Building a long and meaningful career | Nikhyl Singhal (Meta, Google)

Nikhyl Singhal: When I was a kid and I was growing up in the Midwest, entertainment was like going to the dog tracks. The way that they motivated the dogs was they had these fake rabbits. These tails would go around faster than the dogs, which would then motivate the dogs to go around in circles. And what was interesting is the moment that the dogs, if they accidentally touched the rabbit, they would never run again because there was like, “Well, what’s next? I’ve achieved what I was looking for.” So I think this happens a ton, it’s like your listeners are spending time focused on like, “Well, one day I will be X. I will be that vice president. I will have more money. I will have built something. I will have started a company.” But they don’t think about what happens next. What’s the second thing? What’s your career next look like? How do you ensure that you are always going to have something important and motivating to do with your career? Otherwise, you’ll keep working because you know nothing else to do, but you’ll be sadder or you’ll find ways to create war when peace is needed.

Lenny: Welcome to Lenny’s Podcast where I interview world-class product leaders and growth experts to learn from their hard one experiences building and growing today’s most successful products. Today my guest is Nikhyl Singhal. Nikhyl has worked on and led large teams on four different influential consumer products including Facebook, Credit Karma, Google Hangouts, and Google Photos. Currently, he leads product teams for the Facebook app at Meta, overseeing groups, stories, messaging, and the feed. Before that, he served as chief product officer at Credit Karma and held various leadership roles at Google. Nikhyl has also co-founded three different startups, and as you’ll hear in this episode, is extremely passionate about coaching and mentoring, sharing his knowledge through his newsletter and podcast called The Skip.

In our conversation, we cover all aspects of the PM career and what it takes to be successful at every stage of the journey, including the dangers of thinking too short term, the importance of avoiding what he calls ex-growth companies, why you’re probably not getting promoted, what to focus on if you’re a new manager, the rise of the senior IC path, also why top leaders often have huge development areas they don’t know about and how to catch them, and also why people who make it to the top often run into serious mental health challenges. As I say at the end of this episode, this might be my new favorite episode and I’m really excited to bring it to you. With that, I bring you Nikhyl Singhal after a short word from our sponsors.

Nikhyl, welcome to the podcast.

Nikhyl Singhal: Thank you, Lenny. I appreciate it. I’m happy to be here.

Lenny: So I have a very simple question to start. How many product managers have you been a mentor to if you had to put a number on it?

Nikhyl Singhal: Good question. I guess I haven’t thought about it from that perspective. I would say hundreds is probably the way to sort of answer the question, and a little bit has to do with whether how we define being a mentor. I know that was supposed to be a simple question and I’m going to give you a complicated answer, but I think that I started out just helping people 10, 15 years ago, trying to help them through their careers. I find the whole area really interesting. And then what happened was just I started to scale because people were always like, “Hey, can you find time?”

So now what I do is I tend to help and coach hundreds of folks through transitions. So if they’re in a moment where they’re trying to decide between another job, if they’re trying to decide to leave, if they’re having sort of an alert at work, I call them 911 calls. I take a few 911 calls every week and from a relatively large group of people. So I find those are the most substantive times to help people, is when they’re in moments of dilemma or forks in the road, and that’s why the number is more closer to hundreds.

Lenny: Okay. Follow-up question: How many of those people you’ve mentored have been on this podcast?

Nikhyl Singhal: Probably half dozen to kind of close to a dozen at this point.

Lenny: Oh, wow.

Nikhyl Singhal: Yeah, easily half dozen.

Lenny: Amazing. Okay. Is there any names you want to name or should we keep it anonymous?

Nikhyl Singhal: Yeah. We’ll keep it anonymous because I want people to feel they can always call me in and not feel like that. I don’t tend to share the names of most people.

Lenny: Okay. I know the one person that self-identified was Annie Pearl from Calendly, who is a big advocate of the stuff that you do. So we don’t want-

Nikhyl Singhal: Yeah. Annie is someone I learned from and helped talk with, and she’s also part of a community that I also build on the side where we pulled a bunch of CPOs together and they’ve been building community. I’m a big fan of community and learning, and she’s part of that as well.

Lenny: Awesome. I definitely want to talk about that, but maybe just set a little context for our conversation. I feel like you’re in the very high percentiles of people that have seen a variety of careers in product management, both good careers, bad careers, junior people, senior people. So I want to focus most of our time on talking about just the PM career path and what you’ve learned about what is important to have a successful, thriving, happy PM career. Does that sound good?

Nikhyl Singhal: Perfect.

Lenny: Okay. So I’m thinking we break up the chat into early career, mid-career, and late career. So within the early career section, you’ve talked about how people often make a mistake in their early career, specifically being very short-term focused in deciding where they’re going to go. And that’s a very dangerous way of thinking about it. So I’d love to hear just your take on exactly what does that mean, and why is that actually a bad idea?

Nikhyl Singhal: Yeah. I tend to be long-term focused in most of my counsel, and maybe to give you an example of what a short-term focus career kind of framework looks like is, “I really dislike my boss. I feel like this company doesn’t have it anymore. There’s just too hard to ship things.” Those are all maybe true statements, but they probably exist in many of the jobs that one would consider if they were to move for one to another. Lateral moves are by definition not forward moves. So what I try to tell people to think about is work backwards from your end state.

Almost think of career as a product. So if you’re building a good product, you think about, “Well, here’s what a great product would look like,” and then you break it into version one, version two, version three. Well, in some ways the reason I called my newsletter, my podcast The Skip is because I always think about not the next job, but the one after it. Maybe think about not your boss’s job but your boss’s boss’s job and what do I need to think about to get there. And in many ways you may think, “Well, okay, if I need to found a company one day and that’s my job after next,” then you want to look at maybe your current job and then maybe the next job in service of that. And that may lead you to saying, “Hey, maybe I need a grit of doubt and maybe I should stay and maybe I should learn how to deal with some of this ambiguity. That’s why I want people to be a bit more longer term and not so short-term focused.

Lenny: What are some other examples of that short-term thinking? You talked about “my manager sucks, things are moving really slowly.” What other examples where people maybe like, “Oh, okay, I see, this is actually short term. Let me think longer term”?

Nikhyl Singhal: I’d say the biggest one in workplace is focusing career and promotion together. I think that there’s perhaps a light connection between promotion and career addition, but I feel like too many people are, the moment we talk about career, they’re like, “Well, let me talk to you. I want to have a career talk with you.” And I said, “Sure, why don’t you find some time?” We sit down together and they’re like, “Well, what do you think I need to do to get to promotion?” And then I said, “Well, promotion is our system at this company to see you moving forward. And it’s pretty clear in terms of levels and what you’re doing and what the process is and who makes the decision.” And that’s pretty short term because you can ask, “Hey, it’s two years away, how do I make it 18 months?” It’s a classic.

But in reality, if you’re thinking career, you’re thinking about the sort of long term arc and, as I said, maybe the job after next, and then you need to look at the promotion in service because how many people have you and I talked to who said, “Well then, as soon as I get promoted, I’m going to leave”? So then I’m like, “Well, okay, then what’s the promotion in service of?” And you get into that conversation, which tends to be, again, very long-term focused.

Lenny: This makes me think about this interesting two-sided challenge with thinking about your future career and where you want to go. On the one hand, it’s valuable to think about getting more logos in your resume and working at Netflix and Meta and Airbnb and Uber, all these guys, there’s power and value to that. On the other hand, you just keep doing that. And then what is your life turning into? You’re just chasing more fancy logos and feeling better about better brands and your resume and stuff. This might be too big a question, but just how do you advise people to think about how important it’s to get some of these companies in your resume and build that side of it versus just doing things you actually enjoy and having a fulfilling life and doing things that are meaningful to you?

