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

26:58It 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. So this is not as present in hyper growth because the next role always did exist. There was always growth. There was always hiring. There are always hiring people above you below you, etc. 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. And 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.

27:41And that 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.

28:29And leadership takes longer to absorb. It's more soft skills. It's more subtle. It's oftentimes it's based on, you know, impact, which is a lot of times lagging. And that tends to be frustrating. And 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. And so impatience is in 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.

29:08It's substantive. The manager is poor at identifying it. Perhaps he 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 and 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. Amazing. And this super resonates. So just to summarize, the four reasons you may not be getting promoted.

29:53One is there's no advocate that sees your magic and understands that you're awesome too. There's no actual role. That's available. And so there's nothing to get promoted to. And it's so true right now. There's just not there. Like everyone's laying people off. They're getting ready to manage their layers. They totally see that all over the place. Three is you're probably just not being patient for you actually have to work to do. And he shouldn't be promoted. Maybe to follow the thread on that first one if someone doesn't see your magic. I see a lot of people just like complaining that like, I'm doing so well.

30:22I'm so great. And nobody understands it. No one gives me credit. No one really appreciates me. I don't know if this is there was 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. Like what's a sign maybe? Maybe you're not as great as you think you might be. 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, you know, we've run experiments where we said, let's ignore the formal feedback.

31:00Let's have a real conversation with, you know, 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 know, 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.

31:37Then you've missed this. Let me tell you about exactly why that was situation that you're using was, and you have to be great at pulling feedback, listening to it, you have to triangulate it from people like 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, etc. 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.

32:15This reminds me of Jules Walters on the podcast he gave a bunch of advice. I don't know if he 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. I think Jules is a great, probably one of the world's best people in pulling feedback in my experience. I think that even one that is when I talk to Jules, Jules will look for feedback, then he'll repeat it back to me better than I presented it.

32:54And 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 understand the values it. That's the really powerful way is what you're saying is I just interrupt far too often. In some ways, it's almost to a point that it's annoying. Is that a fair assessment? That's not actually not the words I use, but that's what really gets people comfortable in sharing with you what's really going on. Amazing. I think we're discovering some of these people that have worked with you that have been on the podcast slowly.

33:30Maybe we'll all run this topic at and 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? 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 stand up and you are giving notes to people.

34:09So 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, a lot of this came because I got to see this challenge. Now that feedback could be about me or that this project or about the team, and it might be positive. I might be constructive. People hear that and they're like, well, I get recognized for giving this guy feedback. Sign me up. You're always trying to find way to break down that barrier. I love that tip. You talked about managers and how often managers are not great and managers maybe they don't identify development areas.

34:53Maybe they're bad in other areas. Maybe just a question here of just like why are managers often not great? Then too, 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? I'll start by saying that in 100 years, when the archaeologists look back and they see tech in the early years of tech in the first 30, 34 years, you'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.

35:41Most 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 is just 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.

36:33My 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 podcasts might be more meaningful than most L &D departments and most organizations today. That's powerful because you're having a tremendous amount of impact. I think that's learning is essentially a lifelong opportunity. 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, a listening, or maybe someone who's considering it, I think there are probably two quick things that I would say that you have to get very, really thoughtful about as you enter into this journey.

37:18One is your challenge is going to be to share the steering wheel with the person or the set of people you are managing. I think that there's this three modes that people have in their head. They're like, 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 persons driving the motorcycle, and I'm on the sidecar, whether I like it or not, I'm attached, but I have this relatively specific role of giving counsel.

38:04I 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. 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. 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. 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.

38:52Maybe to be specific, if I start managing someone, the thing I'd like to understand is, hey, what can I help you with? 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. One day, they will need help, and I will be in the sidecar waiting to say, perhaps I can assist. 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.

39:38I 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 kind of set of notes that I would share with you. 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 to 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.

40:17Yeah, 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. In this case, management was perceived as a way to drive expansion. 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. 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 happen 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 in the management.

