Microsoft CPO: If you aren’t prototyping with AI you’re doing it wrong | Aparna Chennapragada

0:00

I have a cheesy Chrome extension.

0:00

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?

0:06

How do you see the future of  product development being different?

0:09

If you're not prototyping and building to see  what you want to build, I think you're doing it wrong.

0:14

It becomes even more important  to have that territorial and taste-making at the heart of it because, otherwise,  you just have a Frankenstein product.

0:23

There's this acronym that you  taught me, NLX. What is that?

0:26

Natural language interface. NLX is the new  UX.

0:26

Often I hear a product builders say, "Oh, yeah.

0:32

With AI, the model eats the products."

0:32

That doesn't mean it's not designed.

0:32

You and I are having a conversation. It's a podcast.

0:36

I'll  have another conversation at Microsoft and that's a meeting.

0:41

Conversations also have grammars. They  have structures. They have UI elements. They're invisible.

0:46

What are the new principles, new  constructs in natural language as an interface?

0:52

I just saw that Cursor hit 300 million ARR in  two years.

0:52

Interestingly, you guys were very well positioned to do really well in this  AI coding tool space.

0:58

You guys had Copilot, the first tool in the world at this stuff.

1:02

So ahead of everyone, what happened? I would say...

1:08

Today my guest is Aparna Chennapragada.

1:08

Aparna  is chief product officer at Microsoft where she oversees AI product strategy for their  productivity tools and their work on agents.

1:17

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.

1:27

She was also a long-time engineering leader at  Akamai, and on the board of eBay and Capital One.

1:32

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.

1:45

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With that, I bring you Aparna Chennapragada.

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4:25

Aparna, thank you  so much for being here and welcome to the podcast. Thank you, Lenny. Thanks for having me.

4:37

When I asked a lot of people that work with you, what I should ask you about and what I should know  about you, something that came up again and again, it's something that I think most people don't  know about you, which is that you're big into stand-up comedy, and you take it semi-seriously.

4:48

Just how serious are you about this?

4:48

How much of your life is this and most importantly, how  does this help you build better products?

4:59

It's hard to say I'm serious  about a funny business, but I do watch and do stand-up comedy. I  do open mics. I've done a few shows. Wow.

5:09

I have one set brewing that is around AI,  unsurprisingly AI and tech and Silicon Valley.

5:17

It's really interesting for me.

5:17

This was  an accidental discovery.

5:17

I had always been an SNL fan and Discovery fan, but I went to an open  mic because my son sings, and he went to the open mic for singing and he is like, "Mom, you  should go do this."

5:29

And I was like, "Oh, let me go give it a try," and I found that I enjoyed it  and was good at it.

5:33

To your question though, about building better products, I'd say both have PMF,  I mean, product market fit, punchline market fit.

5:49

Actually, there are a couple of things that  I do find really powerful and useful because in open mics or even when you're testing these  things, it's a very tight cycle of iteration, and you get live...

5:58

Open mics are the real  live experiments.

5:58

You put something out there, you get very clear micro feedback from users,  and then you get tough feedback sometimes.

6:08

And I think as product builders, that's  actually one of the great skills to have, which is you sometimes launch stuff that have a  fantastic vision, but the first version is not quite there.

6:20

And Reid Hoffman says this, "Hey,  if you don't launch the first version and are not embedded, you're doing it too slow."

6:24

Just  that gap in closing that, it's good resilience. Yeah.

6:30

I never saw these corollaries between these  two things.

6:30

I didn't realize you actually did shows, and you're working on a set.

6:34

I wasn't  going to ask you for a joke, but if you're working on a whole thing about AI, is there  something that you can share from that set?

6:44

One joke I'd maybe share is people think about  these AI chat products as women because you don't know what's going on.

6:54

It's a black box, and  you don't know what they're thinking.

6:54

There's an entire set around that, but obviously on  the flip side too, that they're probably more like men in the sense that they hallucinate  a lot.

7:05

They kind of are not yet reliable.

7:12

I'm afraid to laugh with this  a little bit. This is great.

7:16

And even when they don't know the answer,  they make up stuff. They're very confident. This is good.

7:21

Where are we going  to be seeing the show by the way? TBD. Okay. This is great.

7:26

Okay, let's get serious  again.

7:26

So you worked at most of your career at a lot of consumer internet companies.

7:32

You worked  at Google, Robinhood, you're on the board of eBay, you're on the board of Capital One.

7:36

Now, you're at  Microsoft.

7:36

I'm curious just what is most different about working at a company like Microsoft and  building product at a company like Microsoft?

7:46

I think intellectually I knew that, hey,  enterprise, particularly the area that I look at most at Microsoft is focused on enterprise and  productivity and transforming companies through AI.

7:57

And to me, I think two things really strike as  very different.

7:57

One, in fact, I just posted about this the other day 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...

8:15

Every time 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.

8:25

If you think about 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 safe and being able to have auditability and all of those things.

8:37

And often, I  find that when you go from a consumer enterprise, you fall into a trap of either disregarding that  and say, "Oh, we'll just focus on one side of the house," or overly crippling the user experience  side and leaning on the other side.

8:49

So I think there's an art and science and nuance and playbook  there too, so that's one big learning for me.

8:56

The other learning, and especially in the AI era  for me has been about this...

9:02

I think there's a famous trailer from the 2000s on Van Damme  on these two buses [inaudible 00:09:13] splits. Like doing the splits.

9:14

Yeah, doing the splits, exactly.

9:14

I feel like a lot  of the companies, including the tech companies, but certainly the enterprises that I talk  to are in these two modes where one hand, this is the most compressed tech cycle that  we've ever experienced.

