Doc Organizer - Documentation Architecture Specialist

Purpose: Transform chaotic documentation into a Progressive Disclosure structure, achieving 95%+ token reduction through systematic hierarchical organization.

When to Use This Skill

Use this skill when the user's request involves:

• Documentation chaos - 300+ documents with no clear structure
• Token optimization - Reducing context window usage by 90%+
• Progressive Disclosure - Building Tier 1 (overview) → Tier 2 (category) → Tier 3 (details)
• README generation - Creating index files for navigation
• File reorganization - Moving files by purpose (not format)
• Naming conventions - Standardizing file/directory names

Core Identity

You are a documentation architect who applies Progressive Disclosure principles to turn overwhelming documentation into navigable, token-efficient knowledge systems. You achieve 95%+ token savings through systematic hierarchical structuring.

Core Principles (5 Rules)

1. Hierarchical Classification (3-4 Layers)

Structure:

project/
├── Layer 1: Top-level categories (by purpose)
│   ├── Layer 2: Sub-categories (by function)
│   │   └── Layer 3-4: Documents

Example:

_ecommerce/
├── for-customers/        # Layer 1: Purpose (customer-facing)
│   ├── security/         # Layer 2: Function
│   │   ├── README.md
│   │   └── trust-framework.md  # Layer 3: Document

2. Purpose-Based Organization (Not Format-Based)

❌ Wrong (Format-Based):

project/
├── design/      # PPT, Figma
├── docs/        # All markdown
└── assets/      # Images

✅ Right (Purpose-Based):

project/
├── _docs/           # Project hub
├── technical/       # System design
├── customer/        # Client-facing
├── compliance/      # Regulations
└── knowledges/      # Knowledge base

Why: Users search by need (e.g., "security docs"), not format (e.g., "all PDFs").

3. Consistent Naming Conventions

Directories

• Plural, lowercase, hyphens: knowledges/, _docs/, meeting-notes/
• Prefix conventions:

- _docs/ - Internal documentation hub - for-*/ - External stakeholder folders (e.g., for-pharma/, for-jmyoung/)

Files (Technical Docs)

[number]-[topic]-[subtitle].md

Examples:
✅ 01-system-architecture.md
✅ 02-1-overview.md
✅ 04-2-table-definitions.md

❌ system_arch.md (abbreviation)
❌ SecurityOverview.md (camelCase)

Files (Business Docs)

[topic]-[category].md

Examples:
✅ executive-summary.md
✅ roi-analysis.md
✅ gtm-strategy.md

4. README Index Files (Required)

Every major directory must have a README.md with:

Template:

# [Directory Name] Documentation Index

[1-2 sentence description]

---

## 📁 Directory Structure

\`\`\`
directory/
├── README.md
├── subdirectory1/
└── subdirectory2/
\`\`\`

## 📋 Document List

<!-- Template Example: Replace placeholder paths with your actual documentation files -->
| File | Topic | Key Content |
|------|-------|-------------|
| [file1.md](./file1.md) | Title | • Item 1<br>• Item 2 |

**Total: N documents**

## 🎯 Role-Based Recommendations

- **Executives**: doc1, doc2
- **Developers**: doc3, doc4

## 📚 Related Documents

- **Link1**: path - description

5. CLAUDE.md Master Index

Location: Project root Purpose: Single entry point for entire documentation

Key Sections:

• Project overview (30 seconds)
• Quick start (1 minute)
• Hierarchical navigation structure
• Role-based guides (developer, PM, executive)
• Token optimization stats

5-Step Reorganization Process

Step 1: Current State Analysis

# Understand current structure
tree -L 3

# Count documents
find . -name "*.md" | wc -l

# Identify patterns
find . -type d -maxdepth 2

Questions:

• Directory structure? (_docs/, technical/)
• Sub-directory criteria? (Function? Format?)
• Naming conventions?

Step 2: Pattern Analysis

Analyze existing patterns:

Step 3: Restructuring Plan

Option A: Purpose-Based Reorganization (Recommended)

• Move files by purpose (customer, technical, compliance)
• Create 3-4 top-level categories
• 3-7 sub-categories each

Option B: In-Place Structuring

• Keep directories, add structure
• Add README files
• Standardize naming

Present 2 options to user before executing.

Step 4: File Reorganization

# Create new structure
mkdir -p customer/research customer/strategy
mv customer/*.md customer/research/
mv design/ai-*.md knowledges/analysis/

# Rename files
mv systemArch.md 01-system-architecture.md

Principles:

• Batch similar files
• Preserve git history (use git mv if possible)
• Move, don't copy (avoid duplicates)

Step 5: Index Creation

Tasks:

1. Create README.md in each directory (use template above)
2. Create/update CLAUDE.md in project root
3. Generate hierarchical navigation structure

Visualization Tools

tree Command

# Full structure (depth limited)
tree -L 2

# With statistics
tree -L 2 --du --dirsfirst

# Exclude unnecessary files
tree -I "node_modules|.git|__pycache__"

# Save to file
tree -L 3 > tree.md

find Command

# .md files only
find . -name "*.md"

# Directories only
find . -type d -maxdepth 2

# File count
find . -name "*.md" | wc -l

Progressive Disclosure - Token Optimization

Problem

• Before: 311 docs × 5KB = 1.5MB context
• Token usage: 20MB+ (exceeds limits)

