Dive Club 🤿 – Détails, épisodes et analyse

This week's episode is with Ryan Scott who was an early designer at Doordash and then spent years as a design lead at Airbnb. Nowadays Ryan teaches hundreds of designers ranging from seniors to VPs how to make a bigger impact at your company.

This episode is jam-packed with insights about:

• What it’s like presenting at Airbnb CRIT
• Ways to unlock your credibility as a designer
• How to mitigate risk when presenting your ideas
• What it takes to speak the language of the business
• Types of “PM-y” questions that designers should be asking
• How Ryan led a massive redesign of the Airbnb booking flow
• The right (and wrong) way to make a case for investing in UX debt
• How to talk about your work in a way that resonates with non-designers
• a lot more

• Get $100 off of Ryan’s course “Describing the ROI of design”
• Ryan’s case study on redesigning the Airbnb checkout flow
• Past interview with Alex Schleifer (Chief Design Officer at Airbnb)

Investing in my personal brand has been the best investment I’ve ever made in my career. So I wanted to find the perfect designer to give a personal branding masterclass and I think it’s Oliur.

He’s built a massive audience across YouTube, Instagram, Twitter, etc. and he shares his hard-earned knowledge in this episode:

• Oliur’s keys to growing on social media
• Different ways to create leverage in your career
• How he (accidentally) landed a billion-dollar client
• How you can get more confident putting yourself out there
• Specific ways to build meaningful connections with other designers
• What designers need to know to get better at marketing themselves
• a lot more

• Oliur cites James McDonald as an example of someone sharing their work
• Oliur’s iPhone presets and high income streams videos
• We talk about his friend Ali Abdaal (YouTuber, Podcaster, NYT bestseller)
• Jason Levin’s iMessage screenshot of Travis Scott performing
• I referenced Jack Butcher’s “this is pointless” graph
• Dan Petty’s “That Marker Pack”
• The old Audience Building course on Maven (RIP)
• Turkish designer Oguz (Oliur talked about the power of his aesthetic)
• Gabe Valdivia’s new app Almanac that he built with Cursor

This week’s episode is with Kathy Zheng who is currently the Head of design at a Web3 protocol called Optimism. But before that she was the first designer at Patreon and went on to spend over 6 years at Github.

So the goal of this conversation is to look at how Kathy grew as a designer while at Github and identify the specific milestones on her journey to reaching senior and eventually staff designer.

We get into the weeds about:

• How the role of staff and senior designers differ
• The traits shared by the best designers at Github
• How to give your ideas a chance to become memes
• How to avoid conversational spinout on your project
• How to identify opportunities using systems thinking
• How Kathy is growing as a design leader at Optimism
• Specific techniques for storytelling and presenting ideas

Some of the people mentioned in this episode:

• Max Schoening (former Head of design at Github)
• Brian Lovin (bookmarking repo project)
• Kat Fikui (coworker at Github whose .readme we mentioned)
• Connor Sears (old manager at Github)
• Jack Conte (Cofounder of Patreon)

When you think about storytelling in design... Alex Cornell is often the person that comes to mind. And that's a big reason why he's one of the most requested guests on the show. So this episode is a deep dive into the finer details of communication. We talk about:

• The story behind his startup Cocoon
• How Alex leverages his background in video
• Alex’s precision and obsession with language
• Why Alex left linear to work on generative AI at Meta
• Why getting buy-in for your ideas is kind of like a math proof
• Behind-the-scenes of the wild videos Alex made at Facebook
• Lessons learned designing the Substack and Linear mobile apps
• The mental models Alex uses to construct compelling narratives
• a lot more

• Alex’s startup Cocoon
• Alex’s famous Chevron vs. 3 Dot video from Facebook
• Alex’s favorite monospace font is Jet Brains and his favorite serif font is Tiempos
• Klim is Alex’s favorite type foundry
• We discussed the dual-panel approach in the Amie mobile app

• This week’s episode with Maggie Appleton is a deep dive into designing for AI products and LLMs. Maggie shares about her experience as the first designer at Elicit (an AI assistant for research papers) and all of the unique challenges surrounding helping users interface with LLMs.
• We also go deep into:
  • How Maggie’s grown as a frontend developer
  • Why Maggie feels like she’s in a short-run limbo
  • Strategies for improving your technical literacy
  • How writing online has impacted Maggie’s career
  • The AI-native tools that Maggie is drawing inspiration from
  • How advancements in AI will redefine her role as a designer
  • How Maggie’s new understanding of LLMs is shaping the way she designs
  • Why Maggie is more interested in the cognitive applications of AI rather than generative AI

• Maggie is currently leading design at Elicit (they’re hiring)
• “How Trello is different” is where Joel Spolsky explains the differences between horizontal and vertical software
• OpenAI’s introduction of ChatGPT-4o
• We talked about the product tldraw
• The expanding dark forest and generative AI: Maggie’s talk about the possible futures of flooding the web with AI-generated content
• Episode with Soleio where he talks about looking for “time to proficiency” in design candidates

Remember how Michael Wandelmeier told us Metalab hired a storytelling coach? Well that coach is Ian Wharton. He’s an Apple Design Award winner, CEO of Aide Health, and he teaches storytelling techniques to teams like Dyson, BBC, Huge, etc.