9:25

It's in the order of weeks and months versus years and decades.

9:29

If  you think about mobile and cloud and internet, and there's just so much happening, the  intelligence overhang.

9:35

On the other hand, there's also humans and habits that...

9:42

Productivity habits change.

9:42

It's hard to change and change management through the  company is also hard.

9:47

You don't want to be rash on that.

9:53

So it's like the future is unevenly  distributed but even within the companies.

9:59

On the second bucket of the bus that  Van Damme's riding on of governance and adoption and changing behavior and stuff, is there something you've learned about  how to get past that, help that along more?

10:10

The thing not to do is hold back folks who are  early adopters.

10:10

I think that's the other one learning.

10:20

In fact, I think that's one of the  reasons why recently...

10:20

I've been working with folks to say, "Can we have both," which is the  longer-term change management, being able to do it in a trusted way, at the same time do this  program we are calling Frontier program and roll out cutting edge experimental features.

10:37

We  just built this world's first deep research agent made for work, post-trained for work.

10:44

And of  course, it has all sorts of edges, rough edges, but if there are only adopters in an enterprise or  outside, how can we put that in the hands of those folks without insisting that all of the company  be completely developing different muscles?

11:04

This program Frontier you're talking about, I wanted to spend a little time on  it. So what is the idea?

11:06

The idea here is people are working in this futuristic  environment.

11:10

How does that actually work?

11:14

Yeah, I think the idea is exactly this,  which is I want to kind of institutionalize and operationalize my personal model of  living one year in the future and say, "What does this..."

11:22

Imagine a company or a setup  like Frontier Consulting Group or Frontier Inc. , right?

11:30

And if you did live 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?

11:37

What's the kind of work you'd be doing?

11:42

How would you change  how you're going about your work day?

11:42

So that's the premise and you'd say, "Hey, how does it  change an individual?"

11:47

But also down the lane, we want to think about what does a Frontier  team look like.

11:52

We talk a lot about Frontier labs and models.

11:56

I think models layer is  amazing and obviously that's what empowers all these product building to happen, but I want  to push us to think about what does a Frontier product look like?

12:08

And more importantly,  how does a Frontier way of working like?

12:14

What does a team with three people and  tons of compute and AI tools look like?

12:20

So how exactly does this work?

12:20

There's  a team within Microsoft that's like your job is to use all of our latest tools and  build product using that. Does that work? That is the setup.

12:28

We are just  a few weeks into that setup, but meanwhile what we have done is we've  actually set up a fake company and said, "Hey, if you are somebody who wants to  come play with some of the cutting edge science projects and deep research agents  and agents at work, come party here." Wow.

12:51

And it's only a few weeks  in.

12:51

Okay, so TBD how it all goes. Yeah.

12:54

And again, these are micro... Let's  see.

12:54

The meta point here also is that in the traditional way, we've kind of always thought  about across the companies, across industries, really thinking about roll-outs in these macro  ways.

13:03

You build something and you kind of roll it out, you have a general availability for,  and then you take the time.

13:09

And that's really important too because, again, we are talking  about pharma companies, legal companies relying on this.

13:19

So we do want to have that.

13:19

But at the  same time, given the compressed cycles of AI, how do we start to have people experience  what's the one year in the future?

13:29

Let's follow this thread in a few  different directions.

13:29

There's how product development changes, there's  how engineering changes.

13:32

There's also just agents.

13:36

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 or building an agent.

13:42

Lenny, you're doing this wrong.

13:42

You didn't use  the word agents so far into the conversation.

13:50

I try hard to push it out as far as I can.

13:50

It's like every conversation in San Francisco, it's just like how long until I start talking  about AI? It's like three minutes. Average, I bet. Oh, man.

14:00

Okay, 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  does this mean? What is going to change?

14:06

Give us just a glimpse into how you see the world being  different in a world of agents being around more.

14:18

There's a short term and there's a long term,  right?

14:18

There's a lot of hyperventilated, excited talk about the eventual future and all of that.

14:24

I take a much more practical product building lens on this, and I think about these.

14:31

At the end  of the day, there are tools.

14:31

Yes, underneath it, there's stochastic models versus very  deterministic programming models.

14:37

You can tell I'm a computer scientist like the way that worldview  definitely shapes how I think about this.

14:41

To me, the short term is there's an evolution.

14:47

We  had apps, and now I think we are firmly in the assistance era where there's human driving  the...

14:54

That's what we think of as co-pilot, right?

15:00

I think the human driving in the driver's  seat but having a lot of assistance from AI.

15:07

So I think of this as then you look at the  dimension of almost autonomy and delegation and intelligence.

15:13

As the intelligence, for example,  when deep reasoning unlock happened, of course, then you can delegate more to the agent.

15:19

So I  think, to me, there's one dimension where you say, "Hey, agents are somewhat independent software  processes that can kind of run tasks," and you're not just thinking about handholding  and fine motor stuff.

15:33

You're saying, "Hey, here's my goal. Go make this happen."

15:37

I'll  give you an example.

15:37

So we are working on this researcher agent for work.

15:41

And last night,  I said, "Hey, I have an important meeting coming up with the leadership team.

15:48

I really want to  present these frameworks here and this is the roadmap here.

15:52

Go back and look at all the people  that are in the meeting.

15:52

What are their views on this topic and come up with how I should I be  thinking about the right persuasion pitch here?"

16:07

And what's magical about this is not just that  it's saving time.

16:07

Typically, we think about the, so far, AI as summarizing a document or saving  time.

16:11

This is like fighting synapses that I didn't quite have and actually giving me  new insights and giving me, dare I say, superpowers.

16:22

So that's a natural evolution of  AI, I would say.

