Lenny's Podcast: Product | Career | Growth - Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Product Lead at Riverside)

Episode Date: September 22, 2024

Tal Raviv is a product manager at Riverside, where he joined as its first PM. Over his 12-year career as an individual contributor, Tal has been an early PM at Patreon, AppsFlyer, and Wix, working in consumer growth, developer API platforms, and pricing. He started his career by co-founding a profitable SaaS company and also volunteers as a surf instructor for people with disabilities. In our conversation, Tal shares:• Why he has chosen to stay an individual contributor rather than moving into management• The rise of “super ICs” and how companies can support this career path• Advice for succeeding as a long-term IC product manager• How he uses AI to enhance his productivity• How to build self-reliant teams and make yourself redundant• Lessons from failures• Much more—Brought to you by:• Gamma—A new way to present, powered by AI• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Eppo—Run reliable, impactful experiments—Find the transcript and show notes at: https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv—Where to find Tal Raviv:• X: https://x.com/talraviv• LinkedIn: https://www.linkedin.com/in/talsraviv/• Maven course: https://maven.com/tal-raviv/product-manager-productivity-system/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Tal’s background(02:24) Choosing to stay an IC product manager(07:05) The value of IC roles(08:31) Compensation and career path(12:37) Advice for companies on creating space for ICs(14:33) Leveraging AI for productivity(22:44) Build your personal PM productivity system(37:39) Contrarian opinions and insights(44:32) Book smart vs. street smart decision-making(51:51) There’s no one right way to get things done(57:03) Failure corner(01:19:04) Lightning round(01:26:50) Living through conflict—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [e-mail].—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

I've had thousands of people tag my CEO on Twitter calling on him to fire me. I was actually on vacation and I got bored and I was like, I haven't logged into Twitter. I haven't posted anything to Twitter for a while. What's like, what's going on on Twitter? And I see that the notifications number is like maxed out. It's like 999 plus or whatever. And I was like, wait, what? And I clicked the notifications tab and I see the first tweet is has at CEO handle fired at Tall

Review. And I saw that that has like a ton of retweets. I just keep scrolling down and I start to piece together the story. Today, my guest is Tall Revevee. This is a very special episode for me because Tall was one of the first and most active community members when I was just starting my newsletter Slack community. And as a PM I've admired from afar for a very long time, he's got some really unique and insightful takes on how to be a great product leader.

And interestingly, he's decided to stay an IC product manager throughout his entire career up to this point, which is over 12 years as an ICPM. I've never met anyone that stayed in IC for this long. He's been a PM at Patreon, at Wix, at AppsFlier, and most recently joined Riverside as their first ever product manager. Riverside, by the way, is the platform that I used to record my podcast, so this was kind of a meta experience for both of us. He's also former founder, and outside of tech,

he volunteers as a surf instructor for people with disabilities. In our conversation, we talk in-depth about the IC career path, a bunch of tactical advice on how to be more productive as a PM, including a killer example of how he uses chatypt to scale himself. Tall also explains why every tech company has just two departments that matter. The difference between book smart decisions and street smart decisions, we also spend the most time I've ever spent in Failure Corner, where Tall shares all of the times that he's failed in his career

and how those experiences made up stronger. And it was really important for him to share these things because he wants people to understand that successful people fail a lot, and those failures make you better. If you want to learn more from Tall, he's actually about to launch a course on Maven that's called Build Your PM Productivity System, which, based on the conversation that we had, I am confident, is going to be awesome. If you enjoy this podcast, don't forget to follow it and subscribe in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and it helps the podcast tremendously. With that, I bring you Tall Revee.

Tal, thank you so much for being here and welcome to the podcast. Thank you. It's great to be here. This is a long time in the making. It has been a long time in the making. You're interesting in so many ways. We're going to talk about a lot of different things. One of the things that makes you most unique and interesting as a PM is that you've stayed an IC product manager for your entire career for 12 years. I don't think I've ever met a PM that's been an IC for 12 years.

I imagine you've had many opportunities to be promoted. I imagine this has been very intentional. And I also know a lot of people actually think about this a lot. Should I move into management? Can I stay and I see and be successful? So I want to spend some time here to start. And my first question is why? Why have you decided to stay in IC?

Why have you not moved into management? I don't really have a strategy for my career. My strategy is not to have a strategy. For the longest time, I've gone by, am I excited to wake up in the morning? And what's going to make me excited to wake up in the morning? Not every single day, not all the time, but for most of my days that I work,

what's going to make me hop out of bed? And just kind of follow that. And over time, as I got to, you know, have different managers and different product leaders that I've worked with, I've never looked at their schedule or their days or how they spend the highest, you know, high percentage of their time and said, wow, that's what I want to be doing. If I compare their days with mine and the stuff they're, you know, they're busy with and focused on. And at the same time over the years, I've also noticed that the colleagues that I identify with the most, like the ones where I just feel I most relate to them, many of them have that same pattern where they've gone to, you know, team lead or director and so on. And their next role, they request to be an IC, like they insist on being an IC.

