Blaine Billingsley: OpenAI designer on the collaboration problem AI hasn't solved yet

Design Better

Staff designer Blaine Billingsley shares his unconventional journey from studying music and religion to working at OpenAI. The conversation

Key takeaways

• A background in the liberal arts, such as music or religion, provides a unique lens for understanding human behavior in design.
• Corporate jargon acts as 'slop' that obfuscates meaning and prevents teams from reaching genuine agreement on project goals.

Main topics

• Career transitions
• Multidisciplinary thinking

Notable quotes

Ideas are really cheap.

Conclusion

The episode highlights how intellectual curiosity and a commitment to

Transcript preview

Speaker 1 (0:01) Ideas are really cheap. It's easy to come up with a ton of ideas. If we've got two and we're not agreeing on them, let's go get 10 more and we'll find something in there. Let's go find something else different than what we've been talking about is just a way to relax the stress, I think, when people get stuck on something. Speaker 2 (0:19) Blaine Billingsley is a staff designer at OpenAI, and his path getting there was anything but a straight line. He started out in college studying music composition and comparative religion. For a while, he played guitar in Texas for a living and can remember looking at his bank account and seeing $7 and feeling pretty excited about that. Then he drove to San Francisco and took a data entry job at a startup. Some of the engineers he worked with taught him how to script his way through the work in a couple of hours. and then he spent the rest of the day learning from them. From there, he went on to companies big and small, including a long run working on Gmail. Blaine has an allergy to corporate jargon that we found particularly interesting. He's well known amongst his colleagues for rewriting product specs to get absolute clarity on a project, and for raising his hand in a meeting to ask, what do we really mean by create a command center for work? We talk with Blaine about why a Speaker 3 (1:14) design principle only helps if you could reasonably disagree with it, and his counterintuitive advice for working with a pushy PM. The best way to have influence is to be influenced. Then we get into how design actually works inside OpenAI. Blaine walks us through what goes into an eval, and the product design plugin he built with OneEngineer, whose biggest fans turned out to be the PMs and developers who are starved for a design partner. This is Design Better, where we explore creativity at the intersection of design and technology. I'm Speaker 2 (1:42) Eli Wooler. And I'm Aaron Walter. If you're hearing this, you're not currently on our premium subscriber feed. Design Better premium subscribers enjoy weekly episodes. That's four episodes per month rather than just two. And all of them are ad-free. Plus, you'll get an invitation to our monthly AMAs with the smartest folks in design and tech. And if you subscribe at the annual level, You'll also get our toolkit, a collection of our favorite design and productivity tools like Perplexity, Miro, Read AI, and more. You'll hear a preview of this episode, but if you'd like to hear the full conversation, please consider becoming a premium subscriber at designbetterpodcast.com slash subscribe. The podcast is available to everyone through our scholarship program. So if you can't afford a subscription, just shoot us an email at subscriptions at thecuriositydepartment.com. We'll help you out. We'll return to the conversation after Speaker 1 (2:50) this quick break. Speaker 2 (2:58) And now, back to the show. Speaker 3 (3:05) Blaine Billingsley, welcome to Design Better. Thank Speaker 1 (3:08) you so much. It's a pleasure. Speaker 3 (3:09) It's really nice to have you. We want to rewind back to the kind of very beginning of your career because it's kind of unique for somebody who's now finds himself in the tech world and design. But you started in your undergrad, you studied music composition and comparative religion. So maybe you can tell us the story of how you found yourself where you are today. Speaker 1 (3:28) It's a little bit of an... Maybe odd seeming at first, but it made perfect sense every step of the way to me. The hint of becoming a designer was there because early on when I was a kid, we have computers in the house all the time. My grandfather worked for NASA during the Apollo missions. So, you know, he was like a big proponent of technology. And so I was just goofing around on computers a lot. And I would like make posters and websites for my bands in high school. And then in college, I made websites on the side for small businesses in Vermont where I went to college. But I didn't really think of it as a career, really. I was just goofing around with computers and playing around and learning about technology. So I didn't have any. design training per se. I was just into web technology as a hobby to help my musical pursuits. And then I went to college and frankly, I just wanted to study people. Like how do we make decisions? How do we make value judgments? Why do we have sometimes differing value judgments at the same time? Those questions really intrigued me. And comparative religion, also known as a history of religion or sociology of religion, was just a really cool way to... get into that and explore the world through a certain lens. I focused on cargo cults in Papua New Guinea, which I could talk forever about. You know, I was just interested in learning about people. I didn't really have any career aspirations. I was a pretty serious musician. I ended up double majoring just because I was taking a ton of music classes and hanging out around the music department all the time. And then I moved after college back home to Texas and I played guitar for a living. And made absolutely no money doing that. I remember checking my bank account and having like $7 and being pumped, you know. Speaker 2 (5:12) I've been there. Yeah, I was so Speaker 1 (5:15) happy. A friend of mine who was a designer in Vermont had moved to San Francisco. And, you know, he called me up and was like, man, you should come to San Francisco. California is amazing. He was like, if you don't like it, you can always go back. But like spend a year out here. And so a few weeks later, I like I sold a guitar amp. I packed up everything into a car and I drove across the country and lived on his floor for a while and got a job doing data entry at a startup and then learned on the job from there. I started doing data entry, hung out with the engineers. They showed me how to like script my job, which I hope my old boss isn't listening to this right now. But, you know, after a couple of hours, I'd be done with this all day job. And then I would just go hang out with them and slowly started like, oh, how can we tweak this, make this site a little better? Started with SQL queries to clean up content and then started picking up those web skills again and honing them. The rest is history. Since then, I've been working in tech at companies big and small. Speaker 2 (6:12) It's interesting, your multidisciplinary background and following your curiosity and hunches. There seems to be these trends in... you should definitely study the liberal arts and explore a lot of things. And then it's like Peter Thiel paying people to drop out because college is not worth it and you should just study coding. And then, whoops, actually coding is not very valuable because AI solves that. I'm curious what your current perspective is looking back on your origin studying comparative religion. music. Some people would say like, hey, these are disciplines that