AI-Assisted Development Documentation Templates

Purpose: Generic, reusable documentation templates for AI-assisted software development projects
Version: 1.0.0
Last Updated: 2025-12-21

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🎯 What Is This?

This repository contains generic, project-agnostic documentation templates designed to prevent mid-work evaluations and scope creep in AI-assisted development projects. These templates provide:

• AI Onboarding System - Get new AI agents productive in minutes
• Session Management - Track work across sessions and different LLMs
• Multi-Persona Collaboration - 12 specialized AI roles for different perspectives
• Enforcement Mechanisms - Checklists and prompts to ensure consistent usage
• Scope Management - Prevent scope creep through structured documentation

All project-specific details have been removed and replaced with placeholders like [PROJECT_NAME], [DATE], etc.

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📦 What's Included

Core Documentation Files

File	Purpose	When to Use
AI_ONBOARDING.md	Comprehensive guide for AI agents	First time setup, onboarding new AI
AI_PERSONA_GUIDE.md	12 specialized AI personas	When using multiple AI perspectives
PERSONA_HANDOFF.md	Persona-to-persona communication	Cross-session handoffs between personas
SESSION_START_CHECKLIST.md	Mandatory checklist for AI	Every session start (enforced)
PROMPT_TEMPLATES.md	Pre-written prompts for users	Every session (copy/paste)
ENFORCEMENT_GUIDE.md	How to enforce the system	Before starting project

Session Management Files

File	Purpose	When to Use
DAILY_SESSION.md	Session-by-session work log	Every session (read at start, update during)
PROJECT_STATUS.md	Current state dashboard	Every session start
QUESTIONS_BLOCKERS.md	Active questions and blockers	When questions arise
CHANGELOG.md	Chronological change tracking	After completing work

Planning & Tracking Files

File	Purpose	When to Use
DECISION_LOG.md	Architectural decisions (ADR format)	When making design decisions
TECH_DEBT.md	Known issues and technical debt	When finding issues
FILE_INDEX.md	Index of all project documentation	Finding specific documentation

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🚀 Quick Start

For New Projects

1. Copy all files to your project root
2. Customize placeholders in each file:
   • [PROJECT_NAME] → Your project name
   • [DATE] → Current date
   • [DOC_STANDARDS] → Your documentation standards file
   • See each file for full customization list
3. Have AI help customize - Use AI to fill in project-specific details
4. Start using - Follow ENFORCEMENT_GUIDE.md for first session

For AI Agents

1. Read AI_ONBOARDING.md - Full system guide
2. Complete SESSION_START_CHECKLIST.md - Mandatory first step
3. Read DAILY_SESSION.md - See what happened last
4. Read PROJECT_STATUS.md - Understand current state
5. Start working - Update files as you go

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📋 File Customization Guide

Each file contains placeholders that need to be customized for your project. Here's a quick reference:

Common Placeholders

• [PROJECT_NAME] - Your project name
• [DATE] - Current date (YYYY-MM-DD format)
• [DOC_STANDARDS] - Your documentation standards file name
• [DOC_COMMENT_STYLE] - JSDoc, Javadoc, etc.
• [FRAMEWORK] - Spring Boot, React, Django, etc.
• [CLOUD_PLATFORMS] - AWS, GCP, Azure, etc.
• [VISION_DOC] - Your platform vision document name
• [FEATURES_DIR] - Where feature specs live (e.g., features/)

Customization Instructions

Each file includes a "Customization Instructions" section at the bottom with a complete list of placeholders for that file.

Tip: Use AI to help customize - "Please customize all files in this directory for my [PROJECT_NAME] project using [TECH_STACK]"

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🎭 AI Personas

This system includes 12 specialized AI personas for multi-perspective development:

1. Primary Developer - Implements features, writes code
2. QA Reviewer - Reviews code, finds bugs, tests edge cases
3. Security Auditor - Security-focused review, vulnerability assessment
4. Performance Analyst - Performance optimization, scalability analysis
5. Architecture Consultant - Design decisions, patterns, maintainability
6. Documentation Specialist - Code documentation quality
7. Scope Guardian - Prevents scope creep, enforces boundaries
8. User Experience Advisor - UX/UI perspective, usability, accessibility
9. Database Administrator (DBA) - Database design, schema optimization
10. DevOps Engineer - Deployment, infrastructure, CI/CD
11. Technical Writer - User guides, technical documentation
12. Project Manager - Planning, tracking, coordination

See AI_PERSONA_GUIDE.md for full details on each persona.

