Lenny's PodcastAparna Chennapragada: Why prompt sets are killing the PRD
Through Microsoft's Frontier program, prompt sets replace PRDs; live demos beat documents and tastemaking trumps title for AI-era product leaders.
EVERY SPOKEN WORD
120 min read · 24,387 words- 0:00 – 4:28
Introduction to Aparna Chennapragada
- ACAparna Chennapragada
I have a cheesy Chrome extension. Literally, whenever I open a new tab, it just says, "How can you use AI to do what you're going to do right now?"
- LRLenny Rachitsky
How do you see the future of product development being different?
- ACAparna Chennapragada
If you're not prototyping and building to see what you want to build, I think you're doing it wrong. It becomes even more important to have the territorial and taste-making at the heart of it, because otherwise you just have a Frankenstein product.
- LRLenny Rachitsky
There's this acronym that you taught me, NLX. What is that?
- ACAparna Chennapragada
Natural language interface. NLX is the new UX. Often I hear, uh, product builders say, "Oh, yeah, with AI, like, the model leads the products." That doesn't mean it's not designed. You and I are having a conversation. It's a podcast. I'll have another conversation, uh, at Microsoft and that's a meeting. Conversations also have grammars, they have structures, they have UI elements. They're invisible. What are the new principles, new constructs in natural language as a interface?
- LRLenny Rachitsky
I just saw that Cursor hit 300 million ARR in two years. Interestingly, you guys were very well positioned to do really well in this AI coding tool space. You guys had Copilot, the first tool in the world at this stuff. So ahead of everyone. What happened?
- ACAparna Chennapragada
I would say-
- LRLenny Rachitsky
Today, my guest is Aparna Shenapragada. Aparna is chief product officer at Microsoft, where she oversees AI product strategy for their productivity tools and their work on agents. Previously, she was chief product officer at Robinhood; vice president at Google, where she worked on Google Lens, Search, Shopping, augmented reality, AI Assistant; and a lot more. She was also a longtime engineering leader at Akamai, and on the board of eBay and Capital One. In our conversation, we chat about how working in B2B is like being Jean-Claude Van Damme doing the splits across two moving trucks, how she's operationalizing her team living in the future so that they're building towards where things are going, why people still need to learn to code, why the PM role isn't going anywhere, why NLX is the new UX, and so much more. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of a bunch of products, including Linear, Superhuman, Notion, Perplexity, and Granola. Check it out at lemmysnewsletter.com and click BUNDLE. With that, I bring you Aparna Shenapragada. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features, and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. This episode is brought to you by Pragmatic Institute, the trusted leader in product expertise. Pragmatic Institute helps product professionals turn ideas into impact through proven courses, workshops, and certifications designed for real world success. For over 30 years, they've trained more than 250,000 product leaders at companies like Google, Microsoft, and Salesforce, equipping them with practical strategies to build and scale market winning products. Pragmatic's full-time instructors each bring over 25 years of hands-on leadership experience, teaching strategies proven to deliver real world results. And it's not just about what you learn, it's also about who you learn it with. Completing a course connects you to an active community of over 40,000 product professionals. You'll engage in meaningful conversations, collaborate with peers and mentors, and gain direct instructor access to refine your strategies and stay ahead of trends. Get 20% off with code LENNY20 at pragmaticinstitute.com/lenny.
- 4:28 – 7:29
Aparna’s stand-up comedy journey
- LRLenny Rachitsky
Aparna, thank you so much for being here and welcome to the podcast.
- ACAparna Chennapragada
Thank you, Lenny. Thanks for having me.
- LRLenny Rachitsky
When I asked a lot of people that work with you, uh, what I should ask you about and what's that, what I should know about you, something that came up again and again is something that I think most people don't know about you, which is that you're, uh, you're big into standup comedy and you take it semi-seriously. Uh, just how serious are you about this? How, how much of your life is this? And most importantly, how does this help you build better products?
- ACAparna Chennapragada
It's hard to say I'm serious about, like, uh, funny business, but I, I do, I do watch and do standup comedy. I do open mics, I've done a few shows.
- LRLenny Rachitsky
Wow. (laughs)
- ACAparna Chennapragada
Um, I have, uh, one set brewing that is around, uh, uh, AI, (laughs) unsurprisingly AI, and tech, and Silicon Valley. You know, it's really interesting for me. This was an accidental discovery. Like, I'd always been an SNL fan and, like, just comedy fan, but I went to an open mic because, you know, my son sings and he went to the open mic for singing and he's like, "Mom, you should go do this." And I was like, "Oh, let me go give it a try." And I found that I enjoyed it and was good at it. To your question though about building better products, I'd say both have PMF, I mean, product market fit, punchline market fit. (laughs)
- LRLenny Rachitsky
(laughs)
- ACAparna Chennapragada
Uh, and w- but I, I, actually there are a couple of things that I, I do find really powerful and useful, because, you know, in open mics or even when you're testing these things, it's a very tight cycle of iteration and you get live... Like, open mics are the real live experiments, right? You, you put something out there, you get very clear micro-feedback from users, and then you get tough feedback sometimes. And, uh, I think as product builders, that's actually one of the great skills to have, which is, yeah, you, you sometimes launch stuff that you know have a...... fantastic vision, but the first version is not quite there, right? I think Reid Hoffman says this, "Hey, if you don't launch the first version and are not embarrassed, you're doing it too slow." Just that gap in closing that, it's good resilience.
- LRLenny Rachitsky
Yeah. I never saw these corollaries between these two things. I didn't realize we actually did, like, shows and you're working on a set. Uh, I wasn't gonna ask you for a joke, but if you're working on j- on a whole thing about AI, is there something, uh, that you can share from that set?
- ACAparna Chennapragada
One, uh, joke I'd, um, maybe share is, uh, people think about these AI chat products as, uh, women, uh, because, uh, you know, you don't know what's going on. It's a black box, (laughs) and, uh, you don't know what it's, what, what, uh, they're thinking. There's like an entire set around that. But o- obviously on the flip side too that, you know, they're probably more like men in the sense that they hallucinate a lot. They're, uh, they kind of are not yet reliable. (laughs) And they're very confident.
- LRLenny Rachitsky
I'm afraid to laugh at this a little bit. (laughs) This is great. Okay.
- ACAparna Chennapragada
Uh, and they, even when they don't know the answer, they make up stuff. They're very confident. (laughs)
- LRLenny Rachitsky
(laughs) This is good. Where are we gonna be seeing this show, by the way?
- ACAparna Chennapragada
Uh, HBO.
- LRLenny Rachitsky
Okay. (laughs) This is great. Okay, uh,
- 7:29 – 10:00
Transition to Microsoft and enterprise insights
- LRLenny Rachitsky
let's get serious again. So you worked at, most of your career, at a lot of consumer internet companies. You worked at Google, Robinhood, you were on the board of eBay, you were on the board of Capital One. Now you're at Microsoft. I'm curious just what is most different about working at a company like Microsoft and building product at a company like Microsoft?