Nikhyl Singhal: Yeah. I mean I think collecting labels does feel shallow to most builders because if you’re a product person, you probably got into the business because you like building stuff. And frankly, not just product people want to do that, a lot of technical people want to just build stuff. And then the question is, is the things that you’re working on in service of building? And then when you ask people, “Were you happy?” as they always say, “Well, when I was able to build this thing,” and oftentimes they don’t care whether it worked or not, which is kind of ironic. So for me, when I see people chasing logos, I think about it as well. I’m actually really a big fan of a diverse set of experiences, that I think learning about pre-product market fit then seeing smoke turn into fire and witnessing and maybe shepherding that and then taking fire and turning it into something great and being an experience set where you can see the movie in these different frames makes you just a better builder.

So you can’t really go wrong if you’re looking at those experiences. And you’re looking at inside the building problems and outside the building problems, those are maybe consumer problems and business-to-business problems. The more diverse career you have, the better builder you are. And that usually comes up being satisfied. But the idea of just doing that because you think it’s going to make your chances better for the next job maybe scares me and it feels very much in service of some future dream that is not build oriented. And I think that can be leading to sadness.

Lenny: I love that advice, and I say this often actually on this podcast, the power of a diversity of experiences for so many reasons. Maybe just to close this loop, would you agree there is a lot of value in having one of these FAANG ish companies on your resume? Like a lot of opportunity gets unlocked if you work at one of these companies that people are like, “Oh wow, okay, this person’s interesting.” Or not? Or do people maybe overthink that?

Nikhyl Singhal: Generically, the answer is yes. I think it’s especially important for executives. I think that many executives are hired because they are to bring expertise of the next phase of organization to this company. We’re growing, we want to go after the next phase. We want someone who’s has expertise. The MAGMA or FAANG companies, however you want to describe them, they really have challenges and expertise at how to build things at scale, how to manage millions or billions of users and customers. So the advantage is, to be successful at that is an endorsement. Having said that, those specific companies, experiences can be substituted for other later stage companies, but if you’re coming in as an executive to bring someone to the next level and you’ve never experienced it, it’s very difficult thing to get that executive experience and to be like a C-level for that growth company.

Lenny: To point out, FAANG is no longer accurate because Facebook is now Meta. So MAGMA is the term that you prefer.

Nikhyl Singhal: I prefer that. I think it unfortunately kicks out Netflix, but it also doesn’t pay homage to Adobe and Salesforce and a number of other great companies. So I think-

Lenny: FAANG doesn’t. Okay, I like this. Okay, let’s try to make MAGMA the new thing. MAGMA, make that the title of this episode. Just joking.

So the next area I want to touch on is, you wrote this kind of hot take on something you call ex-growth companies and how it’s not good to be at an ex-growth company currently. So can you just talk about what is an ex-growth company and then why is that not a good place to be as a product manager for probably any kind of role?

Nikhyl Singhal: I have a pretty strong opinion on this that I think that for 10 years we created the hypergrowth, blitzscaling type phenomenon, and there was a lot of good reasons for that, some of which were just distribution platforms just got so good. You could take out Facebook ads, you could grow with Google, and you could grow in 18 months that maybe took previous companies 10 years. So I think that the idea was that all of these companies could instantly grow when they found product market fit and that birthed all these unicorns. And then suddenly, 18 months ago, it almost like the music stopped. 0% interest rate went away, and it became a lot harder to find growth through just fueling it with capital. And I think that the sudden change meant that not only capital was harder to raise, but companies started to focus on their core products. You’ve talked about it on this podcast, just how many layoffs and restructuring and managers moving to ICs, and all of that work is happening.

Well, the one funny pocket was there’s these large number of growth companies who have raised substantive dollars. So they’re not going to run out of capital in 2022 or 2023. What’s going to happen is, they actually have quite long periods of time, so you don’t see them raising new rounds, you don’t see them laying off, but in some ways they’re still hiring or they’re still seeking the next product. The sad truth is that many of their contemporary companies that went public are worth 10% or less than what they were worth back then, and these companies are privately held and so they’re sort of sleeping in the shadows.

My fear is, from a career point of view, so many tech professionals are in these organizations or joining these organizations with the expectation that they’ll make money on their equity, that they’ll continue to do fine. And my sense is we’re going to see, even in the second half of this year, lots of boards pulling back, taking their capital back, companies essentially saying, “Hey, we’re capitalized. We’re a scaled ocean liner, and now we need to go find product market fit.” But doing that with 300 people and expectations of hitting a multi-billion dollar valuation just isn’t going to happen. So that’s the reason why I’m like, “Danger. This is not the company to join, this is the company to leave. Find another phase. Time’s a wasting.” And I worry very much that people aren’t getting the message.

Lenny: I know you probably don’t want to name any names of companies, but what are some signs that may be you’re at one of these companies?

Nikhyl Singhal: I think that the moment that you are reframing the core product, trying to find that product market implies that this company’s valuation needs to be a pre-product market fit valuation. So the two questions you ask yourself the day after we listen to this podcast is, “Hey, are we scaling a product? We have customers that love us and we have a tremendous sucking sound? Or are we trying to find that customer sucking sound?” And if the answer is, “We’re still trying to find it,” and then you’re like, “Is your evaluation hundreds of millions or tens of millions?” and if the answer is hundreds or more and you’re still trying to find that sucking sound, you’re an ex-growth company.

Lenny: As a founder listening to this, I bet you’re like, “Damn, we don’t want people leaving. This isn’t the kind of message we want to hear.” On the other hand, as an employee at a company, that is your advice, just generally recognize it and then you should probably leave as soon as possible because things are not going to work out for you.

Nikhyl Singhal: As an employee, I think you have almost no recourse because you almost have to start over in terms of it’s a new four-year investment. I think that as a founder, you can recap your company. You can reset your stock price, you could reissue. You can make those hard decisions and you can maybe return some of the money to the board and still continue, or you can pull the plug and restart the company that maybe you really wanted to. But I think the founder is in a better position, but they also have a lot more to lose and far more constraints. But employees, they’re not… If you listen to this and come to this conclusion, a lot of times, the listeners here, half or more of their compensation is an equity and we just concluded that most of their equity may not be worth anything. In which case, are you willing to take a half pay cut or work for 20% of what you can get on the market? My question is, that seems to be quite concerning, the opportunity cost is just too rich.

Lenny: An important variable in this framework/piece of advice is product market fit. This might be too big of a question, but just, what tells you that something might have not have product market fit when you’re at a company like this? What are signs to you and smoke signals of like, “They may not have product market fit”?

Nikhyl Singhal: For me, it’s always around this pull that sort of how much work do you have to do to basically generate pull? So right now with OpenAI for example, we’re seeing ridiculous pull, but we may not be seeing, for example, massive revenue or profitability. So that’s the reason why I tend to feel like you can kind of tell by how hard it is to acquire your users. When companies are putting very little in marketing and there’re people coming into the door or there’s such an easy sale, you’ve got it. I think that this sucking pull kind of concept feels like the most appropriate way to define it as opposed to the sort of unit economics of acquisition and time to pay back. There are lots of mathy ways to do it, but early on you can tell how hard are you working to bring people in the door.

Lenny: Is there any reason to consider staying at a company like this?

Nikhyl Singhal: There are counter examples. I think the counterpoint is, this is the biggest role that you feel like you could get and you have an appetite to sort of learn like, “I’m on the executive team, I’m not going to get that somewhere else. That experience is career additive. I want that moment.” Great. Sometimes I see loyalty come in, “This was my baby. I feel a commitment to the team, the team that I’ve made, et cetera.”