41:05They 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 like in the part charge of this thing, but they really did the details. And then by the way, before that, I was like 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.

41:44I'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 the 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.

42:19So I think, Lenny, your question, I think the IC track is one of the best things going to have in people career. But to your point, those tracks from a promotion, and from an industry how we perceive it are hard to, 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 be very hard into them as a real promising track for builders. So that's your sense is this is going to become more and more real as these layers have happened, and pullbacks on growth have happened. Yeah, I mean, if you think about it, it's the reality in engineering and design.

43:05So in engineering, you can be the 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 there were managers in our title, we just all became managers. Like, where 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. 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 is like that I'm done with that.

43:39I really enjoy this management layer. And I imagine with engineers, maybe they enjoy the coding. Like when I was an engineer, it's like, that's really, 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. But a lot of your listeners like to build. And actually when they, when a lot of, 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, like what, adjustify resources and headcount. Like I just want to build stuff. I don't want to, you don't build stuff.

44:10So it's, I think there might be some of that. I think that it's not perfect. But I think hopefully builder and IC will become worse and otomous. This episode is brought to you by Epo. Epo is a next generation AB testing platform built by Airbnb alums for modern growth teams. Companies like DraftKings, Zapier, ClickUp, Twitch, and Cameo rely on Epo to power their experiments. Wherever you work, running experiments is increasingly essential. But there are no commercial tools that integrate with a modern growth team stack. This leads to waste of time building internal tools or trying to run your own experiments through a clunky marketing tool.

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45:19Check out Epo at GetEPPO .com that's Getepo .com and 10X your experiment velocity. Coming back to the manager, life and how many managers are not great and also just how to get better as a manager, what have you found actually is effective in helping new managers better? 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. I think 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 is the answer that we'll see more and more.

46:24I think community has a way of creating safety, having authentic conversations, feeling that you're not alone, that others are going to do 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 and 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 and sometimes it's hard to do that with your coworkers and so you need to find another community.

47:20Unfortunately those communities are not 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. Can you actually talk about this community that you've built and this could be a good time to talk about it? It's called a skip. Was that right? Yeah and it was funny it's um it's all kind of fun products. They were always a reaction to something they weren't really intentional. I as you open the podcast you know did you know really enjoy teaching and coaching.

48:00I learned just as much from coaching others as as they learn I think and yet I couldn't really scale and so I had this summer where I had just come off of being a head of product and I had worn more of my people I was talking to were also head of products and 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 answer on Tuesday and it you know what you realize is it's a very lonely job being lonely at the top is not just an adage they don't and it's really everyone's so busy now it's like how do you have time to connect and everything so single player you don't really have community and so I thought well wouldn't what if I took like 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.

48:56I 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 and this was during the pandemic so you really couldn't meet up and you know 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 you know 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 gonna 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 and says six went to 12 and then 12 went to 15 and now we have 28 members and 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 and so for all of you that are building communities it's a tree balancing act but I do think that the goal is to find ways to take all of these these sort of like -minded folks that are in these same situations and connect them together and late stage she 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.

50:35If someone's listening and they're like oh I need to join this thing how do they find out about it and how they potentially apply and try to join? Well we have enough members now there's a LinkedIn you know area called the Skips CEO community and you know 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 perly but that's mid -delight 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 can help create but this one happens to be the pre -existing one I think there are lots of powerful communities that can be created but this particular one is very much focused on the Skips CEOs.

51:28Awesome I'll mention the community around my newsletter just if folks are looking for a community join I try not to promote these sorts of things but it's a good time as well if you're 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 and it's amazing very proud of it people are getting a lot of value it and it's basically open to any level of product manager other functions they're in there too so it's a very different sort of experience but willing to that also in the show that's if you uncheck that.