- ACAparna Chennapragada
I think intellectually I knew, uh, that, hey, enterprise, particularly the, the area that I look at most at Microsoft, is focused on enterprise and productivity and transforming companies through AI. And to me, uh, I think two things really strike, uh, as very different. One, in fact I just posted about this the other day, was saying, in consumer, you're kind of like, oh, we have a playbook for make the product work or make the feature work and make it delightful. But I think in the enterprise, you almost have ev- every time you, you think you have one use case, you have really two, which is how do you make sure that the feature works well and there's governance of the feature? Right? If you think about, like, even something as simple as sharing a link to a document, you want it to be easy, frictionless, but at the same time, you want that to be secure and kind of, uh, safe and being able to have auditability and all of those things. And often, I find that when you go from consumer en- uh, consumer to enterprise, you fall into a trap of either disregarding that, right, and say, "Oh, you know, we'll just focus on one side of the house," or kind of overly crippling the user experience, right, and kind of s- you know, leaning on the other side. So I think the- there's an, uh, art and science and nuance and playbook there too, so that's one big learning for me. The other learning and especially in the AI era for me has been about this, you know, I think there's a famous trailer from the 2000s on Van Damme on these like two trailer, two buses-
- LRLenny Rachitsky
Hmm, like, doing the splits?
- ACAparna Chennapragada
... and he's doing this
- NANarrator
Uh-huh.
- ACAparna Chennapragada
Yeah, doing the splits. Exactly. And I feel like a lot of the, the companies, including the tech companies, but certainly the enterprises that I talk to, are in these two modes where on one hand, this is the most compressed tech cycle that we've ever experienced, right? It's o- in the order of weeks and months versus years and decades if you think about, like, mobile and cloud and internet. And there's just, like, so much happening, uh, the intelligence overhang. Uh, on the other hand, there's also, like, humans and habits that productivity habits change, uh, it's hard to change, and change management through the company is also hard, right? You don't want to kind of be rash on that. So it's like, you know, uh, the future is unevenly distributed, but even within the companies.
- LRLenny Rachitsky
On the second
- 10:00 – 13:28
The Frontier program and AI integration
- LRLenny Rachitsky
bucket of this other, this, the, (laughs) the bus that Van Damme's riding on of governance and, and then adoption and changing behavior and stuff, is there something you've learned about how to get past that, help, help that along more?
- ACAparna Chennapragada
The thing not to do is, uh, hold back, uh, f- folks who are early adopters, right? I think that's the, that's the other one learning. In fact, I think that's one of the reasons why recently we, you know, I've been working with folks to say, "Can we have, can we have both, which is the longer term change management, being able to do it in a trust, uh, trusted way, at the same time, do this program we're calling Frontier Program, and roll out cutting edge experimental features?" We le- we just built this world's first m- agent, uh, de- deep research agent made for work, right, post-trained for work, and of course, it has, you know, all sorts of edges, rough edges. But if there are early adopters in an enterprise or outside, how can we kind of put that in the hands of those folks without kind of insisting that all of the, uh, all of the company be completely different, developing different muscles?
- LRLenny Rachitsky
This program, Frontier, you're talk- you're talking about, uh, I wanted to spend a little time on it. So, uh, what is the idea? The idea here is, like, people are working in this futuristic environment. How, how does that actually work?
- ACAparna Chennapragada
Yeah, I think the idea is exactly this, which is, like, I want to kind of institutionalize and operationalize my personal motto of, like, living one year in the future and say, what does this, uh... Imagine a, a company or a setup, um, like Frontier In- uh, uh, Consulting Group or Frontier Inc., right? And if you did li- lived in that environment where you had all the AI tools and really advanced deep research intelligence on tap, what are the kinds of questions you'd be asking? What are, what's the kind of work you'd be doing? How would you change how you're going about your workday? Uh, so that's the premise. And you'd say, "Hey, how does it change an individual?" But also down the lane, we wanna think about what does a Frontier team look like? We talk a lot about Frontier Labs and models. I think models layer is amazing. And obviously, like, you know, that's what empowers all these product building to happen. But I wanna push us to think about what does a Frontier product look like? Uh, and more importantly, how does a Frontier way of working, right, like, what does a team with three people and tons of, like, compute and AI tools look like?
- LRLenny Rachitsky
So how exactly does this work? There's like a team within Microsoft that's like, your job is to use all of our latest tools and build product using that? Is that how it works?
- ACAparna Chennapragada
Yeah. That is- that is the setup. We're just a few weeks into that setup. But meanwhile what we have done is like we've actually, uh, um, set up in like a comp- external, like a fake company, and said, "Hey, if you are somebody who wants to come play with some of the cutting edge science projects and be research, uh, agents and you know, agents at work, come ha- come party here."
- LRLenny Rachitsky
Hmm. Wow, okay. And it's only a few weeks in. Okay, so TBD how it all goes. Uh...
- ACAparna Chennapragada
Yeah, yeah. And again, like these are micro... Let's see, the meta point here, right, also is that, you know, in the traditional way we've kind of always thought about, across the companies, across industries, really thinking about roll-outs in these, uh, macro ways, right? You build something and you kind of like roll it out, you have a general availability for... and then you take the time. And that's really important too, because again, like we're talking about pharma companies, legal companies relying on this. So we do want to have that. But at the same time, given the compressed cycles of AI, how do we start to have people experience what's- what's the one
- 13:28 – 17:59
Understanding AI agents
- ACAparna Chennapragada
year in the future?
- LRLenny Rachitsky
Let's follow this thread in a few different directions. There's like how product chain development changes, there's how engineering changes. There's also just agents. I know you're spending a lot of time in agents. Feels like you're not an AI company these days if you're not working on agents.
- ACAparna Chennapragada
Yeah.
- LRLenny Rachitsky
Or building an agent. Yeah.
- ACAparna Chennapragada
Lenny, we're doing this wrong. We didn't wor- you didn't use the word agents slo- uh, like-
- LRLenny Rachitsky
(laughs)
- ACAparna Chennapragada
... so far into the conversation.
- LRLenny Rachitsky
I- I try hard to (laughs) push it out as far as I can. Uh, it's like, it's like every conversation in San Francisco, just like how long until they start talking about AI?
- ACAparna Chennapragada
Yeah. Exactly.
- LRLenny Rachitsky
It's like three minutes (laughs) on average, I bet. Oh man. Okay, so- so with agents, I know that you're leading a lot of this work at Microsoft, and a lot of people are wondering what the hell- what the hell does this mean? What is gonna change? Give us just a glimpse into how you see the world being different in a world of agents being around more.
- ACAparna Chennapragada
Look, there's a short term and there's a long term, right? There's a lot of, you know, hyperventilated, excited talk about kind of the w- the eventual future and all of that. I take a much more practical product building lens on this, right? And I think about these. At the end of the day, they're tools, right? Yes, underneath it there's stochastic models versus very deterministic programming models. You can tell I'm a computer scientist by like the way, the- that that worldview definitely shapes how I think about this. To me, the short term is, uh, there's an evolution. Like we had apps, right? And now I think we are formally in the assistance era, where there's like human driving the, uh, you know, that's what we think of as CoPilot, right? Like, I think the human driving kind of the, uh, in the driver's seat, but having a lot of assistance from AI. So I think of this as then you- you- you look at the dimension of almost like autonomy and delegation and intelligence. As the intelligence, for example, when deep reasoning unlock happen, of course then you could say you could delegate more, right, to- to the agent. So I think to me, I think there's one dimension where you say, "Hey, agents are somewhat independent software processes, right, that can kind of like ru- run tasks." And you're not just thinking about hand hol- handholding and fine motor stuff. You're saying, "Hey, here's my goal. Go make this happen." Uh, like I'll give you an example, right? So we're working on this researcher agent for work, and last night I said, "Hey, ho- you know, I'm really, I- I have an important meeting coming up with the leadership team. I really want to present these frameworks here, and this is the roadmap here. Go back and look at all the people that are in the meeting. What are their views on this topic? And kind of come up with how do- how I should kind- be thinking about like, you know, the right persuasion pitch here," right? And what's magical about this is not just that it's saving time. Typically, we think about the so-far AI as summarizing a document or saving time, right? This is like firing synapses that I didn't- I didn't quite have, and I actually giving me new insights and giving me, dare I say, super powers, right? So that's a natural evolution of AI, I would say. So when I think about agents, I think about three things. One is, is an increasing, um, level of autonomy and kind of, uh, uh, independence, that you can delegate higher and higher order tasks. Second thing I think of it is complexity, right? So it's not just a one-shot, "Hey, create this image or do this thing or summarize a document." It's, you know, "Build me this prototype, uh, that expresses my idea of a- an augmented reality app," right? Uh, it's a complex task. And then the third thing I would say is they synchronize. It works when you're not working, right? I think that's the other big thing about these things, that you're not hap- you don't have to s- sit in front of it.
