The Exchanges

Q Being the product leader that you are, your words carry weight, Aparna. How do you communicate in a way that is feedback to be ingested, not a directive to be followed? That's tough.

A Yes, it is. As recently as yesterday, I was in a review where, you know, that's a lesson I've learned over time, which is when you're a senior leader, your whisper is It's heard as a scream, right? You just say, hey, you guys should think about it, and the next thing you know, they've spun up, like, gigantic effort to say, and, like, it's a telephone game. Having seen it a couple of times, I explicitly preface it. I call it, like, this is the iTunes terms of service disclaimer. This is super long preface, and say, hey, by the way, what I'm going to say is I have very strong conviction. This is what we need to do. That's a directive one, and then some other cases, I'm like, you guys should consider this. If you don't do it, to be honest, if you don't do it before the launch, I'm not going to cry a river, but I do think that there's something here, and you guys should explore. As a leader, you have to have to separate that out, and that's probably one of the biggest mistakes me, other product leaders, senior execs make at any company.

AI assessment note: “I explicitly preface it. I call it, like, this is the iTunes terms of service disclaimer.”

Q conversation with Tony. Always so much Character and charisma. Now, I want to bring one that's pretty special that actually went viral on TikTok with close to a million views, with the one and only Alpana Chanapragada, CPO Robinhood. How do you think about structuring product reviews? How often do you do them? Who's invited? Is there an agenda? Like, take me inside the world of product reviews for you.

A Oh, now we have to talk for three hours. I am big on product reviews. I'm also a huge fan of minimum viable process. I don't like process theater, as I see sometimes, where people are just, like, doing a bunch of things, and producing docs, and, like, reviews, and a whole bunch of things, and then that kind of fogs up the space, but I'm a huge fan of product reviews, and I've done that at Google, I do that at Robinhood, and I dedicate, like, a meaningful amount of my time, and I tell my product leaders to do the same, but there are different kinds of reviews. This goes back to what we were talking about earlier on the stages of the products, the solve- Scale and sustain. When the product review is for an early, fragile idea, still in the solve stage, seeking product market fit, you want a small group, and you want the problem solvers in the group, regardless of the organizational hierarchy, and you need a divergent mindset. You don't want to say, okay, what's the action item? Okay, okay, okay, okay, this thing clearly doesn't work because, like, we asked two people and they don't want it. You need that white space, and then you still need somebody to kind of, like, track the action items and all of that Stuff, but you need ideas of fragile, and you can't deal with them the same way you do in a scales, and then at a scaled stage product review, you want to lead with the data. Yo…

AI assessment note: “When the product review is for an early, fragile idea... you want a small group”

Q Terrible liar, Harry, that this was getting easier. I do want to say, because there's a lot of thoughts, there's a lot of feedback, there's a lot of energy in product reviews often. How do you prioritize what to focus on when there is so much feedback and thoughts coming out of them?

A Yeah, and I think I often joke saying one of the best things I learned from Google, wide-eyed, pushy-tailed PM, taking good meeting notes. People think of it as, oh, taking notes, isn't that something somebody else's job? Google was like maniacal about kind of making sure that the Product managers, ones responsible, took the notes, and it was a very good, very specific structure. I forget who it came from, maybe from Jonathan Rosenberg or Marissa Mayer or someone. You had very clear action items, you had specific people, specific things that they had to follow, discussion summary, key decisions made, and then on top of it, the twist I put on top of it, not all action items are made equal to your point. Some are considerations, some are like high priority things, some are like don't even think about doing anything else, like fix And so what I ask is typically the lead who's responsible for that discussion to own the prioritization, and then like publish that back and say, hey, by the way, these are all the things that we need to do. This is a P zero. We're going to go fix that. And that's where you do need the judgment of the product that you leave. If you can't trust that person to kind of make that call, and you're making that call constantly, you're failing.

AI assessment note: “what I ask is typically the lead who's responsible for that discussion to own the prioritization”

Q conversation with Tony. Always so much Character and charisma. Now, I want to bring one that's pretty special that actually went viral on TikTok with close to a million views, with the one and only Alpana Chanapragada, CPO Robinhood. How do you think about structuring product reviews? How often do you do them? Who's invited? Is there an agenda? Like, take me inside the world of product reviews for you.

A Oh, now we have to talk for three hours. I am big on product reviews. I'm also a huge fan of minimum viable process. I don't like process theater, as I see sometimes, where people are just, like, doing a bunch of things, and producing docs, and, like, reviews, and a whole bunch of things, and then that kind of fogs up the space, but I'm a huge fan of product reviews, and I've done that at Google, I do that at Robinhood, and I dedicate, like, a meaningful amount of my time, and I tell my product leaders to do the same, but there are different kinds of reviews. This goes back to what we were talking about earlier on the stages of the products, the solve- Scale and sustain. When the product review is for an early, fragile idea, still in the solve stage, seeking product market fit, you want a small group, and you want the problem solvers in the group, regardless of the organizational hierarchy, and you need a divergent mindset. You don't want to say, okay, what's the action item? Okay, okay, okay, okay, this thing clearly doesn't work because, like, we asked two people and they don't want it. You need that white space, and then you still need somebody to kind of, like, track the action items and all of that Stuff, but you need ideas of fragile, and you can't deal with them the same way you do in a scales, and then at a scaled stage product review, you want to lead with the data. Yo…

AI assessment note: “When the product review is for an early, fragile idea... you want a small group”

Q a tremendous amount of money to say such nice things, but I would love to start with a little bit on you. So, you know, we look at this incredible career working with some of the best product teams with the likes of Google, and obviously now with Robinhood. How did you get your start and come to lead some of the most powerful product talks with Google and Robinhood?

A I have to take you back several decades, Harry, if that's okay. I grew up in India. I was the black sheep of the family. I was literally the only, I am the non-doctor in the family. Like it's a walking Indian cliche. Mom, dad, brother, sister, uncle, aunt, you get the idea. And then I said, oh, I love math. And then they just, they were like just shocked. So I went into computer science. I fell in love with the CS and did my undergrad. And then I joined a PhD program in computer science. And then my mom was like, oh great, at least you'll be a fake doctor. And then I dropped out. But I got my first break, I'd say, in what the kids would call WebOne, MIT company, a spinoff called Akamai. Think about this as the infrastructure layer of the internet, and how do you actually deliver content to any website anywhere in the world? And that kind of, I think, got me hooked into just, like, both building products, making them, like, coding, but also just, like, over time, actually figure out how to build products and scale products. And, of course, at Google, I did a bunch of that.

AI assessment note: “I got my first break, I'd say, in what the kids would call WebOne”

Q I think product management kind of encapsulates all three. I mean, different roles of product management within the three. But I find it's a term that's kind of so loosely thrown around today, and it means a lot to What does product management mean to you, and how do you define product management?

A That's a good one. Exactly. Like, one of the most overloaded terms, I think, and overused terms. The only other one is web three, I think. Close there. To me, I think my definition is a product manager is someone who solves problems for people. That's it. That's the main thing. I mean, as someone said, the main thing is to keep the main thing the main thing. There's a Whole bunch of other things that you need as a product manager to get shit done in a company, but the main job you have is, are you solving problems for people as in customers, could be consumers, enterprise, and each of these is an underlined word. So if you say solves problems, in the beginning, you are the one solving the problem. As you grow in your career, you're getting problem solved. You have a team, you have a machine, like a system that helps Problem solving, like that systematizes problem solving. Problems is also underlined, which is, I don't think it means things that are very well defined in the beginning, again, early stage of products, or even like well into a product, pre-PMF, you actually don't know the problem. You kind of roughly know the space, and some things are articulated, some things are unarticulated, and you just, the art and the science of it is like really teasing apart what's the real problems. It's so cliche to say this, but it's that Jobsian thing about the faster horse versus Like…

AI assessment note: “a product manager is someone who solves problems for people.”

Q according to different cultures, and I'm kind of weirdly passionate about it considering I'm not a product person, but product reviews I find fascinating. When we think about how you as a product leader like to To structure them. How do you think about structuring product reviews? How often do you do them? Who's invited? Is there an agenda? Like, take me inside the world of product reviews for you.

A Oh, now we have to talk for three hours. I am big on product reviews. I'm also a huge fan of minimum viable process. I don't like process theater, as I see sometimes, where people are just, like, doing a bunch of things and producing docs and, like, reviews and a whole bunch of things, and then that kind of fogs up the space. But I'm a huge fan of product reviews. And I've done that at Google, I do that at Robinhood, and I dedicate, like, a meaningful amount of my time, and I tell my product leaders to do the same. But there are different kinds of reviews. This goes back to what we were talking about earlier on the stages of the products, the solve, scale, and sustain. When the product review is for a, like, early, fragile idea, still in the solve stage, seeking product market fit, you want a small group, and you want the problem solvers. In the group, regardless of the organizational hierarchy, and you need a divergent mindset. You don't want to kind of say, okay, what's the action item? Okay, okay, okay, this thing clearly doesn't work because, like, we asked two people and they don't want it. You need that white space, and then you still need somebody to kind of, like, track the action items and all of that stuff, but you need ideas of fragile, and you can't deal with them the same way you do in a scales, and then at a scaled stage product review, you want to lead with the d…

AI assessment note: “When the product review is for a, like, early, fragile idea... you want a small group”

Q I think product management kind of encapsulates all three. I mean, different roles of product management within the three. But I find it's a term that's kind of so loosely thrown around today, and it means a lot to What does product management mean to you, and how do you define product management?

A That's a good one. Exactly. Like, one of the most overloaded terms, I think, and overused terms. The only other one is web three, I think. Close there. To me, I think my definition is a product manager is someone who solves problems for people. That's it. That's the main thing. I mean, as someone said, the main thing is to keep the main thing the main thing. There's a Whole bunch of other things that you need as a product manager to get shit done in a company, but the main job you have is, are you solving problems for people as in customers, could be consumers, enterprise, and each of these is an underlined word. So if you say solves problems, in the beginning, you are the one solving the problem. As you grow in your career, you're getting problem solved. You have a team, you have a machine, like a system that helps Problem solving, like that systematizes problem solving. Problems is also underlined, which is, I don't think it means things that are very well defined in the beginning, again, early stage of products, or even like well into a product, pre-PMF, you actually don't know the problem. You kind of roughly know the space, and some things are articulated, some things are unarticulated, and you just, the art and the science of it is like really teasing apart what's the real problems. It's so cliche to say this, but it's that Jobsian thing about the faster horse versus Like…

AI assessment note: “To me, I think my definition is a product manager is someone who solves problems”

Q You know, one thing I think that everyone does Terribly. I think onboarding, especially in product teams, actually, how do we think about the optimal onboarding process? Again, like, how do you think about lessons you've learned that makes the best onboarding process for product team members joining?

A Oh, this is so timely, given that in Robinhood, obviously, we have both product leaders and product team members joining, and I completely agree with you, like, including my own experience generally, that's like an afterthought, or we assume, especially for senior folks, that, you know, figure it out. Here, I have to plug in one thing that Really helped me is this Coda doc by my good friend, Shishir. He runs Coda, and he has this amazing executive onboarding doc that I use to the hilt, and it talks about how it's onboarding you think about as two steps, actually. One is this, like, first phase of come in, listen, the listen-to-talk ratio needs to be, like, significantly high. You know, just get coffee, do what is needed to kind of actually, like, build that camaraderie with the team. Don't come in guns blazing, hot takes, right? That's Like, really important. It's a learning phase, and then there's a doing phase, but don't wait too long to kind of make sure you're brought in for a reason, right? You gotta kind of get that first win, and for that first win, like, the leader or the manager needs to identify what is that first win for that person, and set them up for success, and tell them who are the key folks that need to be part of their, this person's success.

AI assessment note: “it talks about how it's onboarding you think about as two steps, actually.”

Q My question is, what is not thriving? I don't know. Is it the cadence of their feedback? Is it their involvement in team meetings?

A Yeah, there are two kinds of not thriving that I've seen. One is just they're making poor moves. In the first month, at least, they haven't actually done the thing about like just getting deep into the product and deep into customers and working with like building those relationships with other key folks. Because the place existed before you came. Things were working. Yes, you were brought in to kind of, like, make things significantly better. If you don't kind of acknowledge that, like, there is an existing ecology and you have to fit in, that shows because other people start to say, well, like, this is not being useful at all. So make yourself useful is the first thing that you have to do. That is pretty clear. And that's actually fixable. If you catch that then, I think it's most competent people, they should be able to. The second kind of not thriving is less fixable. Loosely bucketed as culture fit. Or kind of like, they're competent, but they're not a culture fit. They're doing the right things, they're saying the smart things, helping, they're useful in some ways, but they're just so alien to the culture. Every company is an ecology, there's a culture fit, and if you don't fit in there, you get organ rejected.

AI assessment note: “there are two kinds of not thriving that I've seen.”

Q a tremendous amount of money to say such nice things, but I would love to start with a little bit on you. So, you know, we look at this incredible career working with some of the best product teams with the likes of Google, and obviously now with Robinhood. How did you get your start and come to lead some of the most powerful product talks with Google and Robinhood?

A I have to take you back several decades, Harry, if that's okay. I grew up in India. I was the black sheep of the family. I was literally the only, I am the non-doctor in the family. Like it's a walking Indian cliche. Mom, dad, brother, sister, uncle, aunt, you get the idea. And then I said, oh, I love math. And then they just, they were like just shocked. So I went into computer science. I fell in love with the CS and did my undergrad. And then I joined a PhD program in computer science. And then my mom was like, oh great, at least you'll be a fake doctor. And then I dropped out. But I got my first break, I'd say, in what the kids would call WebOne, MIT company, a spinoff called Akamai. Think about this as the infrastructure layer of the internet, and how do you actually deliver content to any website anywhere in the world? And that kind of, I think, got me hooked into just, like, both building products, making them, like, coding, but also just, like, over time, actually figure out how to build products and scale products. And, of course, at Google, I did a bunch of that.

AI assessment note: “I got my first break, I'd say, in what the kids would call WebOne, MIT company, a spinoff called Akamai”

Q What do you think are the biggest mistakes that people make when conducting product reviews? Where do they go wrong?

A One is certainly this stage appropriate review, as I call it, right? Like, they do it both ways, right? Which is, you have an early idea, there's like a really passionate engineer and a product person who worked on it, the researcher is saying, here are some really good insights, they might be product market fit here. And then immediately you're thinking, how is this going to scale? This is a Classic big company thing. It's like the South Park thing, right? Step one, interesting idea. Step two, question mark. Step three, how does it scale to billion users? Don't rush to step three. Think about actually, like, sit with that. The other extreme is the cacophony of a review, right? Like, no one knows who owns the, like, what's the agenda? Why are you here for? Is this a decision making? No one's framing the conversation. There are obvious fixes for both of these things, which is actually, like, specific people in charge of it and setting the tone.

AI assessment note: “One is certainly this stage appropriate review... The other extreme is the cacophony”

Q Terrible liar, Harry, that this was getting easier. I do want to say, because there's a lot of thoughts, there's a lot of feedback, there's a lot of energy in product reviews often. How do you prioritize what to focus on when there is so much feedback and thoughts coming out of them?

A Yeah, and I think I often joke saying one of the best things I learned from Google, wide-eyed, pushy-tailed PM, taking good meeting notes. People think of it as, oh, taking notes, isn't that something somebody else's job? Google was like maniacal about kind of making sure that the Product managers, ones responsible, took the notes, and it was a very good, very specific structure. I forget who it came from, maybe from Jonathan Rosenberg or Marissa Mayer or someone. You had very clear action items, you had specific people, specific things that they had to follow, discussion summary, key decisions made, and then on top of it, the twist I put on top of it, not all action items are made equal to your point. Some are considerations, some are like high priority things, some are like don't even think about doing anything else, like fix And so what I ask is typically the lead who's responsible for that discussion to own the prioritization, and then like publish that back and say, hey, by the way, these are all the things that we need to do. This is a P zero. We're going to go fix that. And that's where you do need the judgment of the product that you leave. If you can't trust that person to kind of make that call, and you're making that call constantly, you're failing.

AI assessment note: “lead who's responsible for that discussion to own the prioritization”

Q My question is, what is not thriving? I don't know. Is it the cadence of their feedback? Is it their involvement in team meetings?

A Yeah, there are two kinds of not thriving that I've seen. One is just they're making poor moves. In the first month, at least, they haven't actually done the thing about like just getting deep into the product and deep into customers and working with like building those relationships with other key folks. Because the place existed before you came. Things were working. Yes, you were brought in to kind of, like, make things significantly better. If you don't kind of acknowledge that, like, there is an existing ecology and you have to fit in, that shows because other people start to say, well, like, this is not being useful at all. So make yourself useful is the first thing that you have to do. That is pretty clear. And that's actually fixable. If you catch that then, I think it's most competent people, they should be able to. The second kind of not thriving is less fixable. Loosely bucketed as culture fit. Or kind of like, they're competent, but they're not a culture fit. They're doing the right things, they're saying the smart things, helping, they're useful in some ways, but they're just so alien to the culture. Every company is an ecology, there's a culture fit, and if you don't fit in there, you get organ rejected.

AI assessment note: “Yeah, there are two kinds of not thriving that I've seen.”

Q What do you think are the biggest mistakes that people make when conducting product reviews? Where do they go wrong?

A One is certainly this stage appropriate review, as I call it, right? Like, they do it both ways, right? Which is, you have an early idea, there's like a really passionate engineer and a product person who worked on it, the researcher is saying, here are some really good insights, they might be product market fit here. And then immediately you're thinking, how is this going to scale? This is a Classic big company thing. It's like the South Park thing, right? Step one, interesting idea. Step two, question mark. Step three, how does it scale to billion users? Don't rush to step three. Think about actually, like, sit with that. The other extreme is the cacophony of a review, right? Like, no one knows who owns the, like, what's the agenda? Why are you here for? Is this a decision making? No one's framing the conversation. There are obvious fixes for both of these things, which is actually, like, specific people in charge of it and setting the tone.

AI assessment note: “One is certainly this stage appropriate review, as I call it, right?”

Q How did that change your mindset? What mileage do you think you got out of it?

A The one big thing I got out of it was, like, to Actually, like, have a limited test of the hypothesis. I mean, Google was also the land of abundance in terms of number of people who are ready to jump on an idea. It just grew too fast. Like, there's a bunch of people working on it, and the ROI on, like, what you got out of it was so low. That's one. Like, how do you kind of stage the investment? Especially if you're in a startup and a younger company, that becomes really important. But I think the second one is this. That same idea, I never let go of it. I thought, oh, that's because it's the Pull, but what if it's a push of content? And so that led to a product I worked on called Google Now, and the idea was saying, hey, like, if you have a flight upcoming, or if your regular commute, and there's, like, traffic delays, we should tell you. Like, now that's a very personalized thing, right? Like, your thing will be very different from mine. And that was really helpful for customers. So it's like, sometimes, you know, you're one zip code away from the right idea, and how do you tweak that?

AI assessment note: “The one big thing I got out of it was, like, to Actually, like, have a limited test”

Q A lot of fun, but I get you on the challenge. What would you most like to change about the world of product today in terms of like product thinking?

A Yes. One myth I really want to change. There is implicitly or explicitly, it's all these tech bros with hoodies talking about like, I mean, we have this myth that those are the product guys, the product people, awesome product people come in all colors, all shapes, all forms, all ages. I think that's one myth. Like that somehow there's one type prototype. I think if I can get a bonus thing to change, I think it is really, there's a set of people who talk about products. There's a bunch of other people building products, and often they're not the same. I think like we should get more practitioners to go to the balcony. I mean, many of us are so busy on the dance floor, like so busy doing the things that we're, we don't often get the time to kind of reflect back. And if we can do get more folks, That's why I love what you're doing here. If you can get more folks to kind of, like, actually share their battle scars and share that it's not this glossy, shiny thing that, like, just shows up on cute tweets.

AI assessment note: “One myth I really want to change.”

Q When you've made hiring mistakes, what have those mistakes been?

A Oh, do you have five hours? Okay. Look, if I look at the patterns or the common patterns across hiring mistakes, Both the ones that I've made and friends. One mistake is this timing mistake, which is over hiring, hiring sooner than required. This is an interesting one because I think in product management, by definition, it's an interfacing with multiple functions, et cetera, and like influence is important, but mistaking noise for influence and clout. I think that's one of the things you see that, you know, don't mistake drama and activity for progress that people have made. Sometimes I've kind of been drawn to folks who have, like, big personalities, right, and say, hey, they've, like, really have, like, strong thoughts, deep insights, but if you can't bring people along, you're shit out of luck as a product leader, because it is one of those things, solving problems for people doesn't just happen within an organization. I often say, sometimes this season's firefighters, last season's arsonists, so you have to be careful about, that's one of the anti-patterns, I'd say.

AI assessment note: “One mistake is this timing mistake, which is over hiring, hiring sooner than required.”

Q When you've made hiring mistakes, what have those mistakes been?

A Oh, do you have five hours? Okay. Look, if I look at the patterns or the common patterns across hiring mistakes, Both the ones that I've made and friends. One mistake is this timing mistake, which is over hiring, hiring sooner than required. This is an interesting one because I think in product management, by definition, it's an interfacing with multiple functions, et cetera, and like influence is important, but mistaking noise for influence and clout. I think that's one of the things you see that, you know, don't mistake drama and activity for progress that people have made. Sometimes I've kind of been drawn to folks who have, like, big personalities, right, and say, hey, they've, like, really have, like, strong thoughts, deep insights, but if you can't bring people along, you're shit out of luck as a product leader, because it is one of those things, solving problems for people doesn't just happen within an organization. I often say, sometimes this season's firefighters, last season's arsonists, so you have to be careful about, that's one of the anti-patterns, I'd say.

AI assessment note: “One mistake is this timing mistake, which is over hiring”

Q So then how do you structure them? Is there an agenda? Item one, this product feature. Item two, this product feature. How do you structure them if it's not an FYI? Thoughts.

A Yeah, the FYI thoughts are the worst. I think, again, like, FYI thoughts are fine if it's the earlier stage we were talking about, because it is actually dangerous to prematurely structure the first kind of reviews where they're early solve stage discussions. On the scale and sustained stage reviews, I typically have the area leader. There's one clear, like, Product leader that owns the agenda, right? That owns what needs to be, because it's an expensive meeting. And typically, I do have key cross-functional folks. What that means is, if this product has big implications on marketing, of course, we need to kind of make sure that person's there. If it has significant impact on customer service, let's make sure that, like, those folks are there. Definitely have research and design at the table. I'm a huge, huge proponent of that. I remember even canceling some reviews back in Google when, like, folks would forget Bring the researcher design leads. I'm like, yeah, we're not doing this. That's such a pleasant and positive surprise for me at Robinhood, which is designers and researchers. They're there from the beginning, but it's only financial company that won the Apple Design Award. Design and research need to be at the table, too, for reviews.

AI assessment note: “There's one clear, like, Product leader that owns the agenda”

Q I do want to just ask two more questions before we dive into a quick fire, and the first is, like, when you look back at product decisions that you've made, Can you take me to one that was a mistake, and how did it impact your mindset?

A Oh, again, do you have three hours, Harry? No, I'm kidding. I have a couple of interesting ones, which I feel like I got a lot of mileage out of, like, post facto. At that time, it felt really shitty, but, uh. This is around, I think it was, 2011 or so. Again, like, mobile phones were starting to be a thing, and I had the hunch, which is the right hunch, that personalization was, like, your device is yours, and, like, the humans are adapting to computers. Computers need to adapt to humans. The phone should do a lot more for me, damn it. But where I started, though, is that actually, like, I revved up excitement around personalization as an effort in search. And so, like, you type in something, depending on, like, who you are, maybe, like, you need different results and different content, et cetera. Long story short, that hypothesis didn't pan out, and it turns out that actually the most important signal wants you in something like search is what you specifically or I specifically put in. I mean, other than, like, location, if you, of course, you type in pizza or I type in pizza, you want different results, but for the most part, that wasn't actually, like, making a big difference to customers' happiness.

