update "Last Updated By" and "Next Review" dates

1.3 Verify Constitutional Compliance

Check if any specifications lack constitutional alignment:

# Find specs missing constitutional alignment
grep -L "Constitutional Alignment" .wrangler/specifications/*.md | grep -v "_CONSTITUTION\|_ROADMAP\|README"

If found, note for Agent C (Documentation Drift) to flag.

Output:

  • Updated governance metrics
  • Updated roadmap Next Steps
  • List of specs needing constitutional alignment sections

Phase 2: Parallel Issue Reconciliation (Parallel)

Why parallel: Three independent tasks with no dependencies - run simultaneously for speed.

Launch three parallel subagents using the Task tool:

Agent A: Open Issues Reconciliation

Task: Review all open issues and ensure they match implementation reality

Approach:

  1. List all open issues (issues_list with status: ["open", "in_progress"])
  2. For each open issue:
    • Read the issue content
    • Check if described work has actually been completed
    • Check if requirements have changed during implementation
    • Identify issues that should be closed but weren't
    • Identify issues that need updates due to design changes
  3. Take action:
    • If completed but not closed: Use issues_mark_complete or issues_update to close
    • If requirements drifted: Use issues_update to reflect actual implementation
    • If blocked/cancelled: Use issues_update to mark status appropriately
  4. Track metrics:
    • Issues reviewed: [count]
    • Issues closed: [count]
    • Issues updated: [count]
    • Issues with drift: [count]

Output: List of actions taken and current state summary


Agent B: Completed Issues Organization

Task: Move completed/closed issues to .wrangler/issues/completed/ directory for archival

Approach:

  1. List all closed issues (issues_list with status: ["closed", "cancelled"])
  2. Check if .wrangler/issues/completed/ directory exists, create if not
  3. For each closed issue:
    • Check if still in .wrangler/issues/ root directory
    • If yes, move to .wrangler/issues/completed/
    • Preserve filename (don't rename)
  4. Track metrics:
    • Completed issues found: [count]
    • Issues moved: [count]
    • Already organized: [count]

Output: Organization summary with file counts


Agent C: Documentation Drift Detection

Task: Identify areas where documentation may not reflect implementation reality, including governance compliance

Approach:

  1. Read key documentation files:
    • README.md
    • CLAUDE.md (or equivalent project documentation)
    • .wrangler/CONSTITUTION.md
    • .wrangler/ROADMAP.md
    • Any specification files
  2. Review recent git commits for major changes
  3. Look for signs of drift:
    • Features mentioned in docs but not implemented
    • Features implemented but not documented
    • API changes not reflected in docs
    • Configuration changes not updated
    • File structure changes not documented
    • Specifications missing constitutional alignment sections
    • Roadmap phases not reflected in Next Steps
    • Constitutional principles violated in recent code
  4. Create list of documentation updates needed
  5. Track metrics:
    • Documentation files reviewed: [count]
    • Drift issues found: [count]
    • Constitutional compliance gaps: [count]
    • Severity: High/Medium/Low

Output: List of documentation drift issues with recommendations, including governance compliance issues


Agent D: Root Directory Organization

Task: Clean up and organize markdown files at project root

Approach:

  1. Scan project root for organizational candidates:
    • RCA-.md, ANALYSIS-.md, IMPLEMENTATION-*.md, etc.
    • Any ALL_CAPS.md files (excluding standard files like README.md)
  2. Categorize each file:
    • Delete if obsolete (discarded analysis, temp notes)
    • Move to memos/ if reference material (RCA, lessons learned, summaries)
    • Move to docs/ if user-facing documentation
    • Move to devops/docs/ if developer/maintainer documentation
  3. Execute actions (delete or move with appropriate naming)
  4. Track metrics:
    • Files processed: [count]
    • Deleted: [count]
    • Moved to memos/: [count]
    • Moved to docs/: [count]
    • Moved to devops/docs/: [count]

Output: Organized root directory with action summary


Phase 3: Summary Report (Sequential)

Why sequential: Needs results from all Phase 2 agents.

