Dive Club (Deep Dives) �‪�‬ Ridd

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 developerWhy Maggie feels like she’s in a short-run limboStrategies for improving your technical literacyHow writing online has impacted Maggie’s careerThe AI-native tools that Maggie is drawing inspiration fromHow advancements in AI will redefine her role as a designerHow Maggie’s new understanding of LLMs is shaping the way she designsWhy 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 softwareOpenAI’s introduction of ChatGPT-4oWe talked about the product tldrawThe expanding dark forest and generative AI: Maggie’s talk about the possible futures of flooding the web with AI-generated contentEpisode 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 websiteIan’s business Aide HealthMackinnon 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 chaosHow Amy negotiated her Duolingo offerAmy’s advice to proactively prepare for a layoffThe ways Amy iterated on her portfolio presentationHow Amy’s career coach shaped her interview strategySome hard lessons learned during her job hunt processHow Amy measured everything in her application processa lot more
Show notes:
Amy’s layoff announcement postCareer CompassCharlotte Burns (Amy’s job hunt coach)Levels (transparency database + salary negotiation tools)Amy’s job announcement post
Sponsors:
Framer: How I build websitesJitter: How I animate my designsRaycast: 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 twitterFelt — a better way to work with mapsDaniel 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 codeWhy shipping quality software is like campingHow Raphael identified the MVP of the problemWhat it was like building Cron in YC during COVIDWhy you should design dialogues as first-class citizensWhy Raphael didn’t invest much in the Cron landing pageThe differences between a design toolkit and a design systema lot more lessons from a successful first-time design founderRaphael’s TwitterThe OG Cron websiteScreenshot 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 decisivenessWhy great design leaders are like chefsHow to succeed in executive CRITs at AirbnbHow designers should prepare for an AI futureWhat it means to operate with a “first team” mindsetWhat it takes to achieve Airbnb’s level of craft at scaleWhich elements of the Airbnb culture you can instill for your teama 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)