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

OpenAI’s Head of Design: This is the best time in history to be a designer | Ian Silber Ian Silber is the head of product design at OpenAI, where he has led the design of ChatGPT, Codex, and all of OpenAI’s product experience for the past three years. Before OpenAI, he was at Artifact, the AI-powered news app built by the founders of Instagram. Prior to that, he spent eight years at Instagram, where he worked on products including Reels. Ian is one of the most consequential designers working in AI today, and he takes us inside how OpenAI designs ChatGPT, Codex, and the future of how we will interact with AI. *In our in-depth conversation, we discuss:* 1. Why Ian believes this is the best time in history to be a product designer 2. Why engineers 10x’d with AI but design teams haven’t 3. What OpenAI looks for when hiring designers 4. “Just do less”: Ian’s counterintuitive advice to his designers 5. The future of ChatGPT as a super app 6. Where humans still win: user understanding, invention, and point of view *Brought to you by:* WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more: https://workos.com/lenny Mercury—Radically different banking, now with Command: https://mercury.com/ *Episode transcript:* https://www.lennysnewsletter.com/p/openais-head-of-design-this-is-the *Archive of all Lenny's Podcast transcripts:* https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 *Where to find Ian Silber:* • X: https://x.com/iansilber • LinkedIn: https://www.linkedin.com/in/iansilber • Website: https://iansilber.com *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Ian Silber (02:14) Why designers in general feel anxious about AI (09:01) What makes specific designers thrive in the AI era (13:41) Why Ian says it’s the best time in history to be a designer (17:13) How product roles are converging (22:24) Can AI design great products? (23:54) Where human judgment still matters (27:34) What Ian looks for when hiring designers (30:20) Why systems thinking matters (32:53) Balancing speed and craft (38:05) Designing for vastly different audiences (41:57) Solving the blank-box problem (43:31) How ChatGPT is evolving beyond chat (46:07) The vision for Codex (49:07) What Ian wishes he knew on day one (51:40) Why humility matters in AI (53:41) Advice for designers who are feeling overwhelmed (55:16) AI corner (57:43) Failure corner (01:00:45) Lightning round and final thoughts (01:05:52) Lessons from Groupon *Referenced:* • OpenAI: https://openai.com • How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026 • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • 3 Spiderman Pointing meme template: https://www.kapwing.com/explore/3-spiderman-pointing-meme-template • OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape • Notion: https://www.notion.com • The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead • Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • ChatGPT Work: https://openai.com/chatgpt-work • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Please Stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater • The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna • Maybe Happy Ending: https://www.maybehappyending.com • The Invite: https://www.imdb.com/title/tt14173636 • Rivian: https://rivian.com • Waymo: https://waymo.com • Groupon: https://www.groupon.com ... References continued at: https://www.lennysnewsletter.com/p/openais-head-of-design-this-is-the *Recommended book:* • The Design of Everyday Things: https://www.amazon.com/dp/0465050654 _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email [email protected]._ Lenny may be an investor in the companies discussed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Lenny Rachitsky?

  I've been doing this sentiment survey of the tech workforce. Surprisingly, designers are just the most unhappy on every dimension.

• 0:08Speaker 01

  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.

• 0:17Lenny Rachitsky?

  You believe this is the best time in history to be a designer?

• 0:20Speaker 01

  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.

• 0:36Lenny Rachitsky?

  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.

• 0:43Speaker 01

  Engineers have 10 or sometimes like 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. Still very messy and fluid.

• 0:56Lenny Rachitsky?

  We had a podcast with the head of design club 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.

• 1:05Speaker 01

  There are certain features for ChatGPT where we really obsess and we really spend a lot of time. We try 100 things, 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.

• 1:19Lenny Rachitsky?

  Do you think AI will ever be an extremely good product designer?

• 1:22Speaker 01

  I think it already is an incredible product designer.

• 1:26Lenny Rachitsky?

  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. A huge thank you to Saleo and Joel Lowenstein for suggesting topics for this conversation. Before we get into it, don't forget to check out lennysproductpass.com for a year free of the hottest and most beautifully crafted AI products in the world, available exclusively to Lenny's newsletter subscribers.

• 2:12Lenny Rachitsky?

  With that, I bring you Ian Silber.

• 2:17Lenny Rachitsky?

  Ian, thank you so much for being here.

• 2:20Speaker 01

  I'm so excited to be here. Thanks for having me.

• 2:22Lenny Rachitsky?

  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, where 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, like every actual dimension. They're the most overwhelmed, the most anxious, the most, the least optimistic, the most worried,

• 3:03Lenny Rachitsky?

  the most tired, also the least likely to recommend their role to people entering the workforce.

• 3:11Lenny Rachitsky?

  I'm curious if you're seeing this yourself in the design community? And if you are, what do you think is going on?

• 3:18Speaker 01

  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, you know, and I see, I see a mix for sure. I think like I can speak most of design.

• 3:33Speaker 01

  And I mean, I talk to a lot of designers that are very optimistic and very excited. And so I see, in my world, I see, luckily, I'm, I see a lot of that. But I can totally understand why people might be feeling very uncertain, right? Because there's so much discussion about, well, is the role changing? Should my expectations be different? And, you know, well, do I need to, do I need to do X, Y, and Z? Do I need to be shipping code every day? And, you know, someone who might be sort of classically trained in a certain way of working now feeling like, oh, my gosh, I need to like really change everything.

• 4:18Speaker 01

  And I think it's, to me right now, it feels like the uncertainty of that, I can totally understand, right? Because as an engineer, I think people have, they've already sort of gone through that ship. Like, we see that engineers are working totally different. And we also, you know, one thing I do here, and this came up a lot in my own team, when we did, we do similar surveys internally. One of the big things that came up was, you know, we see that, you know, engineers have 10 or sometimes like 100x their productivity. But our design team hasn't, right? Because the design process still takes time. It's still, sometimes you have to try a bunch of things and throw them out, right?

• 4:59Speaker 01

  Versus maybe working with a coding agent, you ask it to do something, it's pretty binary. Now, at this point, it usually sort of gets it pretty well. And, 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 then you give it to, you know, users or internally, you get internal feedback and it's wrong. And you still have to go through that arduous and kind of messy, but really fun process.

