Skip to main content

Documentation Organization - Implementation Checklist

Status: Ready to Execute Timeline: 2-3 Days (12-16 hours) Owner: [Assign owner] Started: [Date] Completed: [Date]

Day 1: Navigation & Diagram Organization (6-8 hours)​

Morning Session (4 hours)​

Task 1: Master Documentation Index (2 hours)​

  • Create /docs/INDEX.md
    • Add role-based navigation (Executive, Developer, DevOps, Security)
    • Create quick-find alphabetical table with all 33+ documents
    • Add category breakdowns with descriptions
    • Include "Recent Updates" section
    • Link to all existing documents
    • Test all links

Acceptance Criteria:

  • ✅ Every document in repository listed
  • ✅ All links verified working
  • ✅ 4 role-based navigation paths documented
  • ✅ Alphabetical quick-find table complete

Task 2: Visual Documentation Sitemap (1 hour)​

  • Create /docs/DOCUMENTATION-SITEMAP.md
    • Add Mermaid category hierarchy diagram
    • Create document relationship graph
    • Add usage pattern statistics
    • Include navigation tips

Acceptance Criteria:

  • ✅ Mermaid diagram renders correctly on GitHub
  • ✅ All categories represented
  • ✅ Clear visual hierarchy shown

Task 3: Quick Reference Card (1 hour)​

  • Create /docs/QUICK-REFERENCE.md
    • Add copy-paste connection strings (GKE, Cloud SQL, Redis)
    • Create "Most-Used Documents" table
    • Add emergency contacts/resources
    • Include common commands cheat sheet

Acceptance Criteria:

  • ✅ All connection strings tested and working
  • ✅ Commands are copy-paste ready
  • ✅ Links to detailed docs provided

Afternoon Session (2-4 hours)​

Task 4: Reorganize Diagram Structure (2 hours)​

  • Create diagram subdirectories

    • mkdir docs/architecture/diagrams/
    • mkdir docs/architecture/rendered/ (optional)
    • mkdir docs/workflows/diagrams/

  • Move existing diagrams

    • Move diagrams/architecture/c1-system-context.md → docs/architecture/diagrams/c1-system-context.mmd
    • Move diagrams/architecture/c2-container-diagram.md → docs/architecture/diagrams/c2-container-diagram.mmd
    • Move diagrams/architecture/c3-gke-components.md → docs/architecture/diagrams/c3-gke-components.mmd
    • Move diagrams/architecture/c3-networking-components.md → docs/architecture/diagrams/c3-networking-components.mmd

  • Extract workflow diagrams from docs

    • Extract Mermaid from user-registration-flow.md → docs/workflows/diagrams/user-registration.mmd
    • Extract Mermaid from license-acquisition-workflow.md → docs/workflows/diagrams/license-acquisition.mmd
    • Extract Mermaid from heartbeat-mechanism.md → docs/workflows/diagrams/heartbeat-mechanism.mmd
    • Extract Mermaid from zombie-session-cleanup.md → docs/workflows/diagrams/zombie-cleanup.mmd
    • Extract Mermaid from graceful-license-release.md → docs/workflows/diagrams/graceful-release.mmd

  • Update all references to moved diagrams

    • Search and replace old diagram paths
    • Test all links

  • Add deprecation notice

    • Create diagrams/MIGRATION-NOTICE.md with redirect information

Acceptance Criteria:

  • ✅ All diagrams co-located with related documentation
  • ✅ Zero broken links after reorganization
  • ✅ Old diagrams/ directory has clear migration notice
  • ✅ Consistent .mmd extension for all Mermaid files
  • Create /docs/DIAGRAM-GALLERY.md
    • Add architecture diagrams section (4 diagrams)
    • Add workflow diagrams section (5 diagrams)
    • Include preview images (if rendered)
    • Link to source files and related docs
    • Add "Last Updated" for each diagram

Acceptance Criteria:

  • ✅ All 9 diagrams listed
  • ✅ Links to source and documentation working
  • ✅ Clear categorization

Task 6: Diagram Standards (1 hour)​

  • Create /docs/DIAGRAM-STANDARDS.md
    • Document file naming convention
    • Add versioning guidelines
    • Include Mermaid best practices
    • Document rendering options (GitHub, CLI, exports)
    • Add update process workflow

Acceptance Criteria:

  • ✅ Clear naming pattern documented
  • ✅ Examples provided for each diagram type
  • ✅ Mermaid style guide included