16:22

So when I think about agents, I think about three things.

16:28

One is an increasing  level of autonomy and kind of independence that you can delegate higher and higher order tasks.

16:36

Second thing I think of it is complexity.

16:36

So it's not just a one-shot, "Hey, create this image or  do this thing or summarize the document," it's build me this prototype that expresses my idea  of, say, an augmented reality app. It's a complex task.

16:55

And then the third thing I would say is  asynchronous.

16:55

It works when you are not working.

17:00

I think that's the other big thing about these  things that you don't have to sit in front of it.

17:05

This answers the question of  what is an agent essentially, these three bullet points.

17:07

So what are the three again?

17:10

When I think about agents, I think  about these three things.

17:10

So one, it's autonomy like being...

17:15

And it's a spectrum,  it's not a zero-one, it's how do I actually delegate things that it can do.

17:21

Second, I think  of as complexity.

17:21

It's not a one-shot, "Hey, summarize this document, generate this image,  but it's build me this prototype or help me knock this meeting out of the park."

17:32

And then the  third one I think of is it's a much more natural interaction.

17:38

That doesn't just mean chat,  but it may be actually jumping on a meeting with the agent and being able to talk through  all of it or point it to things that I wanted done differently.

17:47

So I think all three things,  the autonomy, the complexity, and the natural interaction are at least product principles  that will shape really good ones, good agents. That is really helpful.

17:58

Along this line of agents, there's this acronym that you taught me as  we were chatting ahead of this podcast, NLX, what is that and how does that relate to agents  and why are people not thinking about this enough?

18:10

Oh, that's one of my Roman empires these days.

18:10

The natural language interface. NLX is the new UX. Here's the deal.

18:16

To me, I think traditionally  we've thought very consciously about GUI because the graphical interfaces are not something  natural, and so they have had to be explicitly designed, but they're rigid interfaces.

18:32

What we  have with conversational interface and natural language is it's a much more elastic, right?

18:38

That doesn't mean it's not designed.

18:38

Often, I hear a product builders say, "Oh, yeah.

18:45

With AI, the model leads to the product.

18:45

So it's just you chat with it."

18:49

You and I are having  a conversation, it's a podcast.

18:49

I'll have another conversation at Microsoft and that's a meeting.

18:55

So conversations also have grammars, they have structures, they have  UI elements, they're invisible.

19:05

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 an  interface?

19:10

I'll give you a few examples.

19:16

And actually a lot of startups as well as big  companies are really experimenting with this stuff.

19:21

One is if you think about it, prompt itself  is a new construct and that's a new UI element just like a dropdown was or a menu was.

19:28

But  others that are emerging, especially for agents, I think are plans.

19:34

So when you give a 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.

19:44

The other one that I think about a lot is  showing the work, progress.

19:44

You see this with different products.

19:53

You see with the Copilot, you  see with ChatGPT, DeepSeek, this idea of thinking aloud and it's kind of showing the work, but how  much do you do it?

19:59

If it's too verbose, it feels like I'm running some cron job and scripts, 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.

20:11

So there are all these new elements.

20:11

So if you are a product whittler, this is a fun new  space to be digging in for product design.

20:22

This is really interesting because I think  people chat with all these chat bots and it just feels like this is just the way it is,  but you actually are designing every element of the interaction, how much to share, but  how much you're thinking, here's my plan, what do you think.

20:36

So I think 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. Yeah.

20:47

Another good example is follow-ups, right?

20:47

You could say, "Look, you asked me a question," and then I could ask a follow-up set of things,  and that's explicitly should be designed for success.

20:59

So for example, if I said, "Hey, create  an image," and it created a black and white like a clip art version of something.

21:07

What are the next  obvious follow-ups that it should be suggesting proactively?

21:12

Now, too much and you are kind  of annoying me, but too little in some sense, you've lost an opportunity to direct  me or guide me into a happy path here.

21:25

This resonates a lot with when we had Kevin Weil  on the podcast, he talked about this question of just how much to show about what you're saying.

21:29

And it's interesting that DeepSeek went the extreme of just showing everything and people  liked it too.

21:34

I think that was interesting.

21:38

Yeah, and I think it's a point in time thing too, Lenny, because in some sense right now these  things are such black boxes.

21:41

They're almost like peeking under the hood for anything.

21:46

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.

21:55

So it just feels like if you just went  silent, I'd be very uncomfortable, I think. I know. Exactly.

22:04

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.

22:09

For example, again  in human, my API would be very different from somewhere.

22:17

My interface is probably different  from others, and I might just want the direct, "Hey, give me the TLDR," versus the, "Oh, so I  went here and then I went there," and I'm like...

22:28

Following the start a little bit.

22:28

We're  talking about just how the future is going to be different.

22:31

There's designing for  these chat experiences, there's agents, 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 going to 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.

22:43

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 succeed in that future?

22:59

I'll start with one stark statement that I say  internally and externally, and I am 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.

23:13

I call it  the prompt sets of the new PRDs.

23:13

I really insist on folks saying if you're building new projects,  new features of course come with prototypes and prompt sets.

23:27

And I think the notion is not to say,  "Hey, now everybody's just a biggest version of a software engineer."

23:36

It is to say you have the  fastest path to seeing and experiencing what's in your mind to be able to communicate, right?

23:46

It's  a much more high bandwidth way of communication.

23:52

I think about that as a really a loop accelerator  in terms of product building. That's number one.

23:57

When in doubt, as someone put it, demos before  memos, right?

23:57

I think that's really number one.

24:04

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 is much  shorter, but the time to a full deployment is going to take longer.

24:19

So I think that there's  going to be an uneven cadence.

24:19

So typically, I think there was much more of a you've been  this thing, you take a few weeks and then you can iterate and so on.

