35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley
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Why do product designers feel a moral obligation to improve everyday digital interactions?
Almost everyone living in a modern economy now is going to have hundreds of interactions with the phone or with a computer. And unfortunately, a lot of those interactions are not gonna be great. We have an obligation as product people to put that emotional energy back into people's lives. You actually have a really unique perspective on just what is design. Design is trying to imagine the future you want to live in and then take the steps to make it real. Saying a company is design-led does not mean it's Designer led. I've never seen somebody grafted on after the fact. It's there at the beginning in the root DNA or it doesn't exist. It wasn't a successful stint at Pinterest. I just sort of bounced off the culture.
I came in thinking I was supposed to behave the way I behaved at Apple, which is very direct, fighting hard. Why did you decide to join Apple? I just seek out opportunities to witness history. The whole company is constantly asking, how can the thing that I'm working on?
on be a little bit better. Why do you think that people that have left Apple, like a lot of amazing things haven't emerged? Today, my guest is Bob Baxley. Bob is a designer, executive, and advisor who's built and led design teams at Apple, Pinterest, Yahoo, and most recently ThoughtSpot. Over the course of his career that spanned over three decades, Bob has played a pivotal role in the design of the Apple Online Store, the Apple App Store, Pinterest, and early in his career, Yahoo Answers. Products that have been used by hundreds of millions. Of people around the world. Bob also mentors individuals and advises organizations that are working to improve the practice, craft, and culture of digital product design.
There is something in this conversation for everyone, from why you should consider having design report to engineering, why it's your moral obligation to build great products, why you should wait as long as possible to draw a picture or create a prototype of your idea, to what the moonland. And can teach us about building better teams and products. I could listen to Bob all day. I learned a ton from this conversation, including a bunch of really unique insights that I've never heard before. A big thank you to Annie Warner, Andrew Hogan, Irene Aw, and Joff Redford for suggesting questions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube.
Also, if you become an annual subscriber of my newsletter, you get a year-free.
What lessons did Bob learn from moving from Apple’s culture to Pinterest and how did that shape his view on company fit?
of a bunch of incredible products, including Linear, Superhuman, Notion, Perplexity, Granola, and more. Check it out at lenny's newsletter.com and click bundle. With that, I bring you Bob Baxley. This entire episode is brought to you by Stripe. There's a reason that I've had more guests on this podcast from Stripe than any other company. It's because they hire the best people and they build incredible products. You probably know them for their payments platform, which powers my newsletter, and also companies like NVIDIA and Salesforce and Zoom and DoorDash. What you may not know is that they have several other products that can help accelerate your revenue. Such as Stripe Billing, which powers billing for companies that you may have heard of: OpenAI, Anthropic, Figma, Atlassian, and over 300,000 other companies.
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Chapters
6 chapters
1
Why do product designers feel a moral obligation to improve everyday digital interactions?
0:00–2:10
2
What lessons did Bob learn from moving from Apple’s culture to Pinterest and how did that shape his view on company fit?
2:10–51:42
3
How can designers develop intuition by observing users of other products?
51:42–57:28
4
Why does Bob treat software as a medium and how does emotion shape design decisions?
57:28–1:03:10
5
What are the risks and benefits of using AI‑generated prototypes and the “primal mark” concept?
1:03:10–1:12:27
6
Which books, movies, and products does Bob recommend and what final lightning‑round questions wrap up the episode?
1:12:27–1:41:55
Speakers
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