AI assessment note: “Long story short, that hypothesis didn't pan out”

Q I do want to just ask two more questions before we dive into a quick fire, and the first is, like, when you look back at product decisions that you've made, Can you take me to one that was a mistake, and how did it impact your mindset?

A Oh, again, do you have three hours, Harry? No, I'm kidding. I have a couple of interesting ones, which I feel like I got a lot of mileage out of, like, post facto. At that time, it felt really shitty, but, uh. This is around, I think it was, 2011 or so. Again, like, mobile phones were starting to be a thing, and I had the hunch, which is the right hunch, that personalization was, like, your device is yours, and, like, the humans are adapting to computers. Computers need to adapt to humans. The phone should do a lot more for me, damn it. But where I started, though, is that actually, like, I revved up excitement around personalization as an effort in search. And so, like, you type in something, depending on, like, who you are, maybe, like, you need different results and different content, et cetera. Long story short, that hypothesis didn't pan out, and it turns out that actually the most important signal wants you in something like search is what you specifically or I specifically put in. I mean, other than, like, location, if you, of course, you type in pizza or I type in pizza, you want different results, but for the most part, that wasn't actually, like, making a big difference to customers' happiness.

AI assessment note: “I revved up excitement around personalization as an effort in search.”

Q When it goes wrong, and you're the leader, and you've got a PM who's hurt, confidence-wise, that hit, How do you bring them up and make sure that their confidence doesn't get too damaged despite a failed product?

A I think part of it is you as a manager and a leader having their back, because I think the worst thing you can do is, like, fault people for having hunch, having a hypothesis, and, like, taking a risk. I think part of it, honestly, is the performance and evaluation and, like, growth culture of the company, and how you encourage those kinds of bets, because if you have a company where you say, hey, like, what metrics did you move, and that's the only way you can actually get recognized and Promoted or evaluated. Then what you end up having is a bunch of risk covers folks who will just all gravitate towards the sure bet, right? Which is not a great company.

AI assessment note: “you as a manager and a leader having their back”

Q On the flip side, what are the signs that a new PM's not working out?

A You know, I've made mistakes here, too. And the mistake I've made in here is sometimes trying to make it work for too long. Because you obviously, like, see the power of this person, and recruiting is a long process. If someone's kind of like, it's the same as customers, like, acquisition is more expensive than retention. You want to kind of figure out and make it work. But the two patterns I've seen there that bite people, one is just like competence. If you're an infrastructure engineer, you can say, okay, these are hard skills that can be like somewhat translated to different environments. If you worked in Uber, it should roughly kind of work in Google. But I think with product management, so much as context and stage and other people dependent, like because you're a piece, you're an important piece of bigger jigsaw puzzle. And so one is just the contextual competence. They may have done really well in a different environment, but they're not thriving. Right. It's an ecology. They're not thriving in this organism because they just don't understand the domain or they haven't kind of like.

AI assessment note: “one is just the contextual competence. They may have done really well in a different environment”

Q Okay, so what questions do you ask to tease out the hustle, the drive, the comfortable being uncomfortable?

A So there's two things. One is, it's what they did versus what they're saying, because some folks interview very well, and that doesn't often always translate. In fact, actually, like, I think studies have over and over proven for things that are kind of like, there's a lot of practitioner judgment and decision-making discipline involved. The interviewing correlation is only weak. So I would look a lot at kind of the back channel on this person, for example, and this sounds like a little bit of a self I'm not criticizing Facebook or Google or any big companies, but there are different phases for big companies. Sometimes like there's all these, you know, amazing tailwinds that help companies grow. You know, if you were working on newsfeed and Facebook or search, of course the web grew with it, mobile grew with it. So you have to differentiate between people who were in the parade versus help the parade. And you certainly have to look for the jerks who pushed everybody aside and somehow got to the front of the parade. That's why having a strong and diverse network Helps here.

AI assessment note: “The interviewing correlation is only weak. So I would look a lot at kind of the back channel”

Q On the flip side, what are the signs that a new PM's not working out?

