Designing with Empathy

Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people’s daily digital interactions.

What you’ll learn:

• Why design should report to engineering, not product

• The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60

• How to create design tenets vs. principles (with real examples)

• The counterintuitive reason to delay drawing or prototyping as long as possible

• Why software is fundamentally a medium, like film or music (not just a tool)

• Why Bob “bounced off the culture” at Pinterest, and lessons from failure

• The lunar landing story that teaches us about championing radical ideas

• How to evaluate if a company truly values design before joining

• The moral obligation of software makers to build great products

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This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.

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Where to find Bob Baxley:

• Instagram: https://www.instagram.com/baxley/

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

• Website: http://www.bobbaxley.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 Bob Baxley

(03:52) Apple's lasting culture

(06:15) Navigating unique company cultures

(13:19) Finding a company that truly values your role

(15:46) What is design?

(17:17) How to help founders understand the value of design

(23:08) How to align product managers and designers

(26:31) Design reporting to engineering

(30:54) Integrating engineers early in the design process

(33:43) The maker mindset

(35:14) Challenging the assumption that design is time-intensive

(38:04) Design tenets vs. design principles

(45:25) The moral obligation of great design

(51:48) Understanding software as a medium

(01:01:20) Reducing ambiguity for product teams

(01:07:04) Giving designers space for creativity

(01:08:48) The "primal mark" concept

(01:12:05) AI prototyping tools: benefits and risks

(01:17:00) AI as a life coach

(01:21:22) Life lessons from the Apollo program

(01:28:24) Lightning round and final thoughts

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Referenced:

• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs

• Walt Disney: https://en.wikipedia.org/wiki/Walt_Disney

• Pinterest: https://www.pinterest.com/

• X: https://x.com/

• Uber: https://www.uber.com/

• Airbnb: https://www.airbnb.com/

• Slack: https://slack.com/

• Ed Catmull on X: https://x.com/edcatmull

• John Lasseter on X: https://x.com/johnlasseter5

• Apple patented a pizza box, for pizzas: https://www.theverge.com/2017/5/16/15646154/apple-pizza-box-patent-come-on

• Humane: https://en.wikipedia.org/wiki/Humane_Inc.

• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive

• Tony Fadell on LinkedIn: https://www.linkedin.com/in/tonyfadell/

• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/

• Tim Cook on X: https://x.com/tim_cook

• ThoughtSpot: https://www.thoughtspot.com/

• Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/

• Ajeet Singh on LinkedIn: https://www.linkedin.com/in/ajeetsinghmann/

• Honeywell: https://www.honeywell.com

• IDEO: https://www.ideo.com/

• Nutanix: https://www.nutanix.com/

• Lego: https://www.lego.com/

• Leica: https://leica-camera.com/

• Porsche: https://www.porsche.com/

• Patagonia: https://www.patagonia.com

• Brian Eno’s website: https://www.brian-eno.net/

• Scenius: why creatives are stronger together: https://thecreativelife.net/scenius/

• The Beatles website: https://www.thebeatles.com/

• Disneyland: https://disneyland.disney.go.com/destinations/disneyland/

• Tomorrowland: https://disneyland.disney.go.com/destinations/disneyland/tomorrowland/

• Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product): https://www.lennysnewsletter.com/p/unorthodox-product-lessons-from-n26-and-more

• Larry Page: https://en.wikipedia.org/wiki/Larry_Page

• Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin

• Design Principles: https://principles.design/

• Tableau: https://www.tableau.com/

• Figma: https://www.figma.com/

• Target self-checkout: https://corporate.target.com/press/fact-sheet/2024/03/checkout-improvements

• 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

• eBay: https://www.ebay.com/

• Williams Sonoma: https://www.williams-sonoma.com/

• Amazon: https://www.amazon.com/

• Monument to a Dead Child | Raw Data: https://podcasts.apple.com/ca/podcast/monument-to-a-dead-child/id1042137974

• Toast: https://pos.toasttab.com/

• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas

• The Plant: https://pixar.fandom.com/wiki/The_Plant

• Microsoft CPO: If you aren’t prototyping with AI you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai

• How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna

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

• John C. Houbolt: https://www.nasa.gov/centers-and-facilities/langley/john-c-houbolt/

• The Apollo program: https://www.nasa.gov/the-apollo-program/

• Archive clip: JFK at Rice University, Sept. 12, 1962—“We choose to go to the moon”: https://www.youtube.com/watch?v=QXqlziZV63k

• Alan Shepard: https://www.nasa.gov/former-astronaut-alan-shepard/\

• Blue Origin: https://www.blueorigin.com/

• Yuri Gagarin: https://en.wikipedia.org/wiki/Yuri_Gagarin

• Wernher von Braun: https://en.wikipedia.org/wiki/Wernher_von_Braun

• Yuri Kondratyuk: https://en.wikipedia.org/wiki/Yuri_Kondratyuk

• John Houbolt’s memo: https://space.stackexchange.com/questions/2823/text-of-john-houbolts-letter-proposing-lunar-orbit-rendezvous-for-apollo

• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx

• Lawrence of Arabia on Prime Video: https://www.amazon.com/Lawrence-Arabia-Peter-OToole/dp/B0088OINTU

• Leica M6: https://leica-camera.com/en-US/photography/cameras/m/m6

• Habitica: https://habitica.com/static/home

• Andor on Disney+: https://www.disneyplus.com/browse/entity-faba988a-a9f5-45f2-a074-0775a7d6f67a

• Edward Tufte quote: https://quotefancy.com/quote/1449650/Edward-Tufte-Good-design-is-clear-thinking-made-visible-bad-design-is-stupidity-made

• Ansel Adams quote: https://www.brainyquote.com/quotes/ansel_adams_106035

• It Takes a Village to Determine the Origins of an African Proverb: https://www.npr.org/sections/goatsandsoda/2016/07/30/487925796/it-takes-a-village-to-determine-the-origins-of-an-african-proverb

• Henry Modisett on LinkedIn: https://www.linkedin.com/in/henrymodisett/

• Perplexity: https://www.perplexity.ai/

• Golden State Warriors: https://www.nba.com/warriors/

• Steph Curry: https://www.espn.com/nba/player/_/id/3975/stephen-curry

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Recommended books:

• From Counterculture to Cyberculture: Stewart Brand, the Whole Earth Network, and the Rise of Digital Utopianism: https://www.amazon.com/Counterculture-Cyberculture-Stewart-Network-Utopianism/dp/0226817423

• Hare Brain, Tortoise Mind: How Intelligence Increases When You Think Less: https://www.amazon.com/Hare-Brain-Tortoise-Mind-Intelligence/dp/0060955414

• The Elements of Typographic Style: https://www.amazon.com/Elements-Typographic-Style-Robert-Bringhurst/dp/0881791326

• Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0060589469

• Time and the Art of Living: https://www.amazon.com/Time-Art-Living-Robert-Grudin/dp/0062503553/

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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.

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