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

1. 0:00 – 2:14

   Introduction to Ian Silber

   1. LRLenny Rachitsky0:00

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

   2. ISIan Silber0:08

      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."

   3. LRLenny Rachitsky0:17

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

   4. ISIan Silber0:20

      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 gonna 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.

   5. LRLenny Rachitsky0:36

      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.

   6. ISIan Silber0:43

      Engineers have 10 or sometimes, like, 100X their productivity, but our design team w- 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.

   7. LRLenny Rachitsky0:56

      We had a podcast with Head of Design Cloud Code, Jenny Wen. She talked about there's been this traditional design process, prototype, mock, test, user research, iterate, and now there's just no time for that.

   8. ISIan Silber1:05

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

   9. LRLenny Rachitsky1:19

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

   10. ISIan Silber1:22

       I think it already is an incredible product designer.

   11. LRLenny Rachitsky1:26

       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. A huge thank you to Saleo and Joel Lewenstein 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. With that, I bring you Ian

2. 2:14 – 9:01

   Why designers in general feel anxious about AI

   1. LRLenny Rachitsky2:14

      Silber. Ian, thank you so much for being here.

   2. ISIan Silber2:20

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

   3. LRLenny Rachitsky2:22

      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, uh, sentiment survey of the tech workforce over the past couple years. I think it's the biggest survey of its kind, where 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 s- 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, uh, 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?

   4. ISIan Silber3:18

      Uh, first of all, it's an incredible survey, and it's such great, I think, information to have as an industry. Um, and I think it's something we need to unpack. And, you know, and I see, I d- I see a mix, uh, for sure. I think, like, I can speak most to design, um, and I mean, I talk to a lot of designers, uh, that are very optimistic and very excited. Um, and so I see, in my world, I see, I luckily, I, I'm, or I, I, 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? Um, and, you know, well, do I need to, d- 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, uh, sort of classically trained in a certain way of working now feeling like, "Oh my gosh, I need to, like, really change everything." And I think it's, to me right now, it feels like the, the uncertainty of, of that I can totally understand, right? Because as an engineer, I think people have al- they've already sort of gone through that shift. Like, we see that engineers are working totally different. And we also, w- you know, one thing I do hear, a- and I, this came up a lot in my own team when, when we did, we do similar surveys internally. One of the big things that came up was, you know, we see that, uh, uh, you know, engineers have 10 or sometimes, like, 100X their productivity, uh, but our design team w- 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? Versus maybe working with a coding agent, you ask it to do something, it's pretty binary now. At, at this point, it usually sort of gets it pretty well. Um, 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 you, you give it to, you know, users or intern- you get internal feedback and it's wrong. And, and you still have to go through that arduous and kind of messy but really fun process. Um, and that hasn't really com- that, it's compressed in that you can get much more ideas out fast, but y- you still need that, that whole sort of feedback loop. There's the alignment of getting many people, uh, you know, especially in a bigger company, like that, it still t- 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, that lack of clarity I can see totally lead to, you know, um, some, some fears, uh, or some unease, I guess. But on the other hand, I've seen that, I mean, our designers What's been, what, what's great, I think, about, at OpenAI is, like, we're such an experimental company. 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 kinda learned and, and have really l- 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, n- 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. Um, it's not like you need to change the way you work, but it's more about encouraging exploration. Um, and when we've done that, when I go and talk to, um, both very senior designers and early career designers at our company, they're so excited because they-- I, I literally was just asking some people before this 'cause 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. They 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, uh, the, the bar is raising. Um, the, the, I think the thinking is getting stronger the more that they're using, um, these tools. So I think for the people that, that, that are starting to embrace this, they're starting to feel really excited and realizing that they have just so much agency as, as designers and, like, um, you know, so much more ability to have, like, really high impact, uh, as, as a, as a designer.

   5. LRLenny Rachitsky7:53

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3. 9:01 – 13:41

   What makes specific designers thrive in the AI era

   1. LRLenny Rachitsky9:01

      today.

   2. LRLenny Rachitsky9:02

      What I'd love to do in this conversation is help folks that are in that bucket of, "Well, this just 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, that-- 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, um, feel amplified, very curious, have time to explore, feel like they can be more creative. Is there any more, anything 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?

