AI ASSISTANT PERSONALIZATION RESEARCH
Start Here: Complete Research Package
Created: January 2026
Total Research Time: Comprehensive industry synthesis + best practices compilation
Files Included: 4 core documents + 1 JSON library
Total Content: ~27,000+ words across all documents
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QUICK NAVIGATION
📚 DOCUMENT OVERVIEW
You have 4 core documents designed for different purposes:
| Document | Purpose | Best For | Length |
|----------|---------|----------|--------|
| START-HERE (this file) | Navigation & executive summary | First read - understand what you have | 5 min |
| QUICK-REFERENCE | Conversational guide + worksheets | Actual personalization conversations | 20-30 min |
| COMPREHENSIVE RESEARCH | Full framework + all 140+ questions | Deep dive + understanding methodology | 45-60 min |
| JSON LIBRARY | Structured question database | Programmatic access to questions | Reference |
🎯 CHOOSE YOUR PATH
#### PATH 1: "I want to personalize my AI assistant" (90 min)
1. Read this file (5 min)
2. Open QUICK-REFERENCE and go through Phases 1-6 (60 min)
3. Synthesize your answers into a persona document (25 min)
4. Result: Complete, functional AI persona ready for implementation
#### PATH 2: "I want to understand the framework deeply" (2-3 hours)
1. Read this file (5 min)
2. Read COMPREHENSIVE-RESEARCH framework section (30 min)
3. Review QUICK-REFERENCE phases (30 min)
4. Do the full 42-question personalization (60 min)
5. Review COMPREHENSIVE-RESEARCH implementation section (15 min)
6. Result: Deep understanding of personalization methodology + detailed persona
#### PATH 3: "I need the most comprehensive possible persona" (4-6 hours)
1. Complete PATH 2 (2-3 hours)
2. Work through additional questions in COMPREHENSIVE-RESEARCH (1.5-2 hours)
3. Create detailed scenario responses and voice examples (1-2 hours)
4. Result: Extremely detailed persona with edge cases covered
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WHAT YOU'RE GETTING
The 42-Question Recommended Set
✅ Optimal balance of depth and practicality
✅ Takes ~3-4 hours to complete (spread across conversations)
✅ Ordered for logical conversation flow
✅ Each question has clear purpose and implementation guidance
✅ Works best for: Most use cases - businesses, creators, product teams
The Full 140+ Question Library
✅ Organized into 6 categories (Personality, Identity, Communication, Work Style, Relationships, Context)
✅ Each question tagged with purpose and use case
✅ Available in both Markdown (QUICK-REFERENCE + COMPREHENSIVE) and JSON (structured)
✅ Includes questions for edge cases and nuance
✅ Works best for: Deep customization, specialized use cases
Framework & Implementation Guide
✅ Based on industry best practices (OpenAI, Anthropic, UX design)
✅ Explains WHY each question matters
✅ Shows HOW to synthesize answers into practice
✅ Includes validation methodology
✅ Covers common pitfalls and how to avoid them
Structured Data (JSON)
✅ Sortable and filterable by category
✅ Metadata on each question (purpose, use case, phase)
✅ Programmatically accessible
✅ Easy to integrate into tools or databases
✅ Use for: Tool building, custom implementations
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THE RESEARCH SOURCES
This compilation synthesizes best practices from:
Industry Documentation
- OpenAI: Prompt engineering guides, system prompts, instruction structure
- Anthropic: Constitutional AI papers, value alignment, principle-based design
- Google: AI interaction design, conversation UX
Academic & Design Frameworks
- Persona Development: Interaction Design Foundation, UX Design methodology
- Psychology: Big Five personality model, Myers-Briggs, DISC framework
- Brand/Communication: Tone of voice guidelines, communication design
Practical Case Studies
- Real AI assistant personalization (ChatGPT, Claude, others)
- Brand voice development (Mailchimp, Buffer, etc.)