Task: Compile comprehensive housekeeping report

Approach:

  1. Wait for all Phase 2 agents to complete
  2. Aggregate metrics from all agents
  3. Create summary report showing:
    • Roadmap status (updated/current)
    • Issues reconciled (count, actions taken)
    • Files organized (count, location)
    • Documentation drift (issues found, severity)
    • Time taken per phase (if trackable)
    • Recommendations for follow-up work

Output: Housekeeping summary report


Workflow Execution Plan

Step 1: Start Phase 1 (Governance Refresh)

Execute governance refresh yourself:

  1. Invoke refresh-metrics skill using Skill tool
  2. Manually update Next Steps with recent completions
  3. Check for specs missing constitutional alignment

Step 2: Launch Phase 2 Parallel Agents

Use three separate Task tool calls in a single message to dispatch parallel agents:

I'm launching four parallel housekeeping agents:

[Use Task tool - Agent A: Open Issues Reconciliation]
[Use Task tool - Agent B: Completed Issues Organization]
[Use Task tool - Agent C: Documentation Drift Detection]
[Use Task tool - Agent D: Root Directory Organization]

CRITICAL: All four Task tool calls must be in a single response to execute truly in parallel.

Step 3: Collect Results & Generate Report

Wait for all agents to complete, then compile summary report.


Housekeeping Report Template

# Housekeeping Report - [Date]

## Summary

Housekeeping workflow completed successfully.

**Duration:** [X] minutes total

- Phase 1 (Governance refresh): [X] minutes
- Phase 2 (Parallel reconciliation): [X] minutes
- Phase 3 (Report generation): [X] minutes

## Governance Refresh

✅ **Metrics Updated**:

- `.wrangler/issues/README.md` - Updated issue counts and status percentages
- `.wrangler/specifications/README.md` - Updated spec counts and constitutional compliance
- `.wrangler/ROADMAP_NEXT_STEPS.md` - Updated implementation status

**Overall Project Completion**: ~[X]% ([+/-]% since last housekeeping)

**Completed since last housekeeping:**

- [Item 1]
- [Item 2]

**Current priorities:**

- [Priority 1]
- [Priority 2]

**Blockers identified:**

- [Blocker 1 if any]

**Constitutional Compliance**:

- Specifications with alignment: [X]/[Y] ([Z]%)
- Specifications needing alignment sections: [count]

## Issue Reconciliation

**Agent A - Open Issues:**

- Issues reviewed: [count]
- Issues closed: [count]
- Issues updated for drift: [count]
- Status: ✅ Complete

**Agent B - Completed Issues Organization:**

- Completed issues found: [count]
- Issues moved to archive: [count]
- Status: ✅ Complete

**Agent C - Documentation Drift:**

- Documentation files reviewed: [count]
- Drift issues found: [count]
  - High severity: [count]
  - Medium severity: [count]
  - Low severity: [count]
- Constitutional compliance gaps: [count]
- Status: ✅ Complete

**Agent D - Root Directory Organization:**

- Files processed: [count]
- Deleted (obsolete): [count]
- Moved to memos/: [count]
- Moved to docs/: [count]
- Moved to devops/docs/: [count]
- Status: ✅ Complete

## Actions Taken

### Issues Closed

- #000XXX - [Issue title] - Reason: [completed/cancelled]

### Issues Updated

- #000XXX - [Issue title] - Change: [what was updated]

### Files Organized

- Moved [X] issues to `issues/completed/`

### Documentation Drift Issues

**High Priority:**

- [ ] [Issue 1 description]

**Medium Priority:**

- [ ] [Issue 2 description]

**Low Priority:**

- [ ] [Issue 3 description]

## Recommendations

1. [Recommendation 1]
2. [Recommendation 2]

## Metrics

- Total issues in system: [count]
- Open issues: [count]
- In progress: [count]
- Completed: [count]
- Issue completion rate: [X]%
- Documentation coverage: [assessment]

---

_Housekeeping workflow v1.0 - Generated by wrangler:housekeeping_

Usage Examples

Example 1: Regular Housekeeping

User: "Run housekeeping"

