Agent Skill
2/7/2026

learning-capture

Multi-trigger, dual-target learning capture patterns. Use this skill to understand how to capture learnings at different points in the development workflow and route them to appropriate targets (codebase docs or plugin improvements).

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daviswhitehead
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npx skills add daviswhitehead/product-playbook-for-agentic-coding-plugin

SKILL.md

Namelearning-capture
DescriptionMulti-trigger, dual-target learning capture patterns. Use this skill to understand how to capture learnings at different points in the development workflow and route them to appropriate targets (codebase docs or plugin improvements).

name: learning-capture description: Multi-trigger, dual-target learning capture patterns. Use this skill to understand how to capture learnings at different points in the development workflow and route them to appropriate targets (codebase docs or plugin improvements).

Learning Capture

This skill provides patterns for capturing learnings at the right moments and routing them to the right places. Learnings compound over time - the more you capture, the more future work benefits.

Three Trigger Points

Learnings should be captured at three key moments, each with different depth and focus:

1. After Chat Session (Lightweight)

When: At the end of any significant agentic coding session

Focus: Quick capture of immediate insights

  • What did we learn?
  • What should be documented?
  • Any quick process improvements?

Depth: Brief, 2-5 bullet points Time: 2-5 minutes

Example Output:

## Session Learning: 2026-01-25

- Discovered that the auth middleware requires explicit error handling
- Found undocumented API endpoint at `/internal/health`
- Process improvement: Always check existing tests before writing new ones

Session Handoff (if work continues later): Also capture state for the next session:

  • What's done and what's next
  • Decisions made with reasoning
  • Docs that need updating (stale conclusions)
  • Where to start next session

2. After Project Completion (Comprehensive)

When: At project milestones or completion

Focus: Thorough retrospective

  • What worked well?
  • What didn't work?
  • What to do differently next time?

Depth: Full retrospective with multiple sections Time: 15-30 minutes

Sections to Cover:

  • Project summary and outcomes
  • What went well (successes, effective practices)
  • What could be improved (challenges, pain points)
  • Process improvements (suggested changes)
  • Template refinements (updates needed)
  • Action items (next steps)

3. After Overcoming Blockers (Targeted)

When: Immediately after solving a difficult problem

Focus: Capture while fresh

  • What was painful?
  • How was it solved?
  • How to prevent next time?

Depth: Focused on the specific blocker Time: 5-10 minutes

Sections to Cover:

  • Context: What were you trying to do?
  • Initial hypothesis: What did you think was wrong?
  • Actual root cause: What was actually wrong?
  • Solution: How was it fixed?
  • Prevention: How to avoid this in the future?

Two Output Targets

Learnings can improve two distinct areas:

Target 1: Codebase Documentation

What goes here: Project-specific knowledge

  • Patterns and gotchas for this codebase
  • Architecture decisions and rationale
  • Debugging solutions for this project
  • Troubleshooting guides
  • API quirks and workarounds

Location: [current-codebase]/docs/ (appropriate subfolder)

Subfolder Guidelines:

Content TypeLocation
Problem solutionsdocs/solutions/
General learningsdocs/learnings/
Architecture decisionsdocs/architecture/
Troubleshootingdocs/troubleshooting/

Target 2: Plugin/Workflow Improvements

What goes here: Process and tool improvements

  • Workflow optimizations
  • New patterns to add to skills
  • Command/agent refinements
  • Template improvements
  • Cross-project patterns

Location: Plugin repository (commands, skills, or docs)

Improvement Types:

TypeAction
Command enhancementUpdate command markdown
New skill patternAdd to skill SKILL.md
Template fixUpdate resources/templates/
New workflowCreate new command or skill

Deep Session Analysis Patterns

When performing a deep retrospective (analyzing SpecStory session files in .specstory/history/), use these patterns to extract insights the agent missed during the session.

Pattern: Repetition Detection

Signal: Same action performed multiple times without progress. How to detect: Scan for repeated file reads (same path 3+ times), repeated errors, repeated user corrections, and solution/revert cycles. What it means: The agent lacked context, had a faulty mental model, or didn't learn from previous attempts. Improvement: Add the missing context to CLAUDE.md or MEMORY.md so future sessions start with it.

Pattern: Frustration Signal Detection

Signal: User communication shifts from collaborative to directive. Severity scale:

  1. Mild — User provides more specific instructions than before
  2. Moderate — Short corrective phrases ("no", "not that", "just X")
  3. Strong — User takes over the task themselves
  4. Severe — User explicitly states frustration Improvement: Identify the specific mismatch and encode it as a behavioral rule.

Pattern: Wasted Effort Detection

Signal: Work that didn't contribute to the final outcome. How to detect: Compare final git diff to all changes during session, look for "let me try a different approach" patterns, count debugging cycles per issue (>2 = wasted). Improvement: Document the correct approach so future sessions don't repeat wrong paths.

Pattern: Scope Drift Detection

Signal: Work expanded significantly beyond original request. How to detect: Compare first user message to final summary. Count files touched vs expected. Improvement: If unintentional, add scope-check trigger to MEMORY.md.

