Session Retrospective

Session Retrospective

Review the current session to extract learnings and propose improvements to CLAUDE.md files and skills, making Claude more autonomous with each session.

Overview

This skill analyzes the conversation history to identify learnings that should be codified into:

• Project CLAUDE.md — Project-specific patterns, commands, and conventions
• Global ~/.claude/CLAUDE.md — Universal coding styles, Claude behaviors, and cross-project patterns
• Skills — Multi-step workflows worth automating (the most valuable output)

Skill proposals are the highest-value output of a retrospective. A single well-designed skill saves more future time than a dozen CLAUDE.md entries. Actively hunt for skill opportunities — do not default to CLAUDE.md when a skill would be more appropriate.

Unlike /revise-claude-md which focuses on missing context, this skill provides broader analysis including corrected approaches, skill opportunity detection, and skill improvement opportunities.

Quick Start

/session-retrospective

No arguments needed. The skill analyzes the current session context automatically.

Workflow

Phase 1: Analyze Session

Gather full session data and reflect on it:

1. Extract full transcript history (Compact で失われた内容も含む完全な記録):

   extract-session-history.ts
   

   stdout に出力されたファイルパスを Read ツールで読み込む。

2. Review extracted history focusing on:

   • Tasks performed and their outcomes
   • Errors encountered and how they were resolved
   • Questions asked to the user (signals missing context)
   • User corrections to Claude's approach
   • Repeated patterns of work
   • Tool usage patterns (Tool Usage Summary セクション参照)
   • Compact boundaries (セッション内のフェーズ遷移を示す)

3. Git activity (if in a git repository):

   git log --oneline -20
   git diff --stat HEAD~5..HEAD
   

4. Current context files:

   • Read project CLAUDE.md (if exists)
   • Read global ~/.claude/CLAUDE.md
   • List existing skills in ~/.claude/skills/

Phase 2: Categorize Learnings

Classify each learning into categories. See references/learning-categories.md for detailed definitions and examples.

Summary of categories:

1. Missing Context — Information Claude needed but did not have

   • Example: "This project uses pnpm, not npm"
   • Example: "Always run nix flake check before darwin-rebuild"

2. Corrected Approaches — User corrections to Claude's behavior

   • Example: "User prefers Japanese commit messages"
   • Example: "Use gh for GitHub URLs, not WebFetch"

3. Repeated Workflows — Multi-step procedures performed multiple times

   • Example: "Check CI → read logs → fix → push → wait (repeated 3 times)"
   • Example: "Every nix change: edit → nix flake check → darwin-rebuild switch"

4. Tool/Library Knowledge — Discoveries about specific tools or APIs

   • Example: "ast-grep requires stopBy: end for relational rules"
   • Example: "Chrome DevTools MCP snapshot should be taken before interaction"

5. Preference Patterns — User style or preference observations

   • Example: "User prefers concise output, dislikes verbose explanations"
   • Example: "User wants draft PRs with English descriptions"

Phase 2.5: Skill Opportunity Scan

After categorizing learnings, perform a dedicated scan for skill opportunities across ALL categories — not just "Repeated Workflows". See references/skill-opportunity-detection.md for the full detection framework.

For every learning in every category, apply these quick checks:

1. The /invoke test: "Would the user type /skill-name for this?"
2. The orchestration test: "Does this involve 3+ steps with tool chaining?"
3. The teaching test: "Did the user describe a multi-step process?"
4. The cross-session test: "Did the user signal this is a recurring task?"
5. The ecosystem test: "Does this resemble an existing skill's structure?"
6. The systematization test: "Did this session consume external knowledge AND encode it into a reusable tool? (Requires 2+ indicators from Signal 6 in skill-opportunity-detection.md)"

If ANY check passes, flag the learning as a skill candidate and carry it forward to Phase 3 routing with a skill proposal bias.

Explicit requirement: Consider at least one skill proposal per retrospective. If no learnings pass the checks above, document why in the results ("No skill opportunities detected because: [reason]"). This forces active evaluation rather than passive defaulting to CLAUDE.md.

Scan existing skills for modification opportunities:

ls ~/.claude/skills/

For each skill that was used or relevant to the session, check:

• Was the skill missing information that was discovered during the session?
• Did the workflow deviate from what the skill prescribed?
• Would a new reference file improve the skill?

Generalization Check

For each identified learning, also ask:

"Is this specific to a narrow context (tool X, environment Y, one-off situation Z), or does it reflect a broader methodological/behavioral principle?"

• If broader principle exists: Document the general principle as the primary entry. Include the specific instance as a concrete example, not as the title/framing. Route to ~/.claude/CLAUDE.md with the general principle.

• If genuinely narrow: Keep specific, but flag it: "Does this narrow symptom suggest a general principle that was missed?"