24:28

But that inner loop of  prototyping and iterating and getting even user research through AI conversations, all of that  gets shortened.

24:35

But I think the bar for scale, therefore becomes much high.

24:42

In some sense, if you  look at it, there's going to be a supply of ideas, a massive increase in supply of ideas in  prototypes which is great.

24:49

It raises the floor, but it raises the ceiling as well.

24:56

In some  sense, how do you break out in these times that you have to make sure that this is something  that rises above the noise?

25:01

So I would say that it's simultaneously thinking about not chasing  after every idea.

25:08

I think is the second one.

25:14

I'd say the third thing is there's a lot  of conversation around full stack builders.

25:19

What does the team of the future look like?

25:19

A  product building team.

25:19

What I think about is I think that is inevitable in terms of there  will be a few folks that are, especially at the prototyping early idea discovery stage that the  lines of blurred, there'll be a few taste makers at the same time.

25:37

I think you can still have a  lot of people experimenting.

25:37

It becomes even more important to have that editorial and taste making  in a Frontier, one or a few at the heart of it because otherwise you just have Frankenstein  product.

25:52

That definitely doesn't change.

25:58

I have one other additional bonus thing, which  is a lot of folks think about, "Oh, don't bother studying computer science or the coding is dead,"  and I just fundamentally disagree.

26:04

If anything, I think we've always had higher and higher layers  of abstraction in programming.

26:12

We don't program in assembly anymore.

26:20

Most of us don't even program  in C, and then you're kind of higher and higher layers of abstraction.

26:26

So to me, they will be  ways that you will tell the computer what to do, right?

26:34

It'll just be at a much higher level of  abstraction, which is great. It democratizes.

26:38

There'll be an order of magnitude more software  operators.

26:38

Instead of Cs, maybe we'll have SOs, but that doesn't mean you don't understand  computer science and it's a way of thinking and it's a mental model.

26:49

So I strongly  disagree with the whole coding is dead. That's awesome. I love that.

26:54

And SO is a software  operator, what is that? What that stands for?

27:00

Yeah, I just made it up but yes. Okay, cool.

27:04

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 a thing everyone has to do?

27:14

Is it just culturally do it or is it like you  must show me a prototype before you show me it.

27:20

Again, the future is here, unevenly  distributed, even in Microsoft I would say, but there is certainly a strong cultural  momentum and shift and desire to say, "Hey, let's actually look at live demos, live  prototypes, and to even communicate the ideas.

27:39

And to me, I mean, it's not always possible  because obviously there are things that are deeply...

27:44

If you're trying to change something in  the bowels of Excel, you probably don't.

27:44

There's even enough depth in the product that what you  need to do, and you don't need to prototype that.

27:56

But if you're especially thinking about new  things and new products, new features, absolutely.

28:01

Okay, let's talk about product management.

28:01

There's this fear that emerged as soon as all these AI coding tools came out of just like  PMs are dead, we don't need PMs.

28:06

We could just build things ourselves.

28:11

What are these people  hanging around for?

28:11

And what I found is it's actually the opposite that now that coding  is easy.

28:16

Now, the question is more and more, what should we be building?

28:22

Why should we  be building it? Is this right?

28:22

Is this the right solution?

28:25

Then getting adoption for  it, which is what PMs are really good at.

28:30

I feel like it's the opposite.

28:30

PMs are the  most important role.

28:30

It'll change too, but let me get your take.

28:35

Just what do you think the  future of product management looks like? Do you think it's dead?

28:38

Do you think it's going to  thrive?

28:38

Do you think it's going to change? Yes.

28:41

Look, if you are a TPS report, mostly  process person, and a lot of companies do get confused about product management  and process and project management, I think then you do have a question of, "Hey,  what is the value add here," especially if AI can read and write 50,000 meeting notes  and track things and send emails and so on, but what I do think on the flip side is the taste  making and the editing function becomes really, really important.

29:21

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 what is the editing function here.

29:34

So that does mean that the bar is higher for  product folks, but I think there's an interesting side effect I am observing in startups that I'm  advising, companies and even within the companies that there used to be more gatekeeping I would  say, in terms of like, "Oh, we should ask the product leader what they think."

29:54

And again,  there is a role for that editing function, but you have to earn it now.

29:58

You just don't  get it because of this title, but there's also just unlock of latent really good ideas  from smart engineers, smart user researchers, smart designers who now have this expert in their  pocket to kind of round out all the other things that they're not typically skilled at to bring  forward their ideas and that's amazing, I think.

30:24

And I think that expert, it's interesting,  I'm working with an engineer on some stuff and he uses ChatGPT to even communicate  to me in a more effective ways like, "Turn his pitch into something that will  convince Lenny, this is a good idea."

30:38

By the way, that is actually  one of my common use cases, which is the WWXD I call it. What  would X do?

30:41

I use it to say, "Hey, what would Satya think about this particular set  of conversations or ideas that we are pitching and so on."

30:55

This is the power of, I think deep  reasoning plus relevant context, right?

30:55

This engineer you're talking about has that context  about you and so it's kind of very interesting.

31:06

If only everyone was 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 understand from the conversations  you've had with that person. Yeah.

31:17

And I think this goes back to actually  what you were saying too, which is I think this idea of what is the...

31:21

There's like a coil spring.

31:21

There's an intelligence overhang that I just see across the board.

31:26

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.

31:32

And that's not as easy, and I've been thinking about why.

31:40

Basically, I mean, I have  a cheesy Chrome extension.

31:40

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?"

31:50

It's very cheesy, but it kind of helps to pause  and think, "Oh, what am I trying to do here?"