- LRLenny Rachitsky
This is answers the question of what is an agent, essentially, these three bullet points. So it's, uh, what are the three again?
- ACAparna Chennapragada
When I think about agents, I think about these three things, right? So one, it's, um, autonomy, like being...
- LRLenny Rachitsky
Autonomy.
- ACAparna Chennapragada
And it's a- it's a spectrum. It's not a zero/one. It's how do I actually, uh, delegate things that it can do? Second, I think of as complexity, right? It's not a one-shot, "Hey, summarize this document, generate this image," but it's, you know, "Build me this prototype or help me knock this meeting out of the park," right? Um, and then the third one I think of is, uh, it's a much more natural interaction. That doesn't just mean chat, but it may be actually jumping on a meeting with the agent and being able to like talk through all of it, or point it to things that I want it done differently. So I think all three things, the autonomy, the complexity, and the natural interaction are at least product principles that'll shape really good ones, good agents.
- LRLenny Rachitsky
That is really helpful.
- 17:59 – 22:28
NLX is the new UX
- LRLenny Rachitsky
Along this line of agents, there's this acronym that you taught me as we were chatting out of this podcast. Uh, NLX. What is that and how does that relate to, uh, agents, and why are people not thinking about this enough?
- ACAparna Chennapragada
Oh, that's one of my Roman Empires these days. The- the, uh, natural language interface. NLX is the new UX. Right? Uh, so I think here's the- here's the, uh- uh, here's the deal. To me, I think traditionally we've thought very consciously about GUI because, uh, the graphical interfaces are not something natural and so they have had to be explicitly designed. They're rigid interfaces, right? Uh, what we have with...... conversational interface and natural language is it's a, it's a much more elastic, right? That doesn't mean it's not designed. So people ha- often I hear, uh, product builders say, "Oh, yeah, with AI, like, the model leads the product. So it's just, you chat with it." Uh, you and I are having a conversation. It's a podcast. I'll have another conversation a- at Microsoft, and that's a meeting. So conversations also have grammars, they have structures, they have UI elements. They're invisible, and so one of the things that I see and I'm really excited about is what are the new principles, new constructs in natural language as a interface? Um, I'll give you a few examples, right? And actually, like, a lot of startups, as well as big companies are really experimenting with this stuff. One is if you think about it, prompt itself is a, is a new construct, and that's a new way, that's a new UI element, just like a dropdown was, uh, or a menu was. But others that are emerging, especially for agents, I think are plans, so when you give a high, high-level goal, what we are seeing is that when the agent comes back with a plan, preferably an editable plan, that's a new construct. Right? The other one that's, um, uh, that I think about a lot is, uh, showing the work, right? Progress. You see this with, uh, uh, different products, right? You see it with the Copilot, you see it with ChatGPT, DeepSeek, this idea of thinking aloud, and it's kind of showing the work, uh, but how much do you do it? If it's too verbose, it feels like I'm running some cron job and scripts, uh, but if it's too terse, then I don't know if it's going in the right path and I don't have the confidence yet. So there are all these new elements. If you're a product builder, this is a fun new space to be digging in, um, for product design.
- LRLenny Rachitsky
This is really interesting-
- NANarrator
Cool.
- LRLenny Rachitsky
... 'cause I think people chat with all these chatbots, and it just feels like this is just the way it is, but you actually are designing every element of the interaction, like how much to share about how much you're thinking. Here's the- my plan, what do you think? Uh, so I think, I think this, this will surprise a lot of people just realizing there's so much that goes into just designing even these what seemingly are simple conversations.
- ACAparna Chennapragada
Yeah. A- another good example is follow-ups, right?
- LRLenny Rachitsky
Mm-hmm.
- ACAparna Chennapragada
You could say, look, you have a que- you, you asked me a question, and then I, I could, uh, ask a follow-up, um, set of things and that's explicitly should be designed for success, right? So for example, if, if I say, "Hey, create an image," and it created a black and white, you know, I don't know, like a, a clip art version of something, what are the next obvious follow-ups that it should be suggesting proactively? Now too much and you're kind of annoying me, right? Like (laughs) , uh, but too little and i- i- in some sense you've lost an opportunity to direct me or guide me into a happy path here.
- LRLenny Rachitsky
This resonates a lot with when we had Kevin Wheel on the podcast. He talked about this question of just how much to sh- show about what you're saying and, you know, uh, and it's interesting that DeepSeek went the extreme of just showing everything, and people liked it too. Tha- I think that was interesting.
- ACAparna Chennapragada
Yeah, and I think it's a point in time thing, uh, too, Lenny, because in some sense right now, these things are such black boxes, they're almost like peeking, a- under the hood, eh, for anything, even if it's verbose. Feels like, oh, I know what's happening. Especially because the compute inference time, it's taking long to think, uh, so it just feels like if you just went silent, I'd be very-
- LRLenny Rachitsky
(laughs)
- ACAparna Chennapragada
... uncomfortable, I think.
- LRLenny Rachitsky
(laughs)
- ACAparna Chennapragada
(laughs) Uh-
- LRLenny Rachitsky
I know.
- ACAparna Chennapragada
... exactly. Uh, so I do feel like there's that point in time, but over time, I also feel like this is an area ripe for personalization. For example, right, like again, in a human, like my API would be very different from somewhere, my interface is probably different from others, and I might just want the direct, "Hey, t- give me the TL;DR," uh, versus the, "Oh, so I went here, and then I went there," and then like...
- 22:28 – 31:16
The future of product development
- ACAparna Chennapragada
(laughs)
- LRLenny Rachitsky
Following this thread a little bit, we're talking about just how the future is gonna be different. There's, like, designing for these chat experiences. There's agents. Uh, kind of zooming out to just product development in general, it feels like you're at the forefront of a lot of the tools that are gonna change the way we build products, and also your teams are working with a lot of these tools that no one else has access to. So let me just ask, how do you see the future of product development being different from today most, and what do you think product builders should be preparing for doing to kind of, to succeed in that future?