• 5:30Speaker 01

  And that hasn't really, it's compressed in that you can get much more ideas out fast, but you still need that, that whole sort of feedback loop. There's the alignment of getting many people, you know, especially in a bigger company like that. It's still has a lot of overhead. So the point is that I think that it's, we're unclear right now, like what is expected of a designer? And that lack of clarity, I can see totally lead to, you know, some, some fears or some unease, I guess. But on the other hand, I've seen that, I mean, our designers, what's been, what's great, I think, about at OpenAI is like, we're such an experimental company.

• 6:10Speaker 01

  We are driven by, you know, research and we treat our company as a research lab and we totally embrace that. And that's a new thing that I really kind of learned and that really come to love about OpenAI is that started as a research lab, that DNA is like deeply embedded in everything we do. And as designers, I think that, you know, you come here, we look for people that are, don't have a background in AI, but are like really curious about the tools and how it can work. And we found that like, just by sort of 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.

• 6:56Speaker 01

  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 they, you know, I think the feeling is that like they have so much more ability to be creative, to express themselves, to try bad ideas and throw them out. You can just like really move through lots of different ideas and it becomes this incredible way to create. And the things that I'm seeing from my team, the bar is raising. The, the, 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

• 7:41Speaker 01

  and realizing that they have just so much agency as designers. And like, you know, so much more ability to have like really high impact as a, as a designer.

• 7:53Lenny Rachitsky?

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• 8:36Lenny Rachitsky?

  or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise-ready and unblocking growth. It's essentially Stripe for enterprise features. Visit workos.com to get started or just hit up their Slack where they have actual engineers waiting to answer your questions. WorkOS allows you to build faster with delightful APIs, comprehensive docs, and a smooth developer experience. Go to workos.com to make your app enterprise-ready today.

• 9:02Lenny Rachitsky?

  What I'd love to do in this conversation is help folks that are in that bucket of, well, 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 like the main, the most, 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, they're seeing that now. They're like, holy shit, I can do so much more. And so just to kind of reinforce the points you're making, the attributes of people that are doing well,

• 9:45Lenny Rachitsky?

  feel amplified, very curious, have time to explore, feel like they could be more creative. Is there any more, think more along those lines of just like 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?

• 9:59Speaker 01

  What I see in, in the folks that I think are really embracing this, right? They are using it every step of the process to kind of help them, right? And it, and I think it helps, you know, we have, we have a community, of course, of designers that are all trying this together. So if there's any way to kind of find that, and that's something that we should think about more as a broader community, how we kind of help each other. But like, I think that learning kind of different ways of working, right? 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 Claude or whatever tool you use, like throw it into, into an agent to help you think about it, to help you prototype it. Just try a different way of working.

• 10:41Speaker 01

  It doesn't necessarily mean that that has to be the exact right way, but I don't know. I think we found that just people that are embracing this, that are adaptable. I think adaptability is like another term that I think we all hear a lot now, but it's like so true. It's like knowing that this stuff changes very quickly. What didn't work yesterday might work today. I mean, literally like within, you know, six months, this entire industry has shifted. I remember I was actually out on, 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 just like it worked, but it just kept kind of running into these hiccups.

• 11:26Speaker 01

  And and then like a month later, like Codex drops and I tried 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 like plop it in there and just try it. And so anyways, I think it's it's just really about like not being scared. I think another thing to think about is that we're so early, we're like so early innings of this entire. Evolution, right? 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, like if you're.

• 12:07Speaker 01

  Early career or late career, or you've never even like actually designed anything, but you've been thinking about it. Is like, we're all figuring this out as we go. Nobody has like some perfect answer. About the how the design process should work.

• 12:25Speaker 01

  And it's whatever you think is working today will probably change again. And so I think what's encouraging about this is that. Nobody should feel like behind right now. I think that if you literally started today, you're going to have a leg up on pretty much most people.

• 12:42Speaker 01

  And just really thinking about like how you can just make great stuff. And there's just so much opportunity to change the way we work or to to just to make great things. And what we think is like really cutting edge today will look so archaic and you know. A year, let alone a month, right? And that's something I've I've learned, you know, I've been at Open Air for three years and I think about the stuff that they. You know, we were working on when we, when I first joined. I mean, I remember getting a demo of of like. Our our early voice mode that we hadn't shipped or computer use that like, you know, barely worked.

• 13:24Speaker 01

  And now it's like become it's it literally has become part of the process of how we design. We use both of those tools to to build software. And so anyways, the point is it's like changing very quickly. We're all extremely early in this process and nobody really has like that it figured out.

• 13:41Lenny Rachitsky?

  I love that. You've also, when we were chatting ahead of this, you're you actually told me you believe this is the best time in history to be designer.

• 13:47Speaker 01

  Yeah, I mean, I I truly believe this. I can't even imagine, you know, so when I, okay, history lesson, when I was getting into design, I mean, I was like.

• 13:59Speaker 01

  In my teenage years, right? And I was like. You know, to learn things, it was like. You know, I I was kind of like learning to design and code and. You could like view source on a HTML webpage and kind of see how things were built. And that was like kind of how you had to learn and, you know. You could, I don't know, it's like Dreamweaver and, you know, like 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 like learn so quickly, you can kind of like have an idea to. Working version of it in like. Like a matter of minutes.

• 14:45Speaker 01

  It's just, you can be so expressive and and you can. I think anybody can be a designer, right? And I think that as more and more software is made, more and more products are made. I think that the. I do think that the human element of design is going to really be. Start to become more and more important. It's always been the case that I think that, you know, companies with great design, you know, can of course stand out. I think that's going to be more and more important, right? I think that products that fully understand their users and that make something delightful.

• 15:29Speaker 01

  When anybody can make anything, you know, that's going to become one of the most important kind of. Like sort of dimensions of a product and that's how people are going to evaluate it. And so I think designers stand like that is that is our core job, right? You know, and and then on top of that. I think that designers are just much more empowered. So, you know.

• 15:54Speaker 01

  You know, I was talking to some friends that are thinking about starting a company and talking about the. Sort of ratio of design to engineer and how like at a startup, maybe that's totally different. It might may have been like you have one designer and. I don't know, 15 engineers or something like that, you know, that maybe a startup, I've seen that sort of ratio. But there was, they were talking about, well, maybe we'll have like two designers and one engineer. One really good engineer who can make sure that like we're really building something that's rock solid, like from from an engineering standpoint. But then we want two really creative people that are going to be thinking about how we kind of build this product. And so thinking about that, I think that there's just like a huge opportunity for designers.