   3. ISIan Silber9:59

      What I see i- in, in the, the folks that I think are really embracing this, right? They are using it every step of the process to kinda 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, uh, find that and that that's something that, uh, we should think about more as a broader community, how we kinda 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, uh, into an agent to help you think about it, to help you prototype it. Just try a different way of working. Um, it doesn't necessarily mean that that has to be the exact right way. But, um, I don't know. I think we've found that just people that are, 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 l- yesterday might work today. I mean, literally, like, within, you know, s- six months, this entire industry has shifted. I remember I was actually out on, on paternity leave, uh, towards the end of last year, and I was working on some side projects. I was trying some, uh, coding agents, and it just, like, it worked, but it just kept kinda running into these hiccups. And, and then, like, a month later, like, Codex drops, and I try it again, and it's like, "Oh my gosh, it just works." Um, 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. Um, 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 in early innings of this entire, um, 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 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. [chuckles] Nobody has, like, some perfect answer, um, about the, how the design process should work. Um, and it's pr- 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 gonna have a leg up on pretty much most people. Um, and, uh, just really thinking about, like, how you can just make great stuff. Um, and, uh, there's just so much opportunity to change the way we work, work or to, to, uh, just to make great things. And what we think is, like, really cutting edge today will look so archaic in, you know, uh, l- a year, let alone a month, right? And that's something I've, I've learned. You know, I've been at OpenAI for three years, and I think about the stuff that they, you know, we were working on when we, when I first joined. Um, 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. Uh, and now it's like become this, uh, 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, the, it figured out. [chuckles]

4. 13:41 – 17:13

   Why Ian says it’s the best time in history to be a designer

   1. LRLenny Rachitsky13:41

      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 a designer.

   2. ISIan Silber13:48

      Yeah. I mean, I, I truly believe this. Um, I can't even imagine, you know, I... So when I, uh, okay, history lesson. When I was getting into design, I mean, I was like, uh, in my teenage years, right? And I was like, uh, you know, to learn things it was like, you know, I would, uh, 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 [chuckles] that was like kind of how you had to learn and, you know, um, you could, I don't know, it's like Dreamweaver and, you know. Like, there were these really to- tools that actually were really cool. Um, 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. Um, uh, it's just you can be so expressive and, and you can, um... I think anybody can be a designer, right? Um, 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 gonna really be, be, start to become more and more important. It's, it's always been the case that I think that, you know, companies with great design, you know, can, uh, of course stand out. I think that's gonna be more and more important, right? I think that products that, um, t- fully understand their users and that make something delightful, when anybody can make anything, you know, that's gonna become one of the most important kind of, uh, like sort of dimensions of a product, and that's how people are gonna evaluate it. And so I think designers, uh, stand, like that is, that is our core job, right? Um, you know, and, and then on top of that, I think that designers are just much more empowered. Uh, so you know, at, at a, um, you know, I was talking to some friends that are thinking about starting a company and talking about the, uh, sort of ratio of design to engineer and how like a- at a startup, maybe that's totally different. It might, it may have been like you're gonna have one designer and, uh, I don't know, 15 engineers or something like that, you know, that maybe a startup I've, I've seen that sort of ratio. Uh, but they were s- they were talking about, "Well, maybe we'll have like two designers and one engineer." [chuckles] One really good engineer who can make sure that like we're really building something that's rock solid f- like from, from an engineering standpoint, but then we want two really creative people that are gonna 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. I think that internally we see that more and more we're l- we, like, designers w- we are, are totally and 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, um, that solves some sort of, uh, unmet need for our customers and, um, that is a designer's job. And so I think that maybe more and more people start to think of themselves as designers. Um, but either way, I think it's like the best, I, I really do think it's the best time to be a designer.

5. 17:13 – 22:24

   How product roles are converging

   1. LRLenny Rachitsky17:13

      So along those lines, when Marc Andreessen was on the podcast, he had this hilarious way of describing the state of the, of the product org right now. Uh, he's like, basically there's this three-way standoff, EV- PMs, engineers, designers. They're all, they all think the other roles are gonna go away, and they're the ones that are gonna win in the end. And so there's this like Spiderman meme where they're all pointing at each other. And I'm curious 'cause 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 1,000X explosion in products being shipped. There's just like endless streams of things to pay attention to. You'd think design would be such a opportunity to differentiate and stand out. 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?

   2. ISIan Silber18:12

      We might start to see that happen more Um, 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. Um, it's not necessarily the same direct output of, like, engineers 10Xing, um, but we are seeing that, that designers, um, are, are able to do a lot more. But no, I mean, I think that, that, that is something we're, we're sort of always thinking about and, and evolving. Um, the other thing I wanted to talk about too is, like, the difference between PM and eng and design, and are they all blurring together? And my point of view is that they, they definitely are, and they-- there's always been overlap as far as I've seen it, right? They're-- I've seen designers that are, like, kind of really good product, you know, manager type archetype, but can design, and I've seen designers that are, like, really good sort of polish engineer type. You know, like, so the... I think I've always found that these, like, single siloed, um, 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, are, I've, I've always kind of seen that. Um, I, I think those, those lines have always been blurry, but they're becoming blurrier for sure. Um, but the other thing is I do still think that, and, 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, uh, 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, you might, it might be hard to find one person that's g- 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, um, sharpen kind of the perspective or, or the problem space that a team is focused on, um, that can help with, like, resourcing, all of those things, right? And so I do think there will still be value in these, um, and people focused on different parts of building a project or a product. Um, that doesn't mean that, um, 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, um, laddering up to something that is gonna work for the broader system.

