Molly Graham is back for round two, and this one is even more powerful. Molly has spent more than 20 years helping organizations and the humans inside them navigate growth and change. She’s held leadership roles at Google, Facebook, Quip, and the Chan Zuckerberg Initiative and is the host of TED’s WorkLife podcast (which she took over from Adam Grant). She also runs Glue Club, a leadership community for senior operators, and writes a popular newsletter called Lessons.

In our in-depth conversation, we discuss:

1. Why Molly’s famous “give away your Legos” career advice no longer holds true in an AI world

2. The grief, loneliness, and burnout sweeping through the tech industry right now

3. Why delegating to AI is fundamentally different from delegating to a human

4. The fear narrative around AI job displacement, and why it’s overblown

5. Which Legos you should never give to AI

6. What the best managers are doing right now

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

DX—Engineering intelligence for the AI era

Where to find Molly Graham

• X: https://x.com/molly_g

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

• Substack: https://mollyg.substack.com

• Website: https://glueclub.com

Referenced:

• The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham

• Myspace: https://myspace.com

• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups

• Safeway: https://www.safeway.com

• The Odyssey: https://www.imdb.com/title/tt33764258

• What happens after coding is solved? | Fiona Fung (Manager of the Claude Code and Cowork Teams): https://www.lennysnewsletter.com/p/building-the-most-ai-pilled-engineering

• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens

• How to step confidently into the unknown with Manoush Zomorodi: https://mollyg.substack.com/p/new-worklife-episode-how-to-step

• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026

• “I Know It When I See It” Doesn’t Scale with Hilary Gridley: https://mollyg.substack.com/p/worklife-hilary-gridley

• Foo Camp: https://en.wikipedia.org/wiki/Foo_Camp

• Tim O’Reilly on LinkedIn: linkedin.com/in/timo3

• Adam Mosseri: AI is a tailwind for authenticity: https://www.lennysnewsletter.com/p/adam-mosseri-ai-is-a-tailwind-for

• 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna?utm_source=publication-search

• Waymo: https://waymo.com

• AI’s third era: the rise of persistent AI coworkers | Tara Seshan (Product Lead ChatGPT Work): https://www.lennysnewsletter.com/p/ais-third-era-the-rise-of-persistent

• Airbnb: https://www.airbnb.com

• Booking.com: https://www.booking.com

• 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

• Hugging Face: https://huggingface.co

• You’re closer to an AI expert than you think with Max Mullen: https://mollyg.substack.com/p/worklife-max-mullen

• OpenAI’s Head of Design: This is the best time in history to be a designer | Ian Silber: https://www.lennysnewsletter.com/p/openais-head-of-design-this-is-the

• Grok Bot: https://x.ai/news/introducing-grok-bot

• Why Clay Has an AI Writing Policy: https://www.clay.com/blog/ai-writing-policy

• Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO): https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future

Recommended book:

• The Reverse Centaur's Guide to Life After AI: https://www.amazon.com/Reverse-Centaurs-Guide-Life-After/dp/037462156X

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.

My biggest takeaways from this conversation:...