• 16:39Speaker 01

  I think that internally, we see that more and more. We're like designers, we are totally completely empowered to to take an idea, to take a. Early research concept and try to figure out how we can actually like package that up into something that people want to use or that. 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 think it's like the best, I really do think it's the best time to be a designer.

• 17:13Lenny Rachitsky?

  So along those lines, when Mark Andreessen was on the podcast, he had this hilarious way of describing the state of the of the product org right now. He's like, basically, there's this three way standoff, PMs, engineers, designers, they're all, 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 less like Spider-Man meme where they're all playing with each other. And I'm curious, because I 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, like there's like a thousand X explosion and products being shipped. There's just like endless streams of things to pay attention to. You think design would be such an opportunity to differentiate and stand out?

• 17:56Lenny Rachitsky?

  I haven't seen that yet in just like an acceleration of design hires and explosion, as you said, like two designers to one engineer. Do you think, 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 is going on?

• 18:12Speaker 01

  We might start to see that happen more.

• 18:16Speaker 01

  Or if anything, what 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 like engineers 10 Xing. But we are seeing that that designers. Are are able to do a lot more. But no, I mean, I think that that is something we're we're sort of always thinking about and evolving. The other thing I wanted to talk about too is like the difference between PM and engine design and are they all blurring together? And my point of view is that they definitely are and that there's always been overlap as far as I've seen it, right? I've seen designers that are like kind of really good.

• 19:02Speaker 01

  Product, you know, manager type archetype, but can design. And I've seen designers that are like really good sort of polished engineer type, you know, like so that I think I've always found that these like. Single siloed. Role definitions don't really make sense. It's just that at big companies, you have to have like a ladder to put people on so you can generally kind of like organize. But in reality, you know, when you look at a team, you see that there are people that are have various strengths and people that play different roles. And so I've always kind of seen that. I think there's those lines have always been blurry, but they're becoming blurrier for sure.

• 19:45Speaker 01

  But the other thing is I do still think that, and maybe this is thinking about it from like a slightly larger company perspective, but. I think you do still need people that have certain responsibilities, right? Because if you have one person that's expected to design, to rally a team around something, you know, to align a whole company. To do all the work that like a PM does, for example, and also be designing it and also be engineering it. It's just maybe not, you might, it might be hard to find one person that's good at all of those different skills. And so I still find a lot of value, for example, in having like an excellent PM that can help rally multiple teams together, that can help.

• 20:26Speaker 01

  Sharpen kind of the perspective or the problem space that a team is focused on.

• 20:33Speaker 01

  That can help with like resourcing, all of those things, right? 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 sort of generally responsible for these different things. Or an engineer who's like really making sure that the output is totally sound and, you know, is actually like. Littering up to something that is going to work for the broader system.

• 21:03Lenny Rachitsky?

  I completely agree. So just to make sure, I understand what you're saying is just, let's 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. Like the Venn diagram, I'm picturing Venn diagrams of product design engineering like converging, but you're saying they're going to continue to stay their own roles. There's going to be a PM, design engineer, but each can do more of the other roles.

• 21:26Speaker 01

  I think that's right. I do think that like for, and again, this is not a blanket statement, right? Because I think if you're at a startup, that's like very different. I would, I would, if I were starting a company right now. I would hire like the best generalist people I could possibly think of, someone who I think could kind of fluidly move between that. But maybe again, that's maybe that's always kind of been true.

• 21:47Speaker 01

  But at a bigger company, I do think that I've seen like designers. That are, you know, maybe incredible at designing, but could really use a product manager who can help them kind of with with like hone. Both their thinking and how and then how they work and the operations of it all. So the point is, I do just think that there are, there are different.

• 22:11Speaker 01

  It's almost like in taking the people out of it, I think that there are different sort of hats that you need to wear to build great software. And I think that those are continued to be important functions, I think.

• 22:24Lenny Rachitsky?

  So this begs the question, do you think AI will ever be an extremely good product designer? And just to like, it's interesting to ask you this question because on the one hand, you're like, oh yeah, open AI like GPT is going to become incredible at everything. On the other hand, it's hard for a head of design to say, oh no, design is going to be done by AI. I'm curious to get your, your take and you know, it's like, sounds crazy, but like engineers never thought it would be able to write code the way it is now. So just, yeah, thoughts on just how good AI will get.

• 22:52Speaker 01

  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 like the best visual designer or best at, you know, information hierarchy or typography, or even, you know, user experience and interaction design. It's not necessarily like the best at any of those. It's impossible to predict where things are going. And like I said earlier, like, you know, how much has changed in three years? Of course they're going to continue to get better.

• 23:36Speaker 01

  But the way we think about it, and I, and I really do believe this is like, we're building tools to enable people to be more creative, to be, to do more, to build more. And so it's, it is already a great designer, but you, it's at your fingertips to kind of figure out how to use it and how to get the best out of it.

• 23:55Lenny Rachitsky?

  Where do you think human brains will continue to be most valuable as AI gets better at product design specifically? What are kind of like the remaining areas for us to be useful?

• 24:04Speaker 01

  Truly understanding what people need. You know, I mean, the human feedback loop of watching people use something and, and understanding that. The, you know, inventing something new. I think, and then of course, there's just the pure like human kind of take, right? Like, oh, somebody made this, somebody had a point of view about this. I just think that, I do think that will stand out more and more. And I think that that's like an important thing for a designer to like really hone. It's like, what is my point of view?

• 24:47Speaker 01

  What, who am I building this for and why? And I don't know, I think like as, as, as AI becomes more and more like better and better, for sure, there will be an opportunity to always kind of stand out and push, how can you push that even further?

• 25:01Lenny Rachitsky?

  Yeah, that touches on a conversation I had with the PM of Codex. Asked him just why is AI not good at design? It's actually gotten better since that conversation, which was just like a month or two ago. And, and he had a number of reasons for it. One is just like, like part of great product design is doing something new. And so if it's trained on all the most interesting websites today, just like, okay, but that's not what, that's not interesting anymore. And the other point he made is like, 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, what do you think it'll take to get AI to be much, much better at product design?

