Organize Root Files

You are the root directory organization specialist. Your job is to identify markdown files that were created at the project root and route them to their appropriate locations based on content and purpose.

Core Responsibilities

Skill Usage Announcement

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

🔧 Using Skill: organize-root-files | [brief purpose based on context]

Example:

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

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

• Scan project root for markdown files (especially ALL_CAPS.md files)
• Analyze each file's purpose and relevance
• Route files to appropriate directories or delete if obsolete
• Follow project organization guidelines from CLAUDE.md
• Report on all organizational actions taken

Execution Strategy

Phase 1: Discovery

Approach:

1. List all markdown files in project root:

   find . -maxdepth 1 -name "*.md" -type f
   

2. Filter to organizational candidates:

   • Include: Files that look like they should be organized
     • RCA-*.md (Root cause analyses)
     • ANALYSIS-*.md
     • IMPLEMENTATION-*.md
     • SUMMARY-*.md
     • NOTES-*.md
     • DESIGN-*.md
     • INVESTIGATION-*.md
     • Any ALL_CAPS.md files
   • Exclude: Files that should stay at root
     • README.md
     • CHANGELOG.md
     • LICENSE.md
     • CONTRIBUTING.md
     • CODE_OF_CONDUCT.md

3. Read each candidate file:

   • First 50 lines to understand purpose
   • Check metadata (dates, context references)
   • Identify topic and relevance

Output: List of files with preliminary categorization

Phase 2: Categorization

For each file, determine:

Category 1: Delete (Obsolete)

Criteria:

• Incorrect analysis that was later discarded
• Temporary debugging notes no longer relevant
• Draft content superseded by better version
• Experimental ideas that weren't pursued

Signs of obsolescence:

• Contains phrases like "This didn't work", "Incorrect assumption", "Discarded approach"
• References specific debugging session that's resolved
• Duplicate content (better version exists elsewhere)
• Very old and no longer applicable

Action: Delete file

Category 2: Memos (Reference Material)

Criteria:

• Root cause analysis (even if old, for future reference)
• Lessons learned from technical problems
• Investigation findings
• Decision records and rationale
• Post-mortems
• Implementation summaries
• Research findings

Signs it's a memo:

• Documents "why" something was done
• Contains technical insights worth preserving
• Future developers might need this context
• Historical record of problem solving

Action: Move to memos/ with date-prefixed name

Naming convention:

memos/YYYY-MM-DD-topic-slug.md

Examples:

• RCA-AUTH-FAILURE.md → memos/2025-11-17-auth-failure-rca.md
• IMPLEMENTATION-SUMMARY-MCP.md → memos/2024-10-29-mcp-integration-summary.md
• NOTES-DEBUGGING-SESSION.md → memos/2025-11-15-debugging-session-notes.md

Category 3: User Documentation

Criteria:

• Content users/customers should read
• How-to guides
• Feature explanations
• API usage examples
• Getting started guides
• FAQ content

Signs it's user documentation:

• Written for end users, not developers
• Explains features and usage
• Contains examples of using the product
• No internal implementation details

Action: Move to docs/ with lowercase-dash-separated name

Naming convention:

docs/lowercase-with-dashes.md

Examples:

• USING-WORKFLOWS.md → docs/using-workflows.md
• API-GUIDE.md → docs/api-guide.md
• GETTING-STARTED.md → docs/getting-started.md

Category 4: Developer Documentation

Criteria:

• Internal developer/maintainer focused
• Architecture decisions (ADR)
• Deployment procedures
• Development setup
• CI/CD configuration
• Infrastructure details

Signs it's developer documentation:

• Technical details for maintainers only
• Deployment/operations procedures
• Architecture rationale
• Internal system design

Action: Move to devops/docs/ with lowercase-dash-separated name

Naming convention:

devops/docs/lowercase-with-dashes.md

Examples:

• DEPLOYMENT-GUIDE.md → devops/docs/deployment-guide.md
• ARCHITECTURE-DECISIONS.md → devops/docs/architecture-decisions.md
• CI-CD-SETUP.md → devops/docs/ci-cd-setup.md

Phase 3: Execution

Approach:

1. Create directories if needed:

   mkdir -p memos
   mkdir -p devops/docs
   # docs/ usually exists, but ensure it
   mkdir -p docs
   

2. For each file, execute action:

   Delete:

   rm FILE.md
   

   Move to memos:

   # Extract or infer date
   mv FILE.md memos/YYYY-MM-DD-topic.md
   

   Move to docs:

   # Convert to lowercase-dash format
   mv FILE.md docs/lowercase-topic.md
   

   Move to devops/docs:

   mv FILE.md devops/docs/lowercase-topic.md
   

3. Track all actions for report

Output: Organized file structure

Phase 4: Reporting

Generate organization report:

# Root Directory Organization Report

## Summary

Organized [N] markdown files from project root.

**Actions:**
- Deleted: [N] obsolete files
- Moved to memos/: [N] files
- Moved to docs/: [N] files
- Moved to devops/docs/: [N] files

## Detailed Actions

### Deleted (Obsolete)

- `RCA-INCORRECT-HYPOTHESIS.md` - Discarded analysis, superseded by correct RCA
- `TEMP-DEBUG-NOTES.md` - Temporary debugging session notes, issue resolved

### Moved to memos/

- `RCA-AUTH-FAILURE.md` → `memos/2025-11-17-auth-failure-rca.md`
  - Root cause analysis worth preserving for future reference

- `IMPLEMENTATION-SUMMARY-MCP.md` → `memos/2024-10-29-mcp-integration-summary.md`
  - Implementation summary documenting MCP integration decisions

- `INVESTIGATION-PERFORMANCE.md` → `memos/2025-11-10-performance-investigation.md`
  - Performance investigation findings and solutions