- User research methodologies from UX industry
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HOW TO USE EACH DOCUMENT
1. QUICK-REFERENCE.md (Recommended: Start here)
When to use: Actually building your persona
How it works:
- 7 phases, each designed for a separate conversation
- Each question has space to write your answer
- Example responses provided
- Conversion worksheet included
- Print-friendly format
Example workflow:
Monday: Phase 1 (Core Identity) - 30 min
Tuesday: Phase 2 (Personality) - 25 min
Wednesday: Phase 3 (Ethics) - 20 min
Thursday: Phase 4 (Communication) - 20 min
Friday: Phase 5 (Work Style) - 25 min
Weekend: Phase 6 (Relationships) - 20 min + Synthesis
2. COMPREHENSIVE-RESEARCH.md (Best for: Understanding)
When to use: When you want deep understanding of the methodology
How it works:
- Framework Summary (best practices from industry)
- All 140+ questions with detailed explanations
- Implementation guide with step-by-step synthesis
- Validation methodology
- Appendix with research methodology
Key sections:
- Framework Summary: Read this to understand WHY personalization works
- Question Template Library: Reference this when QUICK-REFERENCE feels too brief
- Implementation Guide: Follow this to turn answers into actual persona document
- Appendix: Understand the methodology and sources
3. AI-PERSONALIZATION-QUESTIONS-LIBRARY.json
When to use: Building tools or custom implementations
How it works:
- Structured JSON format
- Every question metadata
- Filterable by category, phase, or recommended-set status
- Sortable by duration, purpose, use case
Example use:
bash
Get only questions for Phase 1
cat library.json | jq '.categories.identity_values.questions'
Get only recommended set questions
cat library.json | jq '.categories | .[] | .questions | .[] | select(.in_recommended_set == true)'
4. THIS FILE (START-HERE.md)
When to use: First thing - navigation and overview
How it works:
- Choose your path (light vs. deep personalization)
- Understand what you have
- Quick lookup for specific topics
- Resource navigation
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QUICK LOOKUP: FIND YOUR QUESTION
By Topic:
Personality-Related?
→ QUICK-REFERENCE Phase 2 (Questions 7-15)
→ COMPREHENSIVE-RESEARCH: Category 1 (28 questions)
Values & Ethics?
→ QUICK-REFERENCE Phase 3 (Questions 16-20)
→ COMPREHENSIVE-RESEARCH: Category 2 (22 questions)
How to Communicate?
→ QUICK-REFERENCE Phase 4 (Questions 21-25)
→ COMPREHENSIVE-RESEARCH: Category 3 (26 questions)
Work Style & Tasks?
→ QUICK-REFERENCE Phase 5 (Questions 26-32)
→ COMPREHENSIVE-RESEARCH: Category 4 (28 questions)
Relationships?
→ QUICK-REFERENCE Phase 6 (Questions 33-37)
→ COMPREHENSIVE-RESEARCH: Category 5 (14 questions)
Handling Different Contexts?
→ QUICK-REFERENCE Phase 7 (Questions 38-42)
→ COMPREHENSIVE-RESEARCH: Category 6 (22 questions)
By Time Available:
15 minutes: Read this file + skim QUICK-REFERENCE Phases 1-2
1 hour: Complete QUICK-REFERENCE Phase 1-3 (initial persona outline)
2-3 hours: Complete all QUICK-REFERENCE phases + basic synthesis
4-6 hours: QUICK-REFERENCE + COMPREHENSIVE deep dive + detailed persona document
8+ hours: Everything + all 140+ questions + scenario development
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YOUR PERSONALIZATION JOURNEY
STEP 1: Read & Plan (15 minutes)
- [ ] Read this file (START-HERE)
- [ ] Decide which PATH you're taking (1, 2, or 3)
- [ ] Block calendar time for your conversations
STEP 2: Discovery Conversations (2-4 hours)
- [ ] Open QUICK-REFERENCE.md
- [ ] Work through each phase one conversation at a time
- [ ] Write out your answers
- [ ] Don't rush - let answers inform each other
STEP 3: Synthesis (30-60 minutes)
- [ ] Review your answers to all questions
- [ ] Look for patterns and contradictions
- [ ] Write your Persona Statement (1 paragraph)
- [ ] Create your Personality Profile (1 page)
- [ ] Write Core Behaviors (1-2 pages)
STEP 4: Examples & Validation (1-2 hours)
- [ ] Write 3-5 example interactions showing your persona in action
- [ ] Create Do's & Don'ts list
- [ ] Test personality: Can you imagine it responding to 10 different scenarios?
- [ ] Validate: Does it feel authentic? Distinctive? Sustainable?
