Design Leadership, Growth & the Future of UX with Jayawant Tewari, Partner UX Director @ Microsoft

What does it take to stand out, lead meaningfully, and build products that last for decades? In this episode, we sit down with Jayawant Tewari, a design leader at Microsoft, for a wide-ranging conversation on careers, collaboration, trust, and the future of design in the AI era. From learning through mistakes to tapping into the intuition of industry veterans, Jayawant Tewari shares powerful ways early-career designers can grow faster by leaning on community rather than navigating alone. He opens up about the realities of designing across multiple platforms, teams, cultures, and time zones—and why building great products is always a marathon, never a sprint. As the conversation expands into AI, he shares a compelling vision of a world beyond apps—where intelligent agents orchestrate our tasks, understand our emotions, and reshape the very nature of UX. This is an episode for anyone looking to grow, lead, collaborate, and future-proof their design career. 🔍 Episode Highlights For designers navigating complexity—early-career or senior—this conversation offers frameworks for building trust, sustaining momentum, and creating meaningful impact. JT sheds light on how teams can work across surfaces and systems, how leaders can stay aligned across stakeholders, and why the future of UX will demand new mental models as agents begin to replace apps. Packed with clarity, career guidance, and forward-thinking insights, this episode is a blueprint for standing out—not just once, but consistently. ▶ Chapters 00:00 - Intro: The Paradigm Shift & Going Back to the Primitives of Language 01:01 - Welcome to Jayawant Tewari: Career Trajectory & Microsoft's Unique Value 03:35 - The Scale Challenge: Accountability, Diversity, and Designing for a Billion Users 05:49 - The Trust Imperative: Mitigating AI Hallucination with References and Verification 06:50 - The Mindset: Moving Fast Without Breaking Things (The Cost of Disruption) 09:02 - Productivity vs. Engagement: Focusing on Flow, Continuity, and Time Back 11:47 - Building Intuition and Handling the Absence of Data (Learning from Failure) 14:43 - The Enterprise Reality: Balancing Stakeholders and the Needs of Buyers vs. Users 18:19 - The Ecosystem Approach: Designing Interconnected Experiences (The Orchestra) 21:30 - Collaboration and Influence: Why Storytelling is 50% of the Job 27:39 - When to Be Original: Differentiation is Not the Same as Being Different 34:47 - Leadership Lessons: The Marathon Mentality (Patience & Influence over Ownership) 43:04 - The Future Mindset: Curiosity, Agency, and Becoming a Holistic Product Maker 01:04:12 - Designing for AI: Bridging the Intent-Outcome Gap with Multimodal Input 01:10:29 - Final Thoughts on the Future: Upholding Taste and the Rise of Agents 01:19:44 - Chop Chop Round & Outro 🌟 About the Podcast Behind The Screens is a design leadership podcast series brought to you by Pineapple Design and Industry's Greatest Design Leaders. Our mission is to provoke, inspire, and redefine the boundaries of design through raw conversations with industry luminaries. Get ready to question your perception of product design and UX UI design as we bridge the gap between visionaries and learners. 🎧 Tune in now for a no-holds-barred conversation with Jayawant Tewari that promises to push the limits of design discourse. 📌 Connect with Us: Don't miss out on future episodes – hit that subscribe button now! Follow Pineapple Design on social media for more stimulating content: Instagram:   / pineapple.design_ Twitter:   / pineappleuxui LinkedIn:   / pineappledesignuxui #BehindTheScreens #DesignPodcast #ProductDesign #AI #DesignLeadership #UIUX #UXUIDesign #TechPodcast #Startups