Roleplay: Practice Conversations Before They Happen
Roleplay lets you rehearse difficult or high-stakes conversations with an AI-powered partner before you have them in real life. The AI responds like the actual person would, drawing on their Cloverleaf assessment and personality data. After each session, you receive a scored evaluation with skill-by-skill feedback and actionable suggestions to improve your approach.
Use Roleplay to prepare for feedback conversations, conflict resolution, performance discussions, or any situation where getting your communication right matters.
What you get with every session:
Practice with Purpose: Each Roleplay includes specific objectives so you know what to focus on.
Personality-Informed AI: The AI responds based on the real person's Cloverleaf assessment data.
Completely Private: Your sessions are visible only to you. Experiment freely.
Detailed Feedback: Scored evaluations across multiple communication skills with specific improvement tips.
How to Get Started
The first time you create or start a Roleplay, Cloverleaf displays a one-time consent screen covering three things: the AI-powered nature of the practice session, how your data is handled, and the coaching feedback you'll receive afterward. After you accept, future Roleplays skip directly to the creation step.
How to Create a Roleplay
From the Roleplay dashboard, select + Roleplay in the top right.
In the Describe the Situation field, type what you want to practice. The more specific you are, the more tailored your objectives and AI responses will be.
Example: "I need to give difficult feedback to my direct report about missed deadlines while being supportive."
In the Pick a Person field, search for the colleague you want to practice with. Cloverleaf uses their personality and assessment data to shape how the AI responds.
If you're not targeting a specific person, select Keep it general.
Optionally, select a Quick-Start Chip at the bottom of the screen. These are pre-configured with a person and Roleplay type so you can begin immediately without writing a custom description.
Vague descriptions produce generic Roleplays. Instead of "practice feedback," describe the specific situation and the outcome you're hoping for.
How to Review Your Roleplay Before Practicing
After you submit your Roleplay, Cloverleaf generates a Roleplay Preview screen. Review this before starting. The preview includes:
The Roleplay title and objectives
A Participant Insights section based on the person's Cloverleaf data, including how they typically receive feedback, communicate, and respond to conflict
Use the participant insights to adjust your approach before the conversation begins. This step takes 30–60 seconds and meaningfully improves the quality of your practice.
How to Run a Practice Conversation
Select Start Roleplay to enter the chat interface. The AI plays the role of the other person and responds to your messages in real time, informed by their personality data.
During the conversation:
Text or voice input: Select the toggle at the bottom of the chat to switch between typing and speaking. Practice the way you'd naturally have the conversation.
View Objectives: Select View Objectives at the bottom of the screen to keep your goals visible without losing your place in the conversation.
No time limit: The conversation supports as many exchanges as you need. Go back and forth until you feel ready.
Since sessions are private, use this space to experiment with wording, tone, and strategies you wouldn't try in real life. That's what rehearsal is for.
How to Read Your Evaluation
Select End Roleplay when you're finished.
Cloverleaf generates a detailed performance evaluation with three components:
Overall Score (1–5 scale)
Score | Label |
5 | Excellent |
4 | Good |
3 | Developing |
2 | Emerging |
1 | Needs Work |
Objectives Checklist
Each objective is marked with a status and an explanation:
Achieved: You met the objective clearly.
Partial: You made progress but something was missing. The explanation tells you exactly what.
Additional Recommendations
Beyond scored skills, Cloverleaf surfaces practical suggestions for closing the conversation or reinforcing the relationship.
How to Interpret the Skills Breakdown
Select See details on any skill to expand it. Each skill includes:
What worked: Direct quotes from your conversation showing effective moments.
What to work on: Specific moments where a different approach would have been more effective.
Improvement tip: An actionable suggestion to try in your next session or real conversation.
Use this section to identify patterns across sessions, not just one-off moments.
Tips for Getting the Most Out of Roleplay
Be specific in your description. More detail produces more realistic AI responses and more useful evaluations.
Practice with a real person selected. The AI draws on their personality data, making the conversation feel much closer to the real thing.
Read participant insights before you start. They reveal how the person typically handles feedback and conflict, giving you a strategic edge.
Practice the same Roleplay more than once. Use the evaluation feedback to refine your approach with each attempt.
Check your objectives during the conversation. Select View Objectives if you lose track of what you're working toward.
Managing Your Roleplay
The Roleplay dashboard shows all of your Roleplays in one place. Each Roleplay card displays the title, description, the person you're practicing with, their personality style, the Roleplay status, and when it was created.
Roleplay statuses:
Ready to Practice: Created but not yet started.
In Progress: You've started the conversation but haven't ended it yet.
Completed: You've finished the session and received your evaluation.
Select Continue on any in-progress Roleplay to pick up where you left off.