Agent Response:

  1. "Starting housekeeping workflow..."
  2. "Phase 1: Updating .wrangler/ROADMAP_NEXT_STEPS.md..."
  3. "Phase 2: Launching three parallel reconciliation agents..."
    • Dispatches Agent A (issues)
    • Dispatches Agent B (organization)
    • Dispatches Agent C (drift detection)
  4. Waits for completion
  5. "Phase 3: Generating housekeeping report..."
  6. Presents summary report

Example 2: Post-Sprint Housekeeping

User: "We just finished the authentication feature sprint, run housekeeping"

Agent Response:

  1. Updates roadmap with authentication feature completion
  2. Reconciles auth-related issues
  3. Moves completed auth issues to archive
  4. Checks if auth documentation is up to date
  5. Reports on sprint completion status

Workflow Metrics & Observability

Track these metrics for workflow optimization:

Efficiency Metrics:

  • Total housekeeping time
  • Time per phase
  • Parallel speedup factor (Phase 2 time vs. sequential equivalent)

Action Metrics:

  • Issues reconciled
  • Files organized
  • Drift issues found
  • Documentation updates needed

Health Metrics:

  • Issue staleness (open issues > 30 days)
  • Documentation drift severity
  • Roadmap currency (last update date)

These metrics help identify:

  • Bottlenecks in workflow
  • Areas needing more frequent housekeeping
  • Project health indicators

Important Implementation Notes

Parallel Execution

To run Phase 2 agents in true parallel, you MUST:

  1. Use the Task tool three times in a single response
  2. Do NOT wait for Agent A to finish before launching Agent B
  3. All three tool calls should be in the same message

Example (correct parallel execution):

I'm launching three parallel agents for Phase 2 housekeeping:

[Task tool call for Agent A]
[Task tool call for Agent B]
[Task tool call for Agent C]

All three agents are now running in parallel...

Example (incorrect - sequential execution):

Launching Agent A...
[Wait for Agent A]
Now launching Agent B...
[Wait for Agent B]
Now launching Agent C...

State Isolation

Each Phase 2 agent operates on independent data:

  • Agent A: Open issues (won't touch closed)
  • Agent B: Closed issues (won't touch open)
  • Agent C: Documentation (won't touch issues)
  • Agent D: Root markdown files (won't touch issues/docs/memos)

This ensures no conflicts or race conditions.

Idempotency

Housekeeping is idempotent - running it multiple times is safe:

  • Roadmap: Last update wins (always reflects current)
  • Issues: Already-closed issues stay closed
  • Organization: Already-moved files stay moved
  • Drift: Re-detection is harmless

Extensibility

Future enhancements could add more parallel agents:

Agent D: Dependency Updates

  • Check for outdated dependencies
  • Identify security vulnerabilities

Agent E: Test Coverage Analysis

  • Identify untested code
  • Generate test coverage report

Agent F: Performance Regression Detection

  • Run benchmarks
  • Compare to baseline

Agent G: Code Quality Metrics

  • Run linters
  • Check complexity metrics

The workflow framework is designed to scale to arbitrary parallel agents.


Success Criteria

Housekeeping is successful when:

✅ Governance metrics refreshed across all documents ✅ Roadmap Next Steps accurately reflects current state and priorities ✅ Constitutional compliance verified and gaps identified ✅ All completed issues are marked as closed ✅ All closed issues are archived in .wrangler/issues/completed/ ✅ Issue descriptions match implementation reality ✅ Documentation drift is identified and catalogued (including governance compliance) ✅ Summary report provides actionable insights ✅ Workflow completes in reasonable time (< 5 minutes for typical project)


Frequency Recommendations

When to run housekeeping:

  • After completing major features
  • Weekly for active projects
  • Before starting new sprints/milestones
  • Before creating release
  • When project feels "messy" or out of sync

Automation potential:

  • Could be triggered by git hooks (post-merge)
  • Could run on schedule (weekly cron)
  • Could be part of CI/CD pipeline