31:56

But the reason I find it hard, and when  I talk even people who are living and breathing in this space, they find it hard  is that the updating of the priors is really hard.

32:05

The models couldn't do some things one  year ago.

32:05

I mean, image generation was full of spellings or reasoning.

32:10

You just couldn't  have deeper and smarter answers.

32:10

You couldn't do data analysis.

32:16

So my impression of it  from change, trying it a few months ago, that prior needs to be updated.

32:22

And it's hard to  do that, right?

32:22

You have to do something almost counterintuitive and against the grain  to say, "No, no, ignore what you learned about what this can or cannot do."

32:34

The baby  just grew up to be a 15-year-old in a month.

32:40

I think that last point is so important that we've  tried these tools over the years.

32:40

And 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 things change.

32:52

I think that's actually...

32:52

If you are a  product builder listening to it, that's a really interesting arbitrage thing for you.

32:56

If  you can kind of cut against the grain and say, "No, I won't have that scar tissue around."

33:02

This didn't work a few months ago and keep setting high expectations and demand more of  the AI today, I think you can unlock more.

33:15

There's a lot of alpha in doing that. That's right.

33:19

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33:19

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33:25

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34:05

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34:27

I'm going to come back to this cheesy plugin, say more  about this.

34:35

So this is a plugin that just lets you put a custom message on every new tab, and  you have it say, how can you use AI to do this?

34:45

Yeah, it's as cheesy as that.

34:45

And  it's interesting because it works.

34:51

In the last few weeks alone, I've  been doing this experiment to say, "Hey, how much more AI pill can I get?"

34:56

Both at work and in personal life to say, "When I'm trying to do anything manual,  should I be demanding the AI to do this?" That's so cool.

35:08

Do you know the name of this  Chrome extension by any chance otherwise? No. No. I built it.

35:13

You built a Chrome extension. That's so  cool. Okay.

35:13

Did you use AI to build it? Of course. Wow.

35:21

Which tool did you use to do that?

35:21

Some kind of Microsoft tool I imagine. Yes.

35:25

No, actually, it was just like, I  mean, I live in GitHub and GitHub Copilot, so I just was like, "Okay, let's  go build this Chrome extension."

35:32

Are you releasing this for the general public?

35:36

No, I mean, that's the amazing thing.

35:36

It took me like 10 minutes to do this. Okay, let's link to it.

35:43

Let's get it out there,  open source this thing. Okay.

35:43

You mentioned Satya, I have a question about this.

35:48

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.

35:52

How do their leadership styles differ, and is there just a fun story you  could share about each of them? Yeah.

36:02

I do feel lucky to have a window into  these two amazing leaders of this generation.

36:10

I would say, I mean, again, no surprise as you'd  expect from CEOs of multi-trillion dollar market cap tech companies, they are 99.

36:17

99 percentile in  almost every dimension you'd think of intellect, empathy, leadership, product, strategy.

36:24

There  are, of course, flavors of differences.

36:24

I was the technical advisor for Sundar for the first...

36:32

At Google and set up the office of the CEO there.

36:39

And they're, again, a matter of time and context  because there's a lot more consumer-oriented focus there.

36:45

So what I did find Sundar great  at it is being really calm and measured and thoughtful in terms of making sure that things  have...

36:50

Dealing with the complex ecosystems.

36:58

If you think about the phone ecosystem or even  the search and publisher and advertiser ecosystem, it's a very complex ecosystem.

37:02

He was a master at  that. He's a master at that.

37:02

And I think on Satya, I find it amazing the appetite he has for  learning and fine tuning his mental models and just the zoom levels that he can operate at.

37:15

The macro, the strategy, what's the game?

37:15

Also the micro, "Hey, why are we not..."

37:23

Here's  a specific insight that I saw on Twitter, and you can count on the fact that he's ahead of  pretty much everybody else in terms of spotting those early things too.

37:32

So it's just been  learning from the firehose as they put it.

37:39

What a cool opportunity to work  with two incredible folks.

37:39

Okay, let's go in a whole different direction.

37:42

Let  me just ask you this question that I've been asking people more and more.

37:45

What's the most  counterintuitive lesson that you've learned about building products that goes against common  startup wisdom, common product building wisdom.

37:57

I don't know if it's as common as it should  be, and it's like a counterintuitive thing, but I've repeatedly learned that when  you're doing something new, zero-to-one, the temptation is to kind of think about...

38:10

It's like that South Park episode.

38:10

Step one, think about the problem.

38:16

Step two, question- Underpants.

38:18

I think it's Underpants, step one. Underpants. Exactly, right?

38:20

So I do feel  like there's a temptation to rush and say to go to scale before solve.

38:25

So I've always said  to my teams solve before scale.

38:25

So 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 in roughly in the ballpark.

38:47

So to give you a couple of examples,  I think when you look at the solved stage, there are wide lurches.

38:54

You got to be very comfortable  with the fact that you're day one thinking about, "Hey, a plant detection tool."

39:00

And then day  15, you're like, "Oh, actually, the tech is really good for translating foreign language."

39:06

By  the way, this is not hypothetical.

39:06

This is what we kind of looked at in Google Lens back then and  said, "Okay, what is the intersection and so on?"

39:17

So from the outside, it looks like chaos,  but actually, in the...

39:17

And you should be very comfortable...

39:21

Not only tolerant, I think you  should have an appetite for that because the last thing you want is prematurely fix on one local  hill.

39:26

And then you're climbing that in start-ups 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?"

39:37

So I'd say that's one big counterintuitive.

39:37

When you're trying to think about what mode you're  in, are you in the solved mode?

39:42

Are you in the scale mode?

39:47

One example is kind of making sure  that you're comfortable with the chaos.

