Designing Trustworthy and Empathetic Conversational AI

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In this episode of Unprompted, Nandini Stocker joins Hans van Dam to explore how conversational AI is evolving in the LLM era, from scripting dialogue to designing system behaviour, empathy at scale, cultural context, and governance in high-trust, global AI systems.

In this episode of Unprompted, Hans van Dam, CEO of the Conversation Design Institute, sits down with Nandini Stocker, a global leader in conversational AI with over 25 years of experience designing voice and chat systems across 60+ languages and 120 countries. Drawing on her work at Google, Flipkart, and USAA, they explore how conversation design is fundamentally changing in the era of large language models.

The conversation traces the evolution of conversational AI, from early rule-based and intent-driven systems to today’s generative, adaptive models. Nandini introduces her now-famous “Legos to Play-Doh” analogy, explaining how designers have moved from rigid, modular dialogue blocks to more flexible but unpredictable systems that require new forms of structure, boundaries, and responsibility.

Together, they unpack what this shift means for the role of the conversation designer. Rather than writing every line of dialogue, designers are now shaping system behaviour: defining tone, guardrails, escalation rules, and the conditions under which conversations emerge. Empathy, they argue, must be designed at the utterance level, responding not just to intent, but to emotional context, urgency, and human need.

The episode also covers:

▪️ The shift from scripted dialogue to generative, LLM-driven systems

▪️ Designing system behaviour instead of individual prompts

▪️ Building empathy at scale through rules of engagement

▪️ Global standards versus deep, context-specific design

▪️ Conversational AI for Indian demographics and multilingual markets

▪️ Governance, tone systems, and safety guardrails in high-trust domains

▪️ Empowering designers through tooling, rituals, and shared ownership

Drawing on her experience building Flipkart’s culturally adaptive assistant for hundreds of millions of Indian users, Nandini highlights the importance of designing for lived language, social context, and inclusion, starting with those who face the greatest barriers. She emphasizes that global best practices must be “transcribed,” not copied, to remain authentic and effective across regions.

The discussion also turns inward, exploring career growth and leadership. Nandini shares practical advice on establishing yourself as a design leader, presenting systems thinking in portfolios and interviews, and earning trust across engineering, product, and executive teams by tying design decisions to real outcomes.

Ultimately, the episode makes a clear case: conversational AI is still in its infancy. While LLMs are powerful, meaningful progress depends on designers who can balance technical capability with empathy, ethics, and governance. As conversational systems become more embedded in everyday life, designing with dignity, responsibility, and cultural awareness is no longer optional, it’s the work.

Tune in to hear how conversation design is evolving beyond scripts and prompts, and what it truly takes to build trustworthy, human-centered AI at scale.

Design executive and conversation systems leader with over 25 years of experience shaping how AI speaks across 60+ languages, 120 countries, and 50+ industries. She has guided design strategy and built teams across global tech companies, Fortune 500 enterprises, and consulting practices, uniting platform thinking with cultural fluency to design with dignity at scale.

At Google, she co-patented an adaptive dialog system, scaled global design standards and guidelines, and developed a training methodology that gave thousands of designers and developers tools to shape better conversations. At Flipkart, she created Flippi, India’s first culturally adaptive multilingual e-commerce assistant, and built design and analytics tools that shifted ownership upstream and empowered conversation designers to lead product direction. Today at USAA, she sets standards for voice and chat UX modernization and establishes guardrails for LLM-powered systems in high-trust financial contexts.

Now invested in mentoring the next generation of designers, Nandini is recognized as both a systems architect and a cultural storyteller. Her work blends rigor with empathy, ensuring that as technology evolves, those who need it are never left behind.