And yeah, so that's from the, you know, from the tech world, that's what informs that. and the values I had growing up, just watching my dad, he's a researcher, he's a professor, and he just has a blast every day. Like, he refuses to retire. He's just so enthusiastic about what he does. And he, you know, he's never, like, aspired to be, like, a chairman, provost like that. Like, he just loves what he does, and he stayed there. And I just see the joy, like the fun.

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This episode is brought to you by WorkOS. If you're building a SaaS app, at some point your customers will start asking for enterprise. features like SAML authentication and skim provisioning. That's where WorkOS comes in, making it fast and painless to add enterprise features to your app. Their APIs are easy to understand so that you can ship quickly and get back to building other features. Today, hundreds of companies are already powered by WorkOS, including ones you probably know, like Versel, Webflow, and Loom. WorkOS also recently acquired Warned, the fine grain authorization service. Warrant's product is based on a groundbreaking

authorization system called Zanzibar, which was originally designed for Google to power Google Docs and YouTube. This enables fast authorization checks at enormous scale while maintaining a flexible model that can be adapted to even the most complex use cases. If you're currently looking to build role-based access control or other enterprise features like single sign-on, skim, or user management, you should consider WorkOS. It's a drop-in replacement for OTH Zero and supports up to one million monthly active users for free. Check it out at WorkOS.com to learn more. That's Workos. So much of that resonates with me. There's actually a period of my career where I was not an IC, no, I was an IC and I was just like, I don't want to be promoted any higher. Everyone I look at above me is

just so stressed and I just don't need this. And things are great. Why would I want to change of that. And I love that you stayed close to that. I know a lot of things pull people towards management, there's compensation, their status, more impacts, trying to, you know, like learning to be a manager. Is there anything there that's just like pulled you and you've been just like, I'm going to give that up and I don't need that? Or is it, or life just as good as an I see for you? I won't lie. Over the years, despite like everything I said, if somebody who is my, you know, same amount of experience or same cohort and gets promoted and becomes, a team lead and makes that decision and rises up, it does, you know, like twang in my stomach

and like gets on my ego, I have that moment where I'm like, wait a minute, like, what about me? And should I be doing that? And it makes me question everything. And then I say to myself, okay, so, you know, go for it, you know, tell your manager you change your mind or whatever it is needs to happen. And then I'm like, well, like, do I actually want, I kind of get back to the same logic of like, what, I don't, I don't actually want that. Like, so if I could push a button and and switch with them, I wouldn't. So, but definitely, definitely, you know, very human at the same time. For someone that's trying to pursue this path, trying to avoid these sorts of things, and say just trying to be successful, and as an I see, looking back, is there anything that you've

learned that has helped you be successful and pursue the thing that makes you happy? I think the big elephant of the room is compensation. I think, that's like you know whenever I have this discussion with friends and colleagues like that's always like the well there's two things there's compensation and there's um like can it be interesting like don't you get sick of it right so i think you know that classic book drive you know motivation comes from autonomy mastery and purpose and i think for me the i see role it's definitely very autonomous it's one of the being a product manager is one of the most autonomous roles and most amount of agency you can ask for.

I think mastery, I once heard Marty Kagan say in a workshop, you know, product manager role is just one of those roles where you can just keep doing it, you know, for a really long time because it just keeps changing and you can change industries right without having background in it. The situation changes every time you do it in every different context. It's just so different and interesting. And purpose is one that I, I took for granted in the past

and I learned how important it is. I think if you feel that you're building something that you really want to see happen in the world and you really want to make sure it's done well, you're like, you're like, don't trust anybody else to do it. Like you want to be the one to work on it and make sure that this gets done well in the world because it matters to you,

then I think you're in a really strong place from that point of view. Like that really gets you motivated and you want to be hands on and it keeps you really focused. I want to drill into something. are in compensation and just generally what you've done to be to stay down this path because I know the compensation that's a real thing. Is there anything you've seen or done that has helped

you be more comfortable with that in terms of getting the comp you think you deserve being an I see this long, being like basically a super I see? I think first of all you have to believe your worth. Like you have to genuinely believe and understand that an individual contributor in product management, you know, is worth can have a really big scope, really big ownership, really big impact and matters a lot. And I think the industry is coming around to that, right? We'll talk a little bit more about this, but the great flattening of the last few years.

And, you know, I've seen, like, talking to friends who are founders and the founders here at Riverside are really looking for people really experienced who are really hands-on. Like, that's, like, first of all, we just need people who get stuff done. And just recognizing that in yourself,

believing that, and recognizing that in the industry, and remembering there's a really good analogy here in engineering, where it really makes sense to all of us that you shouldn't have to rise into management in order to increase your compensation. You're equally or just as valuable, right? Not as a manager as like a domain expert. And that's step one,

like really understand that you are, you know, really, really, really valuable as an IC. I think, tactically speaking, one thing that I've done a few times, different interview rounds is when it comes to compensation, you've probably heard the line, well, you know, that's a really high number, but, you know, we can't reach it, but don't worry. We're growing a lot. The product door is going to grow a lot. There's going to be a lot of opportunities to rise into management. So, you know, there's going to be a lot of opportunities to increase compensation over time. And that's like a classic line. You might hear from a recruiter or hiring manager. And in those moments, it's kind of like puts you in a weird position where it's like, well, you know, you don't think you're going to rise up. You can't like debate that so well. And what I say in those moments is, you know, I'm glad you mentioned that. I actually have no intention of going into management or rising up, you know, in those ranks.

