Chapter 23: Session Documentation Skill

Status: Production-Validated (Jan 2, 2026) Difficulty: Beginner Time: 10 minutes ROI: 67% faster documentation (30 min → 10 min)

Problem

Documenting session work requires updating 3 files manually:

Entry file (memory-bank/learned/entry-XXX-topic.md)
Roadmap (CURRENT/{branch}/{branch}-ROADMAP.md)
system-status.json (memory-bank/always/system-status.json)

Pain Points:

Easy to forget one of the 3 files
Roadmap task status gets stale
Entry numbers must be tracked manually
30+ minutes per session to document properly

Solution: Session Documentation Skill

A single /document command that:

✅ Creates Entry with next available number
✅ Updates roadmap (moves completed tasks)
✅ Updates system-status.json
✅ Creates single commit with all changes

Advanced: Pattern Analysis Engine 🆕

For automatic suggestions about creating skills/rules/blueprints:

→ See Chapter 32: Document Automation for:

13-step workflow with pattern analysis
5-type suggestion engine (Skill, Rule, Blueprint, CORE-PATTERNS, Memory)
Decision matrix (when to create what)

This chapter covers the basic /document workflow. Chapter 32 covers the advanced pattern analysis.

Setup (10 min)

Step 1: Create Skill Directory

mkdir -p ~/.claude/skills/session-documentation-skill

Step 2: Create SKILL.md

---
name: session-documentation-skill
description: |
  Automates complete session documentation workflow: Entry creation + roadmap update + 
  system-status.json update. Use when ending a session, documenting completed work, or
  when user says "/document". Saves 67% time (30 min → 10 min).
---

## When to Use

- Session ending with completed work
- User says "/document" or "document this session"
- Major feature/fix completed
- Before creating PR

## Workflow (9 Steps)

### Phase 1: Context Gathering
1. **Git Context**: Run `git status` and `git log --oneline -5`
2. **Analyze Work**: Identify what was accomplished this session

### Phase 2: Documentation (Interactive)
3. **Entry Creation**: Create `memory-bank/learned/entry-XXX-topic.md`
   - Auto-increment entry number
   - Include: Problem, Solution, Evidence, Time savings

4. **Roadmap Update**: Update `CURRENT/{branch}/{branch}-ROADMAP.md`
   - Move completed tasks from "Current" to "Completed"
   - Add Entry reference
   - Show diff to user

5. **Status Update**: Update `memory-bank/always/system-status.json`
   - Add feature to `features` array
   - Update `recent_fixes` array
   - Update `latest_entries`

### Phase 3: Commit
6. **Single Commit**: All 3 files in one commit
   - Message: "docs: Entry #XXX - [topic]"

### Phase 4: Persistence
7. **Memory MCP**: Store session summary
   - `mcp__basic-memory__write_note(folder="sessions")`

## Entry Template

```markdown
# Entry #XXX: [Title]

**Date**: YYYY-MM-DD
**Branch**: {current_branch}
**Status**: ✅ Complete

## Problem
[What issue was being solved]

## Solution
[How it was solved]

## Evidence
- Before: [metrics]
- After: [metrics]
- Improvement: [percentage]

## Files Changed
- file1.js
- file2.md

## Time Savings
- Manual: X minutes
- With skill: Y minutes
- ROI: Z%

Roadmap Update Pattern

## ✅ COMPLETED (This Session)
+ | Task description | ✅ COMPLETE | Entry #XXX |

## 🎯 Current Sprint
- - [ ] Task description

### Step 3: Add Trigger

In `AUTOMATIC-TOOL-TRIGGERS.md`, add:

```yaml
document work/create entry/update roadmap/mark task complete/session documentation:
  → session-documentation-skill
  → Evidence: "Jan 2, 2026 - Automates Entry + roadmap + status updates (67% faster)"
  NEVER: Manual 3-file updates (use /document)

Step 4: Test

Start fresh session and say:

/document

Expected:

✅ Skill activates
✅ Prompts for Entry topic
✅ Creates Entry file
✅ Shows roadmap diff
✅ Updates status JSON
✅ Creates commit

Usage Examples

End of Session

User: /document

Claude: I'll use session-documentation-skill.

Step 1: Git Context
- Branch: dev-Knowledge
- Recent commits: [...]

Step 2: Analyzing work...
- Completed: Pre-prompt optimization
- Evidence: 28k→9k chars (68% reduction)

Step 3: Creating Entry #228...
[Shows Entry content]

Step 4: Updating roadmap...
[Shows diff]

Step 5: Updating system-status.json...
[Shows changes]

Step 6: Creating commit...
docs: Entry #228 - Pre-prompt optimization

✅ Documentation complete!

Mid-Session Checkpoint

User: Document what we've done so far

Claude: I'll use session-documentation-skill.
[Same workflow but marks task as "in progress"]

Benefits

Time Savings

Task	Manual	With Skill	Savings
Entry creation	10 min	3 min	70%
Roadmap update	10 min	2 min	80%
Status update	5 min	2 min	60%
Git commit	5 min	3 min	40%
Total	30 min	10 min	67%

Quality Improvements

✅ Never forget to update roadmap
✅ Entry numbers auto-increment
✅ Consistent Entry format
✅ All changes in single commit
✅ Session history in Memory MCP

Integration with SESSION-PROTOCOL.md

Update memory-bank/always/SESSION-PROTOCOL.md:

## 🏁 SESSION END PROTOCOL

**Before Ending Any Session**:

1. Use `/document` command (activates session-documentation-skill)
2. Review Entry, roadmap diff, and status changes
3. Confirm commit
4. Never stop mid-feature - complete or create checkpoint

Troubleshooting

Issue: Skill not activating

Check trigger:

grep -i "document" memory-bank/always/AUTOMATIC-TOOL-TRIGGERS.md

Add if missing:

document work/create entry/update roadmap:
  → session-documentation-skill

Issue: Entry number wrong

Find latest Entry:

ls memory-bank/learned/entry-*.md | tail -1
# Or:
grep -r "Entry #" memory-bank/learned/ | grep -oE "Entry #[0-9]+" | sort -t# -k2 -n | tail -1

Issue: Roadmap not updating

Check roadmap path:

ls CURRENT/$(git branch --show-current)/*ROADMAP*.md

Chapter 4: Task Tracking System (roadmap basics)
Chapter 12: Memory Bank Hierarchy (Entry organization)
Chapter 13: Claude Code Hooks (automation)
Chapter 31: Branch-Aware Development (ROADMAP templates) 🆕
Chapter 32: Document Automation (pattern analysis) 🆕

Implementation Time: 10 minutes Evidence: Production production (Entry #228, #229 created with skill) Last Updated: 2026-01-19