   3. LRLenny Rachitsky21:03

      I completely agree. So just to make sure I understand, what you're saying is just there's this 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 gonna happen." E- the r- like the Venn di- I'm picturing Venn diagrams of product design engineering, like converging, but you're saying they're gonna continue to stay their own roles. There's gonna be a PM design engineer, but each can do more of the other roles.

   4. ISIan Silber21:26

      I think that's right. I, I do think that, like, for... And a- 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. Um, but at, at a bigger company, I do think that I've seen, like, designers, um, 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, um, both their thinking and how, and, 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... It's, it's almost like in ta- taking the people out of it, I think that there are different sort of hats that you need to wear to build great software.

   5. LRLenny Rachitsky22:19

      Yeah.

   6. ISIan Silber22:19

      And I think that, um, those are continue to be important functions,

6. 22:24 – 23:54

   Can AI design great products?

   1. ISIan Silber22:24

      I think.

   2. LRLenny Rachitsky22:25

      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, you're like, "Oh, yeah, OpenAI, like ChatGPT is gonna become incredible at everything." On the other hand, it's hard for a head of design to say, "Oh no, design's gonna be done by AI." I'm curious to get your, your take. And, you know, it like sounds crazy, but like engineers never thought it would be able to write code the way it is now. Um, so just, yeah, thoughts on just how good AI will get.

   3. ISIan Silber22:53

      Maybe one way to put it is I think it already is an incredible, um, product designer. [chuckles] Um, it, it really is actually already great. The cool thing about it though is it's accessible to every single person. Um, 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, uh, information hier- h-hierarchy or, 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 gonna continue to get better. Um, but the way we think about it, and, and I, and I really do believe this, is like we're building tools to enable people to be more creative, to be, um, to, to do more, to build more. And so it's, it, it, 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

7. 23:54 – 27:34

   Where human judgment still matters

   1. ISIan Silber23:54

      the best out of it.

   2. LRLenny Rachitsky23:55

      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?

   3. ISIan Silber24:05

      Truly understanding what people need. Um, you know, I mean, the human, uh, feedback loop of watching people use something and, and, and understanding that, um- The, you know, inventing something new. Um, I think, uh... 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." Um, I just think that w- 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 is just like, "What is my point of view? What, who am I building this for and why?" Um, 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?

   4. LRLenny Rachitsky25:01

      Yeah. That t- touches on, uh, a conversation I had with, um, the PM of Codex. I asked him just why is AI not good at design, and it's actually gotten better since that conversation, which was just, like, a month or two ago. [chuckles] 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, it's just like, okay, but that's not what p- 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. Uh, thoughts? What do you think, what do you think it'll take to get AI to be much, much better at product design?

   5. ISIan Silber25:40

      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? Um, 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, em- really embracing, um, the sort of like, the fact that the, everybody had mobile phones. And then Snapchat I think is another good example of great design in that it was kind of a, maybe people thought strange, sort of like interaction design, but it completely f- like, flipped on its head the way people might wanna communicate with each other. And to me, that, that is, like, great design. It's, like, truly understanding, like, I, uh, you know, m- the people that, like, people have this problem or there's this unmet need and, and I'm gonna 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 of... And then now with AI, it's like we're designing, like, how do you talk to something that, uh, 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. And so I think that, you know, humans are able to kind of do a, a really good job kind of evaluating, uh, you know, what good is and, um, you know, or at least kind of like trying a bunch of things and, and learning along the way with people. And so, um, I don't know. I, but again, like, all this stuff changes really quickly. It's hard to say. But, uh, I think, um, I think there's a lot of reasons why, uh, having that human in the loop is gonna be so important.

8. 27:34 – 30:20

   What Ian looks for when hiring designers

   1. LRLenny Rachitsky27:34

      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? And what's trending down, if anything?

   2. ISIan Silber27:50

      This might be a luxury of having a slightly larger team, but if you're, you know, at our scale, um, you know, uh, but even at, at a startup or a smaller company, I think, uh, this will 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, or, or the right ratio of sort of generalists that can kind of do everything. But, uh, you know, we also hire like incredible visual designers, or we have like, like a, a really amazing sort of brand team that helps us with kind of like the sort of maybe, uh, e- expression of our brand b- both out and in a, in the product. Um, or great prototypers or, um, you know, um... And so I think that rounding that out, or, or great sort of product thinkers that are m- 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 when you build a team is actually like, um, if you c- if you have the luxury of doing that, is like really valuable. Okay, so that's like my, a 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 in AI," because again, this is evolving so quickly. But we definitely expect high curiosity about it and, and, and, uh, high aptitude to jumping in and, and learning how, how you know, how you're gonna use this in your process, how it works. And not just how you use it in your process, but how, especially for us, like how you're gonna create tools to en- enable more people to use it. Um, and so it's more about the curiosity, I think, um, is something that, like, we really push on, uh, or look for. And then, um, definitely prototyping. Um, prototyping is something I've always valued in my career. Um, but I just think that, you know, it's become more and more accessible. And so that's something that, uh, 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, or just like any of the tools that people have worked on and really thinking that strategic thinking.