And I know that, you know, you and I know that the industry traditionally undervalues the IC role. So it's really important for me to, you know, have that number now. And that works. Wow. Okay. Very straightforward. So maybe along those lines, just the final question there on this track is just for people that are trying to create a space for an IC path at a company or as a company trying to do this, anything you suggest they do to make this a thing for people that actually want to stay ICs to set this up

as a real career path. Have the titles. I think having, you know, good, you know, titles that are clear that you can move up into. First of all, just like creates it as an idea that there is progress, creating clearer levels and the rubric, just like you would for, you know, within any level or within any title. I think saying it out loud, recognizing it, I think it's just, like at the end of the day, you know, we all want respect. We all want to feel that we're growing. We want to feel that that's recognized. So I think putting it in words goes a really long way. So in terms of titles, what are the titles you find as a principal product manager? Is there other titles you've found a couple and how many levels of ICD you line you need it?

The ones I've seen on like LinkedIn is there's there's you know product manager, senior product manager, principal product manager. I've seen a distinguished product manager at last year. Yeah, I think Amazon I think has that too. Amazon too. Yeah. I think those are like the exception of the rule. Yeah. But yeah, I think putting it in words really helps. Okay, so principle and distinguished. Amazing. Distinguishes the highest level you've seen of an ICAPM. And I think you're...

Super IC, I guess. Super IC, and we're going to talk about that. And then in terms of rubric and career ladder, basically it's just the same way you have a career ladder for managers, just have it further, go further for ICAPMs. Yeah, I think product is usually like the last department to really... Just because it's smaller, I think. Yeah.

Yeah. Okay. Amazing. Really helpful. We've talked about this idea of Super ICs, and as you mentioned, there's kind of this been rise of and shift of flattening of orgs, as you said, of people hiring more senior product managers is there's a sense of that, and their companies are expecting more of PMs just doing the work, not managing their PMs.

And I feel like you're such an interesting prototypical example of the PMs people want to hire. And with AI, it's unlocking a whole new lever and opportunity for a lot of PMs where they, in theory can actually achieve this thing that companies are looking for them to achieve, which is just get more done. So any just thoughts along that track of just like more as expected of ICPMs? There's more need for ICPMs and AI making it easier. What have you seen there? Where do you think things might be going? We've seen the last couple of years, you know, I think it was, you had on here, Nikiel Singhal talking about when Facebook had those really big layoffs that they were biased towards keeping individual contributor product managers.

Zuckerberg talked about the flattening. And I've seen here at Riverside during that same time, founders talking about how they're just really looking for, can we just find some really, really senior experienced people who want to stay hands-on? That would be the dream, right? I also have heard from friends in the market, in the hiring market,

that there's just a lot more experienced people competing for the same IC roles as a result of all that. So I do think that the result of that is, you know, a lot of, I think the result of that is, like being a 10x PM, for example, is becoming more and more table stakes, especially like you mentioned with AI. That's just the tailwind for all of that. And we don't have to go too far down the track, but if you actually experience this yourself, have you found really interesting ways to leverage AI and become more effective? Just this week, I have an example. My team, I have one team that's trying to introduce much more rigorous scrum as it hires a lot more development. Part of that is a lot more paperwork as a product manager.

In some companies, it's a whole role that they hire just to do that. And what we did is basically took Chad GBT, told it the format, you know, the stories and epics and so on, and tried something where I just dictated and spoke as if I was doing a kickoff. And I just talked naturally and, you know, out it just put out all this really, really, really amazing detailed stories and so on. And I just had to edit it a little bit. But so that was that was like a, you know, a ha moment for me.

Like, okay, that would have taken either dividing the team into smaller pieces or multiple product managers to be able to keep up. And, you know, obviously the next step is like, we just take the actual kickoff, record that, transcribe that, and like feed that. And we're playing around with that as well. You can imagine what might have taken, you know, 10 years ago, five years ago, a director organization, like a director level organization, and everybody reporting to that director,

to achieve something could probably be achieved with an IC now. And I think this ties in because, like, the product career path is going to be even less about people management and just more and more about, like, leadership, right? And like the core product manager skills. This is an really interesting example of how you're using, I want to definitely spend more time here. Help me understand exactly what you did.

So you had a bunch of, of projects that you were kicking off with a bunch of different teams with a PM leading each one or Scrum Master and leading this is actually we tried this on one team but it was like a really big project okay like a ton of yes ton of stories yeah can you explain what the project is briefly or sure okay um it's a i'll say it's like a pretty fundamental change to the user experience uh so it touches on like everything oh shit over oversight okay yeah man here we go i'm excited Okay, so you have this big project you're kicking off to rethink the experience of Riverside. And normally you're saying you would have had to write all these one-pagers and specs of the components of this project, like the different features and product.