39:47

I think the other lesson I've learned is the danger of  metrics.

39:53

And I think again, if you have worked on Google Search or if you worked on Office  products, you really have a very fine-grained sense of what are the metrics for this product?

40:08

You have the input metrics out, you have the whole shebang, but when you're looking at something  zero-to-one.

40:13

If you decide on a metric two prematurely, that's false precision first of  all, right? I mean, CTR.

40:19

When you have a thousand people, it doesn't mean anything.

40:25

Retention  also may not mean anything.

40:25

So really being very wary of this big guy, big girl of grownup  metrics as I call it, right?

40:32

You are looking for more qualitative, the sound of click, and what  is your...

40:39

The other kind of the handler uses, what is your set timer and play music?

40:46

So if you  look at Alexa and Siri and Google Assistant and all these things, they had a very promising  broad interface.

40:53

You could say anything, but I think there was one or two things that  it was really good at.

40:58

You could set a timer, you could play music, and you could play  trivia.

41:03

And so you've got to nail those things before you say, "Oh yeah, here you can do  anything with it," which is not a good recipe. Not so funny.

41:12

That's exactly  what I use my Google Home for, so basic.

41:16

I don't do the trivia thing  now maybe I got to give this shot. Got to try that. Yeah.

41:21

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 a little framework for helping you know if this is the right time  for this idea.

41:28

How do you think about that? Yeah.

41:33

And when you think about the solved mode,  and this is again sticking with my whole living in one year in the future, I gravitated towards the  zero-to-one and solved mode products completely thinking about new category of products.

41:45

And  what I've found, both the hard way I would say, is that you do want to look for at least two  out of these three factors, inflection points here if you want to make a really good product. Number one is there a...

41:56

Shift is a step function in the tech.

42:02

That's somewhat obvious I would say.

42:02

Deep learning was one for Google lens.

42:02

Back then, speech recognition was a step function for  conversational search.

42:08

I would say for Robinhood, the generational shift was very clearly, and  the fact that phones were a primary means for you could actually have mobile app for finance  that you could use.

42:21

So look for that inflection.

42:27

What is the tech inflection?

42:27

And right now, of  course, like LLMs and reasoning models are that step function, but that's not enough.

42:32

I would say the second factor that we should look for is, what is the consumer  behavior shift?

42:37

So to give you an example, when we started working on Google Lens, what  we said is, "Look, people were taking mostly pictures for sharing, selfies and sunsets and  so on.

42:48

And suddenly, when storage became free, mostly free, and everybody had phones everywhere  all the time, you took pictures of everything.

42:55

And then you had enough of pictures or you use the  camera as the keyboard for your world, for the real world.

43:10

And so how do you then say, "Oh, this  consumer shift is big, and so therefore, as you go order of magnitude more photos, then you want more  to come out of them and you can apply AI to that."

43:24

And I'd say the third inflection point,  particularly I would say in enterprise but also in consumer, is the business model shift.

43:28

Is there an inflection natural inflection point in the business model?

43:34

So any great products, if  you think about all the way from search, again, the second price option and the fact that you had  CPCs, same thing with SaaS and the fact that you could actually charge or monetize enterprise  products in a different way.

43:47

And with AI, of course the monetization is a whole different...

43:54

We've just barely scratched the surface of whether you do seat monetization, usage like on  tap, and then of course outcome-based stuff, outcome-based monetization.

44:08

Hey, have you solved  the problem for me and then I will pay you some fees.

44:14

So all three to me are kind of like, great,  but at least two out of three for a good product. So this essentially...

44:21

When investors  look at startups, they're always asking, why now?

44:24

Why is this the time to start this  thing?

44:24

And so your advice here is there's three ways to look at it.

44:30

Two of these three should  be true.

44:30

There should be a shift in technology, some new technology that has enabled this now  recently.

44:35

There's a shift in consumer behavior, and then there's maybe a new sort of...

44:41

Or you've invented a new business model, any way to monetize something that it gives you  an advantage over folks trying to do it today. Yep, absolutely. Awesome.

44:51

You did mention Robinhood, I think in that example.

44:53

That was  another good example of phones- Yeah, I mean, talk about the business model  of, again, not having a zero fees.

44:56

And again, that combination of all of these things  is what can unlock it.

45:04

You can't just say, "Oh, we'll just have a much more better intuitive  interface and hope that people will switch to it."

45:16

Okay, so speaking of zero-to-one products,  I'm going to take us to a occasional segment on this podcast that I call Hot Seat Corner.

45:21

And I have a question for you that is on my mind and it's come up in a couple recent podcasts  actually.

45:26

So there's these companies like Cursor, VZero, Lovable, Bolt, Replit that are the  fastest growing company's history.

45:31

I just saw that Cursor hit 300 million ARR in two  years.

45:37

Interestingly, you guys were very well positioned to do really well in this space,  this AI coding tool space.

45:43

You guys had Copilot, the first tool in the world at this stuff,  so ahead of everyone.

45:47

You build VS Code, which is what all these companies are forking to  build on.

45:51

You have incredible AI infrastructure, incredible AI talent.

45:56

So this could have been  your market. What happened? What happened, Aparna?

46:02

It's interesting, the framing...

46:02

So I'm a dead  user of GitHub Copilot, and I would say, "Look, if you unpack..."

46:09

I think the beauty of this is  that code generation has become an amazing tool that LLMs have unlocked.

46:17

So it is actually  really good excitement and action that now code generation has just opened up all of these  things that...

46:23

We talked about the whole idea of prototyping, goes from idea to marks and idea  to a clickable prototype in a few minutes.

46:28

Those are the kinds of things that, of course, we  should expect code generation to enable.

