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Aparna Chennapragada is the chief product officer of experiences and devices at Microsoft, where she oversees AI product strategy for their productivity tools and work on agents. Previously, she was the CPO at Robinhood, spent 12 years at Google, and is also on the board of eBay and Capital One.
What you’ll learn:
How “prompt sets are the new PRDs” and why prototyping with AI is now essential for effective product development
The three key characteristics of AI agents: autonomy (delegation of tasks), complexity (handling multi-step challenges), and natural interaction (conversing beyond simple chat)
Why NLX (natural language experience) is the new UX, requiring deliberate design principles for conversational interfaces
Why the PM role isn’t dying in the AI era—it’s evolving to emphasize tastemaking and editing
How living “one year in the future” can be operationalized with programs like Microsoft’s Frontier
How even traditional enterprises can balance cutting-edge AI adoption with appropriate governance through dual-track approaches
Insights on leadership differences between Microsoft’s Satya Nadella (known for multi-level thinking and early trendspotting) and Google’s Sundar Pichai (mastery of complex ecosystems)
The vision for human and AI collaboration in the workplace, where people and agents achieve outcomes greater than either could alone
A practical framework for evaluating zero-to-one product opportunities
Some takeaways:
Enterprise AI requires a “two-product” mindset: Building for enterprise isn’t just about making a feature delightful (like consumer products). You must simultaneously solve for governance, security, and auditability. Neglecting either side leads to failure—either insecure products or crippled user experiences. Mastering this balance is a distinct, crucial skill.
Navigate the “Van Damme split” of AI adoption: Companies are stretched between the incredibly fast pace of AI advancements (weeks/months) and the slower pace of human habit change and organizational adoption. The key is not to hold back early adopters while planning broader, trusted change management. Introduce cutting-edge tools (like Microsoft’s “Frontier” program) to pioneers first.
“NLX is the new UX”—design language interfaces deliberately: Natural language experience (NLX) isn’t just “talking to a model.” It requires intentional design, just like graphical UIs.
“Prompt sets are the new PRDs”—prototype relentlessly: In the AI era, the fastest way to clarify and communicate a product idea is to build a prototype and define its core interactions via prompt sets. Prioritize “demos before memos.” If you’re not prototyping to figure out what you want to build, you’re likely doing it wrong.
PMs evolve to “tastemakers” and editors: As AI floods the world with ideas and prototypes, the PM role shifts away from process management (which AI can handle) and toward editorial judgment and tastemaking. The ability to curate, refine, and guide toward a coherent, valuable product becomes paramount. Influence must be earned through strong judgment, not just title.
Build one year in the future by institutionalizing early-adopter labs. Microsoft’s Frontier program is a new experimental product lab for internal and external early adopters to get hands-on with the most advanced, rough-cut AI tools and agents focused on productivity and work.
Agents defined—a three-pronged definition for designing great agents (and agent-like products):
Autonomy: Increasing capability for agents to independently handle and delegate complex tasks (not just single outputs)
Complexity: Handle multi-step, non-trivial workflows (e.g. “Prep me for a meeting” not “Summarize doc”)
Natural interaction: Go beyond chat—multi-modal, editable plans, meetings, and context-rich communication
The “2 out of 3” rule for 0-to-1 products—for a new product/category to succeed, look for inflection points in at least two of these three areas:
Technology shift: A step-function change (e.g. LLMs, mobile)
Consumer behavior shift: A significant change in how people act (e.g. taking photos of everything)
Business model shift: A new way to monetize or structure the business (e.g. SaaS, freemium)
Where to find Aparna Chennapragada:
• LinkedIn: https://www.linkedin.com/in/aparnacd/
In this episode, we cover:
(00:00) Introduction to Aparna Chennapragada
(04:28) Aparna’s stand-up comedy journey
(07:29) Transition to Microsoft and enterprise insights
(10:00) The Frontier program and AI integration
(13:28) Understanding AI agents
(17:59) NLX is the new UX
(22:28) The future of product development
(31:16) Building a custom Chrome extension
(35:45) Leadership styles of Satya and Sundar
(37:47) Counterintuitive lessons in product building
(41:20) Inflection points for successful products
(45:16) GitHub Copilot and code generation
(48:34) Excel’s enduring success
(50:27) Pivotal career moments
(54:55) The future of human-agent collaboration
(56:25) Lightning round and final thoughts
Referenced:
• Google Lens: https://lens.google/
• Saturday Night Live: https://www.nbc.com/saturday-night-live
• Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/
• Robinhood: https://robinhood.com/
• eBay: https://www.ebay.com/
• Capital One: https://www.capitalone.com/
• Microsoft: https://www.microsoft.com/
• Aparna’s LinkedIn post about enterprise vs. consumer: https://www.linkedin.com/posts/aparnacd_every-enterprise-user-feature-has-a-shadow-activity-7321176091610542080-8X-E/
• The Epic Split: https://en.wikipedia.org/wiki/The_Epic_Split
• AI Frontiers: https://www.microsoft.com/en-us/research/lab/ai-frontiers/
• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai
• Deepseek: https://www.deepseek.com/
• Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/
• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook
• Tobi Lütke’s post on X about reflexive AI: https://x.com/tobi/status/1909251946235437514
• GitHub Copilot: https://github.com/features/copilot
• Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/
• South Park “Underwear Gnomes” episode: https://southpark.cc.com/episodes/13y790/south-park-gnomes-season-2-ep-17
• Google Home: https://home.google.com/welcome/
• Cursor: https://www.cursor.com/
• v0: https://v0.dev/
• Bolt: https://bolt.net/
• Lovable: https://lovable.dev/
• Replit: https://replit.com/
• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons
• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad
• Microsoft Excel World Championship: https://fmworldcup.com/microsoft-excel-world-championship/
• Google Now: https://en.wikipedia.org/wiki/Google_Now
• Hacks on Max: https://www.max.com/shows/hacks/67e940b7-aab2-46ce-a62b-c7308cde9de7
• Granola: https://www.granola.ai/
• Alan Kay quote: https://www.brainyquote.com/quotes/alan_kay_100831
• Sindhu Vee’s website: https://sindhuvee.com/
• Nate Bargatze’s website: https://natebargatze.com/
Recommended book:
• A Brief History of Intelligence: Evolution, AI, and the Five Breakthroughs That Made Our Brains: https://www.amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
Lenny may be an investor in the companies discussed.
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