- ACAparna Chennapragada
I- I'll, I'll start with one stark, uh, s- statement, uh, that I say internally and externally, uh, and I, I'm trying to live it, is that in this day and age, if you're not prototyping and building to see what you want to build, I think you're doing it wrong. I call it the prompt sets of the new PRDs. Right? Like, I really insist on folks saying, "If you're building new projects, new features, of course, come with prototypes and prompt sets." And I think the, the, the an- the, the notion is not to say, hey, now, like, everybody's just, uh, you know, s- uh, like a Vegas version of a, like, a software engineer, right? It is to say, you know, you have the fastest path to kind of seeing and experiencing what's in your mind, uh, to, uh, to be able to communicate. Right? It's a much more high bandwidth way of communication. I think about that as a, really a loop accelerator in terms of product building. That's number one. Uh, when in doubt, uh, as, uh, someone put it, demos before memos, right? I think, like, that's, uh, that's really number one. I would say number two, this one is a little bit tricky, I'd say, is that what I'm seeing is that the time to first demo the- is much s- shorter, right? But the time to like a full deployment is, uh, is going to take longer. So I, I think that there's gonna be an uneven cadence. So typically, I think there was much more of a, hey, you build this thing, you take a few weeks, and then you can iterate and so on. Now, uh, b- but that inner loop of like prototyping and iterating and getting even user research, uh, through AI conversations, all of that gets shortened...... but I think the bar for scale therefore becomes much high, right? I- in some sense, if you look at it, like there's going to be a supply of ideas, right?
- LRLenny Rachitsky
Mm-hmm.
- ACAparna Chennapragada
Like a, a massive increase in supply of ideas in, in prototypes, right? And so, which is great. It raises the floor, but it raises the ceiling as well, right? In some sense, like how do you break out in these times that, uh, you have to, you have to kind of make sure that this is, um, this is something that rises above the noise. So I would say that it's simultaneously thinking about, uh, not chasing after every idea, like, right? I think is the second one. I'd say the third thing is, you know, there's a lot of conversation around full-stack builders, right? What does the team of the future look like? The product building team? What I think about is, um, I think that is inevitable in terms of like, there will be a few folks that are, especially at the prototyping, early idea discovery stage, that the lines are blurred, right? You have... There'll be a few tastemakers at the sa- same time. I think you can still have a lot of people experimenting. It becomes even more important to have that editorial and tastemaking in a partier, uh, one or few, uh, at the heart of it, uh, because otherwise you just have a Frankenstein product, right? That do- that definitely doesn't change. I have a, one other additional bonus thing which is a lot of folks think about, "Oh, you know, don't bother studying computer science," or, you know, "The coding is dead." And, uh, I, I just fundamentally disagree. If anything, I think, you know, we've always had layer... hi- higher and higher layers of abstraction in programming. You know, like we don't program in Assembly anymore. Uh, like most of us don't even program in C, and like, and then y- you're kind of, you know, higher and higher layers of abstraction. So to me, there will be ways that you will tell the computer what to do, uh, right? It'll just be at a much higher level of abstraction, which is great. It democratizes. You'll, there'll be an order of magnitude more software operators. Like instead of SWEs, maybe we'll have SOAs, right? (laughs) Uh, but that doesn't mean you don't understand computer science, and it's a way of thinking and it's a mental model, so I, I strongly disagree with the whole like, coding is dead.
- LRLenny Rachitsky
That's awesome. I love that. Uh, and is, SOA is a, is a software operator? What's that... what that stands for?
- ACAparna Chennapragada
Yeah.
- LRLenny Rachitsky
Interesting.
- ACAparna Chennapragada
I just made it up, but yes.
- LRLenny Rachitsky
(laughs) Okay, cool. Uh, this idea of prototyping as being kind of core to building these days, is there anything you do within Microsoft to operationalize that and make that just like a thing everyone has to do? Is it just like culturally do it, or is it like you must show me a prototype before you show me yeah?
- ACAparna Chennapragada
You know, I think it's, again, like the future is here, unevenly distributed, even in Microsoft I would say. But there is certainly a strong cultural, uh, momentum and shift and desire to say, "Hey, let's, let's actually look at live demos, live prototypes, and to even like communicate the ideas," right? Uh, and, and to me, I mean, it's not always possible because obviously there are like things that are deeply... like if you're trying to change something in like the bowels of Excel, you probably don't... eh, eh, there's even enough depth in the, uh, in the, uh, product that you know what you need to do and you don't need to prototype that. But if you're especially thinking about new things, new products, new features, absolutely.
- LRLenny Rachitsky
Okay. Let's talk about product management. There's this, uh, fear that emerged as soon as all these AI coding tools came out of just like, "PMs are dead. We don't need PMs. We could just build things ourselves. What, what are these people hanging around for?" And what I found is it's actually the opposite, that now that coding is easy, now the question is more and more, "What should we be building? Why should we be building it? Is this right? Is this the right solution?" Than getting adoption for it, which is what PMs are really good at. And so I feel like it's the opposite, like PMs are the most important role and they're, you know, it'll change too, but, uh, well let me get your take. Just what do you think the future of product management looks like? You think it's dead? Do you think it's gonna thrive? Do you think it's gonna change?
- ACAparna Chennapragada
Yes.
- LRLenny Rachitsky
(laughs)
- ACAparna Chennapragada
Meaning, uh, meaning... Look, I mean if you're a TPS report, uh, mostly process, uh, person and like a lot of companies do, uh, get confused about product management and process and project management, I think then you do have a question of like, "Hey, what is the value add here?" Right? Especially if like AI can read and write like 50,000 meeting notes and, uh, you know, track things and send emails and so on. Uh, but I think what, uh, w- what I do think on the flip side is that tastemaking and kind of the edit- editing function becomes really, really important, right? In a world where the supply of ideas, supply of prototypes becomes even more, like an order of magnitude higher, you'd have to think about like what is the editing function here. Um, so that does mean that the bar is higher for, uh, for y- for product, uh, folks. But I think there's a, there's an interesting side effect that I am observing in, you know, startups that I'm advising, companies, and even within the companies that there's... there used to be more gatekeeping, I would say, in terms of like, "Oh, this is... you know, we should ask the product leader what they think." And again, like there is a role for that editing function, but you have to earn it now. You just don't get it because of the, uh, title. But there's also just like unlock of latent really good ideas from smart engineers, smart user researchers, smart designers who can no- who now have like this expert in their pocket, right? To kind of round out all the other things that they're not, they're not, uh, typically skilled at, to bring forth their ideas. And that's fa- amazing, I think.
- LRLenny Rachitsky
And I think that expert, it's interesting. I- I'm working with an engineer on some stuff and he uses, uh, ChatGPT to even communicate to me in a more effective ways. Like turn this pitch into something that will convince Lenny this is a good idea.
- ACAparna Chennapragada
By the way, that is actually one of my, uh, common use cases, which is the WWXD, I call it what would X do? Like I used to say, "Hey, um, what would, uh, Satya think about like this particular set of, uh, uh, uh, conversations or ideas that we are pitching and so on?"This is the power of, like, I think deep reasoning plus relevant context, right? This engineer you're talking about has that context, uh, about you, and so it's kind of, uh, very interesting.
- LRLenny Rachitsky
If only everyone was, uh, as famous as Satya and had so much information out there. But I guess you can import all their emails or whatever tools exist to just, like, understand from the conversations you've had with that person.