Anti-pattern to avoid (from real session):

• ✗ Extracted: "non-interactive environment debugging tip" (env-specific framing)
• ✓ Should extract: "investigation plans must include direct observation means" (general principle) with "non-interactive env" as one concrete example

Artifact Pipeline Check: Beyond generalizing facts, also ask:

"Did this session produce a reusable artifact? If so, is the artifact-creation pipeline itself generalizable across domains?"

If yes, recommend the appropriate mechanism using this routing:

Is the methodology a repeatable workflow the user would invoke by name?
  YES → Skill (standard). Use skill-creator to build it.
  NO → Is it background knowledge that should always be available?
    YES → Skill (user-invocable: false, Reference content).
    NO → Does it need constrained tool access (read-only analysis)?
      YES → Custom Agent (agents/*.md). Use context: fork + agent: from skills.
      NO → Does it augment an existing skill's evaluation criteria?
        YES → Reference file in existing skill's references/.
        NO → Skill (standard) as default. Most flexible option.

Default to Skill (standard) when uncertain — it matches the user's preference for skill-based workflows.

Example:

• Artifact: Evaluation agent derived from Anthropic PDF (specific instance)
• Pipeline: "Methodology document → extract criteria → create evaluation tool" (generalizable)
• Recommended: Skill (standard) — e.g., /review-accessibility [url]
• Alternative: Custom Agent if read-only constraint is needed

Phase 3: Route Proposals

Determine where each learning belongs using routing logic. See references/routing-logic.md for the full decision tree.

Quick routing summary:

• Project-specific (contains project paths, build commands, framework-specific details) → Project CLAUDE.md

• Universal/cross-project (coding style, general tool usage, Claude's behavior) → ~/.claude/CLAUDE.md

• Skill opportunity (detected via Phase 2.5 scan — complex workflow, user-taught process, cross-session repetition signal, or tool orchestration pattern) → New skill or skill modification proposal

• Tool-specific knowledge for existing skill → Skill modification proposal

Phase 4: Draft Proposals

For each routed learning, draft a concrete proposal:

CLAUDE.md additions:

• Format: One line per concept (consistent with /revise-claude-md)
• Show exact placement (after which section heading)
• Use diff format for clarity
• Example:

  ## Development Commands
  + nix flake check - Validate Nix syntax before applying changes
  

New skill proposals (use template from references/skill-opportunity-detection.md):

• Proposed name and invocation example
• When to use (trigger scenario)
• Why-not-CLAUDE.md justification (mandatory — why this needs to be a skill)
• Workflow outline (numbered steps with tools used)
• Parameters (what would be parameterized)
• Similar existing skill (for calibration)
• Estimated complexity (Simple / Medium / Complex)

A skill proposal without a why-not-CLAUDE.md justification is incomplete.

Skill modification proposals:

• Show before/after diff of changes
• Explain rationale for the modification
• Example:

  ## Quick Start
  
  - curl -s https://api.example.com/health
  + curl -sf https://api.example.com/health - Add -f flag to fail on HTTP errors
  

Phase 5: Present and Apply

Present all proposals grouped by target:

## Session Retrospective Results

### Project CLAUDE.md Proposals (N items)
[numbered proposals with diffs]

### Global CLAUDE.md Proposals (N items)
[numbered proposals with diffs]

### Skill Proposals (N items)
[new skills and modifications]

---
Which proposals would you like to apply?
(all / specific numbers like 1,3,5 / none)

After user approval:

• Apply CLAUDE.md changes with Edit tool
• Create new skills (use skill-creator toolchain or direct file creation)
• Apply skill modifications with Edit tool
• Report what was applied

Guidelines

What NOT to Propose

• Information Claude already knows (well-known concepts, standard library usage)
• Temporary or one-off decisions that don't generalize
• Information already present in the target CLAUDE.md or skill
• Overly specific instructions that reduce flexibility

Proposal Quality

• Each proposal should be actionable (specific text to add, not vague suggestions)
• Each proposal should justify its token cost (high signal-to-noise ratio)
• Prefer additions that prevent future mistakes over documenting facts
• Keep proposals concise — one line per concept for CLAUDE.md entries

Respecting Existing Content

• Read existing CLAUDE.md files before proposing additions
• Do not duplicate existing entries
• Match the style and language of the existing file (Japanese or English)
• Place additions in the appropriate section (do not append everything at the end)

Language Matching

When proposing CLAUDE.md additions:

• Detect the primary language of the target file
• Write proposals in that language
• For mixed-language files, match the language of the relevant section

Related Skills

• /revise-claude-md — Focused CLAUDE.md updates based on missing context (narrower scope)
• skill-improver — Evaluates and improves existing skill quality
• skill-creator — Creates new skills from scratch
• skill-tester — Validates skill behavior after modifications