So the high level why we're doing this, you know, usability studies, the design, the vision, all that stuff we did without AI. That was me, director of design and our founder. But then it came time for, you know, the Rupper meets the road. We did a kickoff on the engineers, you know, everybody's bought it and everybody's excited. And now we need to like really make sure that things are really, really well defined and very, very clear and easy for, you know, testing afterwards and just like make all that stuff, the high level stuff really, really specific. And so that means user stories in Jira, in this case, right, for this team, that's how they prefer to work. And the specific format, like, you know, they've asked for. And so it's like a story.

and there's, it's called like Girkin. I'm learning this too. This is new to me. Given this, when that, then that, it's really tedious. When it's small, it's actually really fun to write because it makes you think. But when you have, you know,

so many things I need to change, it's overwhelming. And would either delay the team, that would be the bottleneck or we just have to split it up. And what we did is we took that template. My team lead said, hey, this is the template I would love. I gave it to chat, DIPT.

I said, you know, you're an expert. PM, product owner, scrum master, whatever. This is the template. Do you understand? It's like, yeah, let's go. And then I said, well, actually, before we get going, I want to tell you, I'm like, you know, holding down like the dictation button. Use a whisper AI to dictate. And I was like, you know, let me just tell you a little bit more background. I just started talking to it like I would for a developer, you know, joining the team. And I just started to talk about like why we're doing it and so on.

I was like, so do you understand that? It's like, yeah, cool, let's go. And then it's okay, well, the first thing is we're going to change this area and it's going to work like this. And it's really important that this. and this happens. And I just talked supernaturally to it, just like I would to a person. And when I was done, I hit enter. And it created that user story in that format with all those cases. That would have taken me so long to write.

And I would say the thing that we still really needed a person for was deciding how to break up this really, really big change into those stories. Like what is the logical way to split it up engineering-wise, which, my team lead did. But once you have that, like each one individually worked really, really well. So I'm now experimenting with taking the transcript. I tried this actually. Experimenting with taking the transcript of the actual kickoff that we did and that we recorded on Riverside and had it transcribed. And I copied it and put it into chat dupt. It didn't work as well. So I'm experiment tweaking it to see like how far, how far can we push this? This is awesome. I love that you're

sharing this. So you had basically described the project and all the different components, all the different features and user stories and words using Whisper. And to use Whisper, is it an app or is it within ChatGPT? Where do you actually access this? It's built into ChatGPT's desktop app. Okay, got it. It's like if you dictate that way. I also have like a desktop app on my own that I use because it's just such a great, you know, transcription model. Awesome. It's open source free provided by OpenAI. Right. It's Open AI's

speech to text system. And then they're adding voice mode soon like it's coming out to people. So this is going to be built into chat GPT soon. Amazing. Okay, so you talk about here's all the things we're going to be changing in the product. You give it a template.

Where do you give the template? Is it you put the transcript into chat GPT with a prompt of here is the template? Or are you just even still describing that in the recording? No, the template is something that my team leads. Like, this is how I'd love to have these written.

He just says it as part of the transcript. He sent it to me. He sent it to me on Slack. He's like, this is how I want to written. So the first thing I did, I opened a new thread in chat GPT, and I said, you know, you're an expert, you know, product manager, product owner. This is the template we want to use for user stories. Do you understand? Hit enter. So like, it's like, cool, I get it. And then I start to talk about the changes we want to make. Okay, this is amazing. I could go down this track all day, but let's shift a little bit. Is there anything else you found to be really helpful in having leverage as an ICPM,

kind of along these lines, whether it's A or not, just being that super IC essentially, getting more done as an IC. So the way I think about this is how you manage your own time, how you design your days, your energy, your focus, and then your team, and how you build that culture and those habits to just give you a lot of leverage as an IC. so that still as one person you can own a lot of scope, you can influence a lot, you can manage a lot. So personally, for my time, I really believe, and I think you've written about this as well, in actively designing your days.

And for me, I really strictly split my days between deep work and what I call ping pong. Or ping pong, you can imagine it's like when you're, you open Slack and it's just constant, you know, hitting the belt back and forth. It makes your brain feel like scrambled eggs. You're not going to be doing any deep thinking or reading or strategy. So for me, I'm a morning person and I block off my morning for meetings. You know, a lot of people give that tip. I go even further and I don't open Slack before noon.

I've been doing this for eight years. I don't open Slack at all. It gets really extreme to the point where like if I need to send a message, like it usually fails. I usually open Slack before noon because I need to send a message. And then I realized, like, all these messages don't need to be sent before noon, right? Just because I thought it at 11 a.m. doesn't mean I need to send it at 11 a.m. There's no urgency at that level.