51:58And I think that that would be my put because so many of the managers will say you know hey I'm an IC here's a great 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 with this a bad time to look for a job they should be in your community they would 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 is happening in your community learning is happening in our communities in general that's why I'm pushing so hard on this and this is a good segue to talking about the third bucket which is kind of later career cpo's that's the segway 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 they're hiding behind these superpowers that they have plus people don't like to give real feedback to senior people and so I'd love to hear just what you're seeing there and how maybe people can work with that through that and and how yeah what we can learn about that that issue that you've noticed this came from my kind of notes as I was talking to to a therapist on this I 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 and shadows of superpowers to me is the story of a lot of executives there's an adage this turnaround which is what gets you there isn't what got you here and 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 super power they go into a performance review person says you know you're getting some feedback from your peers that you struggle in collaboration and you know 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 and sometimes it could be more extreme you know 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 makerish they are always the first to have point of view they don't necessarily introduce change particularly often you know you're strong politically but your decisions are unprincipled your structure thinker but lose kind of patience very tough you're an amazing listener but you're very weak to be decisive right so 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 when 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 this person's world class here these are the three things are 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 when they go and almost everyone once they have the name in the face they are able to solve but the face in the name is hard when it's sitting in the shadow as who powers 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 be like no shut up wrong no you don't need a coach what you do need is to listen to contradictory feedback so what 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 dies 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 there are artifacts on my string and often your managers are the one that do the discarding that was just a weird person and they were just into it you know they have it out for you they got reordered they were upset I'm like no no no no no no no no no no no no no no no no no no no no no no no no no perceptions reality talking me about that what that might be that's what I'm looking for fascinating this makes me think about companies I have the same issue companies strengths like say matter for example move fast and break things and then oh that ends up being the biggest to kill you heal uber similar air being via similar challenges like that absolutely this exact thing applies to relationships, this replies to companies, it supplies to a lot, and I'm so happy that I was able to learn about it.

58:55And 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 in myself for those that I coach, I immediately talk through all the things that I bet you exist.

59:43And most of the time we're right. So what is it for you that you said was your superpower and your shadow? 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. And so when you come 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, collect for the collective for good reason. And it's not just to be 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.

1:00:34And I'm like, okay, you start with the sentence like, that's not who you are, and you're definitely doing it right. When you hit your leadership. What was the process like for you to work through that? Like, was it sound, you said it took a long time, what made it effective for you? Was there a coach involved, something else? 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 know, you're not collaborating while your peers don't have the same level respect as they should. And I was like, are you kidding me? Like, that's not who I am, that these things that are being said about are completely wrong.

1:01:09I was like very much struggling, and that's when I said, you know what, I can struggle and blame others, but what if they were right? And if, you know, I'm gonna be doing this for like 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, you know, my self -awareness was strong enough that I was able to say, okay, now that I understand it, I had some peer feedback that helped bring it home from someone I trusted. So that was like a kind of a linchpin to this, but these are tough, tough things to break through.

1:01:49And oftentimes they don't come nicely, I guess is the point. I was gonna 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. 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. Comes back to the power of getting feedback and getting good at that. And making people feel safe and giving it.

1:02:21This is 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? 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. Often, there's so many people struggle with so many basic needs, you know, going through layoffs, going through all these challenges.

1:02:56I mean, these are real issues. But I think that, you know, 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, you know, if Act One is sort of learning and being that sort of builder and then, you know, maybe building the car and then Act Two is building the factory, Act Three is like, what's after that? You know, 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, you know, proverbially retire in their 60s, when they used to actually physically work, now almost all your listeners sit at a desk all day.

1:03:37So they don't need to retire by any means. And the health is getting better. You might see folks work until their 70s or 80s. So that means that their careers are, you know, 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. And 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. And they almost goes hand in hand. So when I was a kid and I was growing up in the Midwest, you know, entertainment was like going to the dog tracks and not even the horse tracks we didn't have horses.