- 31:16 – 35:45
Building a custom Chrome extension
- LRLenny Rachitsky
- ACAparna Chennapragada
Yeah. And I think this is ... This goes back to actually what you were saying too, which is, I think this idea of what is the ... There's like a coil spring, there's an intelligence overhang that I, I just see across the board, and I think the part of product development has to almost rewire ourselves to, I think Tobi from Shopify calls it the reflexive AI usage. Uh, and, and that's not as easy. And I've been thinking about why, like, I basically ... I mean, I have a cheesy Chrome extension. Literally whenever I, uh, open a new tab, it just says, "How can you use AI to do what you're going to do right now?" Just to ... Like, it's very cheesy, but it kinda helps to pause and think, "Oh, w- w- what, what am I trying to do here?" But, um, the reason I find it hard and when I talk to even, like, people who are living and breathing in this space, they find it hard, is that, you know, the updating of the priors is really hard. Like, the models couldn't do some things one year ago. Like, I mean, image generation was full of spellings. Or, like, reasoning. You just couldn't, like, you know, have deeper and smarter answers. It couldn't do data analysis. So, like, my impression of it from change, trying it a few months ago, that prior needs to be updated, and it's hard to do that, right? You have to kind of do something almost, uh, counterintuitive and against the grain to say, "No, no. Like, ignore what you learned about, like, what this can or cannot do." Like, the baby just grew up to be a 15-year-old (laughs) in, in a month.
- LRLenny Rachitsky
I think that last point is so important, that we've tried these tools over the years and it ... Many ... Like, so far, it hasn't been amazing and then all of a sudden it is, and you kind of don't know that. And you've given up almost and, and things change.
- ACAparna Chennapragada
I think that's actually ... If, if you're a product builder listening to it, that's a really interesting arbitrage thing for you. Like, if you can kind of cut against the grain and say, "No, I won't have that scar tissue around like, you know, this didn't work a few months ago," and keep setting high expectations and, like, demand more of the AI today, I think, uh, y- y- you can, you can unlock more.
- LRLenny Rachitsky
There's a lot of alpha in, in doing that.
- ACAparna Chennapragada
That's right.
- LRLenny Rachitsky
Today's episode is brought to you by Coda. I personally use Coda every single day to manage my podcast and also to manage my community. It's where I put the questions that I plan to ask every guest that's coming on the podcast. It's where I put my community resources. It's how I manage my workflows. Here's how Coda can help you. Imagine starting a project at work, and your vision is clear, you know exactly who's doing what and where to find the data that you need to do your part. In fact, you don't have to waste time searching for anything, because everything your team needs from project trackers and OKRs, to documents and spreadsheets lives in one tab, all in Coda. With Coda's collaborative all-in-one workspace, you get the flexibility of docs, the structure of spreadsheets, the power of applications, and the intelligence of AI, all in one easy to organize tab. Like I mentioned earlier, I use Coda every single day. And more than 50,000 teams trust Coda to keep them more aligned and focused. If you're a startup team looking to increase alignment and agility, Coda can help you move from planning to execution in record time. To try it for yourself go to coda.io/lenny today and get six months free of the team plan for startups. That's C-O-D-A dot I-O slash Lenny to get started for free and get six months of the team plan. Coda.io/lenny. I'm gonna come back to this cheesy plugin. Say more about this. So this is a plugin that just lets you put a custom message on every new tab, and it just ... You have it say, "How can you use AI to do this?"
- ACAparna Chennapragada
Yeah. It's as, as cheesy as that. And it's interesting because it works. Uh, in the last few, uh, weeks alone, I've been doing this, like, experiment to say, "Hey, how much more AI pilled can I get?" Like, uh, uh, yeah, both at work and in a person life to say, you know, when I'm trying to do anything manual, I'm like, "Should I be demanding the AI to do this?" (laughs)
- LRLenny Rachitsky
That's so cool. Do you know the name of this Chrome extension by any chance? Otherwise-
- ACAparna Chennapragada
No, no, I built it.
- LRLenny Rachitsky
You built a Chrome extension. That's so cool. Uh, okay. Uh, did you use AI to build it?
- ACAparna Chennapragada
Of course.
- LRLenny Rachitsky
Wow, which tool did you use to do that? Some kind of Microsoft tool, I imagine.
- ACAparna Chennapragada
Yes. Uh, yeah, no, actually it, it was just like ... I mean, I'm, I live in GitHub and GitHub Copilot, so just like, was like, "Okay, let's go build this Chrome extension."
- LRLenny Rachitsky
Wow.
- ACAparna Chennapragada
Yeah.
- LRLenny Rachitsky
Are you releasing this for the general public?
- ACAparna Chennapragada
(laughs) No. I mean, this, this, that's the fun, that's the ma- amazing thing. It took me like 10 minutes to do this, right?
- LRLenny Rachitsky
Hmm. Okay. Let's link to it. Let's get it out
- 35:45 – 37:47
Leadership styles of Satya and Sundar
- LRLenny Rachitsky
there, open source this thing. Okay. Uh, you mentioned Satya. I have a question about this. So, you're one of the very few people that have worked very closely with both Satya and Sundar at Google. Let me ask you this. How do their leadership styles differ? And is there just like a fun story that you could share about each of them?
- ACAparna Chennapragada
Yeah. I do feel, uh, I do feel lucky to have, uh, you know, kind of have a window into these two amazing leaders, um, of this generation. I would say, I mean, again, no surprise, they're ... As you'd expect from CEOs of multi-trillion dollar, uh, market cap tech companies, they are 99.99 percentile in like almost every dimension you'd think of, right? Intellect, empathy, leadership, you know, b- uh, product, uh, strategy. Um, there are of course flavors of differences. Uh, I was the technical advisor for Sundar with the first, uh, at, at Google, and set up kind of the office of the CEO there. Uh, and they are, again, a matter of like time and context because a lot ... There's a lot more consumer-oriented, uh, focus there. So what I did find Sundar great at is being really calm and measured and thoughtful in terms of, um, you know, uh, taking ... Making sure that things have ... Dealing with the complex ecosystems, right? If you think about the phone ecosystem or even like the search and publisher and advertiser ecosystem, it's a very complex ecosystem. He was a master at that.... he's an asset at that. And I think on Satya, I find it amazing the appetite he has for learning and fine-tuning (laughs) his mental models, and just like the, the zoom levels that he can operate at, uh, the macro, the strategy, what's the game, uh, also the micro. "Hey, what, why are we not..." Like, "Here's, like, a specific insight that I saw on Twitter." And, like, you can count on the fact that he is ahead of pretty much everybody else in terms of spotting those early things too. So it's, uh, it's just been like, like, uh, you know, learning from the fire hose as, as they put it.
- LRLenny Rachitsky
What a cool opportunity to work with two incredible folks. Okay, let's go in a, in a whole different direction. Let me just ask you this question that I've been asking people more and more:
- 37:47 – 41:20
Counterintuitive lessons in product building
- LRLenny Rachitsky
What's the most counterintuitive lesson that you've learned about building products that goes against common startup wisdom, common product-building wisdom?
- ACAparna Chennapragada
I don't know if it's, um, I mean, uh, as common as it should be, and it's, like, a counterintuitive thing, but I've repeatedly learned that w- when you're doing something new, zero to one, uh, uh, the temptation is to kind of think about, you know, it's like that South Park episode. Step one, uh, think abo- about the problem, step two, question mark-
- LRLenny Rachitsky
Underpants.
