Session Documentation Skill: > **Purpose:** Enforce comprehensive documentation as part of work completion
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Session Documentation Skill
Purpose: Enforce comprehensive documentation as part of work completion Created: 2025-12-25 Trigger: Feature completion, bug fixes, significant changes, session end, handoff requests
Why This Skill Exists
Documentation debt compounds session over session. Without proactive documentation:
- Future sessions rebuild context from scratch (~50K tokens)
- Handoff errors occur (e.g., Block 10 constraints implemented but not registered)
- Users must prompt 3x for comprehensive docs
This skill ensures documentation is part of "done" - not an afterthought.
When This Skill Activates
Activate automatically when:
- Feature implementation completed - Any new capability added
- Bug fix committed - Any issue resolved
- Significant code change - More than trivial edits
- Session ending - User says "done", "finished", "ending session"
- Handoff requested - User asks for summary/handoff/status
- PR ready - Before creating pull request
Required Documentation Outputs
Minimum Required (ALL must be present)
## What Was Done
- [ ] Bullet list of completed tasks
- [ ] Files created/modified (with line ranges)
- [ ] Tests added/modified
## Why It Was Done
- [ ] Context/motivation
- [ ] Problem being solved
- [ ] Related issue/task reference
## How to Verify
- [ ] Commands to run
- [ ] Expected output
- [ ] Success criteria
## What Remains
- [ ] Incomplete tasks
- [ ] Known limitations
- [ ] Follow-up work needed
Recommended (Include when applicable)
## Decisions Made
- [ ] Design choices and rationale
- [ ] Alternatives considered and rejected
- [ ] Trade-offs accepted
## Gotchas and Warnings
- [ ] Common pitfalls
- [ ] Non-obvious behavior
- [ ] Dependencies or prerequisites
## Related Updates
- [ ] Documentation files updated
- [ ] CHANGELOG entry added
- [ ] README updated (if applicable)
For Session Handoffs (REQUIRED at session end)
## Session Summary
### Current State
- System status (working/broken/partial)
- Database state
- Container status
### Completed This Session
- Task 1 - commit hash
- Task 2 - commit hash
### Blocked Items
- Item 1 - reason
- Item 2 - reason
### Next Steps (Prioritized)
1. Highest priority
2. Second priority
3. Third priority
### Verification Commands
```bash
# Command to verify current state
Key Files
| File | Purpose |
|---|---|
| path/to/file | Description |
---
## Documentation Quality Checklist
Before marking documentation "complete," verify:
### Structure
- [ ] Clear headings and sections
- [ ] Bullet points for scanability
- [ ] Code blocks for commands/examples
- [ ] Tables for structured data
### Content
- [ ] Specific, not vague ("added X to Y" not "made changes")
- [ ] Actionable next steps
- [ ] Verifiable claims (commands to prove it works)
- [ ] No orphan references (linked docs exist)
### Completeness
- [ ] Someone unfamiliar could understand and continue
- [ ] No assumed knowledge not documented
- [ ] Edge cases and exceptions noted
- [ ] Future sessions won't ask "what did we do?"
---
## Output Locations
Documentation should be created in appropriate locations:
| Type | Location | Example |
|------|----------|---------|
| Session handoff | `docs/development/SESSION_HANDOFF_YYYYMMDD.md` | Ending a session |
| Feature docs | `docs/architecture/` or `docs/guides/` | New capability |
| Bug fix notes | Commit message + CHANGELOG | Issue resolution |
| Technical details | `docs/development/` | Implementation specifics |
| Postmortem | `docs/development/POSTMORTEM_*.md` | Session analysis |
---
## Anti-Patterns to Avoid
### Don't: Minimal Response
"Fixed the bug in scheduler.py"
### Do: Comprehensive Response
```markdown
## Bug Fix: Scheduler Timezone Mismatch
### What Was Done
- Fixed UTC/local timezone conversion in `scheduler.py:145-160`
- Added explicit timezone handling in `_calculate_hours()`
- Added test case for HST timezone edge case
### Files Modified
- `backend/app/scheduling/scheduler.py` (lines 145-160)
- `backend/tests/test_scheduler.py` (added test_hst_conversion)
### How to Verify
```bash
pytest backend/tests/test_scheduler.py::test_hst_conversion -v
Root Cause
Scheduler assumed UTC but database stored local time (HST).
---
## Integration with Other Skills
This skill complements:
| Skill | Relationship |
|-------|--------------|
| `constraint-preflight` | Both verify "done" criteria |
| `code-review` | Documentation is part of review |
| `pr-reviewer` | PR descriptions require docs |
| `changelog-generator` | Feeds into release notes |
---
## Verification Script
Run this to check documentation exists:
```bash
# Check for recent session docs
find docs/development -name "SESSION_*.md" -mtime -1 | head -5
# Check for handoff docs
find docs/development -name "*HANDOFF*.md" -mtime -1 | head -5
# Check CHANGELOG updated
git log --oneline -5 | grep -i "changelog\|docs"
Example: Full Session Documentation
# Session Handoff: 2025-12-25
## Session Summary
### Current State
- Backend: Running (Docker)
- Frontend: Running (npm dev)
- Database: 87 assignments in Block 10
### Completed This Session
- [x] Fixed constraint registration gap (commit abc1234)
- [x] Added schema versioning feature (commit def5678)
- [x] Created Docker workaround docs (commit ghi9012)
### Blocked Items
- MCP tool `get_static_fallbacks` - needs backend endpoint
- Heatmap API mismatch - requires backend changes
### Next Steps (Prioritized)
1. Address heatmap API bug (frontend shows unsupported options)
2. Fix swap marketplace permissions for admin role
3. Create person profile for admin user
### Verification Commands
```bash
# Check constraints
docker exec backend python -c "from app.scheduling.constraints.manager import ConstraintManager; print(len(ConstraintManager.create_default().constraints))"
# Check schedule
curl -s http://localhost:8000/api/v1/schedule/block/10 | jq '.assignments | length'
Key Files
| File | Purpose |
|---|---|
backend/app/scheduling/constraints/manager.py | Constraint registration |
docs/development/SESSION_HANDOFF_20251225.md | This handoff |
scripts/verify_constraints.py | Pre-flight verification |
---
## Enforcement
This skill should be enforced through:
1. **Habit** - Check documentation checklist before saying "done"
2. **Prompts** - If minimal docs given, prompt for expansion
3. **PR Review** - Documentation required for PR approval
4. **CI Check** - Verify handoff doc exists for session branches
---
## Related Documentation
- [CLAUDE_HANDOFF_CHECKLIST.md](../../../docs/development/CLAUDE_HANDOFF_CHECKLIST.md) - Handoff protocol
- [AI_RULES_OF_ENGAGEMENT.md](../../../docs/development/AI_RULES_OF_ENGAGEMENT.md) - Work rules
- [POSTMORTEM_BLOCK10_SESSION.md](../../../docs/development/POSTMORTEM_BLOCK10_SESSION.md) - Why this skill exists
---
*Remember: Documentation is not optional polish - it's how future sessions avoid starting from zero.*
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