Lenny: Yeah.

Nikhyl Singhal: I actually respect that. I think that you have to put bounds on that. I think that you should have that conversation. But the learning position, the loyalty tend to be the primary reasons to maybe delay the decision, but fear of finding another job is a bad reason, but is an often common reason as well.

Lenny: Now that we’ve given many listeners an existential crisis, let me move on to another question within the early career phase and then I’m going to move on to mid-career. I guess the question is just, is there any other piece of advice, wisdom for early PMs? Maybe the question is, what do you think they should most get right in their early career?

Nikhyl Singhal: There’s probably two answers that I would share. One is, they want to build something that they as much as possible are world-class in. So if you think about the different types of product ambiguities that exist in industry, you can be a great crafter. You could be incredibly strong at market ambiguity. You could understand how to navigate markets and create something new that doesn’t exist. You can be great at organizational ambiguity. I know how to take complex teams that have complex goals and solve an inside the building problem. You can be a domain expert. I’m an ML expert, I’m a really strong hardware PM. You can be a team expert. I just really thrive in managing managers and I just know how to get the balance right. So, being a product manager means you’re confronted with maybe all five or maybe more of these. I want to know that you pick up one of these as early as possible.

So maybe you become an expert in domain, maybe you become a great crafter, maybe you really think through how to manage growth. Growth is another one that I would add to the list. But picking a lane is kind of goal number one. And then maybe goal number two is having a story to tell to that next employer and that next, next. What I worry about is, sometimes when I’m in an interview, and you and I have probably done hundreds, and you’re talking to someone and then they talk about those early jobs and they just sort of said they were there, this happened and it’s very hard to connect, tell me exactly what you learned and what you did, I want to know that story. So it’s just like Amazon talks about building the press release before they start creating a product. Think about the story, think about the skill, then solve your day to day, your week to week, your month to month, your performance review. That’s my biggest advice I seize.

Lenny: I love that advice. It connects to your other earlier piece of advice, of just try to get a variety of experiences because that’ll help you figure out which of these things is maybe best suited for what you’re interested in, what you enjoy doing.

Nikhyl Singhal: Yep, absolutely.

Lenny: Awesome. So let’s transition to mid-career. Let’s talk about promotions. You mentioned getting promoted earlier. We chatted a bit about that. There’s probably no one ever that didn’t want to get promoted. It’s a common topic in people’s career, but a lot of times people don’t understand why they’re not getting promoted, they’re not sure people are looking for to get promoted. You’ve promoted a lot of people and you’ve gone through a lot of promotions. What would be your advice to give people who are trying to get promoted and just haven’t been promoted? What would you suggest people in that position generally do?

Nikhyl Singhal: Yeah, it’s a great question. I think that we want to kind of understand why, and oftentimes asking your manager won’t reveal the answer. So then you’ll start with that. I think that the answer of what you do is correlated with what’s the real reason. And I think that there may be, I’ll suggest four kind of common things I’ve seen that really hold people back. And then depending on your environment, you have to decide how many of these apply.

So I think the number one is that you just don’t have advocacy. You need someone to see the magic in you to be promoted. There is many of your listeners who have that magic but maybe have a manager or a promotion team, it doesn’t always have to be the manager itself, who doesn’t see said magic. And in that case, if you have the magic, you’re in a bad setting and you just need to change. That could be a shift within the project. You could find a manager who sees it. It could be leaving the company. I think the second that’s very common now, Lenny, and I think it’s coming up a ton, is the next role doesn’t exist.

Lenny: Mm-hmm.

Nikhyl Singhal: So this is not as present in hypergrowth because the next role always did exist. There was always growth, there was always hiring, you’re always hiring people above you, below you, et cetera. Now, I think there’s lots of examples of people who are really qualified and working at the next level, but the job doesn’t exist. So you can’t really create that job and ask them to be working at that next job if their position is mostly the previous one. Again, I feel like it’s not that satisfying because it means you’re still being held back, but it’s radically different than if you’re unqualified. These two are sort of more, the system is not in a position to advocate.

The third is when you are being impatient. And I think the hardest ones that I think I’ve worked with is, the highest performers have succeeded because they have set their goals to be more aggressive than what was essentially average achievable. By default, we expect you to be two years in this role. They’re like, “Great, I’ll see you in a year.” And then they get frustrated when they can’t do that, and leadership takes longer to absorb. It’s more soft skills, it’s more subtle. Oftentimes it’s based on impact, which is a lot of times lagging, and that tends to be frustrating. So if listeners are like, “I know I’m used to being promoted annually and now I’m a leader and I’m not moving as quickly, it’s time for me to go,” I’m like, well, maybe that’s working as intended. So impatience is a number three.

And then the fourth one I think is about 50% of the cases where it’s really, there is a development area but it isn’t quite connected to the individual. The listener has a development area, it’s substantive. The manager is poor at identifying it, perhaps even doesn’t see it, but the promotion committee does, the individual refuses to hear it, which is a very common one. Or they hear it and they just don’t want to change it. And they don’t do it because they’re arrogant, they do it because it’s like, “This is who I am. You want me to be X and I’m Y, and that’s what a Y is and I don’t want to be X.” This is the hardest one because this is where coaching and development and self-awareness come in.

Lenny: Amazing. This super resonates. So just to summarize the four reasons you may not be getting promoted: One is, there’s no advocate that sees your magic and understands that you’re awesome. Two is, there’s no actual role that’s available and so there’s nothing to get promoted to. And that’s so true right now, there’s just not. Everyone’s laying people off, they’re getting rid of manager layers. I totally see that all over the place. Three is, you’re probably just not being patient. Four, you actually have some work to do and you shouldn’t be promoted. Maybe to follow a thread on that first one, if someone doesn’t see your magic, I see a lot of people just complaining that like, “Oh, I’m doing so well, I’m so great and nobody understands it. No one gives me credit. No one really appreciates me.” I don’t know if there is an answer to this, but is there a way to help people see that no, you’re actually not doing great versus you are and people just don’t see it? What’s a sign maybe? Maybe you’re not as great as you think you might be.

Nikhyl Singhal: The cheap answer is you have to get real feedback, not formal feedback. I think that the more scaled the company is, the more they have these systems in place which provide formal feedback. But honestly, we’ve run experiments where we said let’s ignore the formal feedback, let’s have a real conversation with my peers on how our teams are doing. The signal that comes out are dramatically different than the formal feedback. So what you’re looking for when you feel like you’re in this situation where you’re not being seen, and it might be because there’s a real issue, what you really want to dial into is, “Let me get the ground truth as to what people are thinking,” and you have to have very strong listener skills where we all have been in the discussion, where you’re giving feedback to someone and the next thing that they tell you is they justify how you’re wrong, that you missed this. “Let me tell you about exactly why that situation that you’re using wasn’t…”

You have to be great at pulling feedback, listening to it. You have to triangulate it from people that don’t see you all the time, that do see you all the time, your peers. But you have to create an environment of safety where people feel like there is no worry about retaliation or concern, et cetera. And the more comfortable people are about giving feedback to you and the more you have the skills to pull it and you don’t trust formal or you don’t trust manager, the better shot you have of truly understanding what that real issue is and solving it.

Lenny: This reminds me of Jules Walter who’s on the podcast. He gave a bunch of advice. I don’t know if you saw that. I’ve had to accept feedback and get people to give you feedback. And one of its pieces of advice is, ask people for real feedback. And no matter how much you’re melting inside hearing it, just be like, “Thank you so much for that.” Because then, people feel like, “All right, he’s listening.”