1:04:25So it was the dog, Greyhound dog tracks. And so people would, you know, bet on a dog and Greyhound would go across around the ring. And then you would see, you know, I bet on number three, and I'll make it buck or something. And the way that they motivated the dogs was they had these, like fake rabbits, which sounds kind of cruel and horrible. So I don't want the SPH to come after you. But the point is that they'd have these like fake rabbits. And what was interesting is the moment that the dogs, if they accidentally touched the rabbit, you know, the sort of the tail, you know, 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.

1:05:09Sometimes the machines would break. The dogs would actually catch the rabbit. They would never run again. And 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. And so I think this happens a ton, is 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 like what happens next? And when it happens when they succeed, they're North Star, they're entire way of wiring their career themselves.

1:05:48It has been around like getting to that place. And I think that if you're going to get their 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, 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 know anything else to do, but you'll be sadder. Or you'll find ways to create war when pieces need it. Or you'll spend money in an attempt to sort of earn more.

1:06:35And 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. 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. And so I did and then we sold it to Airbnb and then I got to Airbnb and it was just like, what the hell do I do now? I don't have any other goals. And it was pretty, pretty sad exactly that you're describing.

1:07:14It was just like, I guess I'll just work here and, I don't know, maybe I'll start another company, but that's not a, I already did the thing in one of the two. 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 and it has lots and lots of spokes to it. And 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.

1:08:03And so this is reason why, like 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 realize is life after just being a tech professional entrepreneur, there's gotta 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. It's well, it's 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. Yeah, this is my fourth career is what I realized.

1:08:37I was an engineer, then a founder, then a product manager and now this, whatever this is. Whatever this is. 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, you know, content creation, helping people learn stuff. What else have you seen that might work out for people? 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.

1:09:23My North Star is to 200. That's what drives people from, it's non -onchronicity, 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 and you know, Eastern philosophies that have been around for thousands of years talk about this as the sort of end state of, you know, happiness. I think that maybe to be provocative, I think that it's okay for you to 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.

1:10:10But 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 however 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 were able to do that for 30 years and be giving, you 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.

1:10:58And I think that that's a very powerful blend that is hard to achieve in act one and act two, giving constraints and that's the liberation that actually provides. What do you think your act three plus ends up being? You know, many of us mean 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.

1:11:46But scaling that and doing that in a way that is very authentic is really the hardest part. And it's a product problem. And so that's what I'll devote 30 years to. And I look forward to that every day. That is beautiful. I feel like an exactly correct fit for you. And I am here to help you on that journey anyway I can. Thank you, my friend. Absolutely. Is there anything else you wanted to touch on before we get to our very exciting lightning realm? No, I just appreciate your generous offer to have me attend and participate in this wonderful podcast that you created. It's absolutely my pleasure.

1:12:20And it's not over yet. We reached our very exciting lightning round. I've got six questions for you. Are you ready? I am ready. What are two or three books that you've recommended most to other people? So two and both business books. Sorry, I'm going to come across boring. But one is this sort of a little bit of an old school book called Crossing the Casm by Jeffrey Moore. I don't know if other speakers have spoken about this, but it's a book that Jeffrey 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 beach head. And so I like that concept.

1:12:59It's so marketing is something that we don't talk about enough in product. And then the second one is a book that none of your listeners have actually probably heard of called Leadership and Self Deception. And it's a six hour audio that I highly recommend. And 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. And 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.

1:13:36It's a good ride. And I think maybe you'll get something out of it. I'm not heard of that second one. I'm excited to check it out. I have crossing the cast and 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 gonna keep doing it because I totally agree with you. I think there's so much to learn from marketing and it's connected to growth, which is connected to product. So I agree. I yeah, and I think that marketing is a language of connecting products with people.

1:14:15And like 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 the diversity of having both playbooks can make one just a much more powerful builder. So I agree with you though. Marketing folks probably are the best content and at least listen to you. So maybe that's a plug for people to go back to this episode. 100 % that's what everyone should do. And I don't know if you know this, but actually at Airbnb, the product management 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.