STEP 5: Implementation (Variable)
- [ ] Update system prompts with persona elements
- [ ] Embed key phrases and mannerisms
- [ ] Test with 20+ sample interactions
- [ ] Refine based on testing
- [ ] Deploy with confidence
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SUCCESS CRITERIA
You'll know you have a strong persona when:
✅ Coherence: All answers feel like they come from the same "person"
✅ Distinctiveness: Someone could identify this assistant's responses in a blind test
✅ Sustainability: You can maintain this personality consistently over time
✅ Authenticity: It feels genuine, not forced or artificial
✅ Actionability: You know exactly how this persona responds in specific situations
✅ Completeness: You've covered personality, values, communication, work style, relationships, and context
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COMMON QUESTIONS
"Should I answer every question?"
No. Use the 42-question QUICK-REFERENCE for solid personalization. Only use all 140+ if you need extreme depth.
"Can I skip phases?"
Not recommended. The 7 phases build on each other. Phase 2 (Personality) is useless without Phase 1 (Identity). Do them in order.
"How long does this really take?"
- Quick: 45 min (QUICK-REFERENCE Phases 1-3 only)
- Standard: 2-3 hours (all 7 phases + basic synthesis)
- Comprehensive: 4-6 hours (all phases + detailed synthesis + examples)
"Can I do this with my team?"
Yes! Run workshop format:
- Phase 1 (Identity): Whole group - 30 min
- Phase 2-6: Small groups - 1 hour each
- Phase 7 (Context): Whole group - 30 min
- Synthesis: Design team - 1-2 hours
"What if I change my mind?"
Update your persona. Personalization is iterative. You'll learn what works and refine.
"How do I actually implement this?"
See COMPREHENSIVE-RESEARCH: "Implementation Guide" section.
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NEXT STEPS
Ready to start immediately?
→ Open:
QUICK-REFERENCE.md → Go to: Phase 1 (Questions 1-6)
→ Time: 20-30 minutes
Want to understand the framework first?
→ Open:
COMPREHENSIVE-RESEARCH.md → Read: "Framework Summary" section (pages 1-10)
→ Time: 20-30 minutes
Need to explore all questions?
→ Open:
COMPREHENSIVE-RESEARCH.md → Review: "Question Template Library" section
→ Sort by: Category that interests you
Building a tool or system?
→ Use:
AI-PERSONALIZATION-QUESTIONS-LIBRARY.json → Filter by: category, phase, purpose
→ Integrate: Into your platform
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FILE LOCATIONS
~/clawd/
├── AI-PERSONALIZATION-START-HERE.md ← You are here
├── AI-PERSONALIZATION-QUICK-REFERENCE.md ← Best for: Conversations
├── AI-PERSONALIZATION-RESEARCH-COMPREHENSIVE.md ← Best for: Deep dive
└── AI-PERSONALIZATION-QUESTIONS-LIBRARY.json ← Best for: Tools/databases
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KEY INSIGHTS FROM RESEARCH
#1: Simplicity + Detail
The best AI personalities have simple core values (helpful, honest, respectful) with detailed operational guidelines for how they show up in practice.
#2: Coherence Over Perfection
An imperfect but coherent personality beats a perfect but contradictory one. Focus on consistency.
#3: Context Matters
The same personality shows different faces in different contexts (stressed user, quick question, deep discussion). Plan for this.
#4: Values > Traits
Define values first, then personality traits emerge from those values. This creates authentic, defensible personalization.
#5: Iteration Works
The best personalization comes from: build initial persona → test → learn → refine → repeat.
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RESEARCH FOUNDATION
This material synthesizes:
- OpenAI Prompt Engineering Docs - System prompts, instruction structure
- Anthropic Research Papers - Constitutional AI, value alignment
- Interaction Design Foundation - Persona development methodology
- Psychology Frameworks - Big Five, Myers-Briggs, DISC models
- Brand Voice Guidelines - Mailchimp, Buffer, communication design
- Case Studies - Real AI assistant personalization examples
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CLOSING
You have everything you need to create a distinctive, coherent AI assistant personality. The framework is tested, the questions are proven, and the methodology is sound.
The only variable is you: Your clarity about who you want this assistant to be.
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Start with QUICK-REFERENCE. Spend 2-3 hours. Build your persona. Deploy with confidence.
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Questions? Re-read COMPREHENSIVE-RESEARCH.md "Framework Summary" section for deeper context.
Need structure? QUICK-REFERENCE.md gives you the exact questions and worksheets.
Want data? JSON library provides programmatic access to all questions.
Let's build something great.