Manik Gupta (ex-CPO Uber, Google Maps) on how to build consumer apps, why it’s useful to be optimistic about technology, creating inflections in your PM career, the changing CPO role, and more

Lenny (00:00:03):
Manik Gupta has led two of the most successful consumer products in history: Google Maps, where he was director of product for the Maps team, and Uber where he was Chief Product Officer. After leaving Uber, he spent most of his time working on a product to help people avoid getting COVID, called CVKey, and most recently he took on a role at Microsoft as Corporate Vice President leading many of their consumer efforts.

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In our conversation, we cover what he's learned about building successful consumer products, how to structure and higher product teams, building consumer apps, a concept called the consumer stack, company market fit versus product market fit, what it's like to be CPO, what he learned working at Microsoft versus Uber versus Google, and also a ton of career advice for anyone thinking about becoming a CPO someday. I hope that you enjoy this episode with Manik Gupta.

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(00:01:57):
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Casey Winters (00:02:00):
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Lenny (00:02:36):
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Manik, welcome to the podcast.

Manik Gupta (00:03:06):
Thank you, Lenny. It's great to be here, man.

Lenny (00:03:08):
I don't know if it's obvious, but I am quite honored to have you on this podcast. You've had such an illustrious career as a founder leading the Google Maps team, as CPO at Uber for, I believe, four years. Now you're kind of a fancy VP at Microsoft on consumer stuff. It's this incredible career and trajectory. My first question is, looking back at your career, what would you say is maybe the one or two main things that you did that helped you get to where you are today? For folks that are maybe earlier in the career, of what they should be focusing on.

Manik Gupta (00:03:39):
Yeah. Thanks, Lenny, for having me. I'm also a big fan of yours, by the way. I love your newsletter and it's been incredible to just see how you have also grown both the set of topics that you cover and this podcast. Just really a big fan, so again, thanks for having me.

Lenny (00:03:54):
Appreciate that.

Manik Gupta (00:03:55):
Let me start by telling you a little bit about my philosophy of this. I'm maybe a little bit late to the party, but I recently read this book from Morgan Hausel on Psychology of Money. And I highly recommend your listeners read it if they get a chance. There's a chapter in there, he talks about luck and risk. What he says is, when you look at individuals and you think about, or you ask them, or you think about what they have done that have made them successful, we tend to put a greater amount of emphasis on effort and a little less emphasis on luck and risk. I think I strongly subscribe to that. The important thing when you look back is how much luck played a big part, and of course the risk that somebody took played a big part.

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This is something that I've been thinking a lot about myself, which is what are some of the patterns of people who have had multiple careers and have gone through a journey where they've learned a lot and they've contributed and things like that? I think there are two patterns that stand out, both when I look at myself in terms of what I've been through, and also when I talk to a lot of my friends who have also gone on and done interesting things, and I wanted to cover both of that. The first one is really about people. It's about surrounding yourself with the best people you can find.

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It was so funny. I was watching the Warriors game last night, and yeah Warriors, we won the NBA championship. That's great.

Lenny (00:05:22):
Go Warriors.

Manik Gupta (00:05:24):
One of the reporters, I think she asked Steve Kerr, the coach, "What's the secret?" And he goes, "Well just hang around superstars." That's what he said and he just passed the mic over to somebody else and said, "Look, this is a team that's hanging around superstars." And that's exactly what it is. If you're create enough opportunities, especially early on in your career as you asked, around hanging around people who are doing interesting things and they're doing things which really are different, or they're doing things in a different manner and it's exciting, the right things will happen.

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I was lucky in a way that I caught myself in that situation. I grew up in India and when I was 16 I got a scholarship to move to Singapore to do my high school and then my undergrad studies. It just turned out that during those days, Singapore... I mean it still is, but it was a melting pot for the best and brightest folks that you can get from all over the Asia diaspora if you will. Among my colleagues and my fellow students there were a bunch of really, really smart people, so I just learned a lot from them and that gave me a great start to just go on and do something interesting. Right out of college, I started my own company and I did that with two of my classmates. One of them happens to be one of my best friends whom I grew up with who also came on the same scholarship with me to Singapore. We were just part of that ecosystem and it gave me a lot of opportunities to try out different things in college and so on and so forth.

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I think the main thing that I would say here for people who are early in career is just surround yourself with people who are really good at what they do. Learn from them. And by the way, play the long game. Once you find someone like that, stick to them. As long as they want to hang out with you, but just stick to them. Because you will go on to do multiple things over your career with the same set of people. And the shared trust and experience that you build with A plus people is just going to go a long way. Anyway, that's pattern number one. I think that has helped me a lot and I also see a lot of that in other folks whom I talk to.

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Then the second pattern is... This is something I resonate a lot with personally, is I'm a strong technology optimist. There's always a lot of narrative these days around technology and maybe a little bit more pessimism, and I find that bizarre. I'm just such a strong technology advocate and optimist, because I feel technology's such a strong force for good. I grew up as an engineer myself, and I've always been attracted to projects where we can use technology to solve a real human need. I did that with my startup, I did that at Hewlett-Packard, I did that at Google and at Uber as well. The passion that you get if you're a strong advocate of technology and how it can really help, it just gets you to choose a set of things that you want to do at scale.

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For instance, when I joined Google in India to work on Maps, it was all about helping millions of users, around Asia particularly, navigate their world. There wasn't a good solution like that, so how can you bring technology to really solve those problems?

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I think those are the two patterns, Lenny. One is surrounding yourself with A plus people, and the second is just having very strong optimism and passion about technology. At least if I connect their dots looking backwards, those are the things that have really helped me and a bunch of other folks that I see in a similar situation. I'm hoping that folks early in their career thing through that.

Lenny (00:08:40):
I bet there's a big overlap between those two points, technology optimist and just superstars. That's interesting.

Manik Gupta (00:08:46):
Yeah, there definitely is. That's actually really good. I hadn't thought about that. You're right. I think there's definitely that overlap, because folks who are in that mode, they really get around more together. I'm also an angel investor and an investor in a bunch of companies. Lenny, you and I have invested in a bunch of companies together as well. And it's like that. It's really about people who have the same kind of frequency in terms of thinking about the world outlook and they want to go on to do interesting things. I think that's really what drives the narrative forward.