Nikhyl Singhal: I think Jules is a great, probably one of the world’s best people in pulling feedback in my experience. I think that the one that even ones up it is, when I talk to Jules, Jules will look for feedback, then he’ll repeat it back to me better than even I presented it. And then I’d say, “Well, let me now feel safer to even provide.” Because anyone who’s explaining it to a place that they all not only internalize it but they can articulate clearly understands and values it. And that’s the really powerful way is, “So what you’re saying is I just interrupt far too often and some ways it’s almost to a point that it’s annoying. Is that a fair assessment?” “Oh, that’s actually not the words I use,” but that’s what really gets people comfortable in sharing with you what’s really going on.

Lenny: Amazing. I think we’re discovering some of these people that have worked with you that have been on the podcast slowly. Maybe while we’re on this topic, I didn’t expect to go here, but in terms of other tips for getting good feedback, is there anything else that just comes top of mind of how to get better feedback from people? Because it’s hard to do. Most people talk about getting feedback and then don’t, or they just don’t know how. So one is just, you said repeat back exactly what they told you and be like very appreciative. Is there anything else?

Nikhyl Singhal: I’d share out feedback. It’s a little easier when you are a manager, but for example, most managers that are listening have a staff discussion. Maybe it’s sort of awkward, but maybe you have a standup and you are giving notes to people. So as a manager, someone will come to me and they’ll give me a piece of feedback. The next Monday when I have my staff meeting, I’ll make a comment about something and I’ll say, “Well, lot of this came because I got this great piece of feedback from…” and I’ll name the person, and I’m like, “It really helped me see this challenge.” Now, that feedback could be about me or about this project or about the team. And it might be positive, it might be constructive. People hear that and they’re like, “Wow, I get recognized for giving this guy feedback. Sign me up.” You’re always trying to find way to break down that barrier.

Lenny: I love that tip. You talked about managers and how often managers are not great at managers. Maybe they don’t identify development areas, maybe they’re bad in other areas. So maybe just a question here of just, why are managers often not great? And then two, if you’re a new manager, I think a lot of listeners are maybe transitioning to management or about to transition, what’s your advice for being successful as a new manager?

Nikhyl Singhal: I’ll start by saying that, in a hundred years when the archeologists look back and they see tech in the sort of early years of tech, the first 34 years, they’ll say that the biggest surprise was how much we thought it was okay to not train managers. The military probably didn’t make that mistake for very long before they corrected it. And most immature industries really train managers, but boy, if you’re a good coder, you are ready to manage. That’s the way the industry works. If you can talk, you are ready to product manage. If you can product manage and ship something out the door, you should definitely tell people what to do. I think that there’s such a loose coupling between the skills to be successful at building things and teaching people how to build. It’s the difference between if you can make a good car, you must know how to make the factory that makes the car. I don’t think that’s true at all.

I think that this is a massive epidemic, that I think there’s the thousand challenges that stem from this, whether it’s challenges around bias, challenges around enabling coaching and teaching and solving development areas. My hope is that one day as an industry we find ways to improve and fix it. But podcasts like yours are actually quite meaningful steps. I would say that your podcast might be more meaningful than most L&D departments in most organizations today. So that’s powerful because you’re having a tremendous amount of impact, and I think learning is essentially a lifelong opportunity and I think that is the type of resources that just didn’t exist a decade ago.

I think to answer your question around what are the common pitfalls, if you’re a first time manager listening or maybe someone who’s considering it, I think there are probably two quick things that I would say you have to get bravely thoughtful about as you enter into this journey. One is, your challenge is going to be to share the steering wheel with the person or the set of people you are managing. And I think that there’s this three modes that people have in their head. They’re like, “Oh, management is divide and conquering. You go there, I go there, we meet up.”

Or they’ll say it’s like riding a bike, or teaching to ride a bike, I should say. Someone starts out on the bicycle, I hold your hand, I let go, and then I hope that you fly. I think it’s more like the sidecar on the motorcycle, where person’s driving the motorcycle and I’m on the sidecar and whether I like it or not, I’m attached, but I have this relatively specific role of giving counsel. I think that that model of how do you share the steering wheel, not just say you got it or I got it or I got it for a while, and then I hand it to you is the key question.

Nikhyl Singhal: And then I think that the second miss that people tend to have is they tend to, because they have power, by the way, organizational power, not because they’ve earned that power, they start managing whatever they define that to be. And what I find is that you’re more like the vampire knocking on the door of someone. You have to be invited in. You just can’t walk through the threshold. And I think that no matter how senior the person that is the manager, you have to earn the right to be the person’s manager. So maybe to be specific, well, if I start managing someone, the thing I’d like to understand is like, “Hey, well, what can I help you with?” And they can invite me in. Oftentimes, the answer is, “I don’t need you. I actually wasn’t excited about you as a manager. I don’t need another layer between you and the CEO. Get out.” And I’m like, “That’s cool,” because anything I say after that is just going to be annoying and it’s going to backfire.

Now, one day they will need help, and I will be in the sidecar waiting to say, “Perhaps I can assist.” And then when you finally get to that moment where you’re invited in, you pick an area or two, and then you really partner with that person on that area. I can give examples on that, but I generally think that it’s this invitation picking specific and then making sure we’re sharing the responsibility is the key set of notes that I would share with you.

Lenny: What’s your take on the IC path, senior IC path, something that a lot of companies talk about? I know Meta is big on this right now, the layering managers and things like that. I find a lot of times there’s a lot of talk about it and there’s not really a real career opportunity there. I guess, what’s your just take on as that is a real option for most people trying to basically avoid the manager out and staying in IC, PM long term?

Nikhyl Singhal: Yeah, I think that it’s a little bit more acute now because of the backlash that we talked about between growth where management was perceived. So in this case, management was perceived as a way to drive expansion. So if you’re in charge of expansion, you’re managing the people that are doing the build and now we’re doing a lot fewer things. So I think that’s what’s mandated this sort of growth in the IC track, for lack of a better term. I think it is one of the best things that happened to our industry because what’s happened is, in the last 10 years, and you can tell I’m particularly hard on our managers here, they’ve basically been promising ICs that early promoted into management. They didn’t get taught, and now they’re sort of average managers and promising ICs. But now the story that they tell and what they’ve built is not awesome.

If I’m looking to hire, if I’m in a growth company and I’m the next hottest thing and I’m looking to hire someone and someone walks into the interview and said, “Look, I’ve managed two people before and then I was in the charge of this thing, but they really did the details. And then by the way before that, I was early in trying to get this thing out the door and then they picked me to be manager,” I’m like, “Okay, that’s an interesting set of experiences. I’m looking, for me, in my company to build something.”

The next person walks in, it’s like, “I’ve been an IC for that whole time. And during that time I went from learning something to demonstrating it to really being able to take it forward. And I got one of these ambiguities master. I’m an expert in domain. I’m an expert in managing organizations,” I’m like, “I don’t need a team ambiguous expert. That’s not my hard part. My hard part is actually cracking the code on this complex market or this very complicated organization where we have two teams that have different goals. You’re the type of person I want.”

So I think Lenny, to your question, I think the IC track is one of the best things that’s going to happen for people career. But to your point, those tracks, from a promotion and from a industry, how we perceive it, they’re not in cement yet. They’re tender. You wait six months, you wait nine months, they’ll become very, very strong and solid. And I think then, we’ll be able to lean very hard into them as a real promising crack for builders.

Lenny: Your sense is, this is going to become more and more real as these layoffs have happened and kind of pullbacks on growth have happened.