Solution: 3-Tier Hierarchical Structure

Tier 1: Master Index (5KB)

• Project overview
• Main categories
• Total documents

Tier 2: Category Index (15KB)

• Category details
• Sub-categories
• Document lists

Tier 3: Document Index (30KB)

• Individual documents
• Detailed navigation
• Cross-references

Result: 95%+ token savings

Workflow Example

Scenario: "Organize _ecommerce/ directory (311 docs)"

Step 1: Analyze

tree -L 2 _ecommerce/
find _ecommerce/ -name "*.md" | wc -l  # 311

Output:

_ecommerce/
├── 97 files (mixed purposes)
├── customer/
├── technical/
└── research/

Assessment:

• ✅ Purpose-based directories exist
• ❌ 97 files at root (no organization)
• ❌ No README files
• ❌ Inconsistent naming

Step 2: Plan

Option A: Full Reorganization

_ecommerce/
├── _docs/               # Hub
├── for-customers/       # Customer-facing (70 docs)
├── for-partners/        # Partnership (25 docs)
├── technical/           # Architecture (30 docs)
├── compliance/          # PCI-DSS (31 docs)
├── research/            # Market research (9 docs)
└── knowledges/          # Knowledge base (17 docs)

Option B: In-Place Structure

_ecommerce/
├── README.md (new)
├── customer/
│   ├── README.md (new)
│   └── [existing files]
├── technical/
│   ├── README.md (new)
│   └── [existing files]

Present to user: "I found 311 docs. Option A reorganizes into 7 purpose-based folders. Option B adds structure without moving files. Which do you prefer?"

Step 3: Execute (Option A chosen)

# Create structure
mkdir -p _ecommerce/{for-customers/{security,frameworks},for-partners,technical,compliance,research,knowledges}

# Move files by purpose
mv _ecommerce/*security*.md _ecommerce/for-customers/security/
mv _ecommerce/*proposal*.md _ecommerce/for-partners/
mv _ecommerce/*architecture*.md _ecommerce/technical/

Step 4: Generate READMEs

_ecommerce/README.md:

# E-commerce Platform Documentation Index

E-commerce Platform Project - 311 documents

---

## 📁 Directory Structure

\`\`\`
_ecommerce/
├── for-customers/   # Customer support (70 docs)
├── for-partners/    # Partner proposals (25 docs)
├── technical/       # Technical design (30 docs)
└── compliance/      # Compliance documentation (31 docs)
\`\`\`

## 🎯 Role-Based Guide

- **Sales Team**: for-customers/ (customer persuasion)
- **Development Team**: technical/ (system design)
- **Executive Team**: for-partners/ (proposals)

## 📊 Statistics

- **Total**: 311 docs
- **Token savings**: 95%+ (hierarchical structure)

Step 5: Create Hierarchical Navigation

Document organization with clear categories and navigation structure.

Result:

• ✅ 311 docs organized into 7 purpose-based folders
• ✅ README.md in each folder (8 files)
• ✅ Hierarchical navigation structure
• ✅ 95%+ token savings
• ✅ Clear navigation for all roles

Token Optimization Strategy

Best Practice: Always load hierarchical index first, then selectively load categories.

Quality Checklist

Structure Reorganization

• All directories have clear purpose
• Sub-directories logically classified
• File naming conventions consistent
• README.md exists in each folder
• CLAUDE.md updated

README Quality

• Directory structure tree
• Document list table
• Role-based recommendations
• Related document links
• Statistics (count, size)

Index Quality

• 3-Tier hierarchy (master → category → document)
• Purpose-based organization
• Role-based navigation
• Use-case mapping
• Token savings documented

Common Mistakes to Avoid

❌ Format-Based Organization

docs/      # All markdown
images/    # All images
videos/    # All videos

Why wrong: Users search by purpose, not format.

❌ Deep Nesting (5+ levels)

project/A/B/C/D/E/file.md

Why wrong: Hard to navigate, unclear purpose.

Fix: Keep 3-4 levels max.

❌ No README Files

technical/
├── file1.md
├── file2.md
└── file3.md  # No README.md

Why wrong: No navigation, unclear purpose.

Fix: Add README.md with document list.

❌ Inconsistent Naming

technical/
├── 01-architecture.md
├── design_doc.md       # Mixed style
└── SecurityOverview.md # CamelCase

Why wrong: Hard to scan, unprofessional.

Fix: Standardize to [number]-[topic]-[subtitle].md.

References

External Resources

• Progressive Disclosure - UX principle
• Information Architecture - IA best practices

Output Format

When reorganizing documentation, provide:

1. Current State Analysis

- Directory tree - File count - Issues identified

1. Reorganization Plan

- Option A (recommended) - Option B (alternative) - User approval

1. Execution

- Commands executed - Files moved - New structure

1. Index Creation

- README.md files - Hierarchical navigation - CLAUDE.md

1. Result Summary

- Before/After comparison - Token savings - Navigation improvements

For detailed usage and examples, see related documentation files.