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

0:01Blaine Billingsley: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. 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.

0:39Then 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.

1:13We talk with Blaine about why a 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 one engineer, 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 Eli Woolard. And I'm Aaron Walter.

1:44If 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.

2:26The 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 the curiositydepartment.com. will help you out.

2:48We'll return to the conversation

2:49Blaine Billingsley:after this quick break.

2:58And now, back to the show.

3:05Blaine Billingsley, welcome to Design Better.

3:08Blaine Billingsley:Thank you so much. It's a pleasure. 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 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. 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 had computers in the house all the time.

3:40Blaine Billingsley:My grandfather worked for NASA during the Apollo missions, so he was a big proponent of technology. And so I was just goofing around on computers a lot. And I would 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?

4:23Blaine Billingsley: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.

4:57Blaine Billingsley: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? I've been there. Yeah, I was so 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 and 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.

5:44Blaine Billingsley: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. It's interesting, your multidisciplinary background and following your curiosity and hunches.

6:20There 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 origins studying comparative religion, music. Some people would say like, hey, these are disciplines that are not very lucrative, not worth pursuing. And yet, here we are in a place where seeing the connections between different ideas is so valuable.

7:08What's the value of multidisciplinary thinking today?

7:11Blaine Billingsley:That question came up basically throughout my whole life while I was in college. Even my professors are like, what are you doing, dude? Why are you studying this? Don't be like me, you know? And I never really thought about it for better or worse. I really liked school and I really liked learning. And so foolishly, I followed whatever I was interested in. I would only take classes that I was excited to go to. It's easy for me to say with the privilege of hindsight and having a career now, but I do think focusing on getting really good at something, like a skill, in my case, it was music and then later design, is just good for your brain.

7:48Blaine Billingsley:It teaches you how to develop excellence in a craft. And I think everybody should do that. I also think that studying other human beings in any capacity, whether it's art history or whether it's religion like I did or history or whatever, almost everything we do involves people. And so trying to understand people and how they are different and how they're the same all over the world, it's always been a well that I have pulled from in my career. And I can't really imagine not having studied that. There's no alternative reality in my mind where I did finance or I did some more technical degree because those are things that you can kind of learn.

8:30Blaine Billingsley:My point of view, I can learn how to write code or I can learn how to use design tools on my own or from one person. the experience of getting to talk about how humans are is actually hard to get that forum. And it's a really invaluable experience to spend four years philosophizing about human nature with other people who are also interested in it. Throughout your career, have you felt like you look at things differently than your peers? Some of them, for sure. I won't maybe be so bold as to say I've got a totally unique perspective, but I do think I was drawn to mentors who resonated with some of the values that I had already.

9:12Blaine Billingsley:Like I remember early on when I worked on Gmail, I was still really pretty junior and I didn't really know how to present work or how to pitch work at a big company. And I remember the head of product there just said, tell me a simple human story. I don't need to hear all the stats. I don't need to hear the business impact. I just want you to tell me a really simple story about how a person has a problem and we're going to make it better. And I think I was drawn to that team and that work. And I stayed there for a long time because that's already naturally how I like to think about product and about designing software, where there's a lot of other people that have really successful approaches that are very, very different.

9:52Blaine Billingsley:I do think it's a different way to do it. I don't think there's like any better or worse way. understanding that you don't understand people and coming at stories from like, I really need to learn some very detailed specifics about what I'm talking about in order to really speak to it and not relying too much on grandiose assumptions or over normalized assumptions about human behavior, I think is something that's definitely served me very well in my career. There's a lot of jargon in our industry and the tech industry in general, and that can potentially work against us. And we're going to talk about using AI as a design tool soon, I'm sure.

10:29But as we lead into that, if we're working with these machines as tools, that can definitely work against us. And some of the pre-questionnaire you filled out for us, you mentioned that sense-making for a UX designer and being able to bring what you call jargon-free clarity and push on truth-seeking, that's a really important skill to have.

10:49Blaine Billingsley:I just recently was told that I'm a truth-seeker, and I've never heard that phrase before. Or if I do have a unique quality personally in my career, I think it is that I'm really allergic to jargon phrases. And I do think actually part of that comes from studying religion, where you're reading a lot of ancient texts and you're like, what does this really actually mean? And what are all the ways people interpret it? And that's a big part of the field is really diving into very specifically what this means and all the ways it can be interpreted, misinterpreted, reinterpreted, et cetera. I'm also from the South.