Day 2: Templates & Standards (4-5 hours)​

Morning Session (3 hours)​

Task 7: Create Template Directory (30 minutes)​

  • Create /docs/.templates/
    • Add README explaining template usage
    • Include template selection decision tree

Acceptance Criteria:

  • ✅ Directory created with README
  • ✅ Clear instructions for using templates

Task 8: Architecture Document Template (30 minutes)​

  • Create /docs/.templates/ARCHITECTURE-TEMPLATE.md
    • Add complete template structure (frontmatter, sections, footer)
    • Include example Mermaid diagram placeholder
    • Add component documentation pattern
    • Include decision documentation format
    • Add related documentation links section

Acceptance Criteria:

  • ✅ Template is comprehensive yet easy to use
  • ✅ All required metadata fields included
  • ✅ Example content helps guide usage

Task 9: Workflow Document Template (30 minutes)​

  • Create /docs/.templates/WORKFLOW-TEMPLATE.md
    • Add workflow metadata (implementation time, status)
    • Include sequence diagram placeholder
    • Add step-by-step flow structure
    • Include code example sections
    • Add error handling table
    • Include testing section

Acceptance Criteria:

  • ✅ Template covers all workflow aspects
  • ✅ Code example placeholders included
  • ✅ Testing guidance provided

Task 10: Guide Document Template (30 minutes)​

  • Create /docs/.templates/GUIDE-TEMPLATE.md
    • Add prerequisites checklist
    • Include step-by-step structure
    • Add verification steps for each section
    • Include troubleshooting pattern
    • Add "Next Steps" section

Acceptance Criteria:

  • ✅ Template is task-oriented
  • ✅ Verification steps included
  • ✅ Troubleshooting guidance provided

Task 11: Reference Document Template (30 minutes)​

  • Create /docs/.templates/REFERENCE-TEMPLATE.md
    • Add quick reference section
    • Include detailed reference structure
    • Add examples section
    • Include table formats for structured data

Acceptance Criteria:

  • ✅ Template optimized for lookups
  • ✅ Table structures provided
  • ✅ Example patterns included

Afternoon Session (1-2 hours)​

Task 12: Metadata Standard (30 minutes)​

  • Create /docs/METADATA-STANDARD.md
    • Document required frontmatter fields
    • Add optional frontmatter fields
    • Document footer requirements
    • Add change log format (for living docs)
    • Include compliance examples

Acceptance Criteria:

  • ✅ All metadata fields documented
  • ✅ Clear examples provided
  • ✅ Change log format specified

Task 13: Style Guide (1 hour)​

  • Create /docs/STYLE-GUIDE.md
    • Add writing style guidelines (voice, tone)
    • Document formatting conventions (headers, lists, links)
    • Include code block best practices
    • Add table formatting standards
    • Document file naming conventions
    • Add review checklist

Acceptance Criteria:

  • ✅ Comprehensive style guidelines
  • ✅ Clear examples for each rule
  • ✅ Review checklist usable

Task 14: Template Pilot (30 minutes)​

  • Apply templates to 2-3 existing documents
    • Apply architecture template to c1-system-context.md
    • Apply workflow template to user-registration-flow.md
    • Apply guide template to local-development.md
    • Gather feedback/iterate

Acceptance Criteria:

  • ✅ Templates work in practice
  • ✅ No major gaps identified
  • ✅ Improvements documented

Day 3: Content Gaps & Automation (2-3 hours)​

Morning Session (1-2 hours)​

Task 15: API Reference Stub (1 hour)​

  • Create /docs/reference/API-REFERENCE.md
    • Use reference template
    • Add placeholder for each endpoint
    • Document authentication requirements
    • Include example requests/responses
    • Add clear "Status: Work in Progress" banner

Acceptance Criteria:

  • ✅ Structure complete, ready to fill
  • ✅ Clear status indicated
  • ✅ Linked from master index

Task 16: Deployment Guide Stub (30 minutes)​

  • Create /docs/guides/DEPLOYMENT.md
    • Use guide template
    • Add deployment step placeholders
    • Include rollback procedure outline
    • Add verification checklist structure
    • Mark as "Planned for Phase 3"

Acceptance Criteria:

  • ✅ Outline complete
  • ✅ Clear timeline for completion
  • ✅ Prerequisites identified