• 25:40Speaker 01

  I mean, the new thing is interesting, right? Because I think that everything we're doing is trying to design something that hasn't existed before, right? You know, if you look at, if you look at great, great products that have come out in the last, you know, 10, 20 years or whatever, right? It's like, all of a sudden, you know, take the iPhone, we're designing for multi-touch. And that opened up like this whole new interaction paradigm. And there's no training data for that, right? You have to, you're kind of really trying to understand this new thing, right? And then you had something like Instagram that was like really embracing the sort of like the fact that everybody had mobile phones. And then Snapchat, I think is another good example of great design in that it was kind

• 26:25Speaker 01

  of a, maybe people thought strange sort of like interaction design, but it completely like flipped on its head, the way people might want to communicate with each other. And to me, that, that is like great design. It's like truly understanding, like I, you know, the people that like, people have this problem, or there's this unmet need and, and I'm going to build it with this, in this unique way. So yeah, I do think that there's that sort of like fresh, new kind of way. And then now with AI, it's like, we're designing like, how do you talk to something that is, how do you talk to AI with your voice, you know? Or how do you use an agent to like carry out tasks for you? It's like, yeah, there isn't a lot of precedent for this.

• 27:07Speaker 01

  And so I think that, you know, humans are able to kind of do a really good job kind of evaluating, you know, what good is and, you know, or at least kind of like trying a bunch of things and, and learning along the way with people. And so, I don't know, but again, like all this stuff changes really quickly. It's hard to say, but I think, I think there's a lot of reasons why having that human in the loop is going to be so important.

• 27:34Lenny Rachitsky?

  And kind of following that thread of the human in the loop. When you're hiring designers these days, what's kind of 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? What's trending down, if anything?

• 27:49Speaker 01

  This might be a luxury of having a slightly larger team, but if you're, you know, at our scale, you know, but even at a startup or a smaller company, I think that this 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 kind of like your handful of, or the right ratio of sort of generalists that can kind of do everything. But, you know, we also hire like incredible visual designers, or we have like, like a really amazing sort of brand team that helps us with kind of like the sort of maybe expression of our brand, both out and in, in the product.

• 28:32Speaker 01

  Or great prototypers, or, you know? And so I think that rounding that out, or, or great sort of product thinkers that are a little bit more strategic, or people that are like really obsessed over like 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. I think people just naturally are, you know, drawn to certain things. And I think embracing that, and when you build a team is actually like, if you, if you have the luxury of doing that, it's like really valuable. Okay, so that's like my broad statement, but then as far as what we look for, we do definitely, you know, I always tell candidates, we do not expect you to have a background

• 29:16Speaker 01

  in AI, because again, this is evolving so quickly, but we definitely expect high curiosity about it and, and, and a high aptitude to jumping in and learning how, how, you know, how you're going to use this in your process, how it works. And not just how you use in your process, but how, especially for us, like 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 like we really push on or look for. And then definitely prototyping. Prototyping is something I've always valued in my career, but I just think that, you know, it's become more and more accessible.

• 30:01Speaker 01

  And so that's something that I think really does stand out usually when we talk to, to candidates. And then I do think that, yeah, just like having some, having a point of view on, on where, where these things are going, or just like any of the tools that people have worked on and really thinking that strategic thinking. I guess the last, last one on this is like systems thinking is becoming more and more important. And, you know, especially as you're like, in our world, it's interesting because we're trying to build, you know, we're building this super intelligence that has, that has all these different capabilities.

• 30:43Speaker 01

  And we need to think more about the underlying primitives that we can build that can kind of build on top of each other, right? You know, this is something that I think like Notion did really well early on was like, we're going to build these building blocks, right? And then like 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, you know, when someone goes and uses our product, it feels like one cohesive, simple thing and the model can reason about how it can pull up these things together. So that like idea of like really understanding the system and thinking about that is becoming

• 31:26Speaker 01

  even more important, especially because it's kind of complex of all the things that it could possibly do.

• 31:31Lenny Rachitsky?

  This is the fifth podcast in a row I've done where systems thinking has come up as

• 31:35Speaker 01

  Interesting.

• 31:36Lenny Rachitsky?

  a skill that people are more and more looking for. And it's, it's like 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 why, 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, like engineers are shipping 5,000 PRs a day. And so to your point, this idea of building blocks and design system and, and just a platform for people to build on feels incredibly important.

• 32:08Speaker 01

  Totally. It's very hard, but I, I, yeah, it's like, it's funny. I've, we've had these conversations where I'm like, just do less. Like my encouragement has been do less, like 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 kind of, like, you know, extend an existing feature. I think that's an important thing. And, and part of that is like, thinking outside of the bounds of what you're working on, right? And thinking across everything, I think is becoming much more important. And the speed for sure, I think is, is a reason why that's so important right now.

• 32:53Lenny Rachitsky?

  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 design club code, Jenny Wen, and she talked about this, and I think it blew a lot of people's minds. Just, there's been this traditional design process, prototype, mock, test, use of 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 like steering people in a good direction. Does that resonate? How much is that has changed in, in the world of a designer?

• 33:28Speaker 01

  I think that a hundred percent, we, we do work that way. It, it's, it depends. I think for us, it depends on like what sort of what stage you're at in the, in the sort of process or.

• 33:40Speaker 01

  You know, uh, how, uh, maybe how far along the product is. There are certain features for chat GPT where we really obsess and we really spend a lot of time. We try a million things and we throw up, you know, uh, we try a hundred things and we throw out ninety nine. We finally ship one.

• 33:59Speaker 01

  You know, uh, the like, uh, the, or like the composer is like changing every single day. And we try many things we throw out, but or like, and you could take that for many different things within chat GPT. And then there are other things like codecs where, um, you know, I don't know. I mean, a super app is a good example where we definitely just like trying stuff really quick. I think that we really embrace building in public, which is a different way of working. But I think that like, 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.

• 34:40Speaker 01

  But yeah, I mean, it is, uh, moving really fast. And I think it just depends, right? Like, like I said, certain things we really sweat the details and we try, um, you know, and we do tests. We A B tests, we'll do user research, um, and we kind of iterate and evolve a lot. And then other things we, uh, we take big swings and then we learn quickly. But yeah, I don't know. I think you have to, like, I think the biggest thing is like embracing that the technology might change in like a, a month. Or, you know, and maybe, uh, certain interaction or, or setting or, or whatever that you needed doesn't need to exist.

• 35:22Speaker 01

  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 like rethink this. Or whatever, all these capabilities are changing or the intelligence has changed. Or, and so you have to be just like really quick on your feet and, and maybe not be so precious about it. Until it's at the point where, okay, this is kind of hardened. Like, we don't think that this is necessarily gonna change tomorrow because of the technology. So let's make this the best it can possibly be, you know, like we're, we're, we're thinking a lot about how we should evolve. Sort of really think about chat GPT becoming like deeply embedded in a, like your personal life. And how, how should the, how should the app feel?