Nikhyl Singhal: Yeah, I mean, if you think about it, it’s the reality in engineering and design. So in engineering, you can be the sort of VP of engineering or CTO, and in a design, a lot of designers become design managers, a lot of them stay as crafters. And then for whatever reason in product managers, maybe because they were managers in our title, we just all became managers. What about the product? What about the other side? So I actually think it’s a bug that has existed for a long time that actually we’re going to correct permanently now.

Lenny: I wonder if part of it for PMs is, once you become a manager, this happens to me, I didn’t want to be an IC anymore. It’s like, “I’m done with that. I really enjoy this management layer.” And I imagine with engineers, maybe they’ll enjoy the coding. When I was an engineer I was like, “Oh, I don’t want to just sit around and manage. I just want to code.” So I wonder if there’s any part of that.

Nikhyl Singhal: But a lot of your listeners like to build. And actually, when they talk to their managers, they’re like, “I don’t know if that job is awesome. It feels like you spend all your time writing docs and telling your boss’s boss what to justify resources and headcount. I just want to build stuff. You don’t build stuff.” So I think there might be some of that. I think that it’s not perfect, but I think hopefully builder and IC will become more synonymous.

Lenny:

Coming back to the manager life and how many managers are not great and also just how do you get better as a manager, what have you found actually is effective in helping new managers become better?

Nikhyl Singhal: I think I may have come across kind of hard on managers and I think I kind of said, “Hey, your manager and your manager’s manager isn’t really doing much teaching. Find the right podcast, good luck.” And I think that that’s a pretty soulless answer. So maybe the way I describe it is, well, I think learning is changing, and there’s the self-service tools that are getting better and then there’s the structured teaching which I think is weak. And then there’s community, which I think whether it’s within your company or outside of company, I think is the answer that we’ll see more and more. I think community as a way of creating safety, having authentic conversations, feeling that you’re not alone, that others are going through the same thing, and then sharing best practices is so powerful. And what social software has done is it has really empowered community.

And now the tools are awesome. How many great communities have Slack channels or Discord channels or Zoom calls? And we do a lot of that in the CPO community that I created. Whether you’re a new manager or whether you belong to a diverse group, whether you are new to a company, I think that all of your listeners should be part of an active community where they can be very authentic and very safe. Sometimes it’s hard to do that with your coworkers, and so you need to find another community. Unfortunately, those communities are not the easiest to find today, but I believe that the notion of community as a powerful propellant for learning is the critical ingredient and hopefully many people are creating these communities so that new managers can find the right services.

Lenny: Can you actually talk about this community that you’ve built? This could be a good time to talk about it. It’s called The Skip. Is that right?

Nikhyl Singhal: Yeah. It’s funny, it’s all kind of fun products. They were always a reaction to something. They weren’t really intentional. I, as you opened the podcast, did really enjoy teaching and coaching. I learned just as much from coaching others as they learned, I think. And yet I couldn’t really scale. So I had this summer where I had just come off of being a head of product, and more and more of my people I was talking to were also head of products. What would happen is, I would have these conversations and they would ask me a question. I would say, “Well, that’s the same conversation I answered on Tuesday.” What you realize is, it’s a very lonely job. Being lonely at the top is not just an adage. Really, everyone’s so busy now. It’s like, how do you have time to connect? Everything’s a single player, you don’t really have community.

So I thought, “Well, what if I took the half a dozen people I talked to this month?” And I just said, “Hey, all of you are all interested in talking through how to navigate this crazy world of year one, year two, chief product officer. I think you would really gain. I know all of you and I think you can be safe with one another. Why don’t we spend some time together?” So we did a WhatsApp channel and we brought a Zoom call. This was during the pandemic, so you really couldn’t meet up. And we started talking. We started talking every month, and people were so empowered by the fact that the problem they were hitting was not just them. It was, “My crazy CEO is telling me this.” And the next person is like, “Oh yeah? Let me tell you what my person said.” And then they would say, “Oh my gosh, that sounds worse than my situation.”

But then, we would sit down and say, “Hey, the third person said I actually kind of had this and now I figured out a way out, and here’s what I did.” And you’re like, “Wow, that’s amazing. I’m going to try it.” The next day they come back, they’re like, “It works.” And we started to connect and we built this trust, and community building is interesting and powerful work. So six went to 12, and then 12 went to 15, and now we have 28 members. A lot of folks are interested in these types of communities, but I’m so worried about scaling it because it’s the enemy of trust and authenticity. So for all of you that are building communities, it’s like tree balancing act. But I do think that the goal is to find ways to take all of this sort of like-minded folks that are in these same situations and connect them together. Late stage chief product officer happened to be one of the ones that had some of the most substantial importance to me because of all the coaching I did for that group.

Lenny: If someone’s listening and they’re like, “Oh, I need to join this thing,” how do they find out about it? How do they potentially apply and try to join?

Nikhyl Singhal: Well, we have enough members now. There’s a LinkedIn area called The Skip CPO Community, and you should contact any of the members that you know and ask them to join. My request and my requirement is that they are, number one, product leaders in their organization and a company that’s not early, but that’s mid to late. And the reason being is, those sets of problems tend to be the most similar. To be honest, I think this is not the only community that I want to be part of and help create, but this one happens to be the preexisting one. I think there are lots of powerful communities that can be created, but this particular one is very much focused on The Skip CPOs.

Lenny: Awesome. I’ll mention the community around my newsletter just so folks are looking for a community join. I try not to promote these sorts of things, but it’s a good time, may as well. If you’re a paid subscriber to my newsletter, there’s a Slack community you get access to. There’s about 12, 13,000 people in there. There’s meetups happening all over the world every month. It’s amazing. Very proud of it. People are getting a lot of value of it, and it’s basically open to any level of product manager. Other functions are in there too. So it’s a very different sort of experience, but willing to add that also in the show notes if you want to check that.

Nikhyl Singhal: I think that that would be my put, because so many of the managers will say, “Hey, I’m an IC,” here’s a greater one, “I am not being told I have the next job. I just was told to become an IC and I was a manager. I feel like my learning opportunities are stuck, but this is a bad time to look for a job.” They should be in your community. They will learn more from that community than they will learn from managing one random person that they were attached to managing in some project that may or may not see the light of day, yet that’s how our society is programmed. Our industry is like, “No, no, go manage that person because that’s going to make you closer to the top. Forget learning.” And I’m like, “Well, learning isn’t happening. Learning’s happening in your community. Learning is happening in our communities in general.” That’s why I’m pushing so hard on this.

Lenny: This is a good segue to talking about the third bucket, which is kind of later career CPOs. That’s the segue in my mind there. Something that I’ve heard you talk about is that a lot of really senior leaders have real development areas, but they’re hiding behind these superpowers that they have. Plus, people don’t like to give real feedback to senior people. So I’d love to hear just what you’re seeing there and how maybe people can work through that and what we can learn about that issue that you’ve noticed.

Nikhyl Singhal: This came from my notes as I was talking to a therapist on this. They talked about the shadows of superpowers. And I thought it was an incredibly powerful phrase that everyone focuses on your superpowers, but no one ever thinks about what shadows they create. Shadows of superpowers to me is the story of a lot of executives. There’s an adage that’s thrown around, which is, what gets you there isn’t what got you here. It’s sort of the tools that have made you successful today, you need to almost rebuild or relearn to get to the next phase. And I think both of these sort of speak to the same point, that oftentimes people have a great superpower. They go into a performance review, person says, “You’re getting some feedback from your peers that you struggle in collaboration.” And the manager even sometimes is puzzled, but the individual will say, “Are you kidding me? My last five performance reviews told me that I was one of the best collaborators in the company. How in the world is that possible?”