Task 17: Prioritize Remaining Content (30 minutes)​

  • Update content gap prioritization
    • Review table in documentation-organization-plan.md
    • Schedule creation of database-schema.md
    • Schedule creation of REDIS-KEY-REFERENCE.md
    • Schedule creation of TROUBLESHOOTING.md
    • Schedule creation of CONFIGURATION-REFERENCE.md
    • Add to project task list

Acceptance Criteria:

  • ✅ All gaps have priority assigned
  • ✅ Timeline established for each
  • ✅ Owners assigned

Afternoon Session (1 hour)​

Task 18: Documentation Freshness Checker (30 minutes)​

  • Create /scripts/check-doc-freshness.py
    • Implement "Last Updated" field extraction
    • Add staleness calculation (configurable threshold)
    • Generate report of stale documents
    • Add CLI argument parsing
    • Test on docs/ directory

Acceptance Criteria:

  • ✅ Script identifies documents without "Last Updated"
  • ✅ Reports documents older than threshold
  • ✅ Output is clear and actionable
  • Create /scripts/check-links.py
    • Implement markdown link extraction
    • Add relative path validation
    • Check file existence for internal links
    • Generate broken link report
    • Test on docs/ directory

Acceptance Criteria:

  • ✅ Identifies all broken internal links
  • ✅ Clear report with file and line numbers
  • ✅ Handles edge cases (anchors, external links)

Task 20: CI/CD Integration (Optional, 30 minutes)​

  • Create GitHub Actions workflows
    • .github/workflows/doc-freshness-check.yml (weekly schedule)
    • .github/workflows/link-check.yml (on push/PR)
    • Test workflows on test branch

Acceptance Criteria:

  • ✅ Workflows run successfully
  • ✅ Notifications configured
  • ✅ Checks integrated into PR process

Final Verification & Cleanup​

  • Run link checker on entire docs/ directory
  • Fix all broken links
  • Verify all cross-references work

Task 22: Update Root README​

  • Update repository README.md with link to new INDEX
  • Add quick navigation section
  • Reference DOCUMENTATION-SITEMAP

Task 23: Update docs/README.md​

  • Add links to new navigation documents
  • Update organizational description
  • Highlight new templates and standards

Task 24: Team Communication​

  • Announce new documentation structure
  • Share quick reference guide
  • Provide template usage training
  • Gather initial feedback

Success Criteria - Final Check​

Quantitative Checks​

  • Documentation Score: 100/100 achieved
  • Document Count: 40+ documents (up from 33)
  • Cross-References: 100+ links (up from ~50)
  • Template Adoption: 3+ documents using templates
  • Broken Links: 0 broken links
  • Stale Documents: <5% older than 90 days

Qualitative Checks​

  • Navigation: New team member can find setup docs in <1 minute
  • Consistency: All documents have clear audience identification
  • Visual Quality: Diagrams are consistent and professional
  • Maintainability: Templates reduce doc creation time

Rollback Plan​

If issues arise during implementation:

  1. Diagram reorganization broke links:

    • Keep both old and new locations temporarily
    • Use symbolic links as transition mechanism
    • Update references gradually

  2. Templates too restrictive:

    • Mark templates as "recommended" not "required"
    • Iterate based on feedback
    • Create simplified versions

  3. Automation scripts failing:

    • Scripts are optional, documentation works without them
    • Debug and fix post-launch
    • No impact on core deliverables

Post-Implementation​

Week 1 Follow-Up​

  • Monitor usage analytics (if available)
  • Gather team feedback
  • Address quick wins from feedback
  • Update templates based on learnings

Month 1 Review​

  • Measure time-to-find improvements
  • Review template adoption rate
  • Audit document freshness
  • Update documentation roadmap

Notes and Observations​

Use this section during implementation to track:

  • Unexpected challenges
  • Time estimates accuracy
  • Template feedback
  • Improvement ideas
  • Things that worked well

Checklist Version: 1.0 Last Updated: 2025-11-23 Owner: [Assign owner] Status: Ready to Execute

Quick Reference Commands​

cd /path/to/coditect-cloud-infra
python scripts/check-links.py docs/

Freshness Check​

python scripts/check-doc-freshness.py --max-age 90

Find All Markdown Files​

find docs -name "*.md" | sort

Count Documents​

find docs -name "*.md" | wc -l

Search for Broken References​

grep -r "](../" docs/ | grep -v ".git"