9. 30:20 – 32:53

   Why systems thinking matters

   1. ISIan Silber30:21

      I guess last, last one on this is like systems thinking, um, is becoming more and more important in Um, you know, especially as you're, uh, uh, like in our world, we're-- it's interesting 'cause we're trying to build... You know, we're building this super intelligence that has, uh, 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, right? Um, you know, this is something that I think like Notion did really well early on, was like, "We're gonna build these building blocks," right? And then like everything kinda is composable. I think that's becoming really important, too, as you think about like, well, we don't wanna 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. A- and the model can reason about how it can pull all of these things together. So that like idea of like really understanding the system and thinking about that is becoming even more important, especially 'cause it's kind of complex of all the things that it could possibly do.

   2. LRLenny Rachitsky31:31

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

   3. ISIan Silber31:36

      Interesting

   4. LRLenny Rachitsky31:36

      ... the skill that people are more and more looking for.

   5. ISIan Silber31:39

      [chuckles]

   6. LRLenny Rachitsky31:39

      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, 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 langu- and, and just a platform for people to build on feels incredibly important.

   7. ISIan Silber32:08

      Totally. It's very hard, but I, um, I, I, yeah, it's like, uh, it's funny. I've, we've had these conversations where I'm like, "Just do less." Uh, uh, [chuckles] like my encouragement has been do less. Th- there, uh, like don't design it if you don't have to. Maybe there's already a, 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, uh, uh, uh, like, you know, extend an, an existing feature. Um, and 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

10. 32:53 – 38:05

    Balancing speed and craft

    1. ISIan Silber32:53

       right now.

    2. LRLenny Rachitsky32:54

       Just to follow that thread, 'cause that feels like a pretty big change in the design world. There used to be this... We had a podcast with, uh, she was head, head of design at Cloud 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, do user research, iterate. Okay, cool. Ready for engineering. Build it, iterate, ship it. [chuckles] 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 dir- direction. Does that resonate? How much has that uh, has changed in, in the world of a designer?

    3. ISIan Silber33:28

       I think that t- 100% we, we do work that way. It, it's, it depends. Uh, uh, I think for us it depends on like what sort of what stage you're at in the, in the, uh, sort of process or, um, you know, uh, how, uh, 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, and we try a million things, and we throw out, you know, uh, y- we try 100 things and we throw out 99, and we finally ship one. Um, you know, uh, the like, uh, the c- uh, or like the composer is like changing every single day and, and we try many things and we throw them out. But, or like, and you can take that for many different things within ChatGPT. Um, and then there are other things like Codex where, um, you know, I don't know. I mean, the super app is a good example where we definitely are just like trying stuff really quick. I think that we really embrace building in public, [chuckles] which is a different way of working. But I think that like w- 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. Um, but yeah, I mean, it is, uh, moving really fast, and I think it just depends, right? Like so, like, like I said, certain things we really sweat the details and we try, um, you know, and, and we do tests. We A/B test, 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. Um, 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 a certain interaction or t- or setting or, 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 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 w- we're, we're thinking a lot about how we should evolve, sort of really think about ChatGPT becoming like deeply embedded in a per- like your personal life and how, how should the f- how should the app feel. 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, and we're putting it up on, you know, uh, w- you know, 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 f- long before we ever ship something. Um- 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.

    4. LRLenny Rachitsky36:38

       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 a lot.

    5. ISIan Silber36:47

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

    6. LRLenny Rachitsky36:51

       [laughs]

    7. ISIan Silber36:51

       Yeah.

    8. LRLenny Rachitsky36:52

       Yeah. This episode is brought to you by Mercury. Radically different banking loved by over 300,000 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. 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 ask, "How much have I made from X over the past year?" 10 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

11. 38:05 – 41:57

    Designing for vastly different audiences

    1. LRLenny Rachitsky38:05

       FDIC. So I asked, uh, 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. 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 you find that balance knowing you have to cater to both sides.

    2. ISIan Silber38:37

       That's a great question, and it's a really fun part of the way we work. Um, 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. [chuckles] Um, 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 it's right now, but it was a lot of people. Um, but the product was pretty simple, and it was sort of, you know, a couple 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 a recipe to eat tonight, um, 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, au- helping to automate their farm in Japan or something, right? And, uh, it's just like the broadest spectrum ever. Um, generally what we've seen is that, um, w- we, we believe in this idea of this sort of capability overhang, where the, the product, um, you know, like m- vast majority of the people are getting a sliver of the, the true value that they could out of the bottle. Um, that's not necessarily a bad thing. Many, you know, they're still getting tons of value. Um, but we found that like we, you know, make sure to focus on creating a cr- extremely simple, streamlined experience for, for many, many people. Um, and then we put like, uh, all of the, you know, cutting edge stuff. We also make su- 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 Codex, and now ChatGPT 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, and we think about this a lot in design, is like it will tru- like things will truly become like for the 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. Um, 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. 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. Um, but this, it, it makes it fun for sure.