Lenny (00:09:14):
Speaking of technology optimism and technology in general, of the things that you've worked on, what would you say you're most proud of project wise, product wise, feature wise?

Manik Gupta (00:09:23):
Yeah. Again, I've had just the incredible opportunity to be part of phenomenal companies that have created world changing products. I had a small, small, small part to play in that. I always emphasize that. It's not me, it was a team. And I really mean it. I'm not just saying it because I'm on your podcast, but it truly is. I'm particularly proud of the work that I did both at Google and at Uber. I'll give you a couple of examples to illustrate that point.

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When I joined Google in India in 2008, I started off working on Google Maps and I remember how counterintuitive it was for anybody; my friends and family, a bunch of other folks whom I talked to. Counterintuitive in terms of why would anybody ever use maps on their mobile phone in India? The reason was because the norm was that, firstly, the country's unmappable because there's no good addressing system. So how do you even look at places? Then the second one was there were always people around that you can just roll down your car window and just ask people, "Hey, I'm going here and can you just give me guidance or directions?" That was the norm. That's how people navigated for a really long time.

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When I started working on it, I think for me, my belief was, again going back to the tech optimism aspect, is why can't we in India have the same quality maps like we have in the United States? Why not? Why shouldn't we do it? Why are users here not getting the same benefit and same productivity gain, if you will, and less stress in their daily commute and things like that?

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So we started building it. We started building the data. We went ahead and really mapped the country as much as we could. Both ourselves and through a lot of amazing work from our users who co-mapped the world with us. Over time, India became, I think, the second largest country for Google Maps in the world in terms of users. Of course, a lot of that happened because of Android. Android took off and Android had Google Maps on it. But it's just incredible to see how, in a short span of a few years, it just went up to becoming so useful. It's not that we were just distributing Google Maps on Android, people were using it. People were actually using it to go from point A to point B.

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I feel really proud about that. I think the team did an incredible effort. It wasn't even a big team. It was a relatively small team, very passionate about going and doing this, and we made that happen.

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Then at Uber, initially, before I took on the CPO role, I was leading maps and marketplace. When I was doing maps and marketplace, again, how do you get the ETA that you see on Uber when you open the Uber app and you request a car... The average ETA's went down to less than five minutes globally. Just think about that for a minute. In fact, it was 75 countries, more than 300 cities, if I remember correctly, where you could just open the Uber app and get an Uber in, average, less than five minutes. A lot of operational work need to happen for sure, but the technology, the marketplace technology especially to be able to connect the right rider to the right driver, have the mapping infrastructure underneath it to ensure that the car actually reaches you in that amount of time; I just feel very proud of all the work that happened during that time to make Uber really successful in terms of providing that kind of a service.

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One fun anecdote I'll give you where my world came together and it just blows my mind even today, I remember I joined Uber in late 2015 and I made a trip to India to see my parents in sometime around 2016, 2017. I forget. It was around that time. And I was at home in Bangalore and I ordered an Uber. And the guy shows up, the driver comes in, and I sit in the back of the car. He starts the trip using the Uber app, and then he clicks Navigate and he goes to Google Maps. And I was sitting there. I was like, "Man, I built these two to a certain extent." It was just crazy to think about how two of my worlds came together at that point. I still vividly remember that moment where I felt really proud that I had a little bit of a part to play in both those products.

Lenny (00:13:26):
That is some unbelievable impact. It boggles my mind how many people have been impacted by the work that you've done on the teams that you've been on. Like a billion people in India and everyone in the world using Uber. It's unreal. I would feel very proud myself, watching that experience.

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Something people may feel when they see a career like yours, they're like, "Man, Manik's just killing it. He's done everything. Everything just is clicking, always winning." I imagine there's been a few times when you've made mistakes or things have been really challenging. What would you say has been one of the more challenging projects or points in your career?

Manik Gupta (00:13:59):
Yeah. No, absolutely. This is really important to talk about as well, because we glamorize successes and we don't talk enough about challenges. I'm really happy that you're asking this. I would give you two times which... I had a lot of learning from both of them, but they were pretty tough times for me. The first time was, I had started my own company at the height of the dotcom boom. We incorporated our company in June '99, and then in March of 2000 we sold our company to another company from Norway. That was the peak of the dotcom boom. Then within a few months right after that, we had the dotcom bust and it was terrible. Terrible. I know we have a pretty bad economy right now. There's a lot of stuff going on. It was really bad, because people around me, my friends, were losing their jobs.

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Luckily we had some funding. We had secured some of our funding and we had had an acquisition. The parent company was pretty strong in terms of their balance sheet, so we could continue to do it. But things didn't get better, Lenny. 2000 went by, 2001 came in. We kept waiting for things to improve, but they never improved. So we had to pivot. We had to pivot as a company. My co-founders actually left the company at that point. I still wanted to be there, because I really believed that I can keep moving this company forward. Then I was working with the founders of the parent company. We pivoted multiple times, we tried a few things. I even relocated back from Singapore back to India to set up an engineering office so that we can get into a SaaS kind of a model versus an eCommerce company that we were.

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I tried many things over those two or three years. And remember, this was my first, quote unquote, "job" out of college. I was doing a lot of that and it was a very tough time. But at the same time I learned a lot. I learned a lot about myself, I learned a lot about managing ambiguity and just keeping people motivated through a tough time. A lot of that also has to come from keeping yourself motivated, because people can smell fear and pessimism from far. Just like optimism is infectious, so is pessimism. If you're not feeling great as a leader, people will see it. Absolutely. People are not stupid. You have to not fake it. You have to really be motivated to stick it out, and that's what I tried to do at least, and I learned a lot in that. That was one really challenging time for me.

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Then the second one was, man, during Uber. 2017, 2018 was crazy at Uber. Oh my God. There were just so much going on with leadership changes, with the brand issues we were getting. For me, there were times when I would commute up from my house to the office, and while I'm in the car I will be listening to some news or whatever and I'll hear about things that happened at Uber that day from the news before I got to hear it from within the company. It was that crazy during that time. So again, a lot of chaos, a lot of churn at the company as well. It was something where you just had to keep your head down and just keep staying focused on what the core is.

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I think that is where, Lenny, the optimism in me in terms of, what am I really doing? Is this a service that really benefits millions of people around the world? Are we creating true change? Those are things that I just have to dig deep into to make sure that I stay grounded on why am I here and why I remain to be here and then at the same time motivate my team. But yeah, those were the two really challenging times that I have encountered, at least in my career.