So I actually keep a section of my to-do list, which is when I open Slack, here are the messages I'm going to send. And I write them as if I'm about to hit enter in Slack, but they're in my to do-list. And sometimes if I, like, really, really, really rare moments, I'll need to check something. I'll ask the person next to me, like, hey, can you go into this channel and just show me that thing? because all their notifications don't, like, you know, trigger my brain into scrambled eggs again. That's an awesome tip. Yeah. And I know people will hear this and be like, there's no way I can do this.

Is your insight as you can? Yes. Usually when I share this, people are like, well, what if something urgent happens and people are looking for you? This has happened like twice a year. You realize how not urgently needed the PM role ever is. like. And first of all, over time, people really respect it. They learn that this is how you work, and they come to really respect this. And second, the key people that I work with have my phone number. And I tell them, you know, feel free to call me at any time. If I'm not on Slack,

if you really need a response, just call me, WhatsApp me, whatever it takes. And first of all, it's like a barrier, right? It's not like a quick message. So it really is. only for urgent stuff. And, you know, I have like, you know, for twice a year, I'll get like a WhatsApp message from my manager, for my team lead, hey, something urgent is happening in Slack. Like, we really need you. And then I'll open Slack, you know, I'll violate my rule. It's totally fine. But that's like, it's so rare that the system works for me. Amazing. Okay. Anything else along those lines? This is an awesome little tip. I personally keep a weird habit. I realize it's a weird habit. I call it product scrapbooking.

where I have this massive notion database of every opportunity, big or small, that's ever come up. And when a piece of evidence out in the world comes in, it could be like a support ticket or like a CSM sends a gone call. Or like there's a really great slack thread with like an amazing brainstorm happening. And ideas, a piece of data, whatever it is, right? I'll file it. I like actively take a screenshot or whatever is I file it. And I start to like cluster these in this like really messrs. notion. And the reason I do this is that I've learned that, you know, we have these like

roadmaps and strategies that like seem linear, but like life and customers and, you know, insights are not. So when the time does come around to work on that thing and that opportunity comes up, I can pull up that notion. And I already have a bunch of like really, you know, in the weeds, real world clues to start with and even persuade people that we should dig deeper into this. Or for example, another advantage is that if I'm on a conversation with a person from sales or CSM from customer success and they'll mention a request, you know, I can open that up. And I'm like, yeah, this is actually this client and that client and that client also mentioned that. And, you know, you see like in their face that they feel heard. Like, you've been listening all this time. Like,

you've been writing this down. It's a really, I think that's really important as well. I love these tips. I love product scrapbooking as a term. It makes so much sense. And it's just immediately clear what you're going to be doing. And I love how simple the approach there is. Is there anything else along those lines? Or is there something you want to share around kind of this other bucket that I think you hinted at of helping your team set you up for success and get more done?

I believe in cultivating very self-reliant teams. And I think that's really key to having a lot more leverage as an IC. being able to manage multiple teams if needed on much bigger areas of the product. I think the key of that is having this mindset, that product isn't a role. It's a team. And I read a quote once by Ebby Atowari, and she's worked on Netflix and Uber and she's super experienced and she says something like, it's not about waiting for products. You know, products said this or that or waiting for product.

Like, we're all product. And I really try to have that as the cornerstone of a culture of any team that I'm on. That, you know, I had a new teammate come up to me recently. He just joined and he was on engineering. And he came up to me excitedly. And he's like, I found a case that you didn't think about. And I was like, okay, awesome. But Holland's talk about language.

Like product is not a role. It's a team. and whatever it is, I don't even know what it is, but everything that we own, like it's both design was involved, engineering was super involved, you know, yes,

I was there, and it's, let's call it, hey, I found a way to improve the product, or hey, I found something that we didn't think about. It's really,

really important. So first of all, like that language, that culture, that, you know, it's not like this hub and spoke model and like the PM is at the center

and making all these decisions and, you know, passing things through. So first of all, that's like a fundamental mindset. It's really important for each team to have to be more high leverage as an I see. The second thing is personally to seek to not be needed, but be valuable. And the difference is, like, if you think about your day as a product manager,

look for situations where is there a game of telephone that's constantly passing through me? Are there a lot of situations where clearly you're the bottleneck, like your attention, your ability to get to something is the bottleneck, and a lot of people are waiting on you? Do you find like a lot of communication is happening direct messages with you instead of public channels for the team? Are a lot of working meetings just like you and one other person on the team instead of maybe two or three?

You know, not too many either? So all those are like opportunities where you can create a different situation where a culture on the team where people are figuring things out between themselves and maybe involving you at the very end. So one of the things that I really put a lot of energy into is really encouraging people to get conversations out of direct messages and into channels. This is like a really important way to cultivate people with just working together and figuring things out in between one another. And anytime somebody sends me a direct message, I say, this is a great question.

Can you please put it in this channel with the team? I'll answer there. But it's really important for me that any decisions we make are transparent, that it's easy to find it later, that there's a few other people who should probably chime in if they want to. And this could be at the team level. I work at a company that had a really, really big customer success organization. They'd constantly find you as a PM and just DM you these questions.