    3. LRLenny Rachitsky41:39

       That is such a mind-blowing point you're making about the spectrum of usage of ChatGPT and Codex. 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 a Salesforce, you know?

12. 41:57 – 43:31

    Solving the blank-box problem

    1. ISIan Silber41:57

       Yeah. And it, and it makes it really hard too, 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 blank-box problem, right? And people talk about this all the time. It's like, is chat really the final frontier? It's a terminal ba- it's a, you know, a glorified terminal is like some critique that, that, uh, 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? Um, [chuckles] 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, uh, design challenge. And, um, it's like sorta uncharted territory 'cause it can really sh- like, like shape-shift into many different tools. Um, and it's this like, um, incredible at 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, uh, to their lives or to their sort of professional, uh, work or what-whatever the, whatever capacity they're using this in. And then we also wanna, 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. And so designing for that spectrum is something we have to think about a lot. Um, but yeah, it's all a world of spectrums,

13. 43:31 – 46:07

    How ChatGPT is evolving beyond chat

    1. ISIan Silber43:31

       I guess.

    2. LRLenny Rachitsky43:31

       There's a comment that Kevin Weil, your former chief product officer, made on the podcast that has really stuck with me, which is, uh, to your point, people always diss this idea of it 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 chatbot, chatbot. And he made this really good point that what is an interface that is very good at s- uh, spanning a wide spectrum of intelligence? Uh, 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, uh, packaging something that is increasingly smarter and smarter and smarter.

    3. ISIan Silber44:08

       Yeah. And, 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, uh, we don't want you to 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, 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, um, and answer versus having to type everything out, right? Um, 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 j-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, um, you know, write you a letter or, uh, an email, uh, and it now contains that, um, 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 like image generation and creating special tools for that kind of mode. And I think that's where the UI's gonna start to k- uh, 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, uh, l-look different or have different affordances. Um, or you're, you know, a, 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,

14. 46:07 – 49:07

    The vision for Codex

    1. ISIan Silber46:07

       we're thinking a lot about.

    2. LRLenny Rachitsky46:08

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

    3. ISIan Silber46:25

       I think that it will start to become more and more adaptive to, you know, all of the context of your life. Um, I think proactivity is a big untapped kind of part of the experience that we're really excited to think about. Um, 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, um, external kind of context. I think that's gonna become more and more important, um, or kind of shift the way, you know, you use it. I think voice as, you know, we, 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 gonna feel in two, three years as it just gets better and better. I think people-- I, I do love interacting with ChatGPT, especially voice in, like just I wanna 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, um, that's all gonna 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 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, uh, 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, uh, that's like goes back to the balancing the different kind of, you know, personas and user needs. Like, right, of course, we wanna expose that for the right people, but then we wanna make sure that we can- ... get a default experience that works great for, for most people. Um, but yeah, I think it's gonna be really proactive. I do think that we're gonna, like, get much, uh, richer i- sort of input through 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 kinda use over and over. Right now, you know, it, a, a lot of times it feels like you're coming and starting from scratch each time, and we wanna really make this kind of the tool that you can use to, to help you, uh, with whatever sort of task you have.

    4. LRLenny Rachitsky49:04

       This all sounds wonderful. I can't wait.

    5. ISIan Silber49:06

       [chuckles]

15. 49:07 – 51:40

    What Ian wishes he knew on day one

    1. LRLenny Rachitsky49:08

       Uh, just kinda zooming out a little bit, and then I wanna talk a little bit to designers again. But you're in this, uh, 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?

    2. ISIan Silber49:26

       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. Um, you know, uh, I remember like, okay, interviewing. Oh no, I gotta like, uh, you know, I- G- GPT-4 had kinda recently come out and w- GPT, like I, you know, I was like, "What is all this stuff?" Like I, I was using it a- and I was using the te- the stuff, but I d- I didn't feel like I had a true understanding of, of it. And to be honest, I, you know, I s- there's, I still have so much to learn. So that idea of like, you are early, we're, we're figuring this out, like that I think I would w- I would want to hear. And the other thing, like, that I found, uh, you know, a- 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. Um, you know, most of my career I ha- I've managed, uh, 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. Uh, and for a long time I felt like I'm kind of like bad at this, or [chuckles] I'm, you know, uh, I don't know what I'm doing. Um, and then I went and like talked to friends that had led like really large design teams or, um, 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. Um, and so, you know, this is m- 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 sy- 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, uh, challenges and struggles and having that like sort of whether it's a mentor or just like a, a buddy that is like impartial and out of it as was really helpful to me. Um, and, you know, finding that community I think has been, has been helpful. Um, so yeah. So like that, and then understanding that this is all so new and, and evolving really quickly.

    3. LRLenny Rachitsky51:37

       That is extremely helpful to hear.