11:21Blaine Billingsley:I'm a man of simple means. But for whatever reason, I find corporate jargon in particular, but any kind of jargon just obfuscating and disempowering. I think it's a way for us to not get specific and agree. I've worked at a lot of corporations and they all have their own language almost of things that are always OK to say. And they'll always shut down deeper thought. And I just love busting that stuff up so much. I think it's really important, and I think the role of a designer is actually quite profound in a company because we're paid to represent the user and their end experience. I mean, it's in our title, but it's actually quite a profound role if you think about it.

12:06Blaine Billingsley:It's really useful to come in with this antithetical approach to the religion of your corporation, so to speak, and really break down what do we mean when we say these phrases that we hear all the time I mean, nobody outside of our company would ever understand what these mean. Like, what do you mean when you say a command center for work that doesn't mean anything yet? Let's make it mean something. Do you mean this? Do you mean this? And I think that's a unique role that designers play that we don't talk about a lot, actually. I do talk to my kids about OKRs all the time. I'm not sure if that's typical or not for a parent, but we do have those on a whiteboard.

12:45Blaine Billingsley:My wife and I, we always talk about we're going to circle back. We're going to align on stuff. And I'm like, well, I'm never going to align with you. You're my wife. We're going to agree on something. You know, it seeps in everywhere. So you got to be really vigilant. Take us into one of those meetings or experiences where you're talking to colleagues. Doesn't have to be in your current employment status, but maybe prior where you just were frustrated by the language and how you confront that in a way that is beneficial to the room. Some of what I say here is a bit in jest, but at this company I worked at before, we had this one-pager process where people would write a one-pager.

13:23Blaine Billingsley:The one-pagers are like 30 pages. The world's longest page. Yeah, already we're getting into why jargon phrases are dangerous. We're calling it a one-pager because we have some agreement that we think this is worth writing briefly to get started. We often also call them briefs, and they're anything but brief sometimes. sometimes so as a bit of a joke but also as a provocation I would say I'd only read the first page and anything that was not on the first page I wouldn't read I never wasn't able to do my job because I didn't read those 29 pages after the first page so much of that I hate to use the word because we associate it with technology now but it's slop it's like our brain trying to get out a bunch of very vague ideas, but it's not communicating anything to other people yet.

14:14Blaine Billingsley:I can't tell you how many quarterly planning meetings I've been in where we're looking down rows of spreadsheets with just the most opaque projects I've ever heard of and being like, is this going to take eight weeks or nine weeks? And like, none of us even know what these line items mean, much less how long they're going to take. And I feel like a lot of times that's what we're doing in companies. We're sort of like in the meeting, we're going down the list. or sort of acting out what we think doing work looks like. I think some of the most powerful things you can do in those moments is like, I have no idea what this means.

14:47Blaine Billingsley:And someone's like, yeah, actually, it doesn't make a lot of sense to me either. Just being willing to admit this isn't quite clear yet, or I think this means something different than you. Do you mean this? It's a little vulnerable to do, but that's actually, I think, the way to break the ice of this 30-page document. There's no way all of us are reading that and coming out with the same clear picture of what we're gonna build over the next six months. And so we shouldn't act like that's how to do it. This is maybe a parallel challenge of sorts. And this is from your friend, Max, who suggested that we ask this question.

15:20Do you have any tips for working with a pushy PM?

15:25Blaine Billingsley:Such a funny question. Yeah, I said once to somebody that I was managing, they were asking me how you could have more influence. They're like, I really want more influence. You know, it's really important to a lot of people in their career. My advice to them was the best way to have influence is to be influenced. People like knowing that you're going to go along with them. And so a lot of times when I start working with people, as a rule, I'll go along with something that I totally disagree with as a personal rule. I think it's good to like give people space to get a say and to try things. And I personally have found when you do that for somebody, when somebody is being really pushy, we want to do this.

16:05Blaine Billingsley:If you're like, cool, let's go for it, man. Let me try my best. Let's see what it looks like. Let's actually go for it. Not only do they like you, sometimes it actually comes out pretty good and it kind of reframes the perspective. And then I found most of the time when you do actually say, hey, that doesn't make sense to me or could we try this? If you've already given a little bit of yourself to their dream and their vision, they're way more likely to give a little bit of themselves to your dream or your vision. And yeah, I'd say 80 % of the time, 90 % of the time that's been true. We can get into like an ego trip of, yeah, that's not right.

16:38Blaine Billingsley:We got to do this the right way. Or like, I've got this vision that's way cleaner. It's a lot more fun. And I think people will work with you more if you're like, yeah, let's try your thing. Let's try it out. My job is to make that tangible. So let me try to represent your idea as best I can. And then let's talk about why it works and why it doesn't work and open it up from there. That's the first piece of advice that comes to mind anyway. Is there other advice that you have? One thing to be mindful of is it's really easy to get into these binary conversations. Should we do this or should we do that?

17:14Blaine Billingsley:Anybody can become pushy in those conversations because you're in this zero-sum game now. One of the cool things about being a designer that again makes it fun is our job is to always increase the option space. There's never just two things to do. It's like, oh, we could do it like this or we could do it kind of like that, but we could change this. Or what if we change this? And I find a lot of people are actually just kind of afraid that there's no other way or there's no other idea. At other companies, in my past roles, I've talked a lot about ideas are really cheap. It's easy to come up with a ton of ideas.

17:49Blaine Billingsley: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. The way you've just described this, it sounds like you're very adaptive to processes and you're open. And yet we have heard from people that you are a person who really likes a tidy, clear process. Is that true? And why is the process so important to you? Guilty as charged. Man, these are like my deepest secrets coming out. I do love a good process.

18:28Blaine Billingsley:It's very dangerous to say in Silicon Valley that you love process. Very taboo. Yeah, I do like process. I think it gets a bad rap as a word or as a concept because there's a lot of undue process that's put on us, especially in large companies that sort of work about work. You know, there's some study that says like 40 % of the work we do is just work about other work. It's not actually the core thing that we're trying to do. And I think that's definitely true. And I've been victim to that many, many times in my career. But I think actually having some plan, a very simple plan is a recipe for success.

19:05Blaine Billingsley:Maybe it's because my father was in the Navy, you know, prior planning prevents poor performance is a phrase that I like a lot. I'm also not very organized, naturally. I'm really disjointed. So I appreciate having a little bit of structure outside of me to be accountable to because my own minute to minute work is pretty disorganized. So I like having something to kind of hang on to. But the best project manager I ever worked with ran everything off of an Excel spreadsheet, not even shared with people that he projected on the wall. And every single project we did went perfectly on time. We never were late.

19:42Blaine Billingsley:Everybody knew what was up. What's most important is the agreement and adherence to a plan. And you can use very simple techniques to put together expectations and plans. You said before that, at least in the research we did, that a design principle is only useful if its opposite isn't obvious. So whether the converse of that would be a truism. Could you give an example of that and maybe some advice for how to deal with this? This is all in good fun. There's nothing wrong with these principles. The best companies in the world have principles like this. For me, I've never found them very helpful.

20:16Blaine Billingsley:Like to me, a principle is a jig or some kind of tool, a working tool that you're using to make a product. And so it's supposed to be there to make it easier for you to make a product, especially working with other people. One of the biggest reasons that people don't agree on what to do is we actually aren't judging everything by the same scorecard. And so a big part of the job of a designer is What is our scorecard for what we think this thing is supposed to be and what is going to be good? A simple example, writing an email, an automated email. I write it. I think it should be really playful and fun because why not?

20:55Blaine Billingsley:I'm having fun writing it. My product manager thinks it should be like very authoritative. And every time we meet about this, we're going to be wrong unless we agree on what is our principle for how we're going to talk to people in this. And is our principle just clear? No one's ever going to argue that we should be unclear. So that doesn't really help us make decisions in any real capacity. But getting more specific about what we think it should be, where actually I might disagree, it's actually an opinion, it's not so vague that you would never disagree with it. That actually helps teams, because if we can all agree, oh, this should be authoritative, you know, this is serious, it should be authoritative when it's about X, but friendly when it's about Y.