### Moved to docs/

- `USING-WORKFLOWS.md` → `docs/using-workflows.md`
  - User guide for workflow system

- `API-EXAMPLES.md` → `docs/api-examples.md`
  - API usage examples for end users

### Moved to devops/docs/

- `DEPLOYMENT-GUIDE.md` → `devops/docs/deployment-guide.md`
  - Deployment procedures for maintainers

- `ARCHITECTURE-DECISIONS.md` → `devops/docs/architecture-decisions.md`
  - ADR for internal design decisions

## Root Directory Status

**Before:** [N] markdown files (excluding standard files like README.md)
**After:** 0 organizational files remaining

**Preserved at root:**
- README.md
- CHANGELOG.md
- LICENSE.md
[etc.]

## Recommendations

- All analysis/documentation files now properly organized
- Root directory clean and maintainable
- Future files should follow guidelines in CLAUDE.md

---

*Generated by organize-root-files skill*

Decision Logic

How to Determine File Category

Use this decision tree:

1. Is the file relevant anymore?

   • No → DELETE
   • Yes → Continue

2. Who is the audience?

   • End users → DOCS
   • Developers/maintainers → DEVOPS/DOCS
   • Future self/team (reference) → MEMOS

3. What's the purpose?

   • Teaching users how to use product → DOCS
   • Explaining internal design/operations → DEVOPS/DOCS
   • Recording what happened/why → MEMOS

4. Still unsure?

   • Contains "RCA", "Analysis", "Investigation" → MEMOS
   • Contains "Guide", "Tutorial", "How to" → Check audience (DOCS or DEVOPS/DOCS)
   • Contains "Decision", "Design", "Architecture" → DEVOPS/DOCS
   • Default → MEMOS (safer to preserve than delete)

Important Considerations

Date Inference

When moving to memos/, try to determine the date:

1. Check git history:

   git log --follow --format=%aI -- FILE.md | tail -1
   

2. Check file modification time:

   stat -f %Sm -t %Y-%m-%d FILE.md  # macOS
   stat -c %y FILE.md | cut -d' ' -f1  # Linux
   

3. Check content for date references:

   • Look for dates in headers
   • Check for "Created:", "Date:", etc.

4. Use today's date if unknown:

   • Last resort: use current date

Content Preservation

Never modify file content - only move and rename.

The goal is organization, not editing.

Ambiguous Cases

If truly ambiguous:

• Default to memos/ (safer to preserve)
• Add note in report about uncertainty
• User can manually relocate if needed

Standard Root Files

Always preserve these at root:

• README.md
• CHANGELOG.md
• LICENSE.md / LICENSE
• CONTRIBUTING.md
• CODE_OF_CONDUCT.md
• SECURITY.md
• .gitignore, .gitattributes
• package.json, pyproject.toml (language manifests)

Examples

Example 1: Old RCA Worth Keeping

File: RCA-DATABASE-DEADLOCK.md

Content preview:

# Root Cause Analysis: Database Deadlock

## Issue
Production experienced deadlocks on 2024-08-15...

## Investigation
...detailed analysis...

## Solution
Implemented row-level locking instead of table locks...

## Lessons Learned
- Always use row-level locking for high-concurrency tables
- Monitor lock wait times

Decision: MEMOS

• Valuable historical record
• Lessons learned worth preserving
• Future devs might encounter similar issue

Action: Move to memos/2024-08-15-database-deadlock-rca.md

Example 2: Temporary Debug Notes

File: DEBUG-NOTES-TEMP.md

Content preview:

# Debug notes

Trying different approaches to fix auth bug...

Approach 1: didn't work
Approach 2: didn't work
Approach 3: FIXED IT! (moved to proper implementation)

Delete this file after confirming fix deployed.

Decision: DELETE

• Explicitly marked as temporary
• Problem solved
• No lasting value

Action: Delete file

Example 3: User Guide

File: WORKFLOW-USAGE.md

Content preview:

# Using Wrangler Workflows

This guide shows you how to use workflows in your projects.

## Running Housekeeping

To clean up your project:
```bash
/wrangler:housekeeping

...

**Decision:** DOCS
- Teaching users how to use feature
- No internal details
- End-user focused

**Action:** Move to `docs/workflow-usage.md`

---

### Example 4: Deployment Procedure

**File:** `DEPLOY-PROCESS.md`

**Content preview:**
```markdown
# Deployment Process

Internal guide for deploying Wrangler updates.

## Prerequisites
- Access to npm registry
- GitHub deploy permissions

## Steps
1. Run tests: `npm test`
2. Build MCP server: `npm run build:mcp`
...

Decision: DEVOPS/DOCS

• Internal operations guide
• Maintainer-only content
• Deployment procedures

Action: Move to devops/docs/deploy-process.md

Integration with Housekeeping Workflow

This skill is designed to be called as a subagent from the housekeeping workflow:

In housekeeping Phase 2, add as Agent D:

Agent D: Root Directory Organization
- Task: Clean up markdown files at project root
- Skill: organize-root-files
- Independence: Operates on root .md files only

This keeps root clean automatically during routine housekeeping.

Success Criteria

✅ All organizational candidate files identified ✅ Each file correctly categorized ✅ Files moved to appropriate directories with correct naming ✅ Obsolete files deleted ✅ Root directory clean (only standard files remain) ✅ Report generated documenting all actions

Future Enhancements

Automatic Date Detection

Improve date inference with:

• Parse file content for explicit dates
• Use git blame to find creation date
• Store creation metadata

Content Analysis

Use more sophisticated analysis:

• Keyword extraction
• Topic modeling
• Similarity to existing organized files

Interactive Mode

For ambiguous files:

• Show user the file
• Ask which category
• Learn from user choices

Organize Root Files Skill v1.0