16. 51:40 – 53:41

    Why humility matters in AI

    1. LRLenny Rachitsky51:40

       Elena Verna had this really great post, I don't know if you know her, she's Head of Growth at Lovable right now. Uh, 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 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.

    2. ISIan Silber52:06

       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 gonna embrace it and s- and see where it goes."

    3. LRLenny Rachitsky52:13

       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 new things and try them again because maybe it didn't work now, it didn't work before, it now works now.

    4. ISIan Silber52:25

       100%. Yeah. It's like being kind of like, yeah, e- every, every model, every new, every new feature, it's like the people that are poking around at those edges I, I found are, are just having such a blast doing it, you know?

    5. LRLenny Rachitsky52:39

       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."

    6. ISIan Silber52:48

       E- exactly. I mean, that, that goes back to like when, you know, uh, we, we, yeah, I mean, a new model comes out, what, every week?

    7. LRLenny Rachitsky52:58

       Every day.

    8. ISIan Silber52:59

       I, I, I don't know, every day. Like, uh, f- if you count all the labs and, and everything, it's like, it's changing so quickly and, and e- every one gets better. Um, and, uh, I don't know, it's like, yeah, I al- I always try to remind myself. It's like, you know, y- you know, it must be like what, like, I don't know, d- building or designing in like early days of computers when like componentry was like really evolving really quickly and there were these drastic step changes and, um, you know, like you would hit these limitations and all of a sudden those limitations were gone. You know? I, 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 kinda works.

17. 53:41 – 55:16

    Advice for designers who are feeling overwhelmed

    1. LRLenny Rachitsky53:41

       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, uh, 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?

    2. ISIan Silber53:59

       Just recognizing that it's, it's a t- 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, the tooling, or what if I just embraced like, oh, maybe I should prototype more. Let me try, you know, um, try using these tools. But again, like recognizing that I, uh, uh, maybe it helps to hear that I think that we're all still so early and it's, and it's still changing and, and just kind of embracing that. Like, just have fun with it and, and see where it goes. And, a- and I think f- maybe another thing I would say is Really try to focus on the output, the outcome, right? At the end of the day, we're not here to build tool, like processes. We're not here to like build, uh, or Tokenmax or something like that. We're here to make great th- software that people love, or great products, or whatever it is you do. Um, 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

18. 55:16 – 57:43

    AI corner

    1. ISIan Silber55:16

       and directing it.

    2. LRLenny Rachitsky55:17

       So along those lines, I'm gonna take us to a couple recurring corners of the podcast. The first corner is AI corner. Th- the question is just what's one way that you have found AI to be really useful in your job that maybe s- might inspire someone to use, say, uh, ChatGPT or Codex?

    3. ISIan Silber55:34

       As like a designer-designer, I mean, nowadays I spend less time in the pixels. Um, but I really do use it to kind of help me think through broader ideas. Um, or may- 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 that'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. And then like, uh, there's, there's more of the operations side. You know, it's like I have it now, I, like checking and making sure that like important Slack, uh, messages that I need to follow up with are summarized and giving me context before, um, sort of like, uh, you know, important meetings, or for recruiting, or for all, like every pr- every part of my process, I, I, I use this to kind of augment, um, uh, the work that I do.

    4. LRLenny Rachitsky56:40

       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, for example?

    5. ISIan Silber56:48

       ChatGPT Work has been incredible because, um, it now runs fully in the cloud, right? And so the idea is you can kind of just be anywhere and sort of t- 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, um, this thing is." Like may- whether it's helped me think through it or, um, you know, uh, yeah, sometimes I will just have like some ideas that I would love to see like quickly visualized 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, the fact that it's so accessible, right? Um, like I might not even be near a computer or I can, you know, um, uh, I don't know, just kind of like have that, that flexibility I think is really

19. 57:43 – 1:00:45

    Failure corner

    1. ISIan Silber57:43

       fun.

    2. LRLenny Rachitsky57:43

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

    3. ISIan Silber57:46

       Okay.

    4. LRLenny Rachitsky57:46

       Uh, Failure corner.

    5. ISIan Silber57:47

       Yeah.

    6. LRLenny Rachitsky57:48

       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 and to the right and success. What's a story of a time you failed in your career and, and what did you learn from that?

    7. ISIan Silber58:12

       I mean, there are so many times. Um, I think that, i- 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? Um, you know, when I first, uh, joined, I remember, you know, not really even like fully understanding like how I wanted to build a design team and, you know, um, not understanding how to hire or whatever. Um, I mean, it, it just, I felt, I sort of felt like I was kind of failing every day, but just kind of like quickly trying to adjust and learn. Um, I think that that, uh... I don- 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. [chuckles] I, I feel that my whole career has sort of been that way in that I have never really kind of like planned like a- 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. Um, and uh, I've also shipped things that, you know, in, you know, have worked out. But like the r- most, many times I, I've shipped s- or, or you know, you try something and it's kind of a failure. And, uh, 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. [chuckles] Uh, and Reels was like, we, and, and look, I mean, that's a good example 'cause like we had, we, we just like 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. Um, and uh, you know, I, I've seen that many case- many cases of like... And that- 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. Sometimes you try something, and sometimes it is just about having to like put it out in the world and work through it and, um, and get the feedback and, and iterate. And I think that that's like the mo- more importantly is not sort of what you shipped one time, but how you react and how you, um, you know, how you kind of like fix forward and how you continue to iterate and listen to, listen to your users.