And I'd say, great question. put it in this really big channel, that way, and I give a reason. So that way other people on a customer success team can search the channel and find the answer later. It can help other people. And if you do this enough, it becomes a snowball effect because other people on the team will see that other people are posting in public channels and feel more comfortable with it. And that just becomes a chain reaction. Such awesome advice.

It's so counterintuitive also, I think, to a lot of product managers. where you're basically saying, like, remove yourself as a dependency, delegate more, empower everyone in your team, have engineers, come up with ideas, have them write things, like one page respects, things like that, like become less valuable almost, which I think is not the natural tendency. Become obsolete. That's the dream, though? That's my dream.

I love that. But I think they're, like, if I thought of, if I think about trying to do this, I think you need like a real confidence as a PM and be in comfort with chaos. A lot of times PMs, they want to be the hub because the more they can control the narrative, the more they can control what people see, CX pinging engineer, like, oh my God, they're just going to start working on this thing. And we have this roadmap. We have priorities. How do you manage that challenge? Yeah, there's a great phrase I heard a mentor once say, which is culture over process.

You know, process is important and some of these you need to process. to scaffold until you build the culture. But I think it's like you've got to view the team as like this asset you're building, right? This culture is an asset that you're building and you're investing in it and you're, you know, cultivating it. And you want to build something that's stronger than that's a great example. A CX person or a salesperson just directing messaging and engineer or just asking for something. You want to build something that's resilient to that.

Like that's the real product that you're building as a PM, I think, is the team that builds the product. and is resilient to all this thing. It doesn't happen overnight. It's not going to happen in the first quarter that the team is formed, but it happens, you know, over time, gradually with little messages and little interactions and positive feedback and, you know,

asking people to work a little bit differently and giving them a reason why and building trust. And, you know, I think that success in my job is to build a very self-reliant team that's very resilient to all those things I would otherwise, you know, like you said, to keep me up at night and, like, really make me worried. You shared an example of how you do that, these little micro interactions. Like so much of a PM is these micro interactions with team members,

which is so much harder now in a remote world where you can't just walk by and just like do a little chat. The chat you shared, I think, is an awesome example where the language was a really powerful shift in how this person thought. Is there anything else along those lines you could share of how to create this sort of culture? One thing that I try to do is when, somebody take something that would be my job, right, and does that. Like, whether it's on the design side, they, like, you know, lean in more or on the engineering side, they lean in more.

People bring ideas or they say, hey, I took the liberty of doing this. It could be as small as, you know, something bureaucratic or, like, as big as, like, an idea or a suggestion. I just shower them with positivity. I just show them just, you know, how excited I am that they did that. That, you know, I just want that to happen again and then to feel even more. bold and just like when somebody takes something off your plate when somebody you know thing does kind of the PM what you think is like that that's PM thinking what are you doing right just really

want them to feel that that is extremely welcome and imagine there's a bunch of coaching you do to like help engineers designers researchers data people think the way you think almost to kind of become more PME is that a part of this too I don't know if I would call it coaching it's it's like a lot like you said just a lot of little behaviors so one thing I try to to do along those lines is when there's something that's on me to do for someone or like the next logical step. I try to do that live with them. So if somebody asked me a question about, hey, what does the data show about this if we went that direction? I'm like, I don't know. Let's find out. Instead of saying, hey, I'll get back to you. Let's open, you know, mix panel. Let's play around with this.

And I don't tell them, hey, you'd be great. I just show them how easy it was. Like, hey, if I could figure this out? Like, you know, this Fisher Price data for PMs, like this, you could totally figure this out. That's what I'm trying to imply by showing it. Or, you know, if it's a right, create a Gero ticket just to make something happen quickly and document it, I like, hey, let's just do this together on the call right now and make sure I get it right. And what you see is over time, you know, some people more than others, but they start to just naturally want to do that themselves, ask you for that access, start to do those things. Hey, you know, You know, I did this and I wrote the GER ticket for it.

I did this and I did the data analysis. And, you know, that rose over time. You actually have a course that you're launching or is out now or about to launch that teaches a lot of these things. Talk about that. Yeah. This is a passion project I'm working on with Maven, the learning platform. It's a course called Build Your Personal PM Productivity System. And it really goes super deep and super practical into these topics exactly.

how to design your time, how to manage yourself, how to manage your emotions, how to cultivate self-reliant teams, how to give feedback and create a product org, you know, that puts less overhead on you as a PM. And yeah, the idea is to just take all these topics and just make this like really, really, really hands-on. Awesome. I feel like I wish I had this. And I feel like you're such a great person to teach this because as an I see, this is how you succeed. This is the thing that makes it hard to stay as an IC. And again, with the rise of AI, almost creating a space for super ICs as we talked about, feels like this kind of stuff is going to be more and more important. So I'll definitely link to that in the show notes. I want to shift to a different

topic. I think you've kind of shown people this already, but you have a lot of very contrarian opinions about a lot of things. You see things a little differently. And there's a few other things that I've seen you talk about that I want to spend a little time on. So I'm just going to go through a few of them and just share whatever you want to share on. Sound good? Sure. Okay. Okay, cool.