Pattern: CLAUDE.md Growth

Signal: CLAUDE.md size exceeds 32,000 chars or triggers the performance warning (>40k). How to detect: Run wc -c CLAUDE.md. Check for RESOLVED issues still inline, niche guides that belong in docs/guides/, duplicate content (e.g., test commands listed in both Quick Reference and a Common Workflows section). Root cause: The learnings promotion workflow is additive-only — it promotes content UP to CLAUDE.md but never demotes stale content DOWN to docs/guides/ or docs/learnings/. Improvement: Before promoting new learnings to CLAUDE.md, check size and archive stale content. Resolved issues should be moved to docs/learnings/resolved-issues.md. Niche guides should be moved to docs/guides/ with a 1-line reference in CLAUDE.md.


YAML Frontmatter Schema

All learnings should include searchable frontmatter:

---
title: "Brief descriptive title"
date: YYYY-MM-DD
trigger: chat-session | project-completion | blocker-overcome
target: codebase | plugin | both
category: performance | database | integration | workflow | debugging | testing | security | design | generation | infrastructure
tags: [relevant, searchable, keywords]
severity: critical | high | medium | low
module: "affected_module_name"
---

Field Guidelines

trigger: Which trigger point captured this learning

  • chat-session: Quick session insight
  • project-completion: Full retrospective
  • blocker-overcome: Problem solution

target: Where the improvement applies

  • codebase: This specific project
  • plugin: The playbook plugin itself
  • both: Applies to both

category: Primary classification

  • performance: Speed, efficiency issues
  • database: Data layer issues
  • integration: External service issues
  • workflow: Process issues
  • debugging: Investigation patterns
  • testing: Test-related learnings
  • security: Security-related learnings
  • design: Visual design, UX, branding learnings
  • generation: AI content/image generation learnings
  • infrastructure: DevOps, CI/CD, deployment learnings

severity: Impact level

  • critical: Must know, high impact
  • high: Important, significant impact
  • medium: Good to know
  • low: Nice to have

tags: Searchable keywords (3-7 tags)

module: Specific code module affected (if applicable)

Decision Matrix: Which Target?

Use this matrix to decide where learnings should go:

Learning TypeCodebase?Plugin?
Bug fix for specific codeYesNo
General debugging patternMaybeYes
Architecture decisionYesNo
Workflow improvementNoYes
Template enhancementNoYes
Cross-project patternMaybeYes
Project-specific gotchaYesNo
Tool usage tipNoYes

Capture Workflow

Step 1: Identify Trigger

Ask: "What kind of learning moment is this?"

  • End of session → Lightweight capture
  • Project done → Comprehensive retrospective
  • Solved hard problem → Targeted capture

Step 2: Identify Target

Ask: "Who benefits from this learning?"

  • Just this project → Codebase docs
  • Future projects/workflows → Plugin improvements
  • Both → Document in both places

Step 3: Use Appropriate Template

Use template from resources/templates/learnings.md and fill sections based on trigger type.

Step 4: Add Frontmatter

Add YAML frontmatter for searchability.

Step 5: Save to Correct Location

  • Codebase: docs/learnings/YYYY-MM-DD-topic.md
  • Plugin: Create PR to plugin repo

Step 5.5: Deep Analysis (Optional, Project Completion Only)

If session history files are available (.specstory/history/*.md):

  • Spawn a research agent to scan for repetition patterns, frustration signals, wasted effort, scope drift
  • Quantify findings with examples and estimated time impact
  • Compare deep findings against the standard retrospective to identify blind spots
  • Feed improvement actions into Step 6 alongside standard learnings

Step 6: CLAUDE.md Health Check & Promote Key Learnings

Before promoting, check CLAUDE.md health:

  1. Run wc -c CLAUDE.md to check current size
  2. If over 32,000 chars (80% of 40k limit), trigger a trimming pass before adding content:
    • Archive RESOLVED known issues to docs/learnings/resolved-issues.md
    • Move niche/domain-specific guides to docs/guides/
    • Remove content that duplicates the Quick Reference section
    • Condense verbose sections that can be replaced with a 1-line reference + link
  3. If over 40,000 chars, trimming is mandatory before any promotion

Promotion hierarchy (highest = most actionable):

  • Code/scripts (automatic) > CLAUDE.md (always visible) > Templates (on-demand) > Docs (reference)
  • Ask: "Which 2-3 learnings should be promoted? Where should they live?"
  • Implement the promotions (edit CLAUDE.md, create template, update script)

Demotion — content should also move DOWN the hierarchy over time:

  • RESOLVED known issues → docs/learnings/resolved-issues.md
  • Niche workflow guides (used by <1 session/month) → docs/guides/
  • Content duplicated elsewhere in CLAUDE.md → delete
  • Stale milestone-specific content → delete or archive

Integration Points

This skill supports:

  • /playbook:learnings command (primary interface)
  • /playbook:debug (captures blocker-overcome learnings)
  • /playbook:work (suggests session learnings)

Best Practices

  1. Capture while fresh - Don't wait, details fade quickly
  2. Be specific - Vague learnings don't help
  3. Include context - Future you needs to understand why
  4. Add tags generously - Makes finding easier
  5. Link to code - Reference specific files/lines when relevant
  6. Update existing docs - Sometimes better than creating new ones
  7. Review periodically - Old learnings may need updates

Every learning captured makes future work easier. Compound your knowledge.

Skills Info
Original Name:learning-captureAuthor:daviswhitehead