1:14:56And we'll see how that experiment goes, but that's a bold move I thought. Very much so. Very much so, but it's an homage to this concept. Exactly. Okay, back to early in the ground. What is a favorite recent movie or TV show? I'm a huge sports fan. So I have tickets to the Warriors and the Niners and I'm a big Bay Area sports fan. And Yannis is my son's favorite player. He's a basketball player for the Milwaukee Box and they have this Disney plus 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.

1:15:32It's a great Disney plus family show. And it's a great kind of, you know, zero to hero type things. I love that story. I feel like you're gonna have a really good answer to this next one. What is a favorite interview question that you like to ask? I like the format of what's something that everyone takes for granted that you think is essentially hogwash or inaccurate. You know, 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 that actually inaccurate. And you could do that for what do people think about AI?

1:16:13That's inaccurate that everyone believes. You could do that for, you know, domains. You can do all kinds of things. I love it. Is there, is there something you specifically look for there or is it just depends on what year? I'm always looking for people to break this sort of interview mindset. So 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.

1:17:07So when I break that wall, I'm testing as 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. It's going to be all over TikTok soon. Everyone's going to know this. Next question, what's a favorite reason product that you've discovered that you love? The key to answer in me is the arc browser which I think probably a lot of folks are starting to use in that your listeners. Part of the reason is I think it's just great for folks that have hundreds of tabs.

1:17:51And 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. And they've got like gigilians of people using it and billions of installs. And 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. At any time you see a innovation on something that's mature as a product, 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 truza.

1:18:32Yeah, 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, they closes your tabs after 24 hours. Unless you put them in a specific place, which I love because I think it was like, like you think you would do that, but you don't. And then it's like broke so beautifully. 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 fans all use is, and I'm not an investor, just a fan, is the onboarding experience is like the best onboarding experience I've seen.

1:19:02And it's just like, I did it and I just, 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, yeah, it 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 has had a big impact on the team's ability to execute? 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 nuisance or it must have a necessary evil to be able to deliver.

1:19:46Sometimes 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, the 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. Like 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, this is the attendees.

1:20:31And then here's how we make decisions to 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. And 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 and leadership positions in a new company, it's the one thing you can do when you have low context.

1:21:10When 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. So I'm a huge fan of rebooting meetings first. So process first, then people, then product and strategy is sort of the notion I make. And this is this first thing I always do. Final question, what is one thing every PM listening should do to help their career? 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 it.

1:22:02Here's a problem I solved. Here's a 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 promoted or not, that story is compelling.

1:22:43You'll be promoted in career. And that's what we're for. Nikhil, 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. Work and focus finding online if they want to learn more. And also talk about maybe various community, you know, the skip and all that stuff that people can check out. And then how can listeners be useful to you? I'm building this brand around the skip because I'm so passionate. There's two outlets that people can easily connect.

1:23:15One is the podcast, which, you know, much like yourselves is available on Apple and Spotify and others. So, you know, I'd love for people to join my podcast in here. What I'm now moving my podcast to is almost like coaching calls. You know, 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 picking about it. Whether it'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 comp of topic areas.

1:23:51So, 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. And so, between Twitter and LinkedIn, my presence is relatively easy to find. And then how listeners can help me. I mean, one is 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.

1:24:33Because then I can deliver more meaningful content. And 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 professionals. So, I would love to hear from your listeners. Just to make sure people know where to go to do this. For feedback, do you recommend LinkedIn? Yeah, LinkedIn is the ideal, but you can also find me on Twitter. If you're just trying to, if you're trying to follow me, follow me on to LinkedIn, if you're looking for feedback, just tweet me. And then for the skip newsletter, what is the URL to go check that out?

1:25:06It's the skip .substac .com. 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. Mikael, thank you again so much for being here. I'll let you go now. And this was amazing. Yeah, thank you, ready? Appreciate it. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or a leaving review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at LinneesPodcast .com.

1:25:44See you in the next episode.