And then what you realize is that, “Well, you’re collaborating as long as people agreed with your point of view. Now as a leader, we’re asking you to be opinionated, and because you just think you’re an amazing collaborator using the exact same tool set. And it turns out that when you’re dealing with senior people, that may not even be in your function, they may not be product, they may not be tech, they recoil, but you’re moving so fast because it’s your superpower. You would never think that this needs to be rebuilt.” Sometimes it could be more extreme. Great collaborators sometimes are very reticent to present their own opinions because they’re so good at assimilating others. Or people that are amazing at growth struggle to be innovative. People that are world-class storytellers struggle to get in the details. People that are very taste maker, they are always the first to have point of view. They don’t necessarily introduce change particularly often. You’re strong politically, but your decisions are unprincipled. You’re a structured thinker, but blue-sky innovations are very tough. You’re an amazing listener, but you’re very weak to be decisive. I can go on forever.

And what I would say to you is, sometimes even in a 30-minute conversation, walking into the room, just knowing what I know about the person, I can unlock their development area faster than anyone ever before, simply because my secret is, I’ll bet you, because of this person’s world-class here, these are the three things they’re going to hit. And they don’t even realize it because it’s their identity. This is what got me here. If you make me work on that, you will make me change my superpower. And I’m like, “That’s why you’re stuck. That’s why your career is plateauing.” And then they get sad and then they take a long time to process, and then the work actually begins and then they solve and they go. Almost everyone, once they have the name and the face, they’re able to solve. But facing the name is hard when it’s sitting in the shadows of superpowers.

Lenny: Wow. That is an incredibly important point. For someone to recognize this, do you find that they need someone like you that’s like a coach, mentor, person to come in, and be like, “Here’s what I see”? Or is there a way, I guess, as someone that’s a peer or an employee to help them recognize this without them shutting down and being like, “No, shut up. No problem’?

Nikhyl Singhal: No, you don’t need a coach. What you do need is to listen to contradictory feedback. So what was the premise here is you’re being told that something that you hold as your strength is actually in your way or a development area. Do not dismiss that. Recognize most likely you’re doing it correctly. You just have gotten to the next level. So what I’m hoping the listener does is it goes back through all the feedback that they may even have and then looks at all the discard stuff. What’s on the discard pile? Things that were discarded are anomalies because they’re artifacts of my strength. And often, your managers are the ones that do the discarding, “Oh, that was just a weird… That person, they were just into it. They have it out for you. They got reorged or they were upset.” I’m like, “No, no, no, no, no, no, no, no. Perception’s reality. Talk to me about that one. That might be it.” That’s what I’m looking for.

Lenny: Fascinating. This makes me think about companies that have the same issue, companies strengths, like say Meta for example, move fast and break things and then, “Oh, that ends up being the biggest Achilles’ heel.” Uber, similar. Airbnb has similar challenges like that.

Nikhyl Singhal: Absolutely. This exact thing applies to relationships. This applies to companies, this applies to a lot. And I’m so happy that I was able to learn about it. Frankly, it was a critical unlock for me because I was stuck on something for years and I just could not understand how, for me, it was, I was very opinionated about something. And then I realized being loosely held on my opinions didn’t mean that I became a weaker executive, but it was my opinions that got me to be so successful and it required me to rewire who I was as an executive. And that took a lot of time and a lot of energy. But it came from this realization and then I started to apply it for other strength areas. And now, every time I have a strength area of myself for those that I coach, I immediately talk through all the things that I bet you exist and most of the time were right.

Lenny: So what is it for you that you said was your superpower and your shadow?

Nikhyl Singhal: I think that I was, as an entrepreneur, very opinionated about using small amounts of information to make decisions. And then I was very good at driving those things. So when you become an entrepreneur, you’re great at grit, you’re great at opinion, you’re great at being decisive. And then as an executive, you spend a lot of time making sure everyone has context, everyone is heard, your opinions are actually edited for good reason. And it’s not just to placate, it’s actually to improve. But as someone who’s basically been right a lot, that requires almost a complete and you’re like, “Well, that’s not who I am.” And I’m like, “Okay, you start with the sentence like that’s not who I am.” You’re definitely doing it right when you hit your leadership.

Lenny: What was the process like for you to work through that? You said it took a long time. What made it effective for you? Was there a coach involved? Something else?

Nikhyl Singhal: I got a lot of setback. I get a lot of negative feedback. I had a lot of abrupt challenges at work where folks would say, “You’re not collaborating well. Your peers don’t have the same level of respect as they should.” And I was like, “Are you kidding me? That’s not who I am. These things that are being said about are completely ironic.” I was very much struggling and that’s when I said, “You know what? I can struggle and blame others, but what if they were right? I’m going to be doing this for 30 more years, it’s kind of worth it to figure out if they’re right. If they’re wrong, then you don’t lose.” And that’s what kind of forced it. And then the tooling starts, then you start talking through. My self-awareness was strong enough that I was able to say, “Okay, now I understand it.” I had some peer feedback that helped bring it home from someone I trusted. So that was a kind of linchpin to this, but these are tough, tough things to break through. And oftentimes they don’t come nicely, I guess, is the point.

Lenny: I was going to ask what that turning point for you was, and it sounds like it was direct feedback from someone you really trusted that’s like, “Oh, I really need to take this seriously.”

Nikhyl Singhal: You got it. You got it. Because I had a lot of feedback that I was dismissing and then I had feedback from someone, I’m like, “That person I should listen to because they’re giving me the feedback for the right reasons and they have the right language.”

Lenny: Comes back to the power of getting feedback and getting good at that.

Nikhyl Singhal: And making people feel safe and giving it.

Lenny: Mm-hmm. That’s a good segue to maybe the last question. You told me once that a lot of the people that you work with that have kind of made it have a lot of mental health challenges, that they didn’t expect their life to be the way it is necessarily when they got there. Can you just talk about what you see there in that group?

Nikhyl Singhal: Yeah. This is a story that I don’t think is told very well right now, and partly because it’s such a luxury problem, it’s almost a little embarrassing to discuss it openly as so many people struggle with so many basic needs, going through layoffs, going through all these challenges. I mean, these are real issues. But I think that what I’ve noticed is that if you kind of break career as we’ve done in this podcast between sort of act one, act two and act three, if act one is sort of learning and being that sort of builder and then maybe building the car, and then act two is building the factory, act three is like, what’s after that? What do you do after that? And I think that act three in the past wasn’t as long as it is now. Before, people would proverbially retire in their 60s when they used to actually physically work.

Now almost all your listeners sit at a desk all day, so they don’t need to retire by any means. And health is getting better. You might see folks work until their 70s or 80s. So that means that their careers are potentially 60 years long. So even if you’re 20 years or 30 years in your career, you’re only halfway through. So this act three could be a thing. And I don’t think we talk about act three enough. What often happens is, and this is what I’ve been watching for people that are at my age, is they sort of succeed and then they become lost. They almost goes hand in hand.

So when I was a kid and I was growing up in the Midwest, entertainment was going to the dog tracks, and not even the horse tracks, we didn’t have horses. So it was the greyhound dog tracks. So people would bet on a dog and greyhound would go around the ring and then you would see. I bet on number three and I’ll make a buck or something. The way that they motivated the dogs was they had these fake rabbits, which sounds kind of cruel and horrible, so I don’t want the SPCA to come after you. But the point is that they’d have these fake rabbits. And what was interesting is, the moment that the dogs, if they accidentally touched the rabbit, the sort of the tail because the machine broke, because these tails would go around faster than the dogs, which would then motivate the dogs to go around in circles. Sometimes the machines would break, the dogs would actually catch the rabbit, they would never run again.

