The Art of Trusting Judgment in Product Development

Katie Dill is the Head of Design at Stripe. Previously, she was Head of Experience Design at Airbnb and Head of Design at Lyft. Katie has been named one of Business Insider’s 10 People Changing the Tech Industry as well as one of Fast Company’s 100 Most Creative People in Business and received the Girls in Tech “Creator of the Year” award. In today’s episode, she shares:

• What makes a design great

• Advice on building high-performing teams in hyper-growth environments

• A pivotal lesson in leadership she learned at Airbnb

• Stripe’s focus on quality and how it’s tied to growth

• A formula for removing organizational friction

• How to increase productivity

• What to look for when hiring a designer

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Find the transcript for this episode and all past episodes at: https://www.lennysnewsletter.com/p/building-beautiful-products-with

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Where to find Katie Dill:

• X: https://twitter.com/lil_dill

• Threads: https://www.threads.net/@lil_dilly

• LinkedIn: https://www.linkedin.com/in/katie-dill-79168b3/

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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) Katie’s background

(04:47) Katie’s pivotal leadership moment at Airbnb

(10:55) Advocating for design ROI

(16:07) Stripe’s quality focus

(17:50) Stripe’s vast scope

(18:45) How design enhances utility

(21:39) Defining beauty and its role in product growth

(26:19) Operationalizing quality

(28:44) Katie’s insights from dialogues with diverse organizations

(34:47) 15 Essential Journeys: Stripe’s method for holistic UX understanding and unified vision

(44:35) Stripe’s PQR quality review

(46:25) Stripe’s prioritization philosophy

(48:29) Measuring impact beyond metrics

(50:28) Performance = potential – interference

(54:09) Building and managing large teams

(1:01:46) Removing interference at Lyft: a practical example of Katie’s leadership impact

(1:06:10) Stripe’s physical workspace design

(1:07:41) Embracing bold ideas

(1:11:07) Qualities of great designers

(1:15:15) Stripe Press

(1:19:19) Katie’s parting wisdom

(1:23:17) Lightning round

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Referenced:

• Beauty: https://www.amazon.com/Sagmeister-Walsh-Beauty-Stefan/dp/0714877271

• Terry (Olivia Colman) and Richie peel mushrooms—scene from The Bear: https://www.youtube.com/watch?v=f7D8THR_osU

• Building a culture of excellence | David Singleton (CTO of Stripe): https://www.lennyspodcast.com/building-a-culture-of-excellence-david-singleton-cto-of-stripe/

• Figma: https://www.figma.com/

• The Creative Act: A Way of Being: https://www.amazon.com/Creative-Act-Way-Being/dp/0593652886

• Quote by Robert Henri: https://www.goodreads.com/quotes/43397-the-object-isn-t-to-make-art-it-s-to-be-in

• Brian Chesky’s 11-star experience: https://www.product-frameworks.com/11-Star-Experience.html

• How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034

• The Wright Brothers: https://www.amazon.com/Wright-Brothers-David-McCullough/dp/1476728755/

• The Boy, the Mole, the Fox and the Horse: https://www.amazon.com/Boy-Mole-Fox-Horse/dp/0062976583/

• Oppenheimer: https://www.oppenheimermovie.com/

• Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking/umc.cmc.apzybj6eqf6pzccd97kev7bs

• Toniebox: https://www.amazon.com/Toniebox-Starter-Lightning-McQueen-Playtime/dp/B09V7NJCD8

• Stripe Press: https://press.stripe.com/

• Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack

• Stripe’s job board: https://stripe.com/jobs/search

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Books on design craft:

• Dieter Rams: Ten Principles for Good Design: https://www.amazon.com/Dieter-Rams-Principles-Good-Design/dp/3791387324

• The Vignelli Canon: https://www.amazon.com/Vignelli-Canon-Massimo/dp/3037782250

• Forget All the Rules About Graphic Design: Including the Ones in This Book, by Bob Gill: https://www.amazon.com/Forget-Rules-About-Graphic-Design/dp/0823018644

• Emotional Design: Why We Love (or Hate) Everyday Things: https://www.amazon.com/Emotional-Design-Love-Everyday-Things/dp/0465051367

• The Design of Everyday Things: Revised and Expanded Edition: https://www.amazon.com/Design-of-Everyday-Things-audiobook/dp/B07L5Y9HND

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

• In Praise of Shadows: https://www.amazon.com/Praise-Shadows-Junichiro-Tanizaki/dp/0918172020

• Interaction of Color: https://www.amazon.com/Interaction-Color-Anniversary-Josef-Albers/dp/0300179359

• Content Design: https://contentdesign.london/shop/content-design-by-sarah-winters-paperback

• Graphic Design Manual Principles and Practice: https://www.niggli.ch/en/produkt/graphic-design-manual/

• Collaborative Product Design: https://www.oreilly.com/library/view/collaborative-product-design/9781491975022/

• Principles of Form and Design: https://www.amazon.com/Principles-Form-Design-Wucius-Wong/dp/0471285528/ref=asc_df_0471285528

• The Timeless Way of Building: https://www.patternlanguage.com/bookstore/timeless-way-of-building.html

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Lenny may be an investor in the companies discussed.

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