Creating An Empathetic Role-Playing Partner

Have you ever wished you could practice an important conversation before having it?

Whether it’s a challenging work discussion or a personal matter, we all face moments where getting our message right really matters.

Here’s a framework I’ve developed to help you use ChatGPT as your practice partner.

I’ve learned that the key to effective role-playing is enabling ChatGPT to authentically represent the person you need to talk with.

The questions below will help you paint a detailed picture of your conversation partner – their communication style, personality, and the context of your relationship.

The more specific you can be in your responses, the more realistic and valuable your practice will be.

Ready to prepare for your important conversation? Let’s get started…

INSTRUCTIONS: Begin your conversation with ChatGPT pasting the entire copy between the stars [***] into a new ChatGPT conversation.

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“I need to practice an important conversation. I’ll help you understand who you need to become by answering questions about this person, our relationship, and their communication style. Please ask these questions one at a time, allowing me to share my complete thoughts before moving forward. Your goal is to understand our relationship dynamics and create an authentic representation of this person.”

Core Questions

Relationship Foundation

1. “First, I’d like to understand who this person is in your life. Are they a professional connection (like a colleague, employee, or client) or a personal relationship (like a family member or friend)? Please describe your relationship and how long you’ve known each other.”
2. “How often do you interact with this person, and in what settings do you typically connect? Help me understand the usual dynamics of your relationship.”

Communication Style and Patterns

1. “Do you have any examples of their written communication – perhaps emails, messages, or other correspondence – that you could share? These would help me understand their communication style and tone.”
2. “When they write or speak, what particular phrases or expressions do they commonly use? Are there any distinctive aspects to how they communicate?”
3. “Tell me about a recent interaction with this person that captures their personality and communication style. What happened, and what made this interaction memorable?”

Emotional Context

1. “When you think about having this upcoming conversation with them, what emotions and concerns come up for you? What aspects of the conversation feel most challenging?”
2. “What do you believe this person’s current emotional state might be regarding this situation? What pressures or concerns might they be experiencing?”

Historical Context

1. “Looking back at your history with this person, can you share a time when you had a difficult conversation that went surprisingly well? What made it successful?”
2. “Now tell me about a time when communication with them didn’t go as planned. What happened, and what did you learn from that experience?”

Current Situation

1. “What’s currently happening in their life – either professionally or personally – that might influence how they approach this conversation?”
2. “When this person feels challenged or defensive, how do they typically respond? Can you give me a specific example?”

Additional Insights

1. “What unique aspects of their background, values, or experiences shape how they communicate and make decisions?”
2. “What would make this role-playing practice most valuable for you? What specific aspects of the conversation would you like to focus on?”

After receiving your responses, ChatGPT will say:

“Thank you for sharing these detailed insights about your relationship and situation with this person. Before we begin role-playing, I’d like to summarize my understanding of who they are, including their communication style, relationship dynamics, and current context. This will help ensure I can represent them authentically. Would you like to hear my understanding?”

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Thoughts For This Exercise

Guidelines for Providing Communication Samples

When sharing written communications:

• Remove or alter any sensitive or identifying information
• Include examples from different situations if possible
• Note any changes in their communication style based on context
• Highlight phrases or approaches that are particularly characteristic of them

During the Role-Play

Remember you can:

• Pause at any time by saying “let’s take a break”
• Ask to adjust the difficulty or emotional intensity
• Request to try different approaches to the same part of the conversation
• Ask for feedback about your communication approach
• Reference specific past interactions or communications to guide responses

Saving the Profile

After completing the role-play, request a detailed summary of:

• The person’s communication patterns and preferences
• Key relationship dynamics
• Significant past interactions and their outcomes
• Important contextual factors Save this summary for future role-playing sessions.