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🔄 How It Works

Session Start (Mandatory)

1. AI reads SESSION_START_CHECKLIST.md
2. AI reads DAILY_SESSION.md (last session)
3. AI reads PROJECT_STATUS.md (current state)
4. AI checks QUESTIONS_BLOCKERS.md (blockers)
5. AI reads PERSONA_HANDOFF.md (if working as persona)

During Work

• AI updates DAILY_SESSION.md as it works
• AI adds questions to QUESTIONS_BLOCKERS.md
• AI documents decisions in DECISION_LOG.md
• AI adds issues to TECH_DEBT.md
• AI leaves notes in PERSONA_HANDOFF.md (if persona)

Session End

• AI summarizes in DAILY_SESSION.md
• AI updates CHANGELOG.md (if applicable)
• AI updates PROJECT_STATUS.md
• AI resolves questions in QUESTIONS_BLOCKERS.md

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📚 Documentation System Benefits

For Developers

• Continuity - Never lose context between sessions
• Clarity - Always know what was done and why
• Scope Control - Prevent feature creep
• Decision Tracking - Understand why decisions were made
• Multi-AI Support - Different LLMs can work together seamlessly

For AI Agents

• Fast Onboarding - Productive in under 5 minutes
• Clear Context - Always know current state
• Structured Workflow - Know what to do and when
• Persona Support - Specialized roles for different perspectives
• Handoff Support - Communicate across sessions

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🛠️ Setup Instructions

Step 1: Copy Files

# Copy all files to your project root
cp -r ./* /path/to/your/project/

Step 2: Customize

1. Replace all [PLACEHOLDER] values in each file
2. Use AI to help: "Customize these files for my [PROJECT_NAME] project"
3. Update file names if needed (e.g., [PROJECT_VISION].md)

Step 3: Initialize

1. Create initial DAILY_SESSION.md entry
2. Set up PROJECT_STATUS.md with initial state
3. Create DECISION_LOG.md with any existing decisions
4. Review ENFORCEMENT_GUIDE.md for first session

Step 4: First Session

1. Use prompt from PROMPT_TEMPLATES.md
2. Have AI complete SESSION_START_CHECKLIST.md
3. Verify AI read required files
4. Start working!

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📖 Usage Examples

Starting a New Session

Please complete the session start checklist. Read:
1. SESSION_START_CHECKLIST.md
2. DAILY_SESSION.md
3. PROJECT_STATUS.md
4. QUESTIONS_BLOCKERS.md

Then summarize current state and next steps.

Using a Persona

Act as the QA Reviewer and review the file upload implementation

Multi-Persona Workflow

1. Primary Developer: Implement feature X
2. QA Reviewer: Review the implementation
3. Security Auditor: Security review
4. DevOps Engineer: Is this deployment-ready?

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🔧 Customization Checklist

Before using these templates, customize:

• [PROJECT_NAME] in all files
• [DATE] in all files
• [DOC_STANDARDS] file name
• [FRAMEWORK] names (Spring Boot, React, etc.)
• [CLOUD_PLATFORMS] (AWS, GCP, Azure)
• [VISION_DOC] file name
• [FEATURES_DIR] directory name
• Any project-specific terminology
• File names that reference placeholders

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📝 File Descriptions

AI_ONBOARDING.md

Complete onboarding guide for AI agents. Explains the entire system, workflow, and how to use each file.

AI_PERSONA_GUIDE.md

Defines 12 specialized AI personas with roles, perspectives, when to use, and prompt templates.

PERSONA_HANDOFF.md

Communication log for personas to leave notes for each other across sessions or different LLMs.

