Context & Opportunity
Preparing for high stakes meetings with executives requires understanding their communication style, priorities, and decision making frameworks. Traditional preparation involves reviewing past emails, reading interviews, and talking to colleagues who have worked with the executive. This indirect approach provides limited insight into how the executive will actually respond to your specific proposals.
The opportunity was to use AI to create realistic executive personas that could simulate conversations, challenge assumptions, and help refine messaging before the actual meeting. This would allow for direct "practice" conversations that mirror real executive communication patterns, identify potential conflicts early, and help gauge how much time different topics require to ensure efficient use of meeting time.
Before: Indirect Preparation
- Limited insight into executive communication style
- No opportunity to practice actual conversations
- Uncertainty about how they will respond to proposals
- Risk of using wrong level of detail or framing
- Nervousness from lack of rehearsal opportunity
- Missed opportunities to refine messaging
After: AI Powered Rehearsal
- Realistic simulation of executive communication patterns
- Practice conversations with voice interaction
- Test proposals and get simulated feedback
- Identify potential conflicts before the actual meeting
- Gauge time requirements for different topics efficiently
- Refine detail level based on persona responses
- Build confidence through realistic rehearsal
- Iterate messaging based on AI analysis
The Solution
If we provide ChatGPT with comprehensive information about an executive's communication style, priorities, and decision making patterns,
Then it can simulate realistic conversations that mirror the executive's actual responses,
Resulting in improved meeting clarity, increased confidence, and more effective communication strategies.
Approach & Experiment Setup
The implementation used ChatGPT's custom GPT feature to build executive personas based on publicly available information and direct research. ChatGPT was selected specifically for its more fluid voice model, which enables natural spoken conversation practice. The personas were designed to simulate both text and voice conversations for realistic meeting rehearsal.
Persona Building Process
Data Collection
Gather LinkedIn profile, published interviews, company communications, and colleague insights about the executive.
Pattern Analysis
Identify communication style (direct vs. detailed), decision making framework, and stated priorities.
Persona Configuration
Build custom GPT with specific instructions to mirror communication patterns and challenge assumptions.
Voice Rehearsal
Use ChatGPT voice mode for realistic conversation practice and real-time feedback.
Persona Information Sources
Career history, stated expertise areas, writing style from posts and articles, professional network patterns.
Podcast appearances, written Q&As, conference talks reveal priorities, communication style, and decision-making philosophy.
All hands presentations, strategy documents, email patterns show level of detail preference and key focus areas.
First hand accounts of working style, pet peeves, preferred communication formats, and hot-button topics.
Social media posts, press releases, blog articles demonstrate tone, vocabulary, and perspective on industry topics.
Implementation & Results
The custom GPT personas successfully simulated executive communication patterns, enabling realistic rehearsal conversations that improved meeting preparation quality and presenter confidence.
How It Works in Practice
Initiate voice conversation with executive persona, present proposal or update, receive realistic questions and pushback.
Adjust messaging based on persona feedback, test different framing approaches, refine detail level and supporting evidence.
After rehearsal, ask persona for meta-analysis: "What communication patterns would improve clarity?" or "What concerns did I fail to address?"
Multiple practice sessions reduce nervousness, prepare for likely objections, and build fluency with key talking points.
Measurable Outcomes
- Improved clarity: Persona feedback helped identify overly technical language and refine for executive audience
- Increased confidence: Rehearsal reduced anxiety and improved delivery fluency in actual meetings
- Better objection handling: Practice with realistic pushback prepared responses to likely questions
- Optimized detail level: Learned when to summarize vs. dive deep based on persona communication style
- Post session insights: Meta analysis revealed communication patterns to improve for future interactions
Findings & Insights
What Worked Well
- Realistic communication simulation: Personas accurately mirrored executive communication patterns and questioning styles
- Voice mode effectiveness: Speaking out loud with AI response felt significantly more realistic than text-based rehearsal
- Iterative improvement: Could quickly test multiple messaging approaches in single preparation session
- Meta-communication insights: Post session analysis revealed communication patterns invisible during actual conversation
- Transferable skill building: Lessons learned applied to future executive communications beyond specific meeting
Challenges & Considerations
- Information quality dependency: Persona accuracy limited by availability of public information about the executive
- Cannot predict mood or context: AI cannot simulate executive's day of emotional state or external pressures
- Persona calibration needed: Initial sessions required adjusting persona instructions to improve accuracy
- Over preparation risk: Important to avoid becoming too scripted; conversation should remain natural
- Privacy considerations: Must use only publicly available information to build personas ethically
Potential Applications
Executive persona simulation can extend beyond meeting preparation to other high stakes communication scenarios requiring practice and refinement.
Sales Call Preparation
Practice customer conversations by simulating buyer personas based on industry role, company size, and stated pain points.
Presentation Rehearsal
Simulate board presentations or investor pitches with personas that challenge business assumptions and ask tough questions.
Performance Reviews
Practice difficult conversations by simulating employee personas based on past feedback patterns and communication preferences.
Stakeholder Negotiation
Rehearse cross functional negotiations by building personas representing different organizational priorities and constraints.
Key Takeaways
AI persona simulation demonstrates how technology can provide practice opportunities that were previously unavailable. The ability to rehearse conversations with realistic executive responses improves both message quality and presenter confidence.
Success Factors
- Comprehensive persona building: Quality of simulation depends on depth of information gathered about communication patterns
- Voice mode advantage: Speaking practice feels more realistic and builds fluency better than text-based rehearsal
- Iterative refinement: Multiple practice sessions allow testing different messaging approaches efficiently
- Meta communication analysis: Post session review reveals communication patterns invisible during conversation
- Confidence building: Realistic rehearsal reduces anxiety and improves actual meeting performance