So this episode breaks down the key storytelling concepts that he shares in his course Sell the Idea. We talk about the importance of the inciting incident, how to empower others to share your ideas, and a lot more…

But he also presents some compelling ideas about why designers are the most suited people to start companies that solve societal level challenges. All you need is a bias toward action. So if you’ve been considering starting your own thing, there’s a lot we can learn from Ian’s journey as a design founder.

• Ian’s course Sell the Idea (use the code RIDD at checkout for 30% off)
• Ian’s personal website
• Ian’s business Aide Health
• Mackinnon and Saunders (the stop motion company Ian worked with)

~6 months ago Amy Lima was laid off and has been preparing for this episode ever since. So in this interview she gives us an inside look at her process for landing a dream role at Duolingo. If you’re looking for your next role then this conversation is quite the playbook. She has the job hunt process down to a science.

Some topics covered:

• Avoiding burnout amidst the chaos
• How Amy negotiated her Duolingo offer
• Amy’s advice to proactively prepare for a layoff
• The ways Amy iterated on her portfolio presentation
• How Amy’s career coach shaped her interview strategy
• Some hard lessons learned during her job hunt process
• How Amy measured everything in her application process
• a lot more

Show notes:

• Amy’s layoff announcement post
• Career Compass
• Charlotte Burns (Amy’s job hunt coach)
• Levels (transparency database + salary negotiation tools)
• Amy’s job announcement post

Sponsors:

• Framer: How I build websites
• Jitter: How I animate my designs
• Raycast: How I do everything on my computer

• Julius Tarng is the ultimate generalist designer.
  • He started the design tools team at Facebook where he made a massive impact on products like Origami.
  • He then freelanced as a design engineer for companies like Felt, Anthropic, and even prototyped some of the early AI features for the Arc browser.
  • Now he’s in his first-ever engineering role at Linear.

  So this conversation is a deep dive into what it looks like for designers to approach their work with an engineering mindset. We talk about Julius’s deep background in prototyping, how he collaborates with designers at Linear. And we also get into why the current state of design engineering is a missed opportunity.

  If you’re looking to grow as a software designer then you’ll love this episode.

Show notes:

• Julius’s twitter
• Felt — a better way to work with maps
• Daniel Smith (Linear designer that Julius pairs with)
• Origami (Facebook’s prototyping tool)
• Brandon Walkin (ex: Facebook, Apple, now at OpenAI) who made the adaptive pointer for iPad.
• What are GPUs and Shaders? (Julius’s tutorial video)

When it comes to design founder stories, Raphael Schaad’s is one of the best. So this episode is the first-ever telling of how Raphael designed and built Cron (which became Notion Calendar). We talk about:

• Sketching on paper vs. sketching in code
• Why shipping quality software is like camping
• How Raphael identified the MVP of the problem
• What it was like building Cron in YC during COVID
• Why you should design dialogues as first-class citizens
• Why Raphael didn’t invest much in the Cron landing page
• The differences between a design toolkit and a design system
• a lot more lessons from a successful first-time design founder

• Raphael’s Twitter
• The OG Cron website
• Screenshot of the Cron dialogues in Figma

Alex Schleifer was the long-time Chief Design Officer at Airbnb where he grew the team from ~35 to over 600 people. So this conversation is an inside look at what makes design at Airbnb so special. We discuss:

• How to create a culture of decisiveness
• Why great design leaders are like chefs
• How to succeed in executive CRITs at Airbnb
• How designers should prepare for an AI future
• What it means to operate with a “first team” mindset
• What it takes to achieve Airbnb’s level of craft at scale
• Which elements of the Airbnb culture you can instill for your team
• a lot more

Alex’s Twitter and Linkedin

Alex’s “People vs. Algorithms” podcast

Mentioned Airbnb alumni:

• Katie Dill (Head of Design at Stripe)
• Ethan Eismann (SVP Design at Slack)
• Karri Saarinen (CEO at Linear)