    8. LRLenny Rachitsky1:00:34

       That's a very common theme in this corner is just people's careers are like it's mostly failure [chuckles] along the way.

    9. ISIan Silber1:00:39

       [laughs] Uh, yeah, definitely.

    10. LRLenny Rachitsky1:00:41

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

    11. ISIan Silber1:00:43

        Yeah.

    12. LRLenny Rachitsky1:00:44

        Uh, okay.

20. 1:00:45 – 1:05:52

    Lightning round and final thoughts

    1. LRLenny Rachitsky1:00:45

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

    2. ISIan Silber1:00:50

       Uh, if I could distill it, it's like I hope that this is just, like, a really fun time to build stu- 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 I, and that I think that designers are just, like, hopef- uh, 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 gonna 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, uh, that's gonna be more true than ever.

    3. LRLenny Rachitsky1:01:31

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

    4. ISIan Silber1:01:33

       Yes.

    5. LRLenny Rachitsky1:01:34

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

    6. ISIan Silber1:01:38

       Okay. Yes.

    7. LRLenny Rachitsky1:01:40

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

    8. ISIan Silber1:01:46

       I'm not, like... You know, it's funny, I'm not, like, a big, big book recommender. Um, I think, like, when people ask me, uh, 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, I have, I do love The Design of Everyday Things. I think that's, like, such a classic.

    9. LRLenny Rachitsky1:02:07

       Classic. That's the one. That's the one everyone's talking about. Yeah

    10. ISIan Silber1:02:08

        ... that, like, you know, it, it's not like... Yeah, it's not a unique recommendation, um, but it, it is just kind of a classic of thinking about how you-

    11. LRLenny Rachitsky1:02:17

        Yes

    12. ISIan Silber1:02:17

        ... how we think-

    13. LRLenny Rachitsky1:02:18

        Like, you have to read it

    14. ISIan Silber1:02:18

        ... how I think about design. Yeah. Absolutely.

    15. LRLenny Rachitsky1:02:19

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

    16. ISIan Silber1:02:22

        Yeah. [chuckles] Yeah.

    17. LRLenny Rachitsky1:02:24

        Awesome. Uh, anything else there, or should we keep moving?

    18. ISIan Silber1:02:27

        We can keep moving, yeah.

    19. LRLenny Rachitsky1:02:28

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

    20. ISIan Silber1:02:33

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

    21. LRLenny Rachitsky1:02:41

        Yeah

    22. ISIan Silber1:02:41

        ... um, called Maybe Happy Ending. W-w-

    23. LRLenny Rachitsky1:02:44

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

    24. ISIan Silber1:02:47

        You saw it?

    25. LRLenny Rachitsky1:02:47

        Yes.

    26. ISIan Silber1:02:47

        Oh, you saw it. Okay, yeah. H- it was so unique, right? Um, and of course, it kind of hit home a little bit 'cause it's about these, like, super intelligent humanoid, uh, robots and like, you know. Um, but, um, but the, the production was incredible, the set, uh, design, uh, everything about it I thought was, like, so unique, um, which was, um... I thought... But yeah. So if you have the chance to see it, I thought it was really, really good. Um, I also just saw The Invite, which was, I thought... [chuckles] Have you seen it?

    27. LRLenny Rachitsky1:03:23

        Yes. Also love. It's so simple, but so good.

    28. ISIan Silber1:03:26

        It-- That's what I loved about it, is it's, like, so simple. It's like... It actually is, uh, uh, uh, like a play, you know, and it's just four people in one kind of beautiful apartment, and the set design's amazing. Um, uh, but, like, the writing, act... everything about it was, like, incredible, and it's just kind of a wild ride. [chuckles] And I went in ha- knowing nothing about it. I thought it was incredible.

    29. LRLenny Rachitsky1:03:52

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

    30. ISIan Silber1:03:57

        Yeah.
21. 1:05:52 – 1:12:02

    Lessons from Groupon

    1. LRLenny Rachitsky1:05:52

       Okay. Last question. Something I love about your career history, if you look at your LinkedIn, you were a designer at Groupon.

    2. ISIan Silber1:05:58

       [chuckles]

    3. LRLenny Rachitsky1:05:58

       I love that you were at Groupon, and now you're heading design for essentially super intelligence. [chuckles]

    4. ISIan Silber1:06:02

       [chuckles]

    5. LRLenny Rachitsky1:06:03

       Uh, what's something you learned at Groupon that has, is being, is maybe helpful these days building-

    6. ISIan Silber1:06:08

       Oh

    7. LRLenny Rachitsky1:06:08

       ... super intelligent AI?

