Navigating Sharp Problems in Product Development

Ezinne and Oji Udezue have over 50 years of combined product leadership experience at Microsoft, Twitter, Atlassian, WP Engine, Typeform, and Calendly. They’ve witnessed every major shift in product management, and, despite their seniority, they’re taking beginner AI courses and learning from engineers half their age, and Oji is coding more now than in the past decade—from Waterfall to Agile to AI. They are also the authors of Building Rocketships, a guide to building great products. In this conversation, the couple shares hard-won lessons they’ve learned from companies successfully adapting to AI, including their “shipyard” framework and their “sharp problem” methodology.

What you’ll learn:

1. The “shipyard” framework: why the best AI teams embrace controlled chaos

2. Why Oji writes more code now than in the past 10 years—despite being a PM for more than 25 years

3. The three skills that matter most for PMs in 2025: curiosity, humility, and agency

4. How to identify “sharp problems”

5. AI at the core vs. AI at the edge: why companies that are building entirely new AI-centric codebases will beat those just “sprinkling AI” on existing products

6. The counterintuitive truth: engineers are moving so fast with AI that PMs are now the bottleneck

7. Their biggest product lesson from 50 combined years

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Where to find Oji and Ezinne:

• ProductMind on Substack: https://substack.com/@ojiudezue

• ProductMind on LinkedIn: https://www.linkedin.com/company/productmindco

• ProductMind on YouTube: https://www.youtube.com/@ProductMindX/videos

• ProductMind on Spotify: https://open.spotify.com/show/07OVh5pdSv0szHPwWktzQQ

• ProductMind website: https://www.productmind.co/

• Oji on LinkedIn: https://www.linkedin.com/in/ojiudezue/

• Ezinne on LinkedIn: https://www.linkedin.com/in/ezinne/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Oji and Ezinne

(04:14) The evolving role of product managers

(08:01) Challenges and opportunities in product management

(10:34) Sharp problems

(12:37) The shipyard model for product development

(17:02) Hiring PMs in the AI era

(24:55) The importance of staying humble

(27:16) Hands-on learning and personal projects

(39:10) Companies succeeding with AI adoption

(46:25) Lessons from 50 years in product

(49:22) Simplicity in design

(51:24) The role of communication in strategy

(55:17) Career intentions and personal growth

(01:00:00) Ethics and responsibility in product management

(01:03:09) Introducing Building Rocketships

(01:06:42) Lightning round and final thoughts

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Referenced:

• How 80,000 companies build with AI: products as organisms, the death of org charts, and why agents will outnumber employees by 2026 | Asha Sharma (CVP of AI Platform at Microsoft): https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma

• Picking sharp problems, increasing virality, and unique product frameworks | Oji Udezue (Typeform, Twitter, Calendly, Atlassian): https://www.lennysnewsletter.com/p/picking-sharp-problems-increasing

• Atlassian: https://www.atlassian.com/

• Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/

• Brownian motion: https://en.wikipedia.org/wiki/Brownian_motion

• Calendly: https://calendly.com/

• Women in Product: https://womenpm.org/

• Brian Chesky’s secret mentor who died 9 times, started the Burning Man board, and built the world’s first midlife wisdom school | Chip Conley (founder of MEA): https://www.lennysnewsletter.com/p/chip-conley

• Home Assistant: https://www.home-assistant.io/

• What people are vibe coding (and actually using): https://www.lennysnewsletter.com/p/what-people-are-vibe-coding-and-actually

• How many layers should I wear today?: https://layers.today/

• Typeform: https://www.typeform.com/

• David Okuniev on X: https://x.com/okuiux

• Clay: https://www.clay.com/

• Martin Eriksson on LinkedIn: https://www.linkedin.com/in/martineriksson/

• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead

• Dave Mendlen on LinkedIn: https://www.linkedin.com/in/davemendlen/

• Deepfake: https://en.wikipedia.org/wiki/Deepfake

• How to kickstart and scale a marketplace business: https://www.lennysnewsletter.com/p/how-to-kickstart-and-scale-a-marketplace

• Forever on Netflix: https://www.netflix.com/title/81418639

• Paradise on Hulu: https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f

• Sinners: https://www.imdb.com/title/tt31193180/

• Claude: https://claude.ai/

• Nespresso Vertuo: https://www.nespresso.com/us/en/vertuo-coffee-machines

• Gamma: https://gamma.app/

• Framer: https://www.framer.com/

• Lovable: https://lovable.dev/

• 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

• Llama: https://www.llama.com/

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Recommended books:

• Building Rocketships: Product Management for High-Growth Companies: https://www.amazon.com/Building-Rocketships-Management-High-Growth-Companies/dp/1962339068

• Coda version of Building Rocketships: https://www.productmind.co/brpro

• Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067

• The Let Them Theory: A Life-Changing Tool That Millions of People Can’t Stop Talking About: https://www.amazon.com/Let-Them-Theory-Life-Changing-Millions/dp/1401971369/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation: