OpenAI’s Head of Design: This is the best time in history to be a designer | Ian Silber

Lenny Rachitsky (00:00:00): I’ve been doing this sentiment survey of the tech workforce. Surprisingly, designers are just the most unhappy on every dimension.

Ian Silber (00:00:08): We’re unclear right now what is expected of a designer. Someone who might be classically trained in a certain way of working now feeling like, oh my gosh, I need to really change everything.

Lenny Rachitsky (00:00:17): You believe this is the best time in history to be a designer.

Ian Silber (00:00:20): We’re all extremely early in this process. There’s just a huge opportunity for designers. Nobody should feel behind right now. I think that if you literally started today, you’re going to have a leg up on pretty much most people. There’s just so much opportunity to change the way we work, to make great things.

Lenny Rachitsky (00:00:36): If you look at engineering, it’s just a completely new job versus a few years ago. I’m curious how that translates to product design.

Ian Silber (00:00:43): Engineers have 10 or sometimes like 100 excerpt productivity, but our design team hasn’t because the design process still takes time. Sometimes you have to try a bunch of things and throw them out. Still very messy and fluid.

Lenny Rachitsky (00:00:56): We had a podcast with native design Claud Code, Jenny Wen. She talked about there’s been this traditional design process. Prototype, mock, test, use research, iterate, and now there’s just no time for that.

Ian Silber (00:01:05): There’s certain features for ChatGPT where we really obsess and we really spend a lot of time. We try a hundred things and we throw out 99 and we finally ship one. And other things we really embrace building in public. We take big swings and then we learn quickly.

Lenny Rachitsky (00:01:19): Do you think AI will ever be an extremely good product designer?

Ian Silber (00:01:22): I think it already is an incredible product designer.

Lenny Rachitsky (00:01:26): Today, my guest is Ian Silber, head of product design at OpenAI. Ian’s been in this role for three years now, which is a lifetime in AI time. Prior to OpenAI, he was at Artifact, the news app from the founders of Instagram that I absolutely loved. Before that, he spent eight years at Instagram. The role of design is in such an interesting place right now, and Ian has such a unique and insightful and fascinating take on the future of product design and what the AI tools that we use every day will look like in the future.

(00:01:56): A huge thank you to Soleo and Joel Lewenstein for suggesting topics for this conversation. Before we get into it, don’t forget to check out lennysproductpast.com for a year free of the hottest and most beautifully crafted AI products in the world available exclusively to Lenny’s Newsletter subscribers. With that, I bring you Ian Silbert.

(00:02:17): Ian, thank you so much for being here.

Ian Silber (00:02:20): I’m so excited to be here. Thanks for having me.

Lenny Rachitsky (00:02:22): I’m even more excited. Something that I’m very excited to get your take on. I don’t know if you’ve watched me doing this, but I’ve been doing this sentiment survey of the tech workforce over the past couple of years. I think it’s the biggest survey of its kind. We basically survey people in tech about how they’re feeling about their careers, their work, their roles, especially with the rise of AI this last year. And kind of surprisingly, designers and user researchers are just the most unhappy on every dimension, every actual dimension. They’re the most overwhelmed, the most anxious, the least optimistic, the most worried, the most tired, also the least likely to recommend their role to people entering the workforce. I’m curious if you are seeing this yourself in the design community. And if you are, what do you think is going on?

Ian Silber (00:03:18): First of all, it’s an incredible survey and it’s such great, I think, information to have as an industry. And I think it’s something we need to unpack. And I see a mix for sure. I think I can speak most to design. And I mean, I talk to a lot of designers that are very optimistic and very excited. And so in my world, luckily, I see a lot of that, but I can totally understand why people might be feeling very uncertain. Because there’s so much discussion about, well, is the role changing? Should my expectations be different? And well, do I need to do X, Y, and Z? Do I need to be shipping code every day? And someone who might be sort of classically trained in a certain way of working now feeling like, “Oh my gosh, I need to really change everything.” And I think to me right now, it feels like the uncertainty of that, I can totally understand.

(00:04:24): Because as an engineer, I think people, they’ve already sort of gone through that shift. We see that engineers are working totally different. One thing I do hear, and this came up a lot in my own team when we do similar surveys internally. One of the big things that came up was we see that engineers have 10 or sometimes 100X their productivity, but our design team hasn’t because the design process still takes time. It’s still, sometimes you have to try a bunch of things and throw them out versus maybe working with a coding agent, you ask it to do something that’s pretty binary. Now at this point, it usually sort of gets it pretty well. But the design process is really still very messy and fluid and you think you have a great idea and you try it and it sucks. And then you try it again and it sucks and you give it to users or you get internal feedback and it’s wrong.

(00:05:23): And you still have to go through that arduous and kind of messy but really fun process. And that hasn’t really… It’s compressed in that you can get much more ideas out fast, but you still need that whole sort of feedback loop. There’s the alignment of getting many people, especially in a bigger company, that still has a lot of overhead. So the point is that I think that we’re unclear right now what is expected of a designer and that lack of clarity I can see totally lead to some fears or some unease, I guess. But on the other hand, I’ve seen that, I mean our designers, what’s great I think at OpenAI is we’re such an experimental company. We are driven by research and we treat our company as a research lab and we totally embrace that. And that’s a new thing that I really learned and have really come to love about OpenAI is that started as a research lab, that DNA is deeply embedded in everything we do.

(00:06:30): And as designers, I think that you come here, we look for people that don’t have a background in AI, but are really curious about the tools and how it can work. And we found that just by supporting that excitement to explore, that people feel less pressure. It’s not like you need to change the way you work, but it’s more about encouraging exploration. And when we’ve done that, when I go and talk to both very senior designers and early career designers at our company, they’re so excited because they… I literally was just asking some people before this because I wanted to get some different takes. And I think the feeling is that they have so much more ability to be creative, to express themselves, to try bad ideas and throw them out. They can just really move through lots of different ideas and it becomes this incredible way to create.

(00:07:26): And the things that I’m seeing from my team, the bar is raising. I think the thinking is getting stronger the more that they’re using these tools. So I think for the people that are starting to embrace this, they’re starting to feel really excited and realizing that they have just so much agency as designers and so much more ability to have really high impact as a designer.

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(00:09:02): What I’d love to do in this conversation is help folks that are in that bucket of, “This sucks and things aren’t going well.” Because as you said, and this is exactly what we found in that survey, is about half of people are having the best time of their career, having the most fun, the most optimistic about where things are going, and then the half are not, having a really hard time. And exactly what you said, the people that are having a great time report, the strongest correlation is they feel amplified by AI. It’s actually making them better. And that’s the way you described engineers, they’re seeing that now. They’re like, “Holy, I can do so much more.” And so just to kind of reinforce the points you’re making, attributes of people that are doing well feel amplified, very curious, have time to explore, feel like they can be more creative.

(00:09:50): Is there any more thing more along those lines of just patterns of people that are doing really well and having a great time that might be helpful for people to hear that are not having a good time?

Ian Silber (00:09:59): What I see in the folks that I think are really embracing this, they are using it every step of the process to help them. And I think it helps. We have a community, of course, of designers that are all trying this together. So if there’s any way to find that, and that’s something that we should think about more as a broader community, how we help each other. But I think that learning different ways of working. And so it might be, “Okay, I have this idea. Let me just actually start by trying, what if I just threw this right into Codex or Claud?” or whatever tool you use. Throw it into an agent to help you think about it, to help you prototype it. Just try a different way of working. It doesn’t necessarily mean that that has to be the exact right way, but I don’t know.

(00:10:46): I think we’ve found that just people that are embracing this that are adaptable. I think adaptability is another term that I think we all hear a lot now, but it’s so true. It’s knowing that this stuff changes very quickly. What didn’t work yesterday might work today. I mean, literally within six months, this entire industry has shifted. I remember I was actually out on paternity leave towards the end of last year, and I was working on some side projects. I was trying some coding agents and it worked, but it just kept running into these hiccups. And then a month later, Codex drops and I try it again and it’s like, oh my gosh, it just works. And that I think changes a lot of the design process because now all of a sudden, if you do have an idea, you can plop it in there and just try it.

(00:11:40): And so anyways, I think it’s just really about not being scared. I think another thing to think about is that we’re so early. We’re so in early innings of this entire evolution. It feels like things have changed a lot, and it feels like maybe we’re pretty far into this shift. But the good news for anybody who is trying to design or get into design, whether, again, if you’re early career or late career, or you’ve never even actually designed anything, but you’ve been thinking about it, is we’re all figuring this out as we go. Nobody has some perfect answer about how the design process should work. And whatever you think is working today will probably change again. And so I think what’s encouraging about this is that nobody should feel behind right now. I think that if you literally started today, you’re going to have a leg up on pretty much most people.

(00:12:42): And just really thinking about how you can just make great stuff. And there’s just so much opportunity to change the way you work or just to make great things. And what we think is really cutting edge today will look so archaic in a year, let alone a month. And that’s something I’ve learned. I’ve been at OpenAI for three years, and I think about the stuff that we were working on when I first joined. I mean, I remember getting a demo of our early voice mode that we hadn’t shipped or computer use that barely worked. And now it literally has become part of the process of how we design. We use both of those tools to build software. And so anyways, the point is it’s changing very quickly. We’re all extremely early in this process and nobody really has it figured out.

Lenny Rachitsky (00:13:41): I love that. You’ve also, when we were chatting ahead of this, you actually told me you believe this is the best time in history to be a designer.

Ian Silber (00:13:48): Yeah. I mean, I truly believe this. I can’t even imagine… Okay, history lesson. When I was getting into design, I was in my teenage years and to learn things, I was learning to design and code, and you could view source on a HTML webpage and see how things were built. And that was how you had to learn. And you could, I don’t know, it’s like Dreamweaver. And there were these really… tools that actually were really cool. But to compare those to today, if I were just getting into design, the fact that you can learn so quickly, you can have an idea to working version of it in a matter of minutes.

(00:14:46): You can be so expressive and I think anybody can be a designer. And I think that as more and more software is made, more and more products are made, I do think that the human element of design is going to really start to become more and more important. It’s always been the case that I think that companies with great design can of course stand out. I think that’s going to be more and more important. I think that products that fully understand their users and that make something delightful, when anybody can make anything, that’s going to become one of the most important dimensions of a product and that’s how people are going to evaluate it. And so I think designers stand… that is our core job.

(00:15:45): And then on top of that, I think that designers are just much more empowered. So I was talking to some friends that are thinking about starting a company and talking about the ratio of design to engineer and how at a startup, maybe that’s totally different. It may have been like you’re going to have one designer and I don’t know, 15 engineers or something like that. Maybe at a startup, I’ve seen that sort of ratio. But they were talking about, “Well, maybe we’ll have two designers and one engineer. One really good engineer who can make sure that we’re really building something that’s rock solid from an engineering standpoint, but then we want two really creative people that are going to be thinking about how we build this product.”

(00:16:33): And so thinking about that, I think that there’s just a huge opportunity for designers. I think that internally we see that more and more designers, we are completely empowered, to take an idea, to take a early research concept and try to figure out how we can actually package that up into something that people want to use or that solves some sort of unmet need for our customers. And that is a designer’s job. And so I think that maybe more and more people start to think of themselves as designers. But either way, I really do think it’s the best time to be a designer.

Lenny Rachitsky (00:17:13): So along those lines, when Marc Andreessen was on the podcast, he had this hilarious way of describing the state of the product org right now. He’s like, basically there’s this three-way standoff. PMs, engineers, designers, they all think the other roles are going to go away and they’re the ones that are going to win in the end. And so there’s those Spider-Man meme where they’re all pointing at each other. And I’m curious, because I can see a case for each role becoming the dominant role. And I completely agree with you that with all of the tools being shipped, there’s a thousand X explosion in products being shipped. There’s just endless streams of things to pay attention to. You’d think design would be such an opportunity to differentiate and stand out. I haven’t seen that yet in just an acceleration of design hires and explosion, as you said, two designers to one engineer.

(00:18:03): Do you think that’s coming? Why do you think that hasn’t happened yet? Do you think it’s, as you said, just early and people will realize, “Oh wow, we need a lot more designers.”? What do you think’s going on?

Ian Silber (00:18:12): We might start to see that happen more. Or if anything, we might start to see engineers wanting to become a little bit more design focused. I also think that designers are getting more productive. It’s not necessarily the same direct output of engineers 10Xing, but we are seeing that designers are able to do a lot more. But no, I mean, I think that is something we’re always thinking about and evolving. The other thing I wanted to talk about too is the difference between PM and edge and design, and are they all blurring together? And my point of view is that they definitely are, and there’s always been overlap as far as I’ve seen it. I’ve seen designers that are really good product manager type, archetype, but can design. And I’ve seen designers that are really good polish engineer type.

(00:19:12): So I’ve always found that these single siloed role definitions don’t really make sense. It’s just that at big companies you have to have a ladder to put people on so you can generally organize. But in the reality, when you look at a team, you see that there are people that have various strengths and people that play different roles. And so I’ve always seen that. I think those lines have always been blurry, but they’re becoming blurrier for sure. But the other thing is I do still think that, and maybe this is thinking about it from a slightly larger company perspective, but I think you do still need people that have certain responsibilities. Because if you have one person that’s expected to design, to rally a team around something, to align a whole company, to do all the work that a PM does, for example, and also be designing it and also be engineering it, it might be hard to find one person that’s good at all of those different skills.

(00:20:17): And so I still find a lot of value, for example, in having an excellent PM that can help rally multiple teams together, that can help sharpen the perspective or the problem space that a team is focused on, that can help with resourcing, all of those things. And so I do think there will still be value in these and people focused on different parts of building a project or a product. That doesn’t mean that maybe there’s more fluidity that people can move between them, but having somebody who is generally responsible for these different things or an engineer who’s really making sure that the output is totally sound and is actually laddering up to something that is going to work for the broader system.

Lenny Rachitsky (00:21:03): I completely agree. And so just to make sure I understand what you’re saying is just talk about all the roles blurring. There’s like, maybe we’ll all just be builders and we do everything. And you’re saying is like, no, that’s not going to happen. I’m picturing Venn diagrams of product design engineering converging, but you’re saying they’re going to continue to stay their own roles. They’re going to be PM, design engineer, but each can do more of the other roles.

Ian Silber (00:21:26): I think that’s right. I do think that for… And again, this is not a blanket statement because I think if you’re at a startup, that’s very different. If I were starting a company right now, I would hire the best generalist people I could possibly think of, someone who I think could fluidly move between that. But maybe again, maybe that’s always kind of been true. But at a bigger company, I do think that I’ve seen designers that are maybe incredible at designing, but could really use a product manager who can help them with hone both their thinking and then how they work and the operations of it all.

(00:22:06): So the point is I do just think that there are different… It’s almost like taking the people out of it, I think that there are different hats that you need to wear to build great software. And I think that those continue to be important functions, I think.

Lenny Rachitsky (00:22:24): So this begs the question, do you think AI will ever be an extremely good product designer? And it’s interesting to ask you this question because on the one hand you’re like, “Oh yeah, ChatGPT is going to become incredible at everything.” On the other hand, it’s hard for a head of design to say, “Oh, no design’s going to be done by AI.” I’m curious to get your take. And it sounds crazy, but engineers never thought it would be able to write code the way it is now. So just thoughts on just how good AI will get.

Ian Silber (00:22:53): Maybe one way to put it is I think it already is an incredible product designer. It really is actually already great. The cool thing about it though is it’s accessible to every single person. And it’s a tool that anybody can use. I do think it’s really good. Now that doesn’t necessarily mean that it’s the best visual designer or best at information hierarchy or typography or even user experience and interaction design. It’s not necessarily the best at any of those.

(00:23:26): It’s impossible to predict where things are going. And like I said earlier, how much has changed in three years? Of course they’re going to continue to get better. But the way we think about it, and I really do believe this is we’re building tools to enable people to be more creative, to do more, to build more. And so it is already a great designer, but it’s at your fingertips to figure out how to use it and how to get the best out of it.

Lenny Rachitsky (00:23:55): Where do you think human brains will continue to be most valuable as AI gets better at product design specifically? What are the remaining areas for us to be useful?

Ian Silber (00:24:05): Truly understanding what people need. I mean, the human feedback loop of watching people use something and understanding that, the inventing something new. And then of course there’s just the pure human take like, “Oh, somebody made this, somebody had a point of view about this.” I do think that will stand out more and more. And I think that that’s an important thing for a designer to really hone is like, “What is my point of view? Who am I building this for and why?” And I don’t know, I think as AI becomes better and better, for sure there will be an opportunity to always stand out and push, how can you push that even further?

Lenny Rachitsky (00:25:01): Yeah, that touches on a conversation I had with the PM of Codex. I asked him just why is AI not good at design? It’s actually gotten better since that conversation, which was just a month or two ago. And he had a number of reasons for it. One is just part of great product design is doing something new. And so if it’s trained on all the most interesting websites today, it’s just like, okay, but that’s not interesting anymore. And the other point he made is AI researchers aren’t innately great at design, and so they may not understand exactly what it takes to train a model to be really good at this. Thoughts? What do you think it’ll take to get AI to be much, much better at product design?

Ian Silber (00:25:40): I mean, the new thing is interesting because I think that everything we’re doing is trying to design something that hasn’t existed before. If you look at great products that have come out in the last 10, 20 years or whatever, it’s like all of a sudden, take the iPhone, we’re designing for multitouch. And that opened up this whole new interaction paradigm. And there’s no training data for that. You’re really trying to understand this new thing. And then you had something like Instagram that was really embracing the fact that everybody had mobile phones. And then Snapchat I think is another good example of great design in that it was maybe people thought strange interaction design, but it completely flipped on its head the way people might want to communicate with each other. And to me, that is great design. It’s truly understanding, the people have this problem or there’s this unmet need and I’m going to build it in this unique way.

(00:26:50): So yeah, I do think that there’s that sort of fresh, new kind of way. And then now with AI, it’s like we’re designing, like, how do you talk to AI with your voice? Or how do you use an agent to carry out tasks for you? It’s like, yeah, there isn’t a lot of precedent for this. And so I think that humans are able to do a really good job evaluating what good is or at least trying a bunch of things and learning along the way with people. And so I don’t know. But again, all this stuff changes really quickly. It’s hard to say, but I think there’s a lot of reasons why having that human in the loop is going to be so important.

Lenny Rachitsky (00:27:34): And following that thread of the human in the loop. When you’re hiring designers these days, what’s trending up in what you look for? What you think is more and more important in the designers that will be successful today, especially at OpenAI? And what’s trending down, if anything?

Ian Silber (00:27:50): This might be a luxury of having a slightly larger team, but if you’re at our scale, but even at a startup or a smaller company, I think this would still be true. I really believe in hiring a well-rounded team that has many different strengths. So I think it’s important to have the right ratio of generalists that can do everything. But we also hire incredible visual designers or we have a really amazing brand team that helps us with the expression of our brand both out and in the product or great prototypers. And so I think that rounding that out or great product thinkers that are a little bit more strategic or people that are really obsessed over the very cutting edge of where these things are going. And I haven’t found that one designer necessarily checks every single one of those boxes.

(00:28:54): I think people just naturally are drawn to certain things. And I think embracing that and when you build a team is actually, if you have the luxury of doing that, is really valuable. Okay, so that’s a broad statement. But then as far as what we look for, we do definitely… I always tell candidates, we do not expect you to have a background in AI because again, this is evolving so quickly, but we definitely expect high curiosity about it and high aptitude to jumping in and learning how you’re going to use this in your process, how it works. And not just how you use it in your process, but how, especially for us, how you’re going to create tools to enable more people to use it. And so it’s more about the curiosity, I think, is something that we really push on or look for.

(00:29:50): And then definitely prototyping. Prototyping is something I’ve always valued in my career, but I just think that it’s become more and more accessible. And so that’s something that I think really does stand out usually when we talk to candidates. And then I do think that just having a point of view on where these things are going or just any of the tools that people have worked on and really thinking that strategic thinking. I guess last one on this is systems thinking is becoming more and more important. And especially as you’re… In our world, it’s interesting because we’re building the super intelligence that has all these different capabilities. And we need to think more about the underlying primitives that we can build that can kind of build on top of each other.

(00:30:53): This is something that I think Notion did really well early on was like, “We’re going to build these building blocks and then everything kind of is composable.” I think that’s becoming really important too, as you think about like, well, we don’t want to build all these sort of one-off siloed experiences. We want to be able to build and ship systems that can build on top of each other so that when someone goes and uses our product, it feels like one cohesive, simple thing. And the model can reason about how we can pull all these things together. So that idea of really understanding the system and thinking about that is becoming even more important, especially because it’s kind of complex of all the things that it could possibly do.

Lenny Rachitsky (00:31:31): This is the fifth podcast in a row I’ve done where systems thinking has come up as-

Ian Silber (00:31:36): Interesting.

Lenny Rachitsky (00:31:36): … a skill that people are more and more looking for. And it’s so funny. I need a bingo card for systems thinking, but it makes so much sense. And I think it especially makes sense from the designer perspective. If we come back to just my take on why designers are kind of frustrated and stressed right now is just there’s less time to do design, the traditional design process. Things are just moving. Engineers are shipping 5,000 PRs a day. And so to your point, this idea of building blocks and design system language and just a platform for people to build on feels incredibly important.

Ian Silber (00:32:08): Totally. It’s very hard, but yeah, it’s funny. We’ve had these conversations where I’m like, “Just do less.” My encouragement has been do less. Don’t design it if you don’t have to, maybe there’s already an existing system or component or something that we can build on top of, or maybe we don’t even need this feature. We actually just need to extend an existing feature. I think that’s an important thing. And part of that is thinking outside of the bounds of what you’re working on and thinking across everything I think is becoming much more important. And the speed for sure I think is a reason why that’s so important right now.

Lenny Rachitsky (00:32:54): Just to follow that thread, because that feels like a pretty big change in the design world. There used to be this, we had a podcast with, she was head of native design Claud Code, Jenny Wynn, and she talked about this and I think it blew a lot of people’s minds. There’s been this traditional design process. Prototype, mock, test, use research, iterate. Okay, cool. Ready for engineering, build it, iterate, ship it. And now there’s just no time for that. And so the role in her eyes is just move to big picture planning and just steering people in a good direction. Does that resonate? How much that has changed in the world of a designer?

Ian Silber (00:33:28): I think that 100% we do work that way. It depends. I think for us, it depends on what stage you’re at in the process or maybe how far along the product is. There are certain features for ChatGPT where we really obsess and we really spend a lot of time. We try a hundred things and we throw out 99 and we finally ship one. Or the composer is changing every single day and we try many things and we throw them out. And you could take that for many different things within ChatGPT. And then there are other things like Codex where, I don’t know, I mean a super app is a good example where we definitely are just trying stuff really quick. I think that we really embrace building in public, which is a different way of working. But I think that when you get comfortable with it is actually really gratifying or satisfying because you can try stuff and get instant feedback both internally and externally.

(00:34:40): But yeah, I mean it is moving really fast. And I think it just depends. Like I said, certain things we really sweat the details and we try and we do test, we A/B test, we’ll do user research and we kind of iterate and evolve a lot. And then other things, we take big swings and then we learn quickly. But yeah, I don’t know. I think the biggest thing is embracing that the technology might change in a month and maybe a certain interaction or setting or whatever that you needed doesn’t need to exist or now a new one does need to exist or a new capability is there or the latency profile has changed such that you can rethink this or whatever. All these capabilities are changing or the intelligence has changed.

(00:35:36): And so you have to be just really quick on your feet and maybe not be so precious about it until it’s at the point where, okay, this is kind of hardened. We don’t think that this is necessarily going to change tomorrow because of the technology, so let’s make this the best it can possibly be. We’re thinking a lot about how we should evolve. Really think about ChatGPT becoming deeply embedded in your personal life and how should the app feel? That’s something that we’re not going to necessarily design and ship overnight and just put it out there. We’re really thinking about that and we’re trying a bunch of different ideas and we’re putting it up on a whiteboard or we’re doing some design in Figma. We’re prototyping it. We’re probably going to dog food a bunch of different ideas long before we ever ship something. But that’s a bigger project. And then there’s other things where we’re like, idea to ship in four hours.

Lenny Rachitsky (00:36:38): This all makes sense. Essentially what I’m hearing is you pick your battles and you focus the design effort on the things that will be durable and not change.

Ian Silber (00:36:47): Exactly. Yeah, yeah. And it’s hard to know what that is. Yeah.

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(00:38:06): So I asked a bunch of people that know you well what to talk to you about. And Joel Lewenstein, who happens to be the head of design at Anthropic is a good friend of yours, which I love. And he said what he imagines the hardest part of your job is, is balancing the needs of the existing billion monthly active users of ChatGPT with the need to innovate and push and iterate and invent. And so I’m just curious how you just think about that. How do you find that balance knowing you have to cater to both sides?

Ian Silber (00:38:39): That’s a great question, and it’s a really fun part of the way we work. I think that we have vastly different audiences. Really, really different. I’ve never worked in this kind of quite a spread. At Instagram, I spent eight years working at Instagram. We had a billion users or billions of users maybe. I don’t actually know what they’re at now, but it was a lot of people. But the product was pretty simple and it was sort of a couple ways that you could use it. We did think about creators and larger accounts that had special needs, but this is vastly different where you have someone who’s using this to help them come up with a recipe to eat tonight or brainstorm their next haircut or something like that. And then there’s somebody who’s transforming the way they’re doing farming for… helping to automate their farm in Japan or something.

(00:39:41): And it’s just the broadest spectrum ever. Generally what we’ve seen is that we believe in this idea of this is sort of capability overhang where the product, vast majority of the people are getting a sliver of the true value that they could out of the model. That’s not necessarily a bad thing. They’re still getting tons of value. But we found that we make sure to focus on creating an extremely simple, streamlined experience for many, many people. And then we put all of the cutting edge stuff. We also make sure to give that and make sure that’s really accessible for the people that care. The challenge of course is not necessarily over-indexing and putting something that people might not understand in front of a billion users. But generally what we’ve seen is we can experiment early with the people that really care.

(00:40:46): And that’s where we have our desktop app and we have Codex. And now ChatGPT Work is stepping into a much broader audience, which we’re really excited about. And eventually what we know, and we think about this a lot in design is things will truly become for billions of users when they don’t have to think about a switch or a mode or anything like that. And so we know that eventually it has to kind of get distilled into that main experience. But it is a really fun thing to balance. And we have to think about people that are using this for free every day to people that are paying us hundreds of dollars and lots of different needs. It’s just a matter of balancing. And as a designer, it does add a lot of complexity for sure to think… You really have to have empathy for every sort of different type of user, but it makes it fun for sure.

Lenny Rachitsky (00:41:39): That is such a mind-blowing point you’re making about the spectrum of usage of ChatGPT and Codex. I didn’t think about it that way. Has there been a product that has such a wide spectrum from just, “What’s this rash on my finger,” to building a Salesforce?

Ian Silber (00:41:57): Yeah. And it makes it really hard too. It’s so funny, one of the big challenges we’re always thinking about is this blank box problem. And people talk about this all the time. It’s like, is chat really the final frontier? It’s a glorified terminal. It is some critique that I think these chatbots get. And then it’s like, okay, so how do you design something that can kind of shape-shift into anything? It’s like maybe someone is coming here for image generation for fun or they’re trying to generate a PowerPoint. So having this adaptable interface is a really interesting design challenge. And it’s sort of uncharted territory because it can really shape-shift into many different tools. And it’s just incredible at so many different things and trying to figure out how to present that.

(00:42:55): And then thinking about, we think a lot about a novice user, someone who’s sort of brand new to this experience, that we want to help them understand how this can add value to their lives or to their professional work or whatever capacity they’re using this in. And then we also want to get out of the way of people that use this every single day and they use this as a real workhorse tool. And so designing for that spectrum is something we have to think about a lot. But yeah, it’s all a world of spectrums, I guess.

Lenny Rachitsky (00:43:31): There’s a comment that Kevin Weil, your former chief product officer, made on the podcast that has really stuck with me, which is to your point, people always diss this idea of just like, it’s just like a chatbot. Why hasn’t it ever changed from that? Even though it has, but still it’s kind of this chatbot. And he made this really good point that what is an interface that is very good at spanning a wide spectrum of intelligence? It’s actually just talking. If you think about humans, we talk to people of low IQ to very high IQ. We can all just talk to each other and it’s actually a really good interface for packaging something that is increasingly smarter and smarter and smarter.

Ian Silber (00:44:08): Yeah. And I think we’re seeing what’s been really fun design space for us is there’s two things we think about. One is how can we help you express your intent better? We don’t want you to have to think about being a perfect prompt engineer, but how do we even, one, teach you that, oh, this is something that the model can help me with. And then how do we make sure that we best understand what you want? And so we recently shipped some features where if you ask sort of an open-ended question, it can follow up with some follow-up questions that you can just tap through and answer versus having to type everything out.

(00:44:48): Or another good example is, so then once you actually ask it to do something, the chat transcript doesn’t need to be purely text. We’ve seen these now evolve so far from what it was when ChatGPT just launched. It’s no longer just a pure chatbot. It actually has many features within that. So a good example is what we call writing blocks. You ask it to write you a letter or an email and it now contains that email in sort of a block that you can directly manipulate and you can type with it and you can brainstorm and you can edit little bits and parts of it. You can copy just that. And that has made that interaction much better. And we’re seeing the same thing with image generation and creating special tools for that kind of mode.

(00:45:34): And I think that’s where UI is going to start to really continue to evolve is how do we make… If you come at this and you’re a designer, maybe ChatGPT should actually really look different or have different affordances or you’re a data scientist or you’re using this to run your home, your personal life. Maybe it should really work or look differently. So understanding the context and giving you different affordances based on that is something that we’re thinking a lot about.

Lenny Rachitsky (00:46:08): In terms of the vision and future of where all this goes, I know this is always evolving, but is there kind of a sense of what the future of ChatGPT Codex is? I know there’s this idea of a super app. You talked about voice, this personal assistant idea. What’s a way you think about where this goes long-term?

Ian Silber (00:46:25): I think that it will start to become more and more adaptive to all of the context of your life. I think proactivity is a big untapped part of the experience that we’re really excited to think about. We’re starting to see this with ChatGPT Work now where it actually has pretty good suggestions based on your calendar or your Slack or these different sort of inputs and external context. I think that’s going to become more and more important or shift the way you use it. I think voice, we just had a step change in the model that just feels much more natural. And again, I can only imagine how that’s going to feel in two, three years as it just gets better and better. I do love interacting with ChatGPT, especially Voice In. I want to just really quickly say something. And then I think its ability to go not just from asking questions, but actually doing things for you, that’s all going to change.

(00:47:40): And hopefully all of this gets simpler as we do it too. When we think of the super app, I think eventually we really think of the idea of, especially for our broad consumer base, we do think that there should be this one universal input that you can ask that knows when it needs to answer really quickly or should be chatty or whether it should go and go off and do work for you. And so that’s a big excitement that we can get to is how can we just continue to simplify the experience such that you shouldn’t have to think about how this works. You shouldn’t have to think about what model you’re on or what sort of speed you’re using. That goes back to the balancing the different kind of personas and user needs. Of course we want to expose that for the right people, but then we want to make sure that we can get a default experience that works great for most people.

(00:48:34): But yeah, I think it’s going to be really proactive. I do think that we’re going to get much richer input through voice and richer visual outputs that are more interactive. I think that you’ll start to build more durable workflows with ChatGPT that you can use over and over. Right now, a lot of times it feels like you’re coming and starting from scratch each time. And we want to really make this kind of the tool that you can use to help you with whatever sort of task you have.

Lenny Rachitsky (00:49:04): This all sounds wonderful. I can’t wait. Just zooming out a little bit, and then I want to talk a little bit to designers again. But you’re in this epic role right now. I imagine there’s a lot of surprises as you entered OpenAI and took on this role. What’s something you wish you’d known? What’s something you wish you could whisper into Ian of day one to give you some advice?

Ian Silber (00:49:26): I mean, so many things. I think the first one is recognizing that we’re really early and instead… I actually was pretty intimidated coming to OpenAI, if I’m being honest. I remember interviewing. Oh no, I got to… GPT-4 had recently come out and GPT. I was like, “What is all this stuff?” I was using it and I was using the stuff, but I didn’t feel like I had a true understanding of it. And to be honest, I still have so much to learn. So that idea of you are early, we’re figuring this out. That I think I would want to hear. And the other thing that I found, and for me, this is more of a personal thing, it’s less about AI or anything, but I stepped into a really different role most of my career. I definitely managed before, but never at a scale that’s growing so fast and then at a company that is so different that… the role was just every day was something new.

(00:50:38): And for a long time I felt like I’m kind of bad at this or I don’t know what I’m doing. And then I went and talked to friends that had led really large design teams or were in a similar transition as me and they all felt exactly the same or the problems that I had were not unique. And so this is, I guess, more personal advice that it’s like, I think at any stage of your career, there’s that feeling of imposter syndrome and what am I doing? I don’t know how to do this. Finding people you can talk to that are going through the similar things, you’ll find that there’s usually a lot of shared challenges and struggles and having that, whether it’s a mentor or just a buddy that is impartial, out of it, was really helpful to me. And finding that community I think has been helpful. So yeah, so that and then understanding that this is all so new and evolving really quickly.

Lenny Rachitsky (00:51:37): That is extremely helpful to hear. Elena Verna had this really great post. I don’t know if you know her. She’s head of growth at Lovable right now. She had this great post called Stop the AI Confidence Theater, where she just kind of is like all these people just keep posting all these things they’ve done with AI and all the ways it’s changed their life and it’s just the killing it, figure it all out. And really it’s very few people, very few of these things are actually that great and working and it’s just like, stop. Stop pretending like this is actually, you figured it all out.

Ian Silber (00:52:05): I tghink it’s much better to be humble about it and be like, wow, yeah, I don’t know. This changing quickly and I’m just going to embrace it and see where it goes.

Lenny Rachitsky (00:52:13): Yeah. And that connects to what you said was a core component of people that are doing well right now. People that are curious and just kind of poking around and trying to try these things and try them again because maybe it didn’t work now. It didn’t work before, now it works now.

Ian Silber (00:52:25): 100%. Yeah. Every model, every new feature, it’s like the people that are poking around at those edges I’ve found are just having such a blast doing it.

Lenny Rachitsky (00:52:39): And this connects to something else Kevin Weil, former CPO at OpenAI said on the podcast, which has always stuck with me, which is the model we have today is the worst the model will ever be.

Ian Silber (00:52:48): Exactly. I mean that goes back to when we… Yeah, I mean a new model comes out, what, every week?

Lenny Rachitsky (00:52:59): Every day.

Ian Silber (00:53:00): I don’t know, every day? If you count all the labs and everything, it’s changing so quickly and every one gets better. And I don’t know. Yeah, I always try to remind myself. It must be what, I don’t know, building or designing in early days of computers when componentry was really evolving really quickly and there were these drastic step changes and you would hit these limitations and all of a sudden those limitations were gone. I think it’s the same. It’s like these things just change and what was totally broken yesterday now actually just kind of works.

Lenny Rachitsky (00:53:41): So maybe to start to close out the conversation, say a designer is listening to this and they’re in that bucket of overwhelmed, anxious, struggling, stressed, feeling uncertain about their future. What’s one suggestion you have for them to help them move out of that state and into a better place?

Ian Silber (00:53:59): Just recognizing that it’s a totally rational feeling and it’s a great time to just try to explore and see, what if I tried working… What if I tried rethinking about the tooling? Or, what if I just embraced like, “Oh, maybe I should prototype more. Let me try using these tools.” But again, recognizing that maybe it helps to hear that I think that we’re all still so early and it’s still changing and just embracing that. Just have fun with it and see where it goes.

(00:54:36): And I think maybe another thing I would say is really try to focus on the output, the outcome. At the end of the day, we’re not here to build tool processes. We’re not here to build or tokenmax or something like that. We’re here to make great software that people love or great products or whatever it is you do. But that’s the thing that really matters. And if you focus on that, I think that you’ll hopefully find that these tools can help you do that, but you still have a huge role in that as the person that’s steering and directing it.

Lenny Rachitsky (00:55:17): So along those lines, I’m going to take us to a couple recurring corners of the podcast. The first corner is AI Corner. The question is just what’s one way that you have found AI to be really useful in your job that maybe might inspire someone to use say ChatGPT or Codex?

Ian Silber (00:55:34): As a designer designer, I mean, nowadays I spend less time in the pixels, but I really do use it to help me think through broader ideas. Or I’ll have an idea at night or something, and then I’ll just quickly type it in and have it prototype something. And it’ll give me an idea that I can go and talk to the team about and it’ll help visualize something. And so that’s a part of the design process. It’s early ideas or we’re riffing through something and I found that ChatGPT, whether it’s ChatGPT Work or Codex can really help me visualize that. That’s been something that’s been really fun. And then there’s more of the operation side. It’s like I have it now. Checking and making sure that important Slack messages that I need to follow up with are summarized and giving me context before important meetings or for recruiting or for every part of my process, I use this to augment the work that I do.

Lenny Rachitsky (00:56:40): That makes sense. On the prototyping piece, just to give someone a tip on how to do this, are you opening up on your phone and firing off just a Codex thread? What’s the mechanic of doing this at night?

Ian Silber (00:56:49): ChatGPT Work has been incredible because it now runs fully in the cloud. And so the idea is you can just be anywhere and talk to chat and have it really spend the time and come back with a really great artifact. So I’ve found that it’s been really fun to just be like, “Hey, we’re working on whatever this thing is.” Whether it’s helped me think through it or sometimes I will just have some ideas that I would love to see quickly visualized before I even take it further and it will just help me play with it and try it and stuff. And so that’s been really fun. The fact that it’s so accessible. I might not even be near a computer or I can, I don’t know, just have that flexibility I think is really fun.

Lenny Rachitsky (00:57:43): Awesome. Okay, I’m going to take us to another corner, Fail Corner.

Ian Silber (00:57:47): Yeah.

Lenny Rachitsky (00:57:48): So the reason I do this, a lot of people, awesome people like yourself come on the podcast and all people hear is all the amazing things they’ve done, all the ways they’ve been really successful, and they don’t hear all the times things didn’t work out. And I feel like that’s very important for people to hear. It’s not always up into the right in success. What’s a story of a time you failed in your career and what did you learn from that?

Ian Silber (00:58:12): I mean, there are so many times I think that even at OpenAI, I think that I’ve found that I’ve had to learn every step of the way. When I first joined, I remember not really even fully understanding how I wanted to build a design team and not understanding how to hire or whatever. I sort of felt like I was failing every day, but just quickly trying to adjust and learn. I don’t know. I mean that’s maybe kind of a cop-out answer, but really just feeling like every day I’m learning on the go. I feel that my whole career has been that way in that I have never really planned any one step in quickly learning from your mistakes. I’ve shipped plenty of things that did not work out. And I’ve also shipped things that have worked out, but many times you try something and it’s kind of a failure.

(00:59:28): And at Instagram we had flops and then we’d quickly move on. I mean, I worked on IGTV, which was a huge flop, and then we shipped Reels. I mean, that’s a good example because we just kind of baked in some wrong assumptions and we held onto a few constraints. But then we learned from that quickly and we were like, “Okay, actually let’s change that.” And then we sort of redid it and then it became a really successful product. And so I’ve seen that many cases of… And I think that’s helped harden me to the critique and feedback of things because sometimes you get it wrong. Sometimes you try something and sometimes it is just about having to put it out in the world and work through it and get the feedback and iterate. And I think that more importantly is not what you shipped one time, but how you react and how you fix forward and how you continue to iterate and listen to your users.

Lenny Rachitsky (01:00:34): That’s a very common theme in this corner is just people’s careers are like, it’s mostly failure along the way.

Ian Silber (01:00:39): Yeah, definitely.

Lenny Rachitsky (01:00:41): And so I think that’s helpful for people to hear.

Ian Silber (01:00:43): Yeah.

Lenny Rachitsky (01:00:44): Okay. Before we get to our very exciting Lightning Round, is there anything else you wanted to share that we haven’t covered?

Ian Silber (01:00:50): If I could distill it’s like I hope that this is just a really fun time to build stuff. And I hope that we as designers can be really adaptive and focus on making really great stuff. And that I think that designers are just like… I think great companies are seeking designers and seeking great design, and I’ve found that to be really true. There are probably going to be a bunch of companies that will be left behind because they haven’t shifted, but I think that there’s plenty of room for amazing great design and that’s going to be more true than ever.

Lenny Rachitsky (01:01:31): I completely agree. I’m very bullish on design.

Ian Silber (01:01:33): Yes.

Lenny Rachitsky (01:01:34): Well, Ian, with that, we reached our very exciting Lightning Round. I’ve got five questions for you. Are you ready?

Ian Silber (01:01:34): Okay. Yes.

Lenny Rachitsky (01:01:40): All right, here we go. What are two or three books that you find yourself recommending most to other people?

Ian Silber (01:01:47): It’s funny, I’m not a big, big book recommender. I think when people ask me, I do get asked about books for design, and I haven’t found that many that really have stuck with me purely design. Although I will say I do love the Design of Everyday Things. I think that’s such a classic.

Lenny Rachitsky (01:02:07): That’s the one.

Ian Silber (01:02:11): Yeah, it’s not a unique recommendation, but it is just kind of a classic of thinking about how we think how I think about design.

Lenny Rachitsky (01:02:20): You have to read it if you’re in tech or not even in tech.

Ian Silber (01:02:22): Yeah.

Lenny Rachitsky (01:02:24): Awesome. Anything else there or should we keep moving?

Ian Silber (01:02:27): We can keep moving. Yeah.

Lenny Rachitsky (01:02:28): Let’s do it. Favorite recent movie or TV show that you have really enjoyed?

Ian Silber (01:02:33): Okay. So I have one that actually is not a movie or TV show, but I’m in New York. I just saw a Broadway show called Maybe Happy Ending.

Lenny Rachitsky (01:02:43): Yes, I’ve seen it. Love it so much.

Ian Silber (01:02:44): You saw it?

Lenny Rachitsky (01:02:44): Yes.

Ian Silber (01:02:47): Oh, you saw it. Okay. Yeah. It was so unique. And of course it kind of hit home a little bit because it’s about these super intelligent humanoid robots. But the production was incredible. The set design, everything about it I though was so unique, which was I thought… Yeah, so if you have the chance to see it, I though it was really, really good. I also just saw The Invite, which was I thought… Have you seen it?

Lenny Rachitsky (01:03:23): Yes, also love it. It’s so simple, but so good.

Ian Silber (01:03:29): That’s what I loved about it is it’s so simple. It actually is like a play and it’s just four people in one kind of beautiful apartment and the set design’s amazing. But the writing, everything about it was incredible and it’s just kind of a wild ride. And knowing nothing about it, I thought it was incredible.

Lenny Rachitsky (01:03:52): Excellent taste, sir. I love both those so much. And The Invite just came out. It’s in theaters right now.

Ian Silber (01:03:57): Yeah.

Lenny Rachitsky (01:03:58): Next question. Favorite product you’ve recently discovered that you really love?

Ian Silber (01:04:02): I feel kind of like a typical Silicon Valley person recommending this one or something, but I did finally switch to an EV after having many cars for a long time. I got a Rivian and I don’t know, I do respect the design a lot of just how they’ve really made it just all of the… I think of probably Tesla’s similar, but there’s a lot of assumptions that how operating a car should work or have gone away. You just walk up to it unlocks. It’s like you don’t have to turn on and off the car. And it’s cool to see that evolving. Of course I love… Waymos are probably, if I could own a Waymo right now, that is the most magical experience in the world. And I’m waiting on bated breath for that to be broadly accessible for everybody.

Lenny Rachitsky (01:05:03): Do you have a favorite life motto that you find yourself coming back to in work or in life?

Ian Silber (01:05:07): Not necessarily, other than I think trying to sum up how I felt about all of this is have fun with it and just try stuff. And I think don’t feel like… I’ve never felt like you have to fit into a specific box and know that it’s perfectly all right to be very fluid about the way you work or the way you think about things. And I don’t know, be flexible and adaptable. But yeah, it’s not quite a life motto, more of a vibe of just trying to have fun with it and build great stuff.

Lenny Rachitsky (01:05:42): I should shift this question to what’s just the vibe. The vibe that’s been helpful to you because I love that. It’s very a Sam Altman in terms of just you can just build stuff.

Ian Silber (01:05:50): Exactly. Yeah.

Lenny Rachitsky (01:05:52): Okay. Last question. Something I love about your career history, if you look at your LinkedIn, you were a designer at Groupon. I love that you were a Groupon and now you’re heading design for essentially super intelligence. What’s something you learned at Groupon that is maybe helpful these days building super intelligent AI?

Ian Silber (01:06:10): I love that. Groupon was a really fun company. Andrew Mason was a really incredible CEO in just that he brought such character to the product. It was kind of a brand-led product. And there was a comedy team. They were a writer team, but they were all comedians basically. And the product really did not take itself seriously, at least in its early couple years. It didn’t take itself seriously. And I think that the brand really stuck out. You weren’t signing up for Groupon because… Of course the daily deal was great. You were getting 50% off something, but people loved that email because it was really well written and it was funny and it had character. And I thought that early on, the company did a really good job with brand and sort of embracing that side of things.

(01:07:21): And I think the other thing, if I were to carry that forward is I found that every company that I’ve worked for has such unique DNA. And the way you have to work maybe changes a little bit based on that. So Groupon was run one way. Then I went to Instagram, which was this very design and creativity focused. And Kevin Systrom was really an incredible designer and he sort of saw himself or worked in that way with us, which was really cool and it just created a different way of working. And then you have Sam Altman, who’s a completely different way of operating, and OpenAI being a research lab. And so learning that companies have these really different DNAs and understanding how to embrace them and leverage that to your, or help empower that or I guess lean into that has been something that I’ve learned a lot from moving around and getting the opportunity to work at very, very different companies.

Lenny Rachitsky (01:08:26): And also just to add to that, it’s also important to realize you’re not going to change that. You’re not going to come in and change that culture because that’s very hard, especially if it’s very founder-oriented.

Ian Silber (01:08:36): I think it’s about finding like, oh wow, at OpenAI, yeah, sure. We spent more time… At Instagram, we definitely moved slower. And I would say that we changed the product less. And that actually worked really well for most stages of Instagram. But I don’t think that that would work in the current stage of where we’re at with OpenAI in that way of working. Of course, I bring a lot to that. And I think at Instagram we have this motto, do the simple thing first, and we always use that and we really embrace that. I’ve tried to carry that through to the way I think about building product at OpenAI, but that’s not the only way I think of working. Sometimes it’s actually not necessarily the right way to think about it. Sometimes we actually do throw some things out that we’re still experimenting with. And so just being really… I found that having to be flexible and not necessarily trying to change it, but trying to help round it out maybe.

Lenny Rachitsky (01:09:37): Ian, what an incredible place you have in the world right now, just being on the inside of such cool technology, such cutting edge stuff that’s happening. And I feel very fortunate that you found time to chat with us and share what you’re seeing and where things are heading. Two final questions. Where do you want to point people if you want to plug anything? And how can listeners be useful to you?

Ian Silber (01:10:00): Where do I want to point people? I mean, I think that please I guess have fun with the stuff we’re making with ChatGPT and Codex and fire away feedback and thoughts. I’m on Twitter. I love to talk with designers about all sort of stages or not just designers, engineers, PMs, whatever. That’s probably where I’m most reachable and accessible. I think to be useful, again, I love when people do show off the way they’re working and how that’s shifting. And that’s a great way for us to learn how we can build better products, both internally at OpenAI, but just as a design community, maybe showcasing a little bit more of our process because it is becoming a little bit more opaque. Well, how is it working? I think sharing that is such a gift to the community. So doing more of that.

Lenny Rachitsky (01:11:01): Also point people to your website, which I have here now, and I think my face is probably changing colors because the site has all these crazy colors. So if you go to iansilber.com, you could see this insane website, the personal website.

Ian Silber (01:11:14): Yeah, that’s a deep dive into all of my past work. You can see there. Yeah.

Lenny Rachitsky (01:11:21): And the trick is you’ll have to discover the Easter egg where there’s a game involved.

Ian Silber (01:11:25): That’s right. See if you can set the high score.

Lenny Rachitsky (01:11:28): Yeah, this high scores are out of control. I don’t know what’s happening. Someone’s found a cheat code. Ian, thank you so much for being here. Thank you so much for doing this.

Ian Silber (01:11:36): Lenny, this was awesome. Super fun.

Lenny Rachitsky (01:11:38): Same. Bye everyone.

(01:11:41): Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.