SESSION_START_CHECKLIST.md

Mandatory checklist that AI must complete before starting work. Enforced by user prompts.

PROMPT_TEMPLATES.md

Pre-written prompts for users to copy/paste at session start, end, and during work.

ENFORCEMENT_GUIDE.md

Complete guide for users on how to enforce the documentation system and ensure consistent usage.

DAILY_SESSION.md

Session-by-session log of prompts, actions, decisions, accomplishments, and next steps.

PROJECT_STATUS.md

Current state dashboard showing progress, in-progress work, next steps, and blockers.

QUESTIONS_BLOCKERS.md

Active questions and blockers that need answers before work can proceed.

CHANGELOG.md

Chronological log of all changes, decisions, and updates to the project.

DECISION_LOG.md

Architectural Decision Records (ADR format) documenting all design decisions with rationale.

TECH_DEBT.md

Known issues, technical debt, and code smells that need to be addressed.

FILE_INDEX.md

Comprehensive index of all project documentation with purpose and when to read/use each file.

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🤝 Contributing

These templates are designed to be customized for your project. If you find improvements that would benefit others:

1. Fork this repository
2. Make your improvements
3. Submit a pull request
4. Keep it generic (no project-specific details)

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📄 License

These templates are provided as-is for use in any project. Customize as needed for your specific use case.

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🎓 Learning More

• New to AI-assisted development? Start with AI_ONBOARDING.md
• Want to use personas? Read AI_PERSONA_GUIDE.md
• Need to enforce usage? See ENFORCEMENT_GUIDE.md
• Looking for a specific file? Check FILE_INDEX.md

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💡 AI Coding Cheatsheet

Tips to prevent forgetting:

1. Bookmark PROMPT_TEMPLATES.md — Use it every session.
2. Set a reminder — "Use session start prompt".
3. Be consistent — Use the same prompts every time.
4. Verify, don't trust — Ask the AI what it learned from the context files.
5. Use the guide — See ENFORCEMENT_GUIDE.md for details.

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⚡ Auto-Enforcement Options (Highly Recommended)

Don't rely on your memory. Use these tools to automate the workflow:

⚡ Auto-Enforcement Options (Highly Recommended)

Don't rely on your memory. You can set this up manually using the options below, or run the included script to do it all for you.

🤖 One-Click Setup (Optional)

Run this script to automatically create .cursorrules, project snippets, and VS Code tasks:

./setup_automation.sh

Manual Setup Options

Option 1: .cursorrules (For Cursor Users) - Best Option

Create a .cursorrules file in your root directory to "hard-code" the system into the AI's behavior.

# .cursorrules
YOU ARE AN AGENTIC AI WORKING IN THE "PROJECT_START" FRAMEWORK.

CRITICAL RULES:
1. At the very start of a conversation, you MUST check if I have asked you to run the 'Session Start Checklist'.
2. If I haven't, you must politely ask: "Would you like to run the Session Start Checklist before we begin?"
3. You must always read 'DAILY_SESSION.md' and 'PROJECT_STATUS.md' before proposing complex changes.

Option 2: VS Code / Cursor Snippets

Type !start to auto-expand the full prompt.

• Automatic: Run ./setup_automation.sh to install project-level snippets.
• Manual:
  1. Cmd+Shift+P -> "Configure User Snippets" -> "markdown"
  2. Add the JSON for "Session Start".

Option 3: Pinned Tabs

Right-click DAILY_SESSION.md and select "Pin". This keeps the current context always visible in your workspace.

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✅ Success Indicators

You'll know the system is working when:

• ✅ AI starts every session by reading context files
• ✅ AI updates DAILY_SESSION.md as it works
• ✅ AI documents decisions automatically
• ✅ You rarely need to remind AI about the process
• ✅ Context is preserved across sessions
• ✅ Scope creep is prevented through documentation
• ✅ Multiple AI agents can work together seamlessly

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Last Updated: 2025-12-21
Maintained By: Community
Questions? Open an issue or customize for your needs