46:35

The way I think about how we are positioned and  what we do with GitHub is...

46:40

So it's a system, not just a product or a set of features.

46:49

If I think about GitHub, it's for folks who have the repo there and you have...

46:55

Of course,  you have the assistance in terms of autocomplete and you can chat, but now we have the agent board.

47:01

It's one of the fastest loops that we are seeing, really strong positive feedback.

47:08

So in some  sense, when you have a system, what you are looking for in terms of building and designing  it is not just a single product that can grow, but what is the repository? What is your context?

47:18

What are the set of features that grow from your expertise?

47:26

If you're a really expert coder, you  want the assistance this product needs to scale for that.

47:33

If you're a wide coder, you should  still be able to do that and so on.

47:33

So that I think is the way that GitHub is positioned  to build on and growing honestly really well. That's so interesting.

47:46

So the core of  this is everyone ends up in GitHub anyway, no matter what tool they  use and that's kind of the- Yeah.

47:52

The idea again is that code generation as  a tool will unlock lot more products.

47:52

I mean, they're not all competitors to the fact of...

48:00

They're not all kind of doing the same job. I think when you are...

48:07

At the end of the day,  you are building code for companies to run on, you need to have a system.

48:14

You need to have kind  of the ability, an entire Swiss Army toolkit, not just the autocomplete, not just a chat, not just  like a software agent that runs and you kind of hand hold.

48:25

You need all of this to work together,  and that's what the GitHub product is going after.

48:30

All roads lead to GitHub.

48:30

On  the flip side of this question, there have been probably 5,000  startups that have tried to disrupt Excel and you guys just keep winning, so  something there is working really well.

48:46

That is so interesting you say that.

48:46

So when  I came to Microsoft, and I'm an Excel fan, so I actually had a conversation with one of  the OG Excel product folks.

48:51

I was like, "an, what is it about this product?"

48:57

And he said  a couple things that were really interesting for me that just stuck with me.

49:01

One is and I  said, "Hey, Excel is a proof that non-coders also have to program."

49:08

Programming is really  powerful and it's the tool that gives all of the non-coders a really powerful programming ability,  and I thought that was just really striking.

49:22

And then the second thing that I found out  super cool, I don't know if you know this, but I didn't know at least before two years ago  that there are these amazing Excel championships like World Excel championships where you  see folks who can do just magic.

49:31

And to me, I think the insight here is also that  some tools are harder to learn.

49:38

Perhaps in the beginning there's friction in terms of  learning, but great to use.

49:44

So it's a very good case of, hey, the learning curve initially,  the one-time learning curve might be tricky, but it is because there's so  much power and depth in the tool. That's so interesting.

50:02

I never thought of Excel  as a programming language, but it makes sense and I feel like once you get used to it and this  is just the way things work, you're kind of stuck there and everything else has to basically  copy that model, which is hard to be as good. Yeah.

50:13

And I think the depth then the  attention that the team has given, and again, that's the compounding effect  over decades of working on deep, deep signal from people who depend  on it day in and day out. Okay.

50:29

To kind of start to close out our  conversation, I want to ask this question around your career.

50:33

I find that most people  have one moment in their career that changes the trajectory of their career.

50:39

It could be  a manager they had, it could be a project they worked on, it could be just the job they  landed.

50:44

What would you say is the most pivotal moment in your career that eventually led you  to becoming chief product officer at Microsoft?

50:54

Actually, there is one moment where it was a  turning point for me.

50:54

I was in Google Search, I was working on this idea that I thought  should just work and it didn't.

51:00

I said, "Hey, these phones are becoming a thing.

51:08

Personalization  has to be important."

51:08

So I probably banged my head against the wall for a year or so trying to make  personalization work.

51:15

And it turns out when you have a query that you put into Google Search,  the personalization didn't matter as much.

51:27

And so we disbanded the team, but then I think 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 push content.

51:38

It's not about  searching with personalization."

51:38

For example, if you have a flight coming up, we should be  able to say, "Hey," connect the dots and say, "you should leave now given the traffic and where  you need to go," and so on or if you're deeply interested in stand-up comedy with deadpan  artists, you should check out Mitch Hedberg.

52:01

These are kind of these really moments that  the smartphone should be smarter.

52:01

So I let that product through the initial zero-to-one phase, and  that was a pivotal moment.

52:07

It made me realize two things.

52:15

One, I really love seeing around the  corner and kind of seeing where things go and building the product rise to the occasion way more  than the scaling and sustaining products.

52:20

Second, it's harsh, but being early is the same as  being wrong.

52:29

This is pre-LLMs, pre-deep learning a lot of the really amazing ideas in terms  of next token predictor, et cetera.

52:35

We'd been thinking of it but didn't have the horsepower to  go...

52:40

The interface was great, the intelligence wasn't there.

52:45

And I'd say the third thing that  stuck with me is I got to work with some really smart...

52:51

They talk about talent density now,  and I think really smart people who have gone on to do amazing things, and so it gave me a  taste of what a small group of people can do.

53:02

It's such a great story because it didn't  work out in the end.

53:02

Google Now kind of went away.

53:05

And by the way, I super remember  that product. It was very cool.

53:05

I remember looking at it was very delightful  and happy.

53:09

And so I also have this segment on the podcast called Failure  Corner, where people share a story of failure and how that helped them.

53:16

And I  love this as a combination of those two. Yeah.

53:20

I mean, I'm not going to lie.

53:20

I think it  was painful when you do that because you see the vision of what can be and what is, and  sometimes it's hard limitations.

53:26

Sometimes, in this case, it takes five years or 10  years to really unlock the intelligence, but sometimes it's one or two key  click stops away from the product being great and part of figuring out is  knowing when you're in what situation.