    8. ISIan Silber1:06:10

       I love that. Groupon was a f- really fun company. Um, Andrew Mason was, like, a really incredible CEO in just that he brought such character, uh, to the product. You know, it was, like, kind of a brand-led product. Um, and um, you know, like, f- we had, we had a... There was, like, a, a comedy team. Uh, there was, like, a writer team a-at, at, at... But they were, like, all ... comedians basically. And the product really did not take itself seriously, at least in its early, early couple 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 ne- nec- 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, uh, that side of things. Um, and, and, uh, 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 d- DNA, and the way you have to work kind of maybe changes a little bit based on that, right? 'Cause so I, uh, you know, Groupon w- was run one way. You know, then I went to Instagram, which was, like, this very design and, and creativity focused, and Kevin's, you know, Kevin Systrom was, you know, really, like, an incredible designer. Uh, a- and he, he sort of saw himself, uh, or, like, worked in that way with us, which was really cool, and it, 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, uh, you know, I think, uh, you know, and then, and OpenAI being a research lab. And so learning that companies have these really different DNAs and understanding how to sort of embrace them and kinda leverage that to your, uh, like, or help kind of, like, empower that or, like, I guess lean into that, um, uh, uh, has been something that I've learned a lot, um, from moving around and getting the opportunity to work at very, very different companies.

    9. LRLenny Rachitsky1:08:26

       And also just to add to that, it's also important to realize you're not gonna change that. You're not gonna, like, come in and change that culture 'cause that's just, that's very hard, especially if it's very f- founder oriented.

    10. ISIan Silber1:08:36

        I think it's about finding, like, oh, wow, like, at OpenAI, you know, yeah, sure, like, we spent more ti- at, at Instagram we definitely moved slower, and I would say that we, um, we changed the product less, and that actually worked really well for most stages, uh, of, of Instagram. Uh, but I don't think that that would work in, 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, at, at, um, 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, at OpenAI. Um, 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 it. Sometimes we actually do throw some things out that we're still experimenting with. And so just being really f- I, I found that having to, yeah, be flexible and, yeah, not necessarily trying to change it, but try, trying to kinda, like, help round it out maybe.

    11. LRLenny Rachitsky1:09:37

        Ian, what a, what an incredible, uh, place you have in the world right now just being on the inside of such cool technology, such cutting-edge stuff that's happening. Uh, 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 wanna point people, if you wanna plug anything, and how can listeners be useful to you?

    12. ISIan Silber1:10:00

        Where do I wanna point people? I mean, I think that, um, please, you know, I guess use, you know, have fun with, with the stuff we're making with ChatGPT and Codex, and fire away feedback and thoughts. I'm on Twitter. Uh, I love to talk with designers, uh, about all sort of stages, um, or not just designers, engineers, PMs, whatever. Um, that's probably where I'm most, uh, sort of reachable and accessible. Um, and, you know, how can y- uh, yeah, I, 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 kinda shifting, and that's, like, a great way for us to learn how we can, we can build better products both, like, internally at, at OpenAI, but just as a, as a design community. Like, maybe showcasing a little bit more of our process because it is get- becoming a little bit more opaque. Like, well, how is it working? Just, um, I think sharing that is, is, like, such a gift to the community, so doing more of that.

    13. LRLenny Rachitsky1:11:01

        Also pointing people to your website, which I have here now, and I think my face is probably changing colors 'cause-

    14. ISIan Silber1:11:06

        [laughs]

    15. LRLenny Rachitsky1:11:06

        ... the site has all these re- crazy colors.

    16. ISIan Silber1:11:09

        Yes.

    17. LRLenny Rachitsky1:11:09

        Uh, so if you go to iansilber.com, you could see this, uh, insane website.

    18. ISIan Silber1:11:13

        [laughs]

    19. LRLenny Rachitsky1:11:13

        That's your personal website, and there's a-

    20. ISIan Silber1:11:15

        Yeah

    21. LRLenny Rachitsky1:11:15

        ... Easter egg game there

    22. ISIan Silber1:11:16

        That, that's a deep dive into all of my past work, you can see there.

    23. LRLenny Rachitsky1:11:20

        [laughs]

    24. ISIan Silber1:11:20

        Yeah. [laughs]

    25. LRLenny Rachitsky1:11:20

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

    26. ISIan Silber1:11:25

        That's right. [laughs]

    27. LRLenny Rachitsky1:11:26

        Uh, Ian-

    28. ISIan Silber1:11:26

        See if you can set the high score.

    29. LRLenny Rachitsky1:11:28

        Yeah. The high scores are out of control. I don't know what's happening.

    30. ISIan Silber1:11:30

        [laughs]

Episode duration: 1:12:04