• 36:06Speaker 01

  That's something that we're not gonna necessarily design and ship overnight and just like put it out there. We're spending, we're really thinking about that and we're trying a bunch of different ideas or putting it up on, you know, uh, a whiteboard. Or, you know, we're doing some design in Figma, we're prototyping it, we're probably gonna dog food a bunch of different ideas. Long before we ever ship something. That, but that's a bigger project, right? And then there's other things where we're like idea to ship in like, you know, four hours.

• 36:38Lenny Rachitsky?

  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.

• 36:47Speaker 01

  Exactly. Yeah, yeah. And it's hard to know what that is. Yeah.

• 36:52Lenny Rachitsky?

  Yeah. This episode is brought to you by Mercury, radically different banking, loved by over three hundred thousand entrepreneurs. And now with Command, I've been a customer of Mercury's for over six years. I have never once thought about leaving. Mercury is basically what happens when banking is built by product people, not by bankers. They make it so easy, dare I say fun, to send invoices, move money around, set up virtual cards for folks on my team. Does your bank have an API, a terminal native CLI or an AI ready MCP server? I don't think so. And just recently they launched Command, a conversational interface built directly into Mercury, which acts as your financial operator.

• 37:35Lenny Rachitsky?

  I've been using Command to transfer money around, to figure out what categories I've been spending the most money in, analyze my cash flows. And just today I used it to find out how much I've made from a specific sponsor over the past year. I just asked, how much have I made from X over the past year? Ten seconds later, I have an answer. It is so freaking cool. Visit mercury.com to learn more and apply online in minutes. Mercury is a fintech company, not an FDIC insured bank. Banking services provided through Choice Financial Group and Column NA, members FDIC. So I asked a bunch of people that know you well, what to talk to you about. And, uh, Joel, uh, Lowenstein, who happens to be the head of design at Anthropic is a good friend of yours, which I love.

• 38:17Lenny Rachitsky?

  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 chat GPT. 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?

• 38:37Speaker 01

  That's a great question and it's a really fun part of the way we work.

• 38:44Speaker 01

  I think that we have, we have vastly different audiences, like really, really different. I've never worked in this kind of quite, quite a spread.

• 38:55Speaker 01

  You know, I, at Instagram, uh, I, I, I spent eight years working at Instagram. We had a billion user 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's sort of, you know, a couple of ways you could use it. We did think about like creators and, you know, larger accounts that had special needs. But this is like vastly different where you have someone who's, you know, using this to help them come up with the recipe to eat tonight.

• 39:24Speaker 01

  Or, you know, brainstorm their next haircut or something like that. And then there's, uh, somebody who's like transforming the way they're doing farming for their, you know, um, their like, you know, helping to automate their farm in Japan or something, right? And, uh, it's just like the broadest spectrum ever. Generally what we've seen is that, um,

• 39:52Speaker 01

  we, we believe in this idea of this sort of capability overhang where the, the product, um, you know, like vast majority of the people are getting a sliver of the, the true value that they could out of the bottle. That's not necessarily a bad thing. Many, you know, they're still getting tons of value.

• 40:09Speaker 01

  But we found that like, we, you know, make sure to focus on creating a extremely simple streamlined experience for, for many, many people. And then we put like, uh, all of the, you know, cutting edge stuff. We also make sure, make sure to give that and, and make sure that's like really accessible for the people that care. The challenge, of course, is like not necessarily over indexing and, and sort of like putting that, putting, uh, something that, um, people might not understand in front of a billion users. So, but generally what we've seen is we can experiment early with the, the people that really care. And that's where we have like our desktop app and we have codecs.

• 40:49Speaker 01

  And now chat GPT work is kind of stepping into a much broader audience, which we're really excited about. And eventually what we want, what we, what we know, and we think about this a lot in design is like, it will true, like, things will truly become like for billions of users when they don't have to like think about a switch or a mode or anything like that. And so we know that like eventually it has to kind of get distilled into that main experience. But it is like a really fun thing to balance. And, um, we have to think about like 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 sort of balancing.

• 41:27Speaker 01

  And as a designer, it does add a lot of complexity for sure to think to, you really have to have empathy for every sort of different type of user. But this, it makes it fun for sure.

• 41:39Lenny Rachitsky?

  That is such a mind blowing point you're making about the spectrum of usage of chat GPT and codecs. I, I didn't think about it that way. Like, is there, has there been a product that has such a wide spectrum from just like, what's this rash on my finger to building, uh, Salesforce, you know?

• 41:56Speaker 01

  Yeah, and it, and it makes it really hard to, you know, cause I, a lot of, uh, it's so funny, like, one of the big challenges we're always thinking about is this like playing box problem, right? And people talk about this all the time. It's like, is chat really the final frontier? It's a terminal, it's a, you know, glorified terminal. It is like some critique that, 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? You know, it's like, maybe someone is coming here for. Image generation for fun, or you know, they're trying to generate a PowerPoint or you know, so having this adaptable interface is like a really interesting design challenge.

• 42:41Speaker 01

  And it's like sort of uncharted territory because it can really like shape shift into many different tools. And it's this like incredible, so many different things and trying to figure out how to present that. And then thinking about, you know, we think a lot about like 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 sort of professional work, whatever, whatever capacity they're using this in. And then we also want to like get out of the way of people that, you know, use this every single day and they use this as like a real workhorse tool.

• 43:23Speaker 01

  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.

• 43:31Lenny Rachitsky?

  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 chat box. Why hasn't it ever changed from that? Even though it has, but still it's kind of this chat box, chat bot. 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.

• 44:07Speaker 01

  Yeah. And I think we're seeing what's, what's been really fun design space for us is, you know, there's two things we think about. One is like, how do we, how can we help you express your intent better? Right? Like, we don't want you have to think about being a perfect prompt engineer, but like, 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 get, we sort of best understand what you want? And so like, you know, we recently shipped some features where if you ask sort of an open ended question, it can follow up with, you know, some follow up questions that you can like just tap through and answer versus having to type everything out. Right?