53:50

How long was that period from starting out  until just moving on and it's not working?

53:54

Yeah, I would say in that case, one of the  good things is, again, it led the foundation of...

53:59

It was one of the foundations of the  Google Assistant.

53:59

And of course, as the LLMs step function happened now with Gemini, it kind  of works out.

54:04

And I think it's the same thing across the board, which is sometimes you want  to figure out the invariance that do work that then go on to the next version of the product.

54:18

And other times, you just have to start over.

54:23

Is Google Now the first agent before  agents?

54:23

That's what it feels like.

54:27

That was certainly the idea, but it is  fascinating to me that the interface, that there, we had the opposite problem.

54:33

Whether  you think about all the voice assistants, the interface is like we overshot and  the intelligence wasn't there.

54:38

Today, I feel like there's an opposite problem.

54:43

I  think these things have amazing intelligence and the interface we have largely is  like the AOL Dial-Up Modem Chatbot.

54:55

We've covered a lot of ground.

54:55

Is there anything  that you wanted to chat about or leave listeners with, maybe a last nugget of wisdom before  we get to a very exciting lightning round?

55:06

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.

55:12

I think there's some great set of products and experiences to be reimagined.

55:20

That's my other  Roman empire, which is how do we actually have this co-working space where you have the humans  and agents and how do you actually have an output that's much, much more significant than what  any one of us or any few of us can produce?

55:40

Well, I need to hear more about this.

55:40

When do you  imagine a co-working space of humans and agents?

55:44

What does this look like?

55:44

Is this Microsoft teams  or is this a physical place with little robots?

55:51

Oh, I had a thought of the physical place,  but I am thinking a lot about...

55:51

Right now, all of these experiences are very  civil player, and I do think there's an opportunity to think about how do we...

56:00

Again, I'm living one year in the future, how do we actually have collaborate with  each other, but also with agents and really figure out, for example, what tasks can we  delegate? What can we inspect?

56:11

How do we actually have information that flows between  people that agents can mediate, and so on.

56:24

All right, I'm curious to see what  you guys got cooking.

56:24

With that, we've reached our very exciting  lightning round. Are you ready? Let's do it. Let's do it.

56:32

First question, what  two or three books that you find yourself recommending most to other people?

56:38

Oh, I have recency bias, but I've been  reading this book called The Brief History of Intelligence, phenomenal book and like  lots of underlining from me.

56:42

And I think it kind of...

56:50

The premises too, it looks at  the evolution of intelligence like human intelligence and the brain development and  connects that to what we are seeing with AI.

57:01

Do you have a favorite recent movie  or TV show that you've really enjoyed? Hacks. I've been watching this.

57:05

It's about a  woman who's a great standup comedian of...

57:05

I think it's set in the fact that she grew up in the  '70s and '80s and really tried to break through in an industry that hasn't traditionally been very  friendly to women, so really fun and quirky.

57:30

Do you have a favorite product that you've  recently discovered that you really love, could be an app, could be some physical?

57:36

I do use a lot of Microsoft products,  GitHub Copilot being one of them, but I think the one that maybe  I'll pick is Granola, I think, is the name of the app.

57:45

I found it really useful.

57:45

I just gave it a spin the other day and I'm like, "Oh, this is really useful in terms of being  able to, again, without being intrusive, just capture the thoughts, notes, and structure it, put  some..."

57:58

It felt like one of those things where, yep, the confidence of a few things like we  were talking about like the transcription, real-time transcription tech has gotten  really good.

58:08

Voice recognition is great, and then enough of the LLM magic on top of  it to make it structured and contextual.

58:18

I am a huge fan of Granola.

58:18

I'll give  a quick picture here.

58:18

If you become an annual subscriber of my newsletter, you get a  year free of Granola for your entire company. Did not know that.

58:29

There we go, and then just check  that out, lennysnewsletter.

58:29

com, and you click the word bundle  and you'll see how to do that. Very cool. Very cool. Two more questions.

58:34

Do you  have a favorite life motto that you often come back to when you're  dealing with something maybe you share with folks that they find  useful as well in work or in life? I have one.

58:46

In fact, actually, this is my email  signature for, I don't know, for the last 20 years or so.

58:50

It says the best way to predict the  future is to invent it.

58:50

I think it's a quote by Alan Kay.

58:57

I find it useful for two things.

58:57

One is  no one knows anything.

58:57

When you think about all the folks who think about, "Hey, this is exactly  how everything's going to look and this is exactly the sequence," and so on, I think there's  no substitute to experientially building it.

59:16

I think the second part is if you think there's  something that should exist, go build it. I love that. Final question.

59:24

We've talked  about standup comedy a bit.

59:24

Is there a favorite under the radar standup comedian  that you think people should go check out?

59:34

Oh, there's a couple of them.

59:34

So one, I  think, there's an Indian American or I think a British Indian standup comedian.

59:40

Her  name is Sindhu Vee, super smart, mom comedy, and I think the other one that...

59:47

This  is definitely not under the radar, but I just love his stick is  Nate Bargatze. He's just so good.

59:59

Aparna, this was amazing. Two final questions.

59:59

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?

1:00:08

You can find me on LinkedIn and Twitter. Aparna CD is the handle.

1:00:08

I do post stuff a lot more on LinkedIn these days, so would love  to hear thoughts, comments, conversations there.

1:00:24

I'd say one thing that would be super interesting  is if any of this stuff spark conversations, particularly around this, 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. Amazing.

1:00:42

Aparna, thank you so much for being here. Thank you. Bye, everyone.

1:00:46

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1:00:46

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1:00:51

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1:00:57

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1:01:02

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