AI Collaboration Retrospective

Post-session systematic review tool. Eight-dimension deep analysis drives a continuous improvement loop for AI-assisted development.

Core Principles

• Conversation context is the data source: The complete conversation history of the current session is already in context — no external data fetching needed
• Progressive loading: Detailed evaluation criteria live in references/analysis_dimensions.md — load on demand
• Self-reflection first: Examine the AI's own shortcomings before analyzing user-side improvements. This is NOT about criticizing the user — it's about finding efficiency gains in the "AI + Human" collaboration
• Quantify everything: Every finding must reference specific conversation turns, wasted operations, and include counterfactual reasoning ("If X had been done, Y turns could have been saved")
• Dig deep: Don't settle for "no findings." Complete the self-check list for each dimension before declaring it clean

Execution Model

This skill is pure LLM instruction-driven — no scripts, no external dependencies. It works on any AI assistant that can:

1. Access the current conversation history
2. Read reference files from this skill's directory
3. Write output files to the workspace

Capability adaptation: The workflow below references file operations and memory updates. If your AI tool doesn't support a specific capability, skip that step and note it in the report. The analysis itself only requires conversation context access.

Workflow (Six Steps)

Step 1: Conversation Review — Extract Key Events + Tag Waste Points

Scan the entire conversation context and extract these key events into a timeline:

Event Type	Recognition Signal
Tool invocations	Command execution, file reading/writing, web searches, code generation
File changes	Files created, modified, or deleted
Errors & fixes	Error messages, lint failures, debugging cycles
Repeated modifications	Same file/feature modified multiple times, user providing multiple clarifications
Decision points	Technology choices, architecture decisions, trade-offs
Automation/plugin usage	Any skill, agent, plugin, or extension triggered during the session
User clarifications	User adding context because the AI misunderstood intent
Verification rounds	User providing test data/feedback, AI analyzing verification results
AI misjudgments	AI providing wrong conclusions, missing critical issues, or jumping to premature conclusions

Filter rule: System initialization events (bootstrap files, identity setup, etc.) are excluded from analysis.

Critical step — Waste point tagging:

After building the timeline, interrogate each event in reverse:

1. Could this step have been avoided? If something had been done earlier, would this step be unnecessary?
2. Could this step have happened sooner? Did the AI delay something it should have proactively done?
3. Did this step duplicate prior work? Was the AI hand-writing logic that could have been reused?

Tag events where the answer is "yes" with [⚠ Optimizable] and record the reason. These tags are the core input for Step 2.

Output format: Chronological event list with type labels and brief descriptions. Waste points tagged separately.

Step 2: Eight-Dimension Deep Analysis

Load references/analysis_dimensions.md for detailed evaluation criteria, self-check lists, and common patterns per dimension. Analyze conversation events dimension by dimension to identify improvement opportunities.

Eight dimensions overview:

1. AI Self-Reflection ⭐ — AI's mistakes, delayed reactions, missed judgments in this session (highest priority, must be analyzed first)
2. Verification Strategy — Did the AI proactively define verification criteria and expected outcomes, or passively wait for user feedback?
3. Automation Opportunities — Repetitive workflows or hand-written scripts that could be encapsulated into reusable automations
4. Existing Automation Tuning — Were any existing automations/skills/templates used? Did they have gaps, unclear instructions, or output issues?
5. Tool Integration Opportunities — Operations that would benefit from dedicated tool integrations, plugins, or API connections
6. Knowledge Persistence — Preferences, conventions, and technical decisions from this session that should be persisted for future sessions
7. Documentation Updates — Project docs, coding standards, or architecture notes that need updating
8. Workflow Efficiency — Sequential steps that could be parallel, repeated labor, suboptimal tool choices

Analysis requirements (mandatory):

For each dimension:

• Run through the dimension's self-check list (defined in references/analysis_dimensions.md)
• For findings, output: Specific event reference (which turn, what operation) + Counterfactual reasoning (if X had been done, Y could be saved) + Recommendation + Priority
• Only after all self-check items pass can a dimension be declared "no findings" and skipped

Step 3: Generate Retrospective Report

Load assets/report_template.md for the report template. Fill the template with results from Step 1 and Step 2 to produce a complete Markdown retrospective report.

Report save path: {workspace}/retrospectives/{topic}_retrospective.md

Naming rules:

• {topic} uses 2-4 English words joined by hyphens, summarizing the session's core task (e.g., multithread-scope-collection, login-flow-refactor)
• Multiple retrospectives on same topic: If the file already exists, append the new report at the end (separated by --- and a new date heading) — don't create a new file

If the retrospectives/ directory doesn't exist, create it first.

Note: The save path above is a sensible default. Adapt to your project's conventions if they differ.

Step 4: Display Full Analysis in Conversation

The complete analysis must be shown directly in the conversation — don't just output a summary and point to the file. The file is an archive; the primary reading experience is in the conversation.

Output content (show in full, no trimming):

1. Session summary: One-sentence overview
2. Efficiency score: Optimizable turns / total turns
3. Event timeline: Complete table with waste point tags
4. All dimension findings: Each with event reference, problem, counterfactual reasoning, recommendation (this is the core content — never abbreviate or reduce)
5. Pending action list (if any)
6. Report archive location

Format: Use Markdown tables and headings for clear structure. Better to be thorough than to cut valuable analysis.

Step 5: Automatic Execution — Knowledge Persistence

For items identified in the "Knowledge Persistence" dimension (Dimension 6), execute persistence operations available in your AI tool:

• If your tool supports persistent memory (e.g., memory APIs, memory files, .memory directories), write new preferences/conventions directly
• If your tool supports project-level notes or config, update those
• If your tool has no persistence mechanism, list the items that should be persisted and recommend the user save them manually

Briefly state what was updated after each operation. Skip this step if no knowledge needs persisting.

Step 6: Pending Action List

For the following types of improvement suggestions, do not auto-execute — list them for user selection:

Action Type	Examples
Create new automation	Reusable workflow, script template, custom command
Tune existing automation	Modify instructions, parameters, or trigger conditions
Create/update project rules	Coding standards, review checklists, conventions
Update project documentation	Architecture docs, API references, onboarding guides
Create tool integration	Custom plugin, API connection, webhook

List format: Numbered list, each item includes "Action type + Specific content + Expected benefit." User can reply with numbers to select which actions to execute.

If no pending actions, skip this step and state "No additional actions needed for this session."

Edge Cases

Very short sessions: If the conversation is only a few turns with simple content, output a brief summary and state "This session was brief — no significant improvement opportunities identified." Don't force analysis.

Compressed/summarized history: If the conversation history appears compressed or truncated, analyze based on available context and note in the report: "Some conversation history was compressed; analysis is based on visible context."

Tool capability limitations: If the AI tool being used lacks certain capabilities referenced in this workflow (e.g., no file writing, no memory persistence), adapt gracefully — perform the analysis steps that are possible and clearly note any skipped steps with the reason.