- ACAparna Chennapragada
... step three, produ-
- LRLenny Rachitsky
I think it's Underpants is step one. (laughs)
- ACAparna Chennapragada
Underpants. Exactly, right? Uh, so I do feel like there's a temptation to rush and say, uh, to go to scale before solve. So I've always said, uh, to my teams, "Solve before scale," right? So what that, what that does mean is there's a different posture and different mode when you're trying to solve a problem versus scaling something that's either post-product market fit or even at least, like, in the, r- roughly in the ball- ballpark. So to give you a couple of examples, right? I think when we, when you look at the solve stage, there are wide lurches. You gotta be very comfortable with the fact that you're day one thinking about, hey, a plant detection, uh, uh, tool, and then day 15 you're like, "Oh, actually, the tech is really good for translating in a foreign language." By the way, this is not hypothetical. This is what we kind of, like, looked at in Google Lens back, back then and said, "Okay, like where, what is the intersection?" And so on. So from the outside, it looks like chaos, but actually in the in- ... And you should be very comfor- ... Not only tolerant, I think you should be, like, should have an appetite for that, because the last thing you want is prematurely, like, you know, fix on one local hill, and then you're climbing that. And startups and entire product areas and companies, big companies make that mistake, and three years later you're like, "Oh, how do I get off this hill?" So I'd say that's one big counterintuitive thing. Like, when you're trying to think about, uh, what mode you're in. Are you in the solve mode? Are you in the scale mode? Uh, one example is kind of making sure that you're comfortable with the chaos. I think the other lesson I've learned is the danger of metrics, all right? And I think, uh, again, if you have worked on, you know, Google Search or if you worked on, you know, like, Office products, you'd really have, like, a very fine-grained sense of what are the metrics for this product. You have the input metrics, output m- ... You have the whole shebang. But when you're looking at something zero to one, if you decide on a metric too prematurely, that's false precision first of all, right? Like, you kind of, uh, I mean, CTR when you have, like, 1,000 people doesn't mean anything. Uh, you know, retention also may not mean anything. So really being very wary of, like, this, uh, big guy, big girl of grown-up metrics as I call it, right? You are looking for more qualitative, the sound of click, and what is your, as the other, uh, anec- ... uh, you know, kind of the handle I use is, what is your set timer and play music, right? So if you look at, like, Alexa and, like, Siri and Google Assistant and all these things, they had a very promising broad interface. You could say anything, but I think there was one or two things that it was really good at, right? Like, you could set a timer, you could play music, and you could play trivia. And so you got to nail those things before you say, "Oh, yeah, here, you can do anything with it," which is not a good recipe.
- LRLenny Rachitsky
That's so funny. That's exactly (laughs) what I use my Google Home for. Uh, (laughs) so basic. Uh, I don't do the trivia thing, though. Maybe I gotta give it a shot.
- 41:20 – 45:16
Inflection points for successful products
- LRLenny Rachitsky
- ACAparna Chennapragada
(laughs) Gotta try that, yeah.
- LRLenny Rachitsky
There's something along these lines that I've also seen you talk about, which is how to go zero to one with something, just kind of little framework for helping you know, uh, if this is the right time for this idea. How do you think about that?
- ACAparna Chennapragada
Yeah, I, I, ... And when we, when you think about the solve mode, and this is, again, like, uh, sticking with my whole, you know, living in one year in the future, I, I gravitate towards the zero to one and solve mode products completely thinking about new category of products. And what I found, (laughs) both the hard way, I would say, is that you do want to look for at least two out of these three factors', uh, inflection points here if you wanna make a really good product. Number one, is there a shift, is a step function in the tech, right? That's somewhat obvious, I would say. Like, you know, deep learning was one for Google Lens. Back then, speech recognition was a step function for, like, conversational, uh, search. I would say for Robinhood, you know, the, the generational shift was very clearly and the fact that phones were, uh, a primary means for, you know, you could actually have an app, a m- mobile app for finance that you could use. So look for that inflection, right? What is the tech inflection? And right now, of course, like, LLMs and reasoning models are that step function. But that's not enough. I would say the second factor that we should look for is, what is the consumer behavior shift, right? So, uh, to give you an example, when we started working on Google Lens, what we said is, look, people were taking mostly pictures for sharing, right? Selfies and sunsets and so on, and s- suddenly when storage became free, and, mostly free, and m- everybody had phones everywhere, all, a- all, all the time, you took pictures of everything, right? And then you had, like, enough of pictures or, you know, you used the camera as the...... as the keyboard for your, for your world, right? For the real world. And so how do you kind of then say, "Oh, this consumer shift is big," and so therefore, kind of like as it ... as you go order of magnitude more photos, then you want more a- to come out of them, and you can apply AI to that. And I'd say the third, uh, inflection point particularly I would say in enterprise but also in consumer is the business model shift, right? How do you ... Is there an inflection point, natural inflection point, in the business model? So, any great products, if you think about like, you know, all the way from search, again like the, the second price auction and the fact that you had like, you know, s- uh, CPCs. Same thing with SaaS and the fact that you could actually charge, uh, uh, or, or monetize, uh, enterprise products in a different way. And with AI of course, like, the monetization is a whole different like ... I mean you, we've just, uh, barely scratched the surface of, uh, whether you do, you know, seat, uh, monetization, usage, like on tap, and then of course outcome-based stuff, outcome-based monetization. "Hey, have you solved the problem for me? And then I will pay you some fees," right? So, all three, like to me are, you know, kind of like great, but at least two out of three for a good product.
- LRLenny Rachitsky
So there's essentially ... When investors look at startups they're always asking, "Why now? Why is this the time to start this thing?" And so your advice here is, you should ... There's three ways to look at it and you should ... Two o- two of these three should be true. There should be a, a shift in technology, some new technology that has enabled this now, recently. There's a shift in consumer behavior. And then there's maybe a new sort of ... or you've invented a new business model. Like any way to monetize something that, uh, it gives you an advantage over folks-
- ACAparna Chennapragada
Yep, absolutely.
- LRLenny Rachitsky
... trying to do it today. Awesome. And, uh, you didn't mention Robinhood I think in that example. That was another good example of-
- ACAparna Chennapragada
Yeah.
- LRLenny Rachitsky
... following the same-
- ACAparna Chennapragada
Yeah, I mean talk about the business model of kind of, uh, again like, uh, uh, not, uh, having a zero, um, uh, you know, zero fees, right? And again, like, b- the combination of all of these things is what can unlock it, not a- a ... You can't just say, "Oh, we'll just have a much s- much more better intuitive interface and hope that, uh, you know, people will switch to it."
- 45:16 – 48:34
GitHub Copilot and code generation
- ACAparna Chennapragada
- LRLenny Rachitsky
Okay. So, speaking of zero to one products, I'm gonna take us to a occasional segment on this podcast that I call Hot Seat Corner, and I have a question for you that is on my mind, and it's come up on a couple recent podcast actually. So there's these companies like Cursor, v0, Lovable, Bolt, Replit that are like the fastest-growing companies history, uh ... I just saw that Cursor hit 300 million ARR in two years. Interestingly, you guys were very well-positioned to do really well in this space, this AI coding tool space. You guys had Copilot, the first tool in the world at this stuff, so ahead of everyone. You built VSCode which is what all these companies are forking to build on. You have incredible AI infrastructure, incredible AI talent, so this coulda been your market. What happened? What happened to Partner?