Lenny (00:17:26):
Those are awesome examples. I imagine a lot of founders are going through a lot of challenging times right now with the market, and imagine these experiences for you were really important and impacted your ability to take on bigger roles and bigger challenges in the future. Is that how you see it? These are important experiences to have over time as a product leader and just leader in general?

Manik Gupta (00:17:46):
Oh, absolutely. Because like I said, you learn a lot about yourself when you go through a situation like this. You learn both things that bother you or bring you down, and things that give you energy. It's sometimes counterintuitive to think about this. When you're going through a bad time, often then people will say, "Well, during a bad time I only learned things which are bad." But you also learn things that are good. Which is, maybe during a bad time you did something and you suddenly felt relieved or energized, and then you look at that and say, "Wait, I should do more of that even during a good time, because can you imagine the compounding power that I would get? Because stuff is good and I'm doing this and I'll feel even better."

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I learned a lot in terms of my own personal energy, things that get me going, things that really stop me in my tracks. And at the same time, how do you work with a team? How do you motivate them? How do you keep your head down and focus, versus getting distracted? What are some of the decisions you make around your product roadmap?

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I'll give you an example. During my startup, when we were going through that, in order to motivate the team, one of the best tricks that I came up with, and I learned this from a bunch of other people also, is you just give a team a win. Winning really, really drives a lot of energy. We had a choice to make between launching something which will take six months, versus launching something that we can launch in a very small-ish kind of way, but launch it in a month. And we chose the latter, because when we did that, I remember people were giving high five to each other, people were saying, "Hey, you know what? This is great. We put something in front of customers." We had, I think, 10 customers who used it or something, because we were so soft-scaling that feature. But that didn't really matter. The point was that you get confidence from getting things out, putting it out there, and you feel good about being a builder and being someone who is actually creating a difference. That really grounds the team and focuses the team that there is some real value here.

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Some of those things I picked up. Both going through that turbulent time, I picked up. And I have used that even in good times to make sure that we keep building good products.

Lenny (00:19:56):
That's such a good tactical tip. Find a win. Keep people motivated. Speaking of wins, coming back to Google Maps and Uber, they're probably two of the most widely used, successful consumer products in the world. I don't know if I can think of other products that are used by more people for this long. Then now at Microsoft you're helping Microsoft get more into consumer on the communications side. I imagine you know a thing or two about building successful consumer apps, and so I want to ask a couple questions along those lines. What are two or three surprising or counterintuitive things that you've learned about building consumer products?

Manik Gupta (00:20:32):
The good news is that there's just... Because of Twitter and a bunch of other channels, including your newsletter by the way, I feel like people are very well informed these days. And I love that.

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Let me digress for a second and then I'll come back to your question. One thing that I'm observing a lot, Lenny, which I feel very, very happy about, is the quality of learning and insights and frameworks and best practices is so universal at this point. It used to be that you had to be in the Valley or being part of a small group of folks who are doing things at the cutting edge to have those crazy insights about how do you find product market fit and do all that kind of stuff. Today I talk to people from all over the world for various reasons, and it's incredible how fast people pick up all these insights and frameworks and then they apply them to their local setting and so on. I find that to be one of the most wonderful things ever.

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I think folks like you have obviously played a big part, because you have global subscribers and you share some of the best practices. But just generally, that's actually a really good thing for the world, that people have so much access to clarity of thinking. And the best people are actually putting themselves out there, which is great.

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In terms of the counterintuitive stuff, I think two things. One is building consumer products is very hard. I think people think it's easy, because each of us is a consumer. We think of ourselves as a good user, we think of our friends as users, we think of our family as users. And we say, "Well, if we just build it for ourselves and for our family and friends..." By the way, a lot of great consumer products started that way, so I'm not saying don't do that. But man, it's hard. It takes a long time to get things right. Because you're essentially trying to get so many things right when you're building a successful consumer product. You have to be able to reach out to a vast, heterogeneous set of users who have different needs, who have different perspectives. The go to market is always very interesting, because you can't force people to use your product. People have to choose you, you don't choose them. That's the part where... How do you drive virality? How do you drive that real love for a consumer product? And it has to create real value.

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The other thing about time is that, in order for you to find product market fit and then scale from there, you just have to try a lot of different things. There are theoretical playbooks around it, but you got to just get into it. Going back to the point I was making earlier about wins, get some wins and see the results and then iterate from there. I think it's just hard and it takes a lot longer than what people imagine consumer products do. Versus, let's say, enterprise products or products of other nature. That's one counterintuitive thing that at least I've learned.

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The second one is the global patterns that you see in consumer products in terms of the user interface; the core things that people do or expect. At this point along of that is pretty universal. There's always this debate where people would say, "Well, need to have one product for the U.S., another different type of product for Asia, another different type of product for Africa. I think we are past that point. That's again another counterintuitive thing, where people spend a little too much... I've seen this in many companies. People spend too much time debating that, "Oh, the users in market X are different." Well yes, they're different, but they use the product the same way.

(00:24:02):
That's the part which I think... And I'm not making an argument against localization. Of course you need localization around language, pricing. There are some legal requirements, all of that stuff. Obviously you have to do that, otherwise you don't even have a right to exist in that market. But by and large the patterns are very similar. You look at global products, even like Facebook or Google Search or Maps or Twitter or TikTok and so on, all of them have a similar pattern or similar app for the entire world, and they keep on innovating or localizing at the edges.

(00:24:33):
That's the other counterintuitive thing that people should know about consumer products. Build for the world from day one. Understand that there are going to be some nuances that you'll have to solve as you drive adoption in certain markets, but don't over index on building market specific solutions, because consumers have moved on from that kind of a model. Those are the two, in terms of product building, counterintuitive trends at least I have picked up over the years.

Lenny (00:25:02):
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(00:26:04):
Before this chat, we were chatting about this idea of company product fit for bigger companies. How it's an approach to building new products within big companies. Can you just talk about that idea?

Manik Gupta (00:26:17):
Yeah, absolutely. I've been noodling a lot on this, especially since I took on my role at Microsoft as well. And prior to that, even at Google, this was always an interesting discussion. Let's say you are building a new product or leading a new project, if you will, at a larger company. In fact, this also applies to medium-sized companies. I wouldn't say for startups, but medium-sized companies. Usually the narrative in the room when you're discussing this with your team and with your leadership team would be, "Okay, we got to go find product market fit." Absolutely. Yeah. We have to do a bunch of stuff, as we just talked about. Consumer products take time. All of that stuff.

(00:26:57):
But I think there's a question before that question, which is how do you find company product fit? What I define as company product fit. Which is a company essentially is a portfolio of products, and every large company, medium-sized company also has a portfolio. They'll have 10, 20, in some cases hundreds of products in the portfolio. Every company has unique strengths and weaknesses. This is pretty tried, but it's obvious. And I would encourage a lot of folks, when they start embarking on this journey where they're trying to really build out products and so on, is to ask that question. How does that product, assuming it's successful... If it is not successful, it doesn't matter anyway. But assuming it's successful, does it actually serve the right place in a company's product portfolio? Or not? And if it doesn't, don't do it. Why waste time?

(00:27:57):
Oftentimes companies will be like, "I want to do this because some other company is doing it." That is not a good reason. You should only invest in products, or projects for that matter, because you can play to your strengths and you can create some unique consumer, customer value. And by the way, you can do it better than anybody else out there. That's what I mean by company product fit. Take that first step and understand does this even resonate and is it part of the portfolio? Does it make sense?

(00:28:26):
Because if you can answer that question with enough conviction, then your road to the next step on finding product market fit becomes much easier, because you don't have distractions then. Everybody gets it. Everybody gets this is a strategic effort. You have the right sponsorship at the right levels in the company, and you're executing towards it and you're finding it out. Let's say things don't go well. That's okay. People will step in to help. A lot of that will happen, because people innately get it. That this is the right product to go after from a company product fit perspective. That's something that I've been thinking a lot about and also executing as we move forward.

Lenny (00:29:00):
Is there an example of that gone wrong that you can share? Whether it's a company you've worked at or a company you've seen do it badly.

Manik Gupta (00:29:05):
I'll have to think through specific examples, but companies do this all the time, where they do these line extensions. Where they'll say, "Well, we have a lot of traction in a particular segment. Why don't we just go to an adjacent segment? If we just add two more features, suddenly this will be appealing to an adjacent segment." A classic example would be you're doing something for, I don't know, small and medium businesses and you say, "Well, now I just have to add two more features and now I'm going to go up market and I'll get to compete in the enterprise." Or it could be the other way around too, where you have something in the enterprise business and you want to suddenly go down market to SMB.

(00:29:44):
In my view, it's hard. Because again, the capabilities that you need, the thinking that you need, is something you have to really be clear about. This is not to say that it will not fit in the company's portfolio. It's just that when you're making a choice like that, make sure you set it up well to succeed. That's the other part of the equation as well.

Lenny (00:30:02):
Speaking of setting it up to succeed, you also have this idea of a consumer stack concept that I think you've been talking about at Microsoft. Can you talk about what that's all about?

Manik Gupta (00:30:11):
Yeah, sure. One of the things that I'm doing at Microsoft right now is, while I'm working on a lot of the consumer communication products, the other thing that I'm really helping the company think about is how do we get more at scale consumer products built at Microsoft. Part of this is just distilling some of the learnings that I've had over the years. I think there are like five things that I would talk about, which I call the consumer stack, which is essentially a set of capabilities that companies need to have a good chance of success at building a consumer product. Remember, nobody can give a playbook to build a successful consumer product. That does not exist. Because as we were discussing earlier, it's so fickle and so many things have to go right for you to build a successful consumer product. But at least you have a set of capabilities, so you set yourself up the best.

(00:31:01):
The first one I would say is around design-led thinking to delight users. Going back to your days at Airbnb, Lenny, I'm sure this is something that resonates with you. Design for consumer products is such a critical part of how you build the right pull from consumers these days. Poorly designed products have no chance at this point. Your craftsmanship and the design capabilities have to be A plus. And if you don't have that, then you should really invest in that. This is not just about having the best designers. Of course you should. It's just the thinking. It's a attention to detail. It's the attention to how things are pixel to pixel, moving from one screen to another screen and so on. You really have to sweat it out and really be clear in terms of how it's adding value to a consumer. That is, I think, a core capability in these days to build a consumer product. That's number one.

(00:31:54):
Number two is strong focus and prioritization. You can apply strong focus and prioritization to anything in life, but I think it's even more important for consumer products. Because oftentimes people, when they think about solving a problem, they think about coming up with 20 features at the same time, and it's not needed. You don't need 20 features to solve a problem. You just need one or two features which work really well. This whole concept of critical user journeys. How do you make sure that, if you're solving problem X, any feature that you build in the product... Firstly your product should have very few features in the beginning. But even if it has those features, it should be well designed and it should have the focus and prioritization so that you're only getting things for the critical journey so that the user can use it and not get confused. That's the second one.

(00:32:38):
Most PMs totally understand that. That's their job description, to focus and prioritize. But I feel like a lot of times the PMs do get very confused and distracted, because the number of ideas that people have is so large that they want to just throw everything into the product, and that doesn't work. You have to keep a very high bar for focus and prioritization. That's capability number two.

(00:33:00):
Number three is having the right metrics and instrumentation. This talks to the data aspect of the culture, which is, if you don't have the metric with regards to what you're optimizing for at the initial state of the product, middle state of the product, late stage of the product, you're just not going to choose the right things. How will you measure success? How will you convince yourself, your team, and broader stakeholders that this is actually working or not working? Having the right metrics is important, but it's incredible how many times people have the metrics but they don't instrument them. They'll have all these debates, because the product is not instrumented properly. And everybody will talk about the same metric, but they'll have different nuances in terms of, "Oh, what does it really mean? What is a daily active user? Okay, daily means... Okay, I understand it's on a daily basis. What is active?" And there'll be debates about what is active. Pick a definition, instrument it, codify it. No confusion. That's number three.

(00:33:59):
Number four is more on the engineering side, which is how do you get to a very high ship velocity, and the ability to experiment and learn fast. At a broader level, especially during the initial phases, if you're not learning, you are really not doing anything well. You've got to be learning. You've got to be learning good things, bad things, doesn't matter. You've got to be learning. Having the experimentation velocity, having a building culture where engineers are able to check in code, see the results, and then quickly come into another release and stuff like that, I think that's really important for a consumer product.

(00:34:29):
Finally, underpinning all of this is just having strong talent. Assess your talent; your product talent, your design talent, your data talent, your engineering talent, your marketing talent, all these functions. You just have to have a talented pool of people who like to build stuff, and they're the people who understand and have the empathy for consumers.

(00:34:50):
To me, I think these five capabilities... And as a leader, or product leader, or an engineering leader, or anyone who's basically responsible for running products in small company, big company, medium-sized company, it doesn't matter; if you're in the consumer space, my thinking here is that if you look at these five categories and five capabilities, you should really have a report card and say, "Okay. How do I rate these?" If I were to look at my own team, what do I think about design thinking? What do I think about strong focus and prioritization? Are we doing an A job? Are we doing a B job? Are doing a C job or D job? I would argue that if you get to an A job over time, because not everybody will be at A on day one, but if you get that over time, I think you will start seeing results which are very meaningful. That's how I've been thinking about the consumer stack.

Lenny (00:35:34):
Awesome. I was going to ask how you operationalize this. It sounds like it's going to turn into Manik's consumer stack scorecard, and bigger companies can leverage this at their own company and show their manager, "Hey, we're moving really slowly. Maybe this is an area we should focus before we bet big on consumer."

Manik Gupta (00:35:50):
Yeah. I'm trying to operationalize this myself right now in my current job, and I have used some version of this. I mean, this is not something I just came up with. It's something that has been in my mind for a while. I've used it in some shape or form. But during my break, especially before I joined Microsoft, I think this came together for me as something a little bit more tangible that I can use. Then I started applying it, so I think it's been pretty interesting to see.

Lenny (00:36:15):
Awesome. I'm hoping that this proliferates through larger companies and becomes a thing that we can root back to this chat.

(00:36:23):
Shifting a little bit to the CPO role and the VP of product role that you've had at a few companies, in theory this is kind of an end state for a product leader. Every PM, if they stay down the PM career track, they'll become a CPO or VP of product or head of product somewhere. A couple of questions here. One is, do you have a sense of how many PMs actually stay on this track and end up in one of these roles, versus move on to some other role or place?

Manik Gupta (00:36:47):
Yeah. That's a great question. I would say that the percentage for CPO in particular, you having a C title and being a CPO, I think that percentage is still relatively small. This is just my sense. I haven't done the numbers to give you a more accurate picture here, but I think my sense is relatively smaller. Because I think a large part of it depends on how companies are organized. Companies can be organized functionally, companies can be organized through business units, and oftentimes these days it's a mix of both. If you look at any company, they'll have some C level functional executives, but underneath them they'll have GMs. The organization design is just such an evolving field always. And as they say, companies will go one... they'll swing the pendulum one way and they'll say, "Oh, over time it's not working," and then they'll swing the pendulum the other way and then they keep going back and forth. I think the percentage for CPO in particularly in my mind is probably not as big as what people think it is. Like I said, because of the way that companies are organized.

(00:37:50):
I think the interesting thing here is I am just seeing personally, having been a CPO myself and also talking to a lot of people in my network and just observing a bunch of different companies, I think the CPO role is evolving. Or the head of product role is also evolving. I think a lot of it is morphing more into the GM model where you're running not just product management but also perhaps PM and engineering, and design to a certain extent and data science too. You're essentially becoming the overall technical product leader at the company.

(00:38:27):
The reason why I feel that is happening is because it's all about accountability. It's about who has the single threaded leadership model where this person can make all the decisions when it comes to trade offs and running the roadmaps and all of that kind of stuff. It's not ideal, by the way, in all cases. Because what that means is, for somebody to be doing that, that person has to be really, really good at all those other functions too so that everyone who is in their organization respects that. Otherwise people feel like I'm the second class citizen in this model where this person doesn't know anything about, whatever; my function and so on. So it's harder, but I do feel that for optimization around decision making, around having a single threaded leadership and accountability, I feel like that's the direction where the product leadership role itself is going more and more. At least based on my experience.

Lenny (00:39:19):
Is your sense that maybe CPO might fade away as a title and GMs become the common path across companies?

Manik Gupta (00:39:26):
If you were to push me on this, I would say that's probably the direction we will go. I think it's interesting to also think about CTO. If you look at the CTO roles versus SVP of engineering or a VP of engineering, I think it's an interesting debate too, what's happening with CTO roles. If a company is organized purely functionally, I think that's absolutely the right call. But as companies are changing and thinking about how they drive more accountability and more business units and so on, I just feel it probably will become more GM oriented. That does not mean that the VP product is going to go away or the VP engineering is going to go away. I think those roles will still stay. But the C-level title, reporting into the CEO but you're just running that one function; if I look at over time, maybe that role is lot less prevalent than what we have right now.

Lenny (00:40:15):
Do you think that's partly because there's this weird overlap between CPO and CEO, and there's often tension of who's leading the product? Is that something you've seen?

Manik Gupta (00:40:24):
Yeah. I think that's definitely an interesting one as well. I mean, if you think about it, just based on my experience, what does the CPO really do? What is their job description? I think it's useful to think through that. Generally speaking, and again, we can always talk in generalizations because that's how you should think. And every company is unique. But generally you would say the CPO is responsible for driving the product vision for the company, and that product vision cannot be divorced from the company vision. Oftentimes this is actually what also creates conflict within the leadership team, where the product vision is... people are coming up with these grandiose plans. Like, "Oh, we'll do this, we'll do that," but then it's not really grounded in the reality of where the company is. Anyways, it's around product vision and making sure it's coherent with the company vision.

(00:41:09):
Then the second big part of a CPO job is execution of the roadmap on the priorities. People sometimes think that, hey, I get to a C-level position. I don't have to worry about execution. Absolutely not. If you're a CPO in particular, even the CTO and the head of engineering, execution matters a lot. The operational excellence. Because things are so complex. I mean, we are in a situation where a lot of people are working remotely, there are all these different tool sets, there are all these different technologies that are coming up, you have different competitors. Execution is super important. And if people don't understand that that's a big part of their job when they get to the senior level, I think they're mistaken. The execution is another one.

(00:41:50):
The third is, for a CPO, especially for a tech company, because you are really driving the product roadmap, it's a very leveraged job. Meaning you have to really work with all your other peers, whether the marketing person, or the sales person, or the business unit person and so on, and just make sure that you are really even deeply connected in terms of what is really needed, so that your product roadmap is how things are going to actually come to life. It's a very cross-functional, on steroids kind of job in that sense.

(00:42:19):
In terms of the CEO, CPO, I think the important thing again is... And this is actually advice I've given to CEOs of some companies as well, when they first start looking for a VP of product or a CPO. This is almost like a questionnaire that I give them. The first question I ask the CEO is, what do you want to do? That's the most important question. Because a lot of times the CEO has either been the technical founder, or they have been the product founder. They can be a sales founder too. All that is fine. But what do you want to spend your time on? Because if you are going to get a CPO or a VP of product and then still want to own the product roadmap and own the execution, then don't do that. Because what is that person going to do? That's the first question that I tend to clarify between a CEO who's looking for a CPO or VP of product.

(00:43:10):
Then the other thing is really about, are you trying to optimize for process? Are you optimizing for strategy? Are you optimizing for team building and attraction? I think that's a really big one. Sometimes you have to get the right level of leader to attract more talent to the team. Because people say, "Oh, this person is working there. Now I want to go work in their organization." How do you think about engineering and data science and design? How do you think about GM and operations? There are a bunch of all these things in terms of the design that you need to do before you decide whether VP of product, CPO is somebody you want to get and what kind of person you want to get.

(00:43:43):
I think that's where the intersection of the work between this... especially for a tech company, the CEO, CPO have to be... And even the CTO I would throw in the mix. That has to be very clearly articulated, otherwise it creates a lot of confusion. Those are some of the things, at least that I observe from different patterns and different companies that I've worked with and also guided and advised, those are things that always come up.

Lenny (00:44:06):
It's interesting how much similarity there is to that experience as there is to the first PM at a company. It feels like they have to have the same conversations with the founder. What do you want to work on? What am I going to take on? How do we avoid stepping on each other's toes the whole time?

Manik Gupta (00:44:21):
That's actually a... I never thought about it that way, Lenny. I think that's a really good point. You're totally right. Obviously, if you're at a bigger company, then you're looking for a VP of product. Or if you're a super big company, then you're looking for a CPO. But you're right. The first product hire that you make as a founder, you'll pretty much have the same conversations to ensure that there are clear swim lanes and accountability for that group.

Lenny (00:44:39):
Interesting. I want to make sure to ask you, as kind of a big deal leader of product at larger companies, I'm curious, what do you look for in PMs that are looking to get promoted, or just deciding somebody's ready for promotion or ready for more responsibility? What do you look for and what should people focus on if they want to come across as promotion material?

Manik Gupta (00:45:01):
I'm a big fan of looking at both the what and the how. So what did they accomplish and how did they accomplish. Because they're a package. And if you just look at one versus the other, then I think you end up making a mistake. Usually. On the what, I think the what is usually more objective. What I look for... And again, it depends on the level of the person. Don't try to calibrate someone based early in their career. You have to think through that. That they're in learning phase. If they're more senior than you have to of course calibrate them differently. But ultimately, if I were to boil it down on the what, it's really about real demonstrated impact. An ideal example is someone who had a strong product hypothesis, they rallied a bunch of people around them. They may not have come up with the hypothesis. That's fine. Somebody else could have come up with it, it doesn't matter. But they believed in it, they rallied the team behind it, they drove towards it and created impact.

(00:45:58):
The impact not necessarily always has to be positive. It could also be a lot of stuff that we learned, but we learned from it and then we moved on and we did the next rev. By the time we did the next rev, we were smarter about it. Clear demonstrated impact from an end to end product cycle to me is probably one of the better indicators of readiness for someone to take on more. And you basically want to give them more, because now they have a pattern of doing things properly. That's one.

(00:46:23):
On the how, I just love people who are able to create both energy and create clarity. Think of the flip side. PMs who don't create clarity is such a time sink and the teams struggle so much. I'm sure all of us, when we think about back in the day, maybe we were in that position at some point. But we also worked with folks who were always confused and didn't really summarize, or didn't really follow up, or didn't really create that level of clarity in terms of what we need to do and so on, and how broken that felt. People who can create the clarity and then have the energy around them to get things done, I think that's the how in my opinion. Which is really important for determining somebody's career trajectory.

(00:47:11):
Then the last thing I would say is followership. Really important for PMs. Do people want to work with them? Do people at some point, as they go up and become more senior, do people want to work for them? Ultimately people make choices. And if you have a bunch of smart people and they're making smart choices and they're choosing this person to follow or to be with and work with them and reach out to them, and you keep hearing things about, hey, so and so wants to work with this person because this person is amazing; there is a ton of value in that.

(00:47:45):
Those are the three things that, if I were to really boil it down, not looking at a certain level, I think I always look for those attributes.

Lenny (00:47:51):
Those are awesome. So simple and clear and succinct. I like the way that you framed it as followership versus leadership. There's a lot of PM attributes leadership, and there's something really nice about just a way to understand that as how many people are following you and excited to work on the things that you're trying to get them to work on. That's very cool.

(00:48:11):
Along the same lines, when you think about PMs that had an inflection point in their career, do you find that there's anything correlated with something that leads to a large inflection in the progress of someone's career where they all of a sudden started doing incredibly better?

Manik Gupta (00:48:24):
I've gone through a few inflection points myself, and almost always they've happened because something in the organization changed, so I got a shot. There's always that luck factor, going back to the first question that we discussed.

(00:48:37):
But generally speaking, I think the inflection points happen in two places. One is when someone has really successfully changed the dynamic, or the trajectory rather, of a particular product. That's a huge inflection point. That doesn't happen very often, to be fair. But when it happens, you know it. You know, as a leader, this person worked on this and they actually led this change and now we are playing a different game. We are playing a bigger game, we are playing a different game, all of that kind of stuff.

(00:49:16):
In other words, what I'm saying is the inflection point for a career is correlated strongly with the inflection point in the product. If you can connect those, the cause and effect... If there's causality and not just correlation, if there's causality in that, I think that absolutely means that you've got a winner. And you really want to bet on them and you have to give them a lot more to do, because they have the ability to do it. That's one.

(00:49:38):
The second is, oftentimes as people go up in their career, they start managing teams. They become a manager, and then you become a manager of managers, and then you become more senior. I mean, that's the organizational trajectory that happens. One inflection point that I've seen is, when you go from being a manager, a first line manager, to becoming a manager of managers, and if you're able to navigate that with very strong effectiveness, then you know. If you're their manager or if you're their leader you know this person has got their act together. Because managing ICs is so different from managing managers, because then you now need to create a structure. You need to be able to determine how much you delegate. How do you coach? How do coach your managers to do the right thing? If you see somebody making that transition effectively... And you have to give them some time, but if you see that and you know that they're actually doing it, and again, a lot of followership, a lot of other things are happening, good things are happening, then you know they're at that inflection point where they're ready to take on more.

(00:50:41):
Both product inflection in terms of real output and this management prowess inflection in terms of being able to effectively lead going from one step to another, a manager to becoming a manager of managers; I think those are the two places where I feel like, if I see somebody doing well, I know they're ready to put more onto them.

Lenny (00:51:00):
Do you find that second piece is this filter for PMs that do well in this manager manager role and go on to do better and better and then a lot just fall away because they can't handle that?

Manik Gupta (00:51:12):
Yeah, I think so. Maybe I'm a little bit more traditionist on this point. I know there are other schools of thought on this, which I respect. Which is there are a lot of times where people are like, "Well, oftentimes the best PMs are PMs who are IC PMs. They have this crazy, incredible, unbounded energy and they don't want to waste their time on management and whatnot and do that. Because a large part of a PM's job, by the way, is managing by influence. PMs typically don't have large organizations. In fact, one of the most leveraged teams in almost every company... Because you talk about PM manage ratios, PM design ratios, they're never one-ish to one, or one-ish to five, or one-ish to six. Sometimes it' going to be one-ish to 10. At Google it used to be one-ish to eight to one-ish to 10.

(00:51:52):
I personally see that transition... If somebody's making that transition successfully and they're getting good scores out of it and delivering the product and the output of the team is significant, I definitely see that as a good filter criteria for someone whom we can bet on.

Lenny (00:52:06):
Do you find there's common habits or pitfalls PMs make to shoot themselves in the foot in their career, especially early on?

Manik Gupta (00:52:14):
Oh, I see that all the time. There's a few of the things that I have picked up. And by the way, I was doing this too early on and I learned the hard way. The first one I would talk about is you are early in your career and everyone expects you to just manage things and manage the process and all of that. Make sure that trains are running on time and all of that. Which, by the way, is really important for an early in career PM to understand. That that's actually a big part of your job. Let's not over glamorize a PM. A large part of being a PM initially is just basically doing whatever the team needs you to do. But I think one of the pitfalls of that is, if you start putting process over progress, that's a problem.

(00:52:58):
What I mean by that is, you want to introduce process into almost everything that the team does and not be flexible on shipping things out there and all the things that can come in the way of progress. If process is helping progress, great. But if process is hurting progress, you should not be the person saying, "No, no, no, no. We can't do it, because I'm just so married to the process. Because as a PM, that's what I own." I mean, as a PM you don't write code typically, you don't write design specs, you write product specs. Sometimes you feel like, what is the set of attributes that I own? Especially early in career PMs. And you're like, "I own this process. I own this weekly standup meeting, or I own this sprint planning, or whatever." And then you get so married to it that you forget the fact that that's just a means to an end and the end is what you're going to be actually measured on. That's one mistake that I see people making early on.

(00:53:48):
The second one is becoming really too self-centered. It's all about me, not the team. I'm the PM. There's this myth that keeps going around. The PM is the CEO of the product. That's one of the most incorrect things in the world. The PM is an enabler. I said earlier, it's a leverage job. Your job is to really make the team successful. Of course you have to have the product thinking and the roadmap and all of that, but sometimes this can go to their head. Then people become too self-centered and that's a red flag.

(00:54:21):
Then the third one would be just not admitting your mistakes or learning from them. Early in career, the only thing you should optimize for is learning. Sure, you'll make a lot of mistakes. You don't know much yet. You're just coming into this journey and you should be humble and you should be learning and you should be saying, "Oops, I screwed up over here." And that's okay. That's fine. And by the way, if you work in a company where that is not accepted, you should not work in that company. What's the point? You should really be optimizing for learning and learning from other people. And people should be saying, "Yeah, don't worry. It's okay. You made the mistake. Learn from it. Don't make the mistake again. That's fine." But that's the kind of culture you want to choose for yourself.

(00:55:01):
Those are the three pitfalls that I see people get into, especially early on in their career.

Lenny (00:55:05):
You touched on how different companies work in different ways and look for different things in different PMs. And something I wanted to ask you is just to chat a bit about the difference between working at Google versus Uber versus Microsoft as a PM, and also just generally how product is built differently at these companies. It's something I'm trying to do with this podcast as much as possible. Just give an overview of what product is like at different companies. You've worked at three of the biggest, and so I'm curious to hear what you can share around that.

Manik Gupta (00:55:32):
Yeah. It's actually really interesting. I mean, all the three companies are so different. Google, the core DNA of the company was very much engineering. In fact, there used to be a framework which was around technology insights drive innovation. It was always about what is the best tech we can come up with, which is going to indeed drive innovation, and have a longish view so that the market will get there. That was the Google philosophy always. As a PM, your job at Google... It might have changed in the last six, seven years that I've not been there, but at least when I was there from 2008 to 2015, especially working on Google Maps, it was all about how do you take good long-term bets grounded in strong technical insights, and then use the power of Google Search distribution to really get your product out there. That was it.

(00:56:33):
On the Maps team, our innovation was pretty much around crowdsourcing everyone's location signals for traffic. Huge, huge accomplishment. We had the best traffic models in the world. And then being able to do this crazy route optimization for driving directions. Then on top of that, we had the search stack, which came from Google Search anyway. So that you can search for any address, any business and so on.

(00:56:55):
Anyway, as a PM it was partnering very closely with engineers and really amplifying the engineer's ideas and so on. I think at that point also a lot of Google PMs were very technical. Very, very technical. Because that was just part for the course. It was expected that you will be able to at least have engineering discussions. A large part of what I did as a PM at Google, especially initially, was getting into the technical details with my engineers and really geeking out on what we can do. That was the Google model.

(00:57:25):
By the way, one thing I should say about Google before I go to... At Google as a PM, at least all the way up to the time even when I became a director, I never had to think about business models, man. Never. It was fascinating. You were in this weird state where you could just build and have the consumer traction and all of that, but you never thought about P&L, never thought about revenue and so on.

(00:57:48):
Then I landed at Uber, which was very different. Uber was very operations, very business driven, very P&L. In fact, one of the most incredible things that Uber did was they had a dashboard which every employee in the company could look at, and it had last week's revenue, last week's number of trips that we did, and you could slice and dice it and all of that. I think that changed over time as we became a public company and so on. But the point was that it was really in your face all the time. When there were weekly newsletters sent out, it was all about growth, it was all about business, all of that kind of stuff. It was very operational and business, so as a PM over there it was a lot about managing a bunch more stakeholders. The operations teams, the marketing teams, the policy teams and so on. And how do you work with them to deploy your product into each of these markets. Of course then a large chunk of your work was still working with the engineering team. It was different in that sense.

(00:58:47):
I think at Uber the other thing was it was also much more of a real time business. I mean, Google was also real time. Google Maps was real time. Billions of users were using it. But Uber was... every day there was something going on in the market and you had to keep on that hustle in terms of how do you make sure that your staying competitive, your product is working well, there are no outages. All of that kind of stuff was really important.

(00:59:09):
Then finally, on Microsoft... I mean, Microsoft has been around for quite a while. The company went through so many different things and then over the last several years, especially under Satya's leadership, it has done so well. Incredibly well in terms of how the company has changed the culture, the kind of products that they have in the market, the traction they have in the market.

(00:59:29):
I think I would describe Microsoft as both... first and foremost, it's a very strong tech company. The engineers here are incredible. Oh my God. I am so privileged to work with some of the best engineers that I've worked with in my career. At the same time there's a lot of legacy. There are a lot of products that have been around for a really long time, which is good and bad. The good part is that they have seen pretty much every pattern there is to see. In fact, they came up with a lot of those patterns themselves. The bad part sometimes can be that change is hard. How do you convince people that we're going to go down a different path? As a PM, a lot of it is around bringing outside in perspective, bringing clarity of like, "Hey, this is how it has actually worked somewhere else." Bring a specific example. Let's try it out and see how that works.

(01:00:13):
The final thing I would say about it is the company is so grounded in trust. If there's one word that I would say about Microsoft is trust. They really care a lot about customers. Customers trust Microsoft a lot. I've been in some of the customer meetings myself and I can totally hear what customers say. It's all about trust. They expect resilience, they expect the products to work, and they expect that when they have a problem on the surface, that Microsoft will take care of it. They built that over time. A lot of that goes into your mind as a PM when you're working in that company, that a lot of the stuff that we are doing here is to really help our customers.

Lenny (01:00:48):
Going back to your point about company-product fit, these cultures and the way they work just fits perfectly with the thing they end up building. I wonder which one comes first.

Manik Gupta (01:00:57):
It's true. That's a whole nother conversation we can have at some point. I have a lot of thoughts on that. But I'll just echo what you just said, which is that's the reason why it's so important for companies, when they embark on new initiatives, to be really, really thoughtful. Is this the right area for us to get into? Or rather, what are the conditions and the reasons why we are getting into something? We have to be super clear on that. Because if the starting conditions are not right, then you will just trash the team. The team will keep working on something and people will never find the right internal fit. So that's super important.

Lenny (01:01:35):
You worked on Google Maps and Uber, which I imagine you still use often and maybe billions of people use every day. Is there a feature that you wish that you built back when you were on the team, or that you think should be killed, that annoys you about either of those products?

Manik Gupta (01:01:50):
Wow. Okay. This is a super interesting one. I don't know if that's something that I could have built at Google Maps, but one of the things that's interesting is the self-driving technology has just not gotten there fast enough. I feel like the best and brightest actually worked on it and are still working on it and it will get there. I'm a big believer. But of course the timelines have shifted for various reasons, because it is a really hard problem. It's actually really interesting to see what Cruise is doing right now in SF. They have started the pilots and so on, so I'm really happy to see some progress happening. I know Waymo's been doing a bunch of this already.

(01:02:29):
But it would've been amazing. One of the things that we used to talk about all the time at Google on Maps was how would we design a navigation product when people are in self-driving cars? We had some really interesting ideas at that point, but we never got to it. Not because we didn't prioritize it, but the technology isn't there. I still keep a close watch on that and see at what point are we going to get there. It's going to take years, but it is just such a different paradigm. It's like computers talking to computers, algorithms talking to other algorithms. Then there's a human in the mix in terms of serving the human at the end, but it's like the human is not initiating that much. It's just, stuff is happening around it.

(01:03:08):
Anyway, that's one thing that is unfinished business, if you will, in my mind. And hopefully, as the technology comes together, that will happen.

Lenny (01:03:16):
Amazing. Manik, you've been extremely generous with your time. Just two last quick questions. Where can folks find you online if they want to reach out maybe, or learn more about what you're doing? And then how can listeners be useful to you?

Manik Gupta (01:03:28):
Yeah. You can find me on Twitter, you can find me on LinkedIn. Those are the two places. I have not been very active on both those recently. I've not been active as a contributor, but I'm very active on those two platforms as a consumer. If you have any questions, if you have any thoughts, would love to hear from you, so please send me a note.

(01:03:47):
In terms of how listeners can be helpful, I just want to learn what's new and what's out there. I've had the privilege of being in these incredible companies. The reason why I'm still doing what I'm doing is because I still want to learn. If there are better patterns out there that you're seeing, particularly around how to build products, would love to know if there are other ways people think about finding product market fit. Because that's such an elusive thing that I just keep thinking a lot about. If you have some techniques, some tips, some best practices that you have learned and it has worked for you, please, please, please reach out to me. I would love to learn that, because it's so important for us to keep having that conversation.

Lenny (01:04:24):
Awesome. It's always such a pleasure chatting. I always learn a ton. And this did not disappoint, so thank you again for being here.

Manik Gupta (01:04:30):
Lenny, thank you so much for asking all these questions and giving me the opportunity to share my learnings over the years. Thank you.

Lenny (01:04:36):
Absolutely my pleasure. That was awesome. Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast. You could also learn more at lennyspodcast.com. I'll see you in the next episode.