End-of-session debrief to capture learnings and keep documentation current.
When to Run
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Before ending a productive session
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When context window is getting full
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After significant conversations about preferences, workflows, or decisions
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Periodically as maintenance
Workflow
Phase 1: Gather Context
Read current state:
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.claude/memories/about-taylor.md
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Current profile
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.claude/memories/index.json
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Existing memories
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CLAUDE.md
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Current instructions (skim for relevant sections)
Get today's date:
date +%Y-%m-%d
Phase 2: Analyze Conversation
Review the conversation for memory-worthy moments:
Preferences (category: preference )
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"I like X better than Y"
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"I prefer...", "I don't want..."
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Choices made when given options
Corrections (category: workflow or context )
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"Actually...", "No, that's not right"
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Clarifications about how something works
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Misunderstandings corrected
Personal Context (category: personal or context )
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Life events (moves, job changes, milestones)
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Schedule or routine changes
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Health, relationships, living situation
Workflow Insights (category: workflow )
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How Taylor actually uses tools vs. assumptions
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Shortcuts or patterns observed
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Friction points identified
Decisions (category: project or workflow )
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Architecture or design choices
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Tool/technology selections
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Process changes
Phase 3: Present Findings
Present findings one category at a time:
Proposed Memories
Memory 1: [Brief title]
Category: preference Content: Taylor prefers X over Y because Z. Source: [Quote or paraphrase from conversation]
Action? [Save / Skip / Edit]
Phase 4: Updates to about-taylor.md
Check if any new information should be added to the profile:
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Job status changes
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New skills or interests
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Updated preferences that are significant enough for the profile
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Life changes (location, situation)
Suggested Profile Updates
Update 1: [Section]
Current: [What it says now, if anything] Proposed: [New or updated text] Reason: [Why this matters]
Action? [Apply / Skip / Edit]
Remember: about-taylor.md has a 300-line limit. Only add significant, lasting information.
Phase 5: Updates to CLAUDE.md
Check if any workflow or instruction changes should be documented:
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New conventions established
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Process improvements agreed upon
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Corrections to existing instructions
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New skills or capabilities added
Suggested CLAUDE.md Updates
Update 1: [Section]
Location: [Which section] Change: [What to add/modify] Reason: [Why this should be documented]
Action? [Apply / Skip / Edit]
Phase 6: Execute Approved Changes
For approved memories:
- Create JSON file: .claude/memories/YYYY-MM-DD-NNN.json
{ "date": "YYYY-MM-DD", "category": "preference|workflow|context|project|personal", "content": "Concise description (1-2 sentences)", "source": "conversation|observation|correction" }
- Update .claude/memories/index.json
For approved profile/CLAUDE.md updates:
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Apply edits to the relevant files
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Confirm changes
Phase 7: Summary
Debrief Complete
Memories saved: N Profile updates: N CLAUDE.md updates: N Skipped: N
Next debrief recommended: [if context is still full, suggest continuing]
Memory JSON Format
{ "date": "2026-01-20", "category": "preference", "content": "Taylor prefers not to over-engineer tooling for rare edge cases.", "source": "conversation" }
Tips
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Be selective - not every detail needs a memory
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Memories should be durable (still relevant in weeks/months)
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Profile updates should be significant life/work changes
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CLAUDE.md updates should be reusable conventions, not one-off fixes
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When in doubt, ask rather than skip