- ACAparna Chennapragada
You know, it's interesting, the framing, uh ... So, I'm a daily user of GitHub Copilot, uh, and I would say, look, uh, the, the f- like l- if you unpack, I think the thing, the, the beauty of this is that code generation has become an amazing tool, uh, that LLMs have unlocked, right? So it is not so ... It is actually really good excitement and action that now code generation has just opened up all of these things that we've talked about the whole idea of like prototyping. Go, go from idea to marks and idea to kind of a clickable prototype in like, in a few minutes. Those are the kinds of things that of course we should expect code generation to, uh, enable. The way I think about, uh, uh, you know, how we, uh, we are positioned and like what we, what we do with GitHub is ... So it's a system, not just a product or a set of features. If I think about GitHub, it's for folks who are, who have their rep- repo there, right, and you have kind of, uh ... Of course you have the assistance in terms of auto-complete and you can chat, but now we have the agent mode. It's one of, one of the fastest, um, you know, kind of loops that we are seeing, really strong positive feedback. So in some sense, when you have a system, uh, what you are looking for in terms of building and designing it is not just a single product that can go, grow, but it's the what is the repository, what is your context, what are the set of features that grow from your expertise, right? If you're a really expert coder, you want kind of like the, you know, assistance. The sca- this product needs to scale for that. If you're a wide coder, you should still be able to do that and so on. Right? So that I think is the way that, um, uh, that GitHub is positioned to, uh, build on and like growing, honestly, really well.
- LRLenny Rachitsky
That's so interesting. So ba- it like ... The core of this is everyone ends up in GitHub anyway, no matter what tool they use, and that's kind of the-
- ACAparna Chennapragada
Yeah, and I think the, the, yeah, the idea again is that, you know, code generation as a tool will unlock lot more products. I mean, they're not all competitors to the fact, uh, of, uh ... They're not all kind of, um, uh, you know, uh, doing the same job. I think when you're ... At the end of the day, like you're building, uh, code for companies to run on, you need to have a system, you need to have kind of the ability to ha- an entire Swiss Army tool- toolkit, right? Not just the auto-complete, not just a chat, not just like a software agent that runs and you kind of like hand-hold. You need all of this to work together, and that's what the GitHub, uh, product is going after.
- LRLenny Rachitsky
All roads, uh, lead to GitHub.
- 48:34 – 50:27
Excel’s enduring success
- LRLenny Rachitsky
- ACAparna Chennapragada
(laughs)
- LRLenny Rachitsky
Uh, on the flip side of this question, (laughs) uh, there have been, uh, probably 5,000 startups that have tried to disrupt Excel, and you guys just keep winning. So, something there is working really well.
- ACAparna Chennapragada
That is so interesting you say that. So when I, um, came to Microsoft, uh, and I'm an Excel fan, so I actually had a conversation with one of the OG, uh, Excel product folks. I was like, "Man, what is it about this, th- this, uh, product?" And he said a couple things that were really interesting for me that just stuck with me. One is, you know, he said, "Hey, you know, Excel is a proof that non-coders also have to program," right? Programming is really powerful.And it's the tool that gives all of the non-coders a really powerful programming, uh, uh, you know, ability. And I thought that was just, like, really, um, striking. And then the second thing that I found out, super cool, uh, did, I don't know if you know this, but I didn't know at least before, uh, two years ago, that there are these amazing Excel championships-
- LRLenny Rachitsky
Mm-hmm.
- ACAparna Chennapragada
... like World XM Championships, where you see folks who can do just magic. And to me, I think the insight here is also that some tools are harder to learn, perhaps, in the beginning, there's friction in terms of learning, but great to use, right? So, it, it's a very good, uh, uh, uh, case of, hey, the learning curve initially, the one-time learning curve might be tricky, but it is because there's so much power, uh, and depth in the, in the tool.
- LRLenny Rachitsky
That's so interesting. I never thought of Excel as a programming language, but, but it makes sense. And I feel like once you get used to it, and this is just the way things work, you, you're kind of stuck there, and everything else has to basically copy that model, which is hard to be as good.
- ACAparna Chennapragada
Yeah, and I think the, the depth and the attention that the, that the team is given-
- LRLenny Rachitsky
Mm-hmm.
- ACAparna Chennapragada
... and again, that's the compounding effect over, you know, decades of working on, like, deep, deep, uh, signal, right, from people who live, uh, who depend on
- 50:27 – 54:55
Pivotal career moments
- ACAparna Chennapragada
it day in and day out.
- LRLenny Rachitsky
Yeah. Okay. To s- to kind of start to close out our conversation, I want to ask this question around, uh, your career. And I find that most people have a p- like, one moment in their career that changes the trajectory of their career. It could be, like, a manager they had, it could be a project they worked on, it could be just a job they landed. What would you say is the most pivotal moment in your career that eventually led you to becoming Chief Product Officer at Microsoft?
- ACAparna Chennapragada
Actually, the, there is one moment where, you know, it was a turning point for me. I was in Google, uh, Search. I was working on this idea that I thought should just work, and it didn't, right? Like, I ve, I s- I said, "Hey, um, these phones are becoming a thing. Personalization has to be important." So I, I probably banged my head against the wall for a year or so, uh, trying to make personalization work. And it turns out when you have a, you know, query, uh, that you put into Google Search, like, the personalization didn't matter as much. And so, you know, we disbanded the team. But then I think, um, I started working on this product called Google Now, which was a twist on that, which said, hey, actually on the phone, we should be able to, like, push content. It's not about, like, you know, searching, uh, uh, with personalization. For example, if you have a flight coming up, it shou- we should be able to say, hey, connect the dots and say, "You should leave now for the, you know, g- given the traffic and where, where you need to go," and so on. Or if you're deeply interested in, I don't know, standup comedy with deadpan artists, you should check out Mitch Hedberg. Like, these are kind of, like, these, uh, really moments that the f- smartphone should be smarter. So h- I led that product through the, kind of the initial zero to one phase, and that was a pivotal moment. It made me realize two things. One, I really love seeing around the corner and kind of seeing wh- where things go and building the product to rise to the occasion, uh, way more than, you know, the, the scaling and sus- sustaining, uh, products. Second, it's harsh but being early is, is the same as being wrong. (laughs) You know, this is pre-LLMs, pre-deep learning, uh, lot of the really amazing ideas in terms of next token predictor, et cetera, we'd, we'd been thinking of it, but, you know, didn't have the horsepower to go. The interface was great, the intelligence wasn't there. And I'd say the third, uh, thing that stuck with me is I got to work with re- some really smart, like, they talk about talent density now, right? And I think really smart people who have gone on to do, like, amazing things. And so kind of, like, it gave me a taste of what a small group of people can do.
- LRLenny Rachitsky
That's such a great story because, 'cause it didn't work out, right? In the end. Like, Google Now kind of went away, right? And by the way, I super remember that product. It was very cool. I remember looking at it as very, like, delightful and happy. And so I, I also have this segment on the podcast called Failure Corner, where people share a story of failure and how that helped them, and I love this is a combination of those two.
- ACAparna Chennapragada
Yeah, I mean, I, I'm not gonna lie, I think it was, uh, it was, um, it's painful when you do that, because you s- you see the vision of what can be and what is, and sometimes it's hard limitations. Sometimes it takes, like, you know, in this case it takes, uh, five years or 10 years to kind of, like, really unlock the intelligence. But sometimes it's, uh, it's one or two key clicks, click stops away from the product being great. Uh, and part of figuring out is knowing when, (laughs) when you're in what situation.