A You know, I've made mistakes here, too. And the mistake I've made in here is sometimes trying to make it work for too long. Because you obviously, like, see the power of this person, and recruiting is a long process. If someone's kind of like, it's the same as customers, like, acquisition is more expensive than retention. You want to kind of figure out and make it work. But the two patterns I've seen there that bite people, one is just like competence. If you're an infrastructure engineer, you can say, okay, these are hard skills that can be like somewhat translated to different environments. If you worked in Uber, it should roughly kind of work in Google. But I think with product management, so much as context and stage and other people dependent, like because you're a piece, you're an important piece of bigger jigsaw puzzle. And so one is just the contextual competence. They may have done really well in a different environment, but they're not thriving. Right. It's an ecology. They're not thriving in this organism because they just don't understand the domain or they haven't kind of like.

AI assessment note: “one is just the contextual competence. They may have done really well in a different environment”

Q Okay, so what questions do you ask to tease out the hustle, the drive, the comfortable being uncomfortable?

A So there's two things. One is, it's what they did versus what they're saying, because some folks Interview very well. That doesn't often always translate. In fact, actually, like, I think studies have over and over proven for things that are kind of like, there's a lot of practitioner judgment and decision-making discipline involved. The interviewing correlation is only weak. So I would look a lot at kind of the back channel on this person. For example, there are different phases for big companies. Sometimes, like, there's all these, you know, amazing tailwinds that help companies grow. You know, if you were working on newsfeed and Facebook or search, of course the web grew with it. Mobile grew with it. So you have to differentiate between people who were in the parade versus help the parade. And you certainly have to look for the jerks who pushed everybody aside and somehow got to the front of the parade.

AI assessment note: “interviewing correlation is only weak. So I would look a lot at kind of the back channel”

Q Okay, so what questions do you ask to tease out the hustle, the drive, the comfortable being uncomfortable?

A So there's two things. One is, it's what they did versus what they're saying, because some folks Interview very well. That doesn't often always translate. In fact, actually, like, I think studies have over and over proven for things that are kind of like, there's a lot of practitioner judgment and decision-making discipline involved. The interviewing correlation is only weak. So I would look a lot at kind of the back channel on this person. For example, there are different phases for big companies. Sometimes, like, there's all these, you know, amazing tailwinds that help companies grow. You know, if you were working on newsfeed and Facebook or search, of course the web grew with it. Mobile grew with it. So you have to differentiate between people who were in the parade versus help the parade. And you certainly have to look for the jerks who pushed everybody aside and somehow got to the front of the parade.

AI assessment note: “So I would look a lot at kind of the back channel on this person.”

Q Okay, so we figured out that I need this. This is the person that we're going for. How do I structure a hiring process for a PM? I've never hired a PM before. Like, what does it look like? What does the first meeting look like? Second? How do I do it?

A You know, obviously, the Google stage hiring process is different from, like, what I've been doing building the team in Robinhood. I think across the board, there's one invariant, which is you have to decide up front what stage are you hiring for, right? So in this, your case, if you're saying, like, it's an early stage The most important factor I would look for is just like the hustle and drive at that stage. At a later stage, and for a different product, the domain experience may matter a lot more, but my bias or my preference is really higher for the hustle, and extremely strong high tolerance for ambiguity and uncertainty, because, like, if they get queasy on the roller coaster ride, they're not the right people.

AI assessment note: “The most important factor I would look for is just like the hustle and drive”

Q Okay, so what questions do you ask to tease out the hustle, the drive, the comfortable being uncomfortable?

A So there's two things. One is, it's what they did versus what they're saying, because some folks interview very well, and that doesn't often always translate. In fact, actually, like, I think studies have over and over proven for things that are kind of like, there's a lot of practitioner judgment and decision-making discipline involved. The interviewing correlation is only weak. So I would look a lot at kind of the back channel on this person, for example, and this sounds like a little bit of a self I'm not criticizing Facebook or Google or any big companies, but there are different phases for big companies. Sometimes like there's all these, you know, amazing tailwinds that help companies grow. You know, if you were working on newsfeed and Facebook or search, of course the web grew with it, mobile grew with it. So you have to differentiate between people who were in the parade versus help the parade. And you certainly have to look for the jerks who pushed everybody aside and somehow got to the front of the parade. That's why having a strong and diverse network Helps here.

AI assessment note: “interviewing correlation is only weak. So I would look a lot at kind of the back channel”