The first is you have this phrase that, or this concept that every tech company basically has just two departments that matter. So yeah, over time working at a bunch of hypergrowth companies, I've started to notice that there's some departments that are the reason that company won, the market. and also started to realize that, and this is sometimes true of the department that I'm in product, that even if product did a 10x job, it wouldn't be a 10x outcome for the company over the decade.

But for example, it could be if marketing did a 10x job, the company would have a 10x outcome over the decade. And I started to observe this over the years, and I noticed, it's roughly, usually like two things, two companies, sorry, two departments. It's roughly like two departments that this boils down to in each company. So I'll just make this really concrete without naming names. The companies that I worked at, the two departments at one company was product design and support. Like, if those two departments were 10x, then the company would win.

another company was data accuracy and customer success. Another company was the thing that made them win in the market was trust slash brand, like trusted brand, and payments. And another company that I worked at looking back, what made them win in the market was marketing and engineering, like scalability. So product, sometimes is on this list.

So one of the companies I worked out, like I mentioned in product design product, if that department does 10X impact, then the company will succeed 10X in the market. But it's, in my career, it mostly hasn't been product. Product has to do a good job, but it's not the, you know, not the biggest lever for that company,

even though it's a tech product company. And I think this really crystallized for me when I finally worked in a company where product is that department. You feel that. Okay. So the $64,000 question, whatever, billion dollar question is, how do you know which of these, how do you know which two departments matter most? First of all, look at what really drives the growth?

Like, what's the growth model? You know, what are the levers? Ask those questions. How does it work? Ask officially and ask as part of your back channeling and, you know, reference checking. And the second thing is if you're really seriously, you know, checking out a company, evaluating a company. truly understand that customer and like what are they actually paying for in this industry?

You know, what is the thing that, what is the real product? What's the real value that they're getting? Clearly they're paying for a product or a service, but like what is beyond that, what are they actually paying for? Ask those questions and I think that'll make it clear. I think maybe one trick here is just see what team drives growth. Oftentimes it's going to be sales. Oftentimes it's going to be product experiments they're running. could be marketing. Exactly. And that department,

whatever role you have, if you're in that department for that company, that's going to be your career defining work. Like that's why it's so worth it. That's kind of, you're going to attract,

like, you know, the best colleagues, your careers are going to, you know, have a step function jump. Like it's a totally different experience. And this is when people say a company's engineering driven,

product driven, marketing, driven, this is exactly what they mean, which team matters most to the company because they are driving most growth. So if you're a salesperson on a sales driven company, you will be valued more highly than being a product person at a sales driven company.

Yeah, when I graduated from college at a friend gave me advice, he was like, don't be a finance guy at a tech company and don't be a tech guy at a finance company. This was 2009, so like, yeah, anyways. Yeah. And I think this is where a lot of people struggle with their PM at a company that's very not product driven and they read all these books about being empowered and having agency and autonomy and instead they're just the team that people they're just feature factories because other teams

are in the show and we don't need your opinions we know we know how to grow this thing just build this thing for us and here's the thing that's okay like that's what that company needs you know to succeed in the market you know you think about the olympics this is an analogy that came to mind recently it's like let's say you can think like how a marathon runner looks and how a swimmer looks right they have very different they look very different you can you can spot them you know in the row of athletes and if you imagine you know product being a lap muscle that's product department you know you can be a lap muscle for a marathon runner you can be one for a swimmer and a marathon runner needs one and it needs to work but right it's you want where do you want to be the

that lap muscle on the swimmer on the on the marathon runner. I love that. This episode is brought to you by Epo. Epo is a next generation AB testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Muro, ClickUp, and Draft Kings rely on Epo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. And Epo helps you increase experimentation, velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own.

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That's get-EPPO.com slash lenny. Let's move on to another, let's say, hot take that you have. You have this kind of phrase that there's a big difference between book, smart decision making and street smart decision making. What's that about? Yeah, this one comes out of a lot of mistakes I've made myself and seen around me as well. So I'm so guilty of this. Book smart decision making as a PM is all the stuff we talk about all the time. That's data, you know, design, technology, strategy frameworks, all that stuff. And it's really important and you know, it's why we're strong of it. Street smart decision making is

taking all that and then seeing something from somebody else's point of view. This goes beyond empathy. Alexana what I mean? It's like giving the customer's perception just as much weight as you would to logic. A really big example of this, and I won't name the company, I was at this company that changed the structure of the pricing. And the change was actually not. not meant to make more money. It was meant to unblock a payments roadmap and like enable all these feature requests that were stuck behind this fundamental change. And in preparing for this, the company did a lot of analyses and just made sure that, you know, this was really, actually really good for customers and that this would, this would only, like, the numbers and

the predictions and the models, we're like, this is a positive thing. And I know all the people that were involved were the most empathetic really did this because they really cared about this customer. Generally, I've never seen people that are, you know, at the executive level, at the product level, at the data level, like, these are the people who really genuinely wanted the best for this customer. And they rolled out the change. And in reality, what, bottom line, it was a big, you know, revolt on the internet. It was a big deal. And it was rolled back.