The reason why they wouldn’t run again is because there was like, “Well, what’s next? I’ve achieved what I was looking for.” So I think this happens a ton. It’s like, your listeners are spending time focused on like, “Well, one day I will be X. I will be that vice president. I will have more money. I will have built something. I will have started a company.” But they don’t think about what happens next, and when it happens, when they succeed, their North Star, their entire way of wiring their career, themselves, it has been around getting to that place. And I think that if you’re going to get there 30 years in and you have a 60-year career, a lot of the discussion I’ve been having with myself and with others has been, you probably need to start working on that North Star now.

What’s the second thing? What’s your career next look like? How do you ensure that you are always going to have something important and motivating to do with your career? Otherwise, you’ll keep working because you had no nothing else to do, but you’ll be sadder, or you’ll find ways to create war when peace is needed, or you’ll spend money in an attempt to earn more, or you’ll find habits that are bad. And I really want us to have long 60-year, 70-year careers, not just 30-year or 10-year, which is why I enter this into the vocabulary out there.

Lenny: That is really resonating with me. I had a similar experience. I had a startup, and my whole goal was just like, “I just want to start a company.” That’s my goal. That’s all I got in life. I want to start a company and then maybe sell it, maybe go somewhere with it. So I did and then we sold it to Airbnb and then I got to Airbnb and I was just like, “What the hell do I do now? I don’t have any other goals.” And it was pretty sad. Exactly how you’re describing. It was just like, “I guess I’ll just work here and I don’t know, maybe I’ll start another company, but I already did the thing I wanted to do.”

Nikhyl Singhal: Your story is I think very inspiring because what you did is you said, “I think the thing that I want to do is give, but I want to do it in my own way and I want to create something, but I want to do something that I think I can do for 30 years and I want to do it.” It has lots and lots of spokes to it. So you reinvented yourself professionally, but you created a new North Star.

My sense is, for every one of you, Lenny, there’s a hundred that could do that, that could do giving, that could do things that could scale, but that end up falling into what got them to be successful in act two and they get stuck. So this is the reason why when you hit your skip, keep looking for the next skip, is the point I’m trying to make. And I think you’re an inspiration for a lot of folks who have seen you transition and realizes life after just being a tech professional entrepreneur, there’s got to be ways to do more of this for all of your listeners. And I think it’s never too early to start thinking through. It’s actually quite powering to think that you have such a long career. You can make mistakes and you can do some amazing things down the road.

Lenny: Yeah. This is my fourth career, is what I realized. I was a engineer, then a founder, then a product manager, and now whatever this is.

Nikhyl Singhal: Whatever this is.

Lenny: Whatever this is. I guess, just to give people something inspiring, productive, what are maybe some examples of North Stars you’ve seen that people can evolve into? I guess one path is this path of content creation, helping people learn stuff. What else have you seen that might work out for people?

Nikhyl Singhal: I think that all variations here come into two categories. One categories are ways to drive more scaled economics. I’ve made millions. My North Star is to now make it tens. I’ve made tens. My North star is to do hundreds. That’s what drives people from, it’s not entrepreneurship, it’s investing; it’s not investing, it’s private equity, et cetera. Whether we describe that as a bad quest or a good quest is a decision for your listener. The other arc is around giving. Eastern philosophies that have been around for thousands of years talk about this as the sort of end state of happiness. I think that maybe to be provocative, I think that it’s okay for you in act one and act two to not predicate yourself around the notion of giving to others because this is maybe the time on the planet where you need to take and you need to create.

Nikhyl Singhal: But boy, if you’re going to work on an act three and you have 30 years, regardless of where you are economically, if you feel like you can take that off the table, if you can find ways to give, whatever that means to you, however that translates to you, is that content, is that volunteer, is that starting a company that is more mission based, that is not my role, but I think that if you are able to do that for 30 years and be giving, not only is that going to be more fulfilling than your act one and act two, but it’s tremendous for society, very empowering. And that’s where I commend you because you’re giving through your passion but also making a livelihood. And I think that that’s a very powerful blend that is hard to achieve in act one and act two given constraints. And that’s the liberation that act three provides.

Lenny: What do you think your act three plus ends up being?

Nikhyl Singhal: Many have asked me about this. I would say that I’ll use the word, and then I’ll tell you I won’t use that word. So it is around my passion around coaching and giving to others. But because I’m a product person, because I’ve seen success in building products, thinking about scale, thinking about community, I definitively plan to devote my act three towards coaching and giving to others and lifting up those that with the right advice at the right time can change their trajectory. But scaling that and doing that in a way that is very authentic is really the hardest part and it’s product problem. So that’s what I’ll devote 30 years to and I look forward to that every day.

Lenny: That is beautiful. That feels like an exactly correct fit for you, and I’m here to help you on that journey any way I can.

Nikhyl Singhal: Thank you, my friend.

Lenny: Absolutely. Is there anything else you wanted to touch on before we get to our very exciting lightning round?

Nikhyl Singhal: No, I just appreciate your genuine offer to have me attend and participate in this wonderful podcast that you created.

Lenny: It’s absolutely my pleasure. And it’s not over yet. We’ve reached our very exciting lightning round. I’ve got six questions for you. Are you ready?

Nikhyl Singhal: I am ready.

Lenny: What are two or three books that you’ve recommended most to other people?

Nikhyl Singhal: So two, and both business books. Sorry, I’m going to come across boring. But one is this sort of little bit of an old school book called Crossing the Chasm by Geoffrey Moore. I don’t know if other speakers have spoken about this, but it’s a book that Geoffrey Moore wrote, and it’s a book that really talks about how to get your first product on base. So it’s this concept of creating a beachhead. I like that concept. Marketing is something that we don’t talk about in enough and product.

And then the second one is a book that none of your listeners have actually probably heard of called Leadership and Self-Deception. It’s a six-hour audio that I highly recommend. It’s a story about a person who has hit a wall and who’s getting all this feedback that they don’t know what to make of, and it’s around their mindset being stuck in a box. That was very powerful when I listened to it in my late 20s. So I encourage all of your listeners to grab that one. It’s not one that anyone normally would hit, but it’s a fun story. It’s a good ride, and I think maybe you’ll get something out of it.

Lenny: I have not heard of that second one. I’m excited to check it out. I have Crossing the Chasm back behind me on that shelf somewhere. And you talk about how marketing isn’t something product leaders and managers think about enough, and I have many marketing-oriented guests on this podcast and those episodes do the least well, but I’m just going to keep doing it because I totally agree with you. I think there’s so much to learn from marketing. It’s connected to growth, which is connected to product. So I agree.

Nikhyl Singhal: Yeah, and I think that marketing is a language of connecting products with people. That is what a product manager does, but we often lack the language. We lack the thinking around how to explain it, and yet we spend all our time on data and features for that. The diversity of having both playbooks can make one of just a much more powerful builder. So I agree with you. Marketing folks is probably some of the best content and the least listen to. So maybe that’s a plug for people to go back to those episodes.

Lenny: 100%. That’s what everyone should do. I don’t know if you know this, but actually, at Airbnb, the product manager function has been renamed to product marketing. So all the product managers are product marketers because Brian is so big on, you’re not just building product, your job is also to make sure people use it. We’ll see how that experiment goes, but that’s a bold move I thought.

Nikhyl Singhal: Very much so. Very much. But it’s an homage to this concept.

Lenny: Exactly. Okay, back to landing ground. What is a favorite recent movie or TV show?

Nikhyl Singhal: I’m a huge sports fan, so I have tickets to the Warriors and 49ers, and I am a big Bay Area sports fan. Giannis is my son’s favorite player. He’s a basketball player for the Milwaukee Bucks, and they have this Disney+ story called the Rise story, and it’s a story about his childhood and how he struggled to find notoriety and how he made it into the professional leagues. It’s a great Disney+ family show and it’s a great kind of zero to hero type thing. So I love that story.

