Where human judgment still matters

Jenny Wen leads design for Claude at Anthropic. Prior to this, she was Director of Design at Figma, where she led the teams behind FigJam and Slides. Before that, she was a designer at Dropbox, Square, and Shopify.

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We discuss:

1. Why the classic discovery → mock → iterate design process is becoming obsolete

2. What a day in the life of a designer at Anthropic looks like, including her AI tool stack

3. Whether AI will eventually surpass humans in taste and judgment

4. Why Jenny left a director role at Figma to return to IC work at Anthropic

5. The three archetypes Jenny is hiring for now

6. Why chatbot interfaces may be more durable than most people expect

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Episode transcript: https://www.lennysnewsletter.com/p/the-design-process-is-dead

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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 Jenny Wen:

• X: https://x.com/jenny_wen

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

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

• Website: https://jennywen.ca

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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 Jenny Wen

(04:23) Why the traditional design process is dead

(06:33) The two new types of design work

(10:00) How widespread this shift will be

(13:00) Day-to-day life as a designer at Anthropic

(18:45) Jenny’s AI stack

(20:03) Why Figma still matters for exploration

(22:25) Advice for working with engineers

(24:19) How to maintain craft, quality, and trust in the AI era

(27:35) Will AI ever have “taste”?

(31:38) The future of chatbot interfaces

(35:33) Moving from director back to IC

(41:00) The 10-day build of Claude Cowork

(46:06) Hiring: the three archetypes

(50:44) Advice for new and senior designers

(54:42) The value of “low leverage” tasks for managers

(57:52) Why the best teams roast each other

(01:01:45) The legibility framework

(01:07:22) Lightning round and final thoughts

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Referenced:

• Figma: https://www.figma.com

• Anthropic: https://www.anthropic.com

• v0: https://v0.app

• Navigating a Design Career with Jenny Wen | Figma at Waterloo: https://www.youtube.com/watch?v=OHcBPMh2ivk

• Claude Cowork: https://claude.com/product/cowork

• Use Claude Code in VS Code: https://code.claude.com/docs/en/vs-code

• Claude Code in Slack: https://code.claude.com/docs/en/slack

• Lex Fridman’s website: https://lexfridman.com

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

• OpenClaw: https://openclaw.ai

• 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

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• Socratica: https://www.socratica.info

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice

• Evan Tana’s ‘legibility matrix’ on X: https://x.com/evantana/status/1927404374252269667

• How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early

• Palantir: https://www.palantir.com

• Stripe: https://stripe.com

• Linear: https://linear.app

• Notion: https://www.notion.com

• Julie Zhuo’s website: https://www.juliezhuo.com

• Sentimental Value: https://www.imdb.com/title/tt27714581

• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD

• Noah Wyle: https://en.wikipedia.org/wiki/Noah_Wyle

• ER on Prime Video: https://www.amazon.com/gp/video/detail/B0FWZSDYRP

• Retro: https://retro.app

• Granola: https://www.granola.ai

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Recommended books:

• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509

• The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394480767

• Insomniac City: New York, Oliver Sacks, and Me: https://www.amazon.com/Insomniac-City-New-York-Oliver/dp/162040494X

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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.