• 44:48Speaker 01

  Or another good example is, you know, so then, then once you actually ask it to do something, there's, the chat transcript doesn't need to be purely text, right? We've seen these now evolve so far from what it was with, when ChatGPT just launched. You know, it's no longer just a pure chatbot. It actually has many features within that. Right? So a good example is what we call writing blocks. You ask it to, you know, write you a letter or an email and it now contains that, that email and 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 like image generation and creating special tools

• 45:32Speaker 01

  for that kind of mode. And I think that's where the UI is going to start to really continue to evolve is how do we make, if you're, if you come at this and you're a designer, maybe ChatGPT should actually really look differently, look different or have different affordances. Or you're, you know, a data scientist or, you know, you're using this for, to run your home, you know, like your, your personal life. Maybe it should really kind of work or look differently. So like understanding the context and giving you different affordances based on that is something that, you know, we're thinking a lot about.

• 46:08Lenny Rachitsky?

  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 like a way you think about where this goes long term?

• 46:25Speaker 01

  I think that it will start to become more and more adaptive to, you know, all of the context of your life. I think proactivity is a big untapped kind of part of the experience that we're really excited to think about. You know, we're starting to see this with ChatGPT work now where it actually has pretty good suggestions based on, you know, your calendar or your Slack or these different sort of inputs and external kind of context. I think that's going to become more and more important or kind of shift the way, you know, you use it.

• 47:09Speaker 01

  I think voice as, you know, we, we just had a step change in the model that just feels much more natural. And again, like, you know, I can only imagine how that's going to feel in two, three years. This is just get better and better. I think people, I do love interacting with ChatGPT, especially voice in like just, I want to just kind of like really quickly say something. And, and then I think like its ability to kind of go sort of like, not just from asking questions, but actually doing things for you. That's all going to change. And hopefully all of this gets simpler as we do it too. Right? You know, 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 sort

• 47:54Speaker 01

  of this one universal input that you can ask that knows when it needs to answer like really quickly, or it should be chatty, or whether it should go and like go off and do work for you. And so that's a big like 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, you know, that like, that's like, goes back to the balancing, the different kind of, you know, personas and user needs like, right? 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, for most people. But yeah, I think it's going to be really proactive.

• 48:35Speaker 01

  I do think that we're going to like get much richer sort of inputs, your voice and like richer visual outputs that are more interactive. I think that you'll start to build more durable kind of workflows with ChatGPT that you can kind of use over and over. Right now, you know, it, a lot of times it feels like you're coming and starting from scratch each time. We want to really make this kind of the tool that you can use to, to help you with whatever sort of task you have.

• 49:04Lenny Rachitsky?

  This all sounds wonderful. I can't wait. Just kind of 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, of day one and to give you some advice?

• 49:26Speaker 01

  I mean, so many things. I think, you know, the first one is like recognizing that we're really early and instead, like I actually was pretty intimidated coming to OpenAI, if I'm being honest. You know, I remember like, okay, interviewing, oh no, I gotta like, you know, GPT four had kind of recently come out and what GPT, like I, you know, I was like, what is all this stuff? Like 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, you know, I still have so much to learn. So that idea of like, you are early, we're figuring this out, like that, I think I would, I would want to hear.

• 50:11Speaker 01

  And the other thing like that I found, you know, and for me, this is more of like a personal thing. It's less about AI or anything, but I stepped into a really different role. You know, most of my career, I've managed, I definitely managed before, but never like at a scale that's growing so fast and, and then at a company that is like so different, you know, that it, the role was just every day was something new. And for a long time I felt like I'm kind of like bad at this or I'm, you know, I don't know what I'm doing. And then I went and like talked to friends that had led like really large design teams

• 50:51Speaker 01

  or, 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, you know, this is, I guess, yeah, more personal advice that it's like, I think at any stage of your career, there's that feeling of like imposter syndrome and like, what am I doing? I don't, 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 kind of challenges and struggles and having that list, or whether it's a mentor or just like a buddy that is like impartial and out of it as, was really helpful to me. And, you know, finding that community, I think has been, has been helpful. So yeah, so like that, and then understanding that this is all so new and evolving really

• 51:36Speaker 01

  quickly.

• 51:37Lenny Rachitsky?

  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 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 they're killing it, figured it all out. And really it's like very few people, like very few of these things are actually that great and working and, and it's just like, stop, stop pretending like this is actually, you figured it all out.

• 52:05Speaker 01

  I think it's much better to be humble about it and be like, wow, yeah, I don't know, this is like changing quickly and like, I'm just going to embrace it and see where it goes.

• 52:13Lenny Rachitsky?

  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.

• 52:25Speaker 01

  A hundred percent. Yeah. It's like being kind of like, yeah, every, every model, every new, every new feature, it's like the people that are poking around at those edges, I found are, are just having such a blast doing it, you know?

• 52:39Lenny Rachitsky?

  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.

• 52:48Speaker 01

  Exactly. I mean, that, that goes back to like when, you know, We, yeah, I mean, a new model comes out, what, every week?

• 52:58Lenny Rachitsky?

  Every day?

• 52:59Speaker 01

  I don't know, every day, like, if you count all the labs and everything, it's like, it's changing so quickly and everyone gets better.

• 53:09Speaker 01

  And I don't know, it's like, yeah, I always try to remind myself, it's like, you know, you know, it must be like, what, like, I don't know, building or designing and like, early days of computers when like, component tree was like, really evolving really quickly and there were these drastic step changes and, you know, like, you would hit these limitations and all of a sudden those limitations were gone, you know, I think it's the same, right? It's like, these things just change and they're what was totally broken yesterday now actually just kind of works.

• 53:41Lenny Rachitsky?

  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?

• 53:59Speaker 01

  Just recognizing that it's, 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, you know, think, rethinking about the tooling? Or what if I just embraced like, oh, maybe I should prototype more, let me try, you know, try using these tools. But again, like, recognizing that, maybe it helps to hear that, I think that we're all still so early and it's, and it's still changing and just kind of embracing that, like, just have fun with it and see where it goes. And, and I think maybe another thing I would say is really try to focus on the output, the outcome.

• 54:43Speaker 01

  Right? At the end of the day, we're not here to build tool, like, processes, we're not here to like, build a, or token max 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, you know, I think that you'll hopefully find that, you know, these tools can help you do that. But you still have a huge role in that as, as the person that's kind of steering and directing it.

• 55:17Lenny Rachitsky?

  So along those lines, I'm going to take us to a couple of 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, GPT or Codex?