Lenny: I feel like you’re going to have a really good answer to this next one. What is a favorite interview question that you like to ask?

Nikhyl Singhal: I like the format of, what’s something that everyone takes for granted that you think is essentially hogwash or inaccurate? Sometimes I’ll ask a manager, “Look, you’ve managed hundreds of people in your career, what’s conventional wisdom that you bet against that you have found is actually inaccurate?” And you can do that for what do people think about AI, that’s inaccurate, that everyone believes you could do that for domains, you can do all kinds of things.

Lenny: I love it. Is there something you specifically look for there, or is it just depends on what you hear?

Nikhyl Singhal: I’m always looking for people to break this sort of interview mindset. Everyone always prepares for interviews and then their entire conversation is predicting what you think you want me to say. And as a result, you can have high-quality people that you dismiss because they weren’t genuine. There’s no way to answer that question without being genuinely opinionated because it starts with, “What is the thing that you think I want to say here? And then tell me why it’s inaccurate.” So when I break that wall, I’m testing, is this person authentic? Because sometimes I’m dismissing them because they told me nothing new, but I don’t want the interview process to penalize them. And this was my save question, but I can’t use it now that I’ve told everyone.

Lenny: It’s going to be all over TikTok soon. Everyone’s going to know this. Next question, what’s a favorite recent product that you’ve discovered that you love?

Nikhyl Singhal: The geeky answer in me is the Arc Browser, which I think probably a lot of folks are starting to use and your listeners. Part of the reason is, I think it’s just great for folks that have hundreds of tabs, and if you work at a scaled organization, you just have lots of tabs. But I think it’s also, as a product guy, I thought Chrome was pretty good. They’ve got gajillions of people using it and billions of installs. So at some point, you kind of come to the conclusion that this is probably good enough. And then you see a product obviously built with a much smaller team and you’re like, “Huh, there actually is opportunities to innovate.” And any time you see a innovation on something that’s mature, as a product person, I think that’s just fascinating. And I was just blown away at how they created something that’s better than something I hold as a true set.

Lenny: Yeah. We had Josh on the podcast, we talked about a lot of their philosophies. And on the tab thing, I think the key there is it closes your tabs after 24 hours unless you put them in a specific place, which I love because I was like, you think you would do that, but you don’t. And then it’s broke so beautiful, you wake up in the morning, everything’s gone, but you can save stuff that you want. The other thing I’ll mention with Arc, by the way, also huge fan, that’s all I use, and I’m not an investor, just a fan, is the onboarding experience is the best onboarding experience I’ve seen. I was just like, I did it and I got a tweet about this. This is so good. And actually, if you go to that episode, there’s a link to get past the wait list and just-

Nikhyl Singhal: Oh, that’s right. Yeah.

Lenny: Yeah. You gave me many thousands of invites. Okay, keep going. What is something relatively minor you’ve changed in the way you develop products and your team that’s had a big impact on the team’s ability to execute?

Nikhyl Singhal: A little bit of this is just because of scale, but oftentimes we think a lot about the products and the features and the decisions that we’re working on, and then we think that meetings are a nuisance or a must-have necessary evil to be able to deliver. Sometimes I realize that at a scaled organization, the meeting operating system is as important as the products that we’re building because it sort of speaks to how we scale and how we ensure we have the right degree of delegation, the right conversations, and then the right acceleration on the right decisions.

So what’s interesting is every quarter, in my current teams, even in my past teams, I talk about our meetings like a product. We’re on version seven in my team, and so we’re like, “Hey, version seven, every 90 days, these are the meetings, these are the discussions, this is how we organize, these are the attendees, and then here’s how we make decisions. This is the cadence of the week. This is when people can work from home, hybrid, whatever it might be.” And then I take feedback two months in and then every three months we make another route.

What it finds is that people then can plan and they can make meeting time effective. And meeting time is such precious time. It’s the most expensive time in a company. So when I was in a startup, I couldn’t imagine doing this, but now this is like my bread and butter as a leader. It’s the process part. And frankly, for new folks that are new in leadership positions in a new company, it’s the one thing you can do when you have low context. When you don’t know how the product works, you can look at things with fresh eyes and see inefficiencies when everyone that’s been in the system can’t see it. I’m a huge fan of rebooting meetings first. So process first, then people, then product, then strategy is sort of the notion I make, and this is this first thing I always do.

Lenny: Final question, what is one thing every PM listening should do to help their career?

Nikhyl Singhal: Ensure that the story you will tell about the work you’re doing today is meaningful for your skip job. So if you sit down and you write down, “In six months, in 12 months, in 24 months, when I achieve or finish this role, here’s the paragraph I’ll write. Here’s a problem I solved. Here’s the skill I built. Here’s the headwind I faced. Here’s what I did to overcome it.” Use I in the sentence, do not use we. We will do good things. You are who we are thinking about, your career. We’re not looking for we. Master the story now. Understand the story. If the story sucks, you probably should be thinking through how to make the story not suck. But that to me is a very good career decision and I think everyone is building their story today. I want to know that story. I want that story to be incredibly compelling because whether you promote it or not, that story’s compelling. You’ll be promoted in career. And that’s what we’re here for.

Lenny: Nikhyl, this is the first time we’ve ever met. I’m such a fan instantly. This might be my new favorite episode. I’m so excited for people to listen to this. There’s so much value here. Two final questions before we wrap up. Where can folks find you online if they want to learn more? And also, talk about maybe various community, The Skip, and all that stuff that people can check out. And then how can listeners be useful to you?

Nikhyl Singhal: I’m building this brand around The Skip because I’m so passionate. There’s two outlets that people can easily connect. One is the podcast, which much like yourselves is available on Apple and Spotify and others. So I’d love for people to join my podcast and hear. What I’m now moving my podcast to is almost like coaching calls. Because I have so many of them, I’m saying like, “Hey, 30 minutes, let me walk you through a problem and hear how I’m thinking about it, whether that’s a transition discussion or compensation discussion, et cetera.” And then the other one is this sort of newsletter that I have on Substack, which is a bit of a mirror of the podcast. It’s different forms of the same topic areas. So, would love for your listeners to connect with that.

I think as far as getting in touch with me, LinkedIn is where I spend most of my time professionally. So between Twitter and LinkedIn, my presence is relatively easy to find. And then how listeners can help me, I mean, one, you can build the most fulfilling career story and be your best, but also give back and pull others forward. Whether that’s through your act three or whether that’s just helping others, I mean, I think that would be the most fulfilling to me. I think feedback from your listeners to me on things they wish I would spend time talking about is incredibly empowering for my content because then I can deliver more meaningful content. It’s very different from yours, but I think it’s all around the arc of trying to help people gain forward and be more effective tech professionals. So I would love to hear from your listeners.

Lenny: Just to make sure people know where to go to do this. For feedback, do you recommend LinkedIn?

Nikhyl Singhal: Yeah, LinkedIn is the ideal, but you can also find me on Twitter if you are just trying to add a quick… If you’re trying to follow me, follow me on LinkedIn. If you’re looking for feedback, just tweet me.

Lenny: And then for The Skip newsletter, what is the URL to go check that out?

Nikhyl Singhal: It’s theskip.substack.com.

Lenny: Amazing. And you don’t publish often, but each issue is incredibly valuable, so we’ll definitely link to that all in the show notes. Nikhyl, thank you again so much for being here. I will let you go now. This was amazing.

Nikhyl Singhal: Yeah, thank you, Lenny. Appreciate it.

Lenny: Bye, everyone.

Lenny: Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

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