Model introspection and evals reveal product gaps

Cat Wu is Head of Product for Claude Code and Cowork at Anthropic, building one of the most important AI products of this generation. Before joining Anthropic, Cat spent years as an engineer and briefly worked in VC. Today, she’s interviewing hundreds of product managers who are trying to break into AI—and seeing firsthand what separates those who thrive from those who fall behind.

We discuss:

1. How Anthropic’s shipping cadence went from months to weeks to days

2. The emerging skills PMs need to develop right now

3. Why you need to build products that don’t yet fully work, so you’re ready when the next model closes the gap

4. Cat’s most underrated AI skill: asking the model to introspect on its own mistakes

5. Why Claude’s personality is core to its success

6. Why Anthropic’s mission alignment eliminates the friction that slows most large organizations

7. Why “just do things” is the most important principle for working at AI-native companies

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Episode transcript: https://www.lennysnewsletter.com/p/why-half-of-product-managers-are-in-trouble

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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0

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Where to find Cat Wu:

• X: https://x.com/_catwu

• LinkedIn: linkedin.com/in/cat-wu

• Newsletter: https://catwu.substack.com

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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 Cat Wu

(01:29) Working with Boris Cherny

(04:29) What Anthropic looks for when hiring PMs

(06:18) How to help your teams move fast

(08:58) How PRDs and roadmaps have evolved at Anthropic

(10:28) The Mythos model and Anthropic’s shipping velocity

(11:54) What happened with the Claude Code source code leak

(12:53) Integrating with OpenClaw

(14:19) How the PM team is structured at Anthropic

(15:42) How engineer and PM roles are merging

(17:54) Why product taste is the most valuable skill

(20:10) Where human brains will continue to be useful

(22:23) How to stay sane in constant chaos

(24:16) What gets sacrificed when you ship so fast

(27:47) The /powerup command

(28:32) Why Anthropic has been so successful

(32:28) When to use Claude Code vs. Desktop vs. Cowork

(35:58) Tips for getting started with Cowork

(38:44) Demo: Using Cowork to build slide decks overnight

(41:48) Cat’s PM tech stack and internal tools

(46:47) Which teams use the most tokens

(51:15) The emerging skills PMs need for AI companies

(55:00) Why building evals is underappreciated

(58:44) Why Claude’s character and personality matter so much

(1:00:44) How new models force product changes

(1:05:11) The vision for Claude Code and Cowork

(1:07:22) Advice for thriving in an AI-driven world

(1:09:18) Why 95% automation isn’t good enough

(1:11:58) Build apps you use every day, not prototypes

(1:13:41) The divide between AI skeptics and believers

(1:15:19) Lightning round

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Referenced: https://www.lennysnewsletter.com/p/how-anthropics-product-team-moves

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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.