Conversation Design Case Study: Helping Young Adults Set Healthy Boundaries

1. Context & Objective
During my time at Wysa, I worked on a script titled “Setting Good Boundaries”—initially sent in as an application assessment, it eventually helped me practice my skills and later was fleshed out and evolved into a foundational module used for both user-facing conversations and internal training.

User Persona:
The primary audience was young adults (19–25 years old) struggling with people-pleasing tendencies. They often felt pressured by family and friends, carried a strong sense of obligation, and experienced guilt when trying to prioritise their own needs. For them, saying “no” or asserting themselves felt selfish.

Objective:
The conversation aimed to:
- Normalise the act of putting oneself first.
- Reduce guilt associated with boundary-setting.
- Help users communicate their needs clearly and respectfully.
- Equip users with practical tools to manage and uphold boundaries.

2. Initial Draft & Iterations
The first draft followed a straightforward narrative arc:

a. Introduction: Why boundaries matter—what we can and cannot adjust to.
b. Self-assessment: How good are you at setting boundaries? (Good / Not good)
c. For users who struggled: What aspect is difficult? (Recognising / Following through)
d. Delivery of relevant strategies.

As the script matured:
+ A 5-question self-assessment was added to gauge the user's boundary-setting challenges.
+ A slider carousel of 8 popular techniques was integrated, letting users explore tools at their pace.

These elements not only helped in user engagement but made the script interactive and educational.

3. Design Approach
The conversation flow was designed to be both structured and empathetic:

- Happy Path: A clear linear flow for users who resonated with the default options.
- Branching Paths: Alternative routes for users expressing confusion, contradiction, or unsureness—helping them feel seen and supported.
- Sentiment Categorisation: Responses were grouped into emotional buckets to shape empathetic replies.
- Personalisation Layer: User inputs from earlier free-text responses were stored and replayed later in the script, creating a sense of continuity and care.

This layered design aimed to mimic the fluidity of a real conversation while providing psychological safety and space for self-reflection.

4. Research & Strategy
interpersonal communication. The goal was to identify techniques that not only help users understand boundaries but also offer them language and tools to express these boundaries in emotionally intelligent ways.

The 8 strategies chosen were distilled from common, evidence-based practices and included:

Validation, Gratitude, Mediation, Non-negotiables, Sympathy, Restatement, Alternate Solutions, Consequences.

Each of these was introduced through micro-interactions within the chatbot. Users could scroll through these strategies using a slider, explore one or many at their pace, and even return to review favorites. The tone was kept warm, supportive, and non-clinical—mirroring how a thoughtful peer might offer advice.

5. Outcome & Impact
What started as a practice script soon became a core part of the internal training toolkit at Wysa. New joiners and junior conversation designers used this script to practice:

- Conversation wireframing
- Twining (via Twinery.org)
- Parsing chats into structured JSON formats

The script served a dual purpose—supporting users in emotional self-care, and mentoring new team members in practical, hands-on conversation design.

6. Reflections & Learnings
This project helped solidify my approach to human-centered design—how research, structure, empathy, and technical flow all come together in a well-crafted conversation.

Key takeaways:
- Empathy is not just in tone, but in anticipating emotional responses and designing for them.
- Personalisation (even light-touch) can significantly increase engagement.
- A flexible flow allows for richer, more inclusive experiences.
- Internal training content can emerge organically from thoughtful design exercises.