- LRLenny Rachitsky
How long was that period from, from starting on it till they're just, like, "Move it on." And it's not working out?
- ACAparna Chennapragada
Yeah, I would say in that case one of the good things is again, like, the f- the, it led the foundation of, it was one of the foundations of the Google Assistant. And, of course, as the LLMs, you know, step function happened, now with Jim and I, it kind of, like, w- works out. Uh, and I think it's the same thing across the board, which is, uh, sometimes you want to kind of figure out the invariants that do work, right, that can then, tha- then go on to the next version of the product, and other times you just have to start over.
- LRLenny Rachitsky
(laughs) Was Google Now the first agent before agents? That's what it feels like.
- ACAparna Chennapragada
That was certainly the idea. Uh-
- LRLenny Rachitsky
Yeah.
- ACAparna Chennapragada
... you know, inter- but it is f- fascinating to me that the interface, that, there we had the opposite problem. Like, whether you think about all the voice assistants, right? The, um, interfaces, like, we overshot and the intelligence wasn't there. Today, I feel like there's an opposite problem. I think these, these things have amazing intelligence and the interface we have largely is like the AOL, AOL dial-up modem chat bot.
- 54:55 – 56:25
The future of human-agent collaboration
- ACAparna Chennapragada
(laughs)
- LRLenny Rachitsky
We've covered a lot of ground. Is there anything that you wanted to chat about or leave listeners with, maybe a last nugget of wisdom before we get to our very exciting lightning round?
- ACAparna Chennapragada
I think I would say one thing that I'm really excited about is this idea of figuring out how we as people and agents collaborate together-Right? I think there's, like, some great set of products and experiences to be reimagined. That's my other Roman empire, which is how do we actually have this co-working space where, uh, you know, you have kind of, like, the, uh, the humans and, uh, agents, and how do you actually kind of have an output that's much, much more significant than what any one of us or any few of us can, uh, produce?
- LRLenny Rachitsky
Well, I need to hear more about this. What do you... When do you imagine a co-working space of humans and agents? What does this look like? Is this like Microsoft Teams or is this like a physical place with little robots?
- ACAparna Chennapragada
Oh, I hadn't thought of the physical place, but I, I, I, I am think- I am thinking a lot about kind of... You know, right now all of these experiences are very single player, right? And I do think there's an opportunity to think about how do we... Again, I'm living one year in the future. How do we actually have, like, you know, collaborate with each other, but with also with agents and really, uh, figure out, for example, uh, what task can we delegate? What can be kind of, like, in fact, how do we actually have information that flows between people that agents can mediate and so on?
- LRLenny Rachitsky
Hmm. All right.
- 56:25 – 1:01:12
Lightning round and final thoughts
- LRLenny Rachitsky
I'm curious to see what you guys got cooking. With that, we've reached our very exciting lightning round. Are you ready?
- ACAparna Chennapragada
Let's do it.
- LRLenny Rachitsky
Let's do it. First question, what are two or three books that you find yourself recommending most to other people?
- ACAparna Chennapragada
Oh, I have recency bias, but I've been reading this book called, uh, The Brief History of Intelligence. Um, phenomenal book and, uh, you know, like lots of, uh, lots of underlining from me. And I think it kind of, uh, the, the premises to it, it looks at the evolution of intelligence, like human intelligence and kind of the, the brain development and, uh, co- connects that to what we're, uh, what we're seeing with AI.
- LRLenny Rachitsky
Do you have a favorite recent movie or TV show that you really enjoyed?
- ACAparna Chennapragada
Hacks. I've been watching, uh, this. It's about a woman who, uh, uh, who's this, like a great standup comedian of, uh, I think it's set in kind of like the, um... The fact that she, she grew up, uh, I think in the, uh, s- '70s and '80s and kind of like really tried to break through in an industry that hasn't traditionally been like very, uh, friendly to women. So, really fun and, uh, quirky.
- LRLenny Rachitsky
Do you have a favorite product that you recently discovered that you really love? Could be an app, could be something physical.
- ACAparna Chennapragada
I ha- I do use a lot of Microsoft products, GitHub (laughs) Copilot being one of them. But I think the one that I maybe, I, I'll pick is, um, Granola, I think is the name of the app. I, I found it really useful. Uh, I just gave it a spin the other day and I'm like, "Oh, this is really useful in terms of being able to, um," you know, again, like without being intrusive, just, uh, just capture the, uh, thoughts, notes and structure it. Put some... It, it, it felt like one of those things where you have the confluence of a few things like we were talking about, right? Like the transcription, real-time transcription, Tech has gotten really good. Voice recognition is great. And then enough of the LLM magic on top of it to kind of make it structure and contextual.
- LRLenny Rachitsky
I'm a huge fan of Granola. I'll give a quick pitch here. If you become an annual subscriber of my newsletter, you get a year free of Granola for your entire company.
- ACAparna Chennapragada
Did not know that. Okay.
- LRLenny Rachitsky
There we go. So, and then just check that out, lennysnewsletter.com and you click the word bundle and you'll see how to do that.
- ACAparna Chennapragada
Very cool.
- LRLenny Rachitsky
Very cool. Uh, two more questions. Do you have a favorite life motto that you often come back to when you're dealing with something, so maybe you share with folks, they, they find useful as well in work or in life?
- ACAparna Chennapragada
Uh, I have one. In fact, actually this is my email signature for, I don't know, for the last, uh, uh, 20 years or so. Uh, it says, "The best, uh, way to predict the future is to invent it." I think it's a quote by Alan Kay. I find it useful for two things. One is, you know, no one knows anything. Like when you think about like all the folks who are pro- uh, you know, kind of think about, "Hey, this is the, this is exactly how everything is going to look and this is exactly the sequence and so on." I think there's no substitute to experientially like building it. And, uh, and I think the second part is, you know, like if you think there's something that is, that should exist, go build it.
- LRLenny Rachitsky
I love that. Final question. We've talked about standup comedy a bit. Is there a, is there like a favorite under the radar standup comedian that you think people should go check out?
- ACAparna Chennapragada
Oh, uh, there's a, there's a couple of them. So one, I think there's a, um, there's an Indian American or a, I think, I think a British-Indian, uh, standup comedian. Uh, her name is Sindhu Vee, super smart, you know, mom comedy. And I think the other one that he... This is definitely not under the radar, but like, I'm just like, love his, um, s- schtick is, uh, Nate Bargatze. He's just so good.
- LRLenny Rachitsky
Aparna, this was amazing. Two final questions. Where can folks find you online if they want to reach out maybe and follow up on anything you shared, and how can listeners be useful to you?
- ACAparna Chennapragada
You can find me on LinkedIn and, uh, Twitter. Uh, AparnaCD, uh, is the handle. Uh, I do post stuff a lot more on LinkedIn these days, so, um, you know, would love, uh, would love to hear, um, thoughts, comments, conversations there. I'd say one thing that would be super interesting is if any of this stuff spark conversations, particularly around like kind of, you know, this, uh, what do, what can a small team with a lot of AI tools do? Or new products that folks are really excited about saying that they should exist, hit me up.
- LRLenny Rachitsky
Amazing. Aparna, thank you so much for being here.
- ACAparna Chennapragada
Thank you.
- LRLenny Rachitsky
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.
Episode duration: 1:01:12
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