• 55:34Speaker 01

  As like a designer designer, I mean, nowadays I spend less time in the pixels, but I really do use it to kind of help me think through broader ideas, or maybe like, you know, I'll have an idea at night or something and then I'll just like quickly, you know, type it in and have it like prototype something and it'll give me like an idea that I can go and talk to the team about and it'll help visualize something. And so there, that's like a part of the design process, it's like early ideas or we're riffing through something and, and I can, I found that ChatGPT, whether it's ChatGPT work or Codex can like really kind of help me visualize that. That's been something that's been really fun.

• 56:15Speaker 01

  And then like, there's, there's more of the operation side, you know, it's like, I have it now, like checking and making sure that like important slack messages that I need to follow up with are summarized and giving me context before, sort of like, you know, important meetings or for recruiting or for all, like every, every part of my process, I, I use this to kind of augment the work that I do.

• 56:40Lenny Rachitsky?

  It 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 like a Codex thread? What's like the mechanic of doing this at night?

• 56:48Speaker 01

  ChatGPT work has been incredible because it now runs fully in the cloud, right? And so the idea is you can kind of just be anywhere and sort of like, talk to chat and have it, like, really spend the time and, and come back with like a really great artifact. So I've found that it's been really fun to just be like, hey, you know, we're working on, you know, whatever this thing is, like, whether it's helped me think through it or, you know, yeah, sometimes I will just have like some ideas that I would love to see like quickly visualize before I even like take it further and it will just like kind of help me like play with it and try it and stuff. And so that's been really fun.

• 57:31Speaker 01

  The fact that it's so accessible, right? Like I might not even be near a computer or I can, you know, I don't know, just kind of like have that flexibility, I think is really fun.

• 57:43Lenny Rachitsky?

  Awesome. Okay, I'm going to take us to another corner, fail corner.

• 57:47Speaker 01

  Yeah.

• 57:48Lenny Rachitsky?

  So the reason I do this, a lot of people, awesome, 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 until the right and success. What's a story of a time you failed in your career and, and what did you learn from that?

• 58:12Speaker 01

  I mean, there are so many times, I think that, I mean, even at OpenAI, it's like, I, I think that I've found that I've had to learn every step of the way, right? You know, when I first joined, I remember, you know, not really even like fully understanding like how I wanted to build a design team and, you know, not understanding how to hire or whatever. I mean, just, I sort of felt like I was kind of failing every day, but just kind of like quickly trying to adjust and learn.

• 58:51Speaker 01

  I think that that, I don't know, I mean, that's like, maybe kind of a cop out answer, but like really just feeling like every day I'm kind of like learning on the go. I feel that my whole career has sort of been that way and that I have never really kind of like planned like any, any one step and I've in, in sort of like quickly learning from your mistakes. I've shipped plenty of things that did not work out. And I've also shipped things that, you know, you know, have worked out, but like the most, many times I've shipped or, you know, you try something and it's kind of a failure.

• 59:28Speaker 01

  And, you know, at Instagram, we had flops and then we, you know, we'd like quickly move on. I mean, I worked on IGTV, which was like a huge flop and then we shipped reels. And reels was like, we, and, and I mean, that's a good example because like we had, we, we just like kind of baked in some wrong assumptions and we held on to 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, you know, I, I've seen that many cases, many cases of like, and that's helped, I think that's helped harden me to the sort of critique and feedback of things because, you know, sometimes you get it wrong.

• 1:00:12Speaker 01

  Sometimes you try something and sometimes it is just about having to like put it out in the world and work through it and, and get the feedback and iterate. And I think that that's like the most, more importantly is not sort of what you shipped one time, but how you react and how you,

• 1:00:29Speaker 01

  you know, how you kind of like fix forward and how you continue to iterate and listen to, listen to your users.

• 1:00:34Lenny Rachitsky?

  This is a very common theme in this corner is just people's careers are like, it's mostly failure along the way.

• 1:00:40Speaker 01

  Definitely.

• 1:00:40Lenny Rachitsky?

  And so I think that's helpful for people to hear.

• 1:00:43Speaker 01

  Yeah.

• 1:00:44Lenny Rachitsky?

  Okay. Before we get to our very exciting lightning round, is there anything else you wanted to share that we haven't covered?

• 1:00:49Speaker 01

  If I could distill it, it's like, I hope that this is just like a really fun time to build, build stuff. And I hope that we, you know, as designers can be really adaptive and focus on making really fun, making really great stuff. And I, and that, I think that designers are just like, hopefully, you know, I think, I think great companies are, are seeking designers and seeking great, great design. And I've found that to be really true. There probably are going to be a bunch of companies that will be left behind because they haven't shifted. But I think that, that there's plenty of room for amazing, great design and that's going to be more true than ever.

• 1:01:30Lenny Rachitsky?

  I completely agree. I'm very bullish on design.

• 1:01:33Speaker 01

  Yes.

• 1:01:34Lenny Rachitsky?

  Well, Ian, with that, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

• 1:01:38Speaker 01

  Okay, yes.

• 1:01:40Lenny Rachitsky?

  All right, here we go. What are two or three books that you find yourself recommending most to other people?

• 1:01:46Speaker 01

  I'm not like, you know, it's funny, I'm not like a big, big book recommender.

• 1:01:52Speaker 01

  I think like when people ask me, I do get asked about like books for design and I'm not, I haven't found that many that really have stuck with me, like purely design, although I will say I have, I do love the design of everyday things. I think that's like such a classic.

• 1:02:07Lenny Rachitsky?

  That's the one, that's the one.

• 1:02:08Speaker 01

  That like, you know, it's not like, yeah, it's not a unique recommendation. But it is just kind of a classic of thinking about how you, how we think, how I think about design. Yeah.

• 1:02:19Lenny Rachitsky?

  You have to read it if you're in tech or not even in tech.

• 1:02:22Speaker 01

  Yeah.

• 1:02:24Lenny Rachitsky?

  Awesome. Anything else there or should we keep moving?

• 1:02:27Speaker 01

  We can keep moving, yeah.

• 1:02:28Lenny Rachitsky?

  Let's do it. Favorite recent movie or TV show that you have really enjoyed?

• 1:02:33Speaker 01

  Okay, so I have one that actually is not a movie or TV show, but it's a, I'm in New York. I just saw a Broadway show called Maybe Happy Ending.

• 1:02:44Lenny Rachitsky?

  Yes, I've seen it. Love it so much. Yes.

• 1:02:47Speaker 01

  Oh, you saw it. Okay, yeah. It was so unique, right? And of course, it kind of hit home a little bit because it's about these like super intelligent humanoid robots and like, you know. But, but the production was incredible, the set design, everything about it, I thought was like so unique. Which was, I thought, yeah, so if you have the chance to see it, I thought it was really, really good. I also just saw The Invite, which was, I thought, have you seen it?

• 1:03:23Lenny Rachitsky?

  Yes, I also love it. It's so simple, but so good.

• 1:03:26Speaker 01

  That's what I loved about it is it's like so simple. It's like, it actually is like a play, you know? And it's just four people in one kind of beautiful apartment and the set design is amazing. But like the writing, everything about it was incredible and it's just kind of a wild ride. And I wouldn't have, knowing nothing about it, I thought it was incredible.

• 1:03:52Lenny Rachitsky?

  Excellent taste, sir. I love both those so much. And The Invite just came out. It's in theaters right now.

• 1:03:57Speaker 01

  Yeah.

• 1:03:58Lenny Rachitsky?

  Next question. Favorite product you've recently discovered that you really love?

• 1:04:02Speaker 01

  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, they just, I do respect the design a lot of just kind of how they've really made it just

• 1:04:26Speaker 01

  all of the, like, I think, you know, probably Tesla's similar, but like, there's a lot of assumptions that how operating a car should work or have gone away. You just walk up to it and it unlocks, you know? It's like, you just like, you don't have to like turn on and off the car. And it's cool to see like that evolving. Of course, I love, you know, at Waymos or probably if I could like own a Waymo right now, that is the most magical experience in the world.

• 1:04:55Speaker 01

  And I, I'm waiting on bated breath for that to be broadly accessible for everybody.

• 1:05:02Lenny Rachitsky?

  Do you have a favorite life motto that you find yourself coming back to in work or in life?

• 1:05:07Speaker 01

  Not necessarily, other than I think like kind of trying to sum up like how I felt about all of this is like, have fun with it and like just try stuff.

• 1:05:17Speaker 01

  And, you know, 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 like have fun with it and build great stuff.

• 1:05:42Lenny Rachitsky?

  I should shift this question to what's just like the vibe. What's 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.

• 1:05:50Speaker 01

  Exactly, yeah.

• 1:05:52Lenny Rachitsky?

  Okay, last question. Something I love about your career history, if you look at your LinkedIn, you're a designer at Groupon. I love that you're at Groupon and now you're heading design for essentially super intelligence.

• 1:06:04Lenny Rachitsky?

  What's something you learned at Groupon that is maybe helpful these days building super intelligent AI?

• 1:06:10Speaker 01

  I love that. Groupon was a really fun company.

• 1:06:16Speaker 01

  Andrew Mason was like a really incredible CEO and just that he brought such character to the product, you know, it was like kind of a brand led product. And, you know, like, we had, there was like a comedy team, there was like a writer team,

• 1:06:44Speaker 01

  but they were like all comedians, basically, and the product really did not take itself seriously, at least in its early, early couple of years. It was like, it was, it didn't take itself seriously and I think that the brand really stuck out, right? You weren't signing up for Groupon because, I mean, of course, the daily deal was great. You were getting like 50% off something. But people loved that email because it was like really well written and it was funny and it was, and it had character. And I thought that like the, early on, the company did a really good job with, with brand and sort of embracing that set of things.

• 1:07:21Speaker 01

  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 kind of maybe changes a little bit based on that, right? So I, you know, Groupon was run one way, you know, then I went to Instagram, which was like this very design and creativity focused. And Kevin's, you know, Kevin Systrom was, you know, really like an incredible designer. And he sort of saw himself or like worked in that way with us, which was really cool and it just created a different way of working. And then you have like Sam Altman, who's like a completely different way of operating and he's like, you know, I think,

• 1:08:04Speaker 01

  and then an OpenAI being a research lab. And so, learning that companies have these really different DNAs and understanding how to sort of embrace them and kind of leverage that to your, like, or help kind of like empower that or like, I guess, lean into that.

• 1:08:20Speaker 01

  Has been something that I've learned a lot from moving around and getting the opportunity to work at very, very different companies.

• 1:08:26Lenny Rachitsky?

  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 like come in and change that culture because that's, that's very hard, especially if it's very founder oriented.

• 1:08:36Speaker 01

  I think it's about finding like, oh, wow, like at OpenAI, you know, yeah, sure, like we spent more time. At Instagram, we definitely moved slower and I would say that we, 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 and that way of working. Of course, I bring a lot to that and I think like, you know,

• 1:09:07Speaker 01

  at Instagram, we had this motto, like 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, you know? Sometimes it's actually not necessarily the right way to think about. Sometimes we actually do throw some things out that we're still experimenting with. And so just being really, I found that having to, yeah, be flexible and, yeah, not necessarily trying to change it, but trying to kind of like help round it out, maybe.

• 1:09:36Lenny Rachitsky?

  Ian, what a, 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.

• 1:09:48Lenny Rachitsky?

  And I feel very fortunate that you found time to chat with us and share what you're seeing, 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?

• 1:10:00Speaker 01

  Where do I want to point people? I mean, I think that, please, you know, I guess you use, you know, 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 at all sort of stages. Or not just designers, engineers, PMs, whatever. That's probably where I'm most sort of reachable and accessible. And, you know, how can, yeah, I think to be useful, again, it's like, I love when, when people do show off the way they're kind of working and how that's kind of shifting and that's like a great way for us to learn how we can, we can build better products,

• 1:10:43Speaker 01

  both like internally at OpenAI, but just as a, as a design community, like maybe showcasing a little bit more of our process because it is becoming a little bit more opaque, like, well, how is it working? Just, I think sharing that is like such a gift to the community. So doing more of that.

• 1:11:01Lenny Rachitsky?

  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, this is your personal website.

• 1:11:15Speaker 01

  Yeah, that's a deep dive into all of my past work. You can see there, yeah.

• 1:11:21Lenny Rachitsky?

  And the trick is, yeah, you'll have to discover the Easter egg where there's a game involved.

• 1:11:25Speaker 01

  That's right. See if you can set the high score.

• 1:11:28Lenny Rachitsky?

  Yeah, the 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.

• 1:11:36Speaker 01

  Lenny, this was awesome. Super fun.

• 1:11:38Lenny Rachitsky?

  Same. Bye, everyone. 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.