And the bottom line, why there was such a gap between, you know, everything. Actually, by the way, all the analyses proved out to be correct. All the models, all the predictions, like everything played out the numbers as predicted. The problem was the perception, the narrative behind it, what it looked like when you've logged into the product. And you saw only the negative, but you didn't see all the positive because a positive was. you know, would happen 30 days later and you saw the negative immediately, you know, a lot of things like that. And I would have made exactly the same mistake. I would, you know, not a criticism. I would have probably made more mistakes. But that's like what opened my mind to, oh my God,

you have to really think more than just logical, more than just like, you know, utilitarian. Another example of this is there's a company I worked out where all the features that were on a higher plan, were invisible to the lower plans just because everything was built really fast and it was just, it was time to make them visible so people could upgrade. So we got that ready. And we did this and we're about to release it

and we realized, you know, tomorrow morning, a bunch of customers are going to log into the product and there's all these features that they've been asking us for because they didn't know that we have them because they were locked and only on the higher plan. Suddenly, from their point of view, the company built everything they'd asked for, and all of it requires paying more money.

How are they going to feel? And so we didn't roll it out. That way, we rolled it out in smaller pieces and, you know, in different ways, because we realized, like, that's going to feel really shitty. If you think about it, you know, but practically speaking, or theoretically speaking, We didn't upsell anything. We didn't start to, you know, these are all things we already had built. Everything is above board.

That's the perception that was going to happen. And that's like an example. Is there anything that triggered that recognition or is it just people sitting around being like, oh, what about this? Or is it because the first example you had a great point where customers were telling you this isn't necessarily what they want. And you're like, no, no, no. You're going to do great.

Trust us. It's going to be really good for you. But there's feedback, at least in the second examples, or something that's like, and what I'm asking about is like how can people develop the skill? Because I love this advice. I think that intuition came from spending time in the customer community and support tickets and just noticing smaller versions of that that people have feedback on. And you kind of start to see, you know, what our customers, you know, at the time with like what

they would tend to, like what their suspicions always were. they're very like, you know, trigger-happy to blame the company for XYZ. And if you see enough, you know, raw data from customers, or if you get on a customer call and they mention nickel and diming and all these things, right, like, you start to understand, like, this is the target persona. This is how they think. This is what they're sensitive to. It's interesting because at Airbnb, there was a lot of that, a lot of hosts being really

upset about changes, like constantly. Everything that changed, they're, and usually the changes are to help. the business in some way, help the guest in many ways. And it's always this balance of we're just going to, we got to do this. This is just the future. Is there anything there? Just real quick of just like learning when we got to do this anyway, even though they're going to be pissed versus like, oh shit. Yes.

Yes. Yes. For sure. This is just like what I'm talking about is to recognize it. What you do with it, right, is a different thing. But, you know, I joke when we, when we do changes to like redesigns or changes to the and we're going to get inevitable, you know, complaints. I just tell my team, we're going to deploy this, and we're all going to log out of social media for two weeks. And that's the strategy.

Great. That's extreme. We don't actually do that. And of course, but that's what we wish we could do sometimes. And the insight there is just social media will amplify one person's loud voice versus like how many people actually are upset about this. How important are they to the business, right? It's like, don't pay attention to the loudest person. or also I think the key there is the two weeks

because if people are still complaining after two weeks okay then there's something here but in those two weeks there's going to be a lot of feedback that comes from a resistance to change that they're going to adapt to and we won't be able to remember what was before but sometimes you make mistakes and people will

if there's a real mistake you'll know about it for a long time yeah and obviously you'll pay attention to like support tickets on all that stuff. Yeah, obviously, yeah. And disclaimer, like, during those two weeks, we look at every support ticket and we look at everything on social media. We, yeah, for sure.

Okay. Two more examples about the Street Smart Books, Smart that are really important. Oh, please. Let's do it. Let's do it. This has happened twice to me where I worked on a team that made a very logical U.S. change and quickly found out that we ruined. the sales demo. So for the users of the product, the experience became a little bit smoother.

It was an optimization. It wasn't something critical. But then for the sales demo, it communicated the value less. It was harder to, for people to really understand, you know, in one glance. So a lot of times this comes from taking something that's very visual and making it very efficient and small. So you might gain fewer clicks, but it'll make it harder for the sales team to, you know, to communicate and for that ha moment to happen on a call to the point where we made this change and then salespeople would send me gong link recordings, you know, in the past and in the current demos and just show me the difference. And it would pain me to watch these. And I was like, oh, we got to fix this. Like people aren't getting the vet.

value how they even going to experience it. Okay, I know that you have a couple more hot takes that I wanted to make sure we have time for. One that I love that I agree with, and it's kind of the thesis of this podcast almost, which is that there's no right way to get things done in a product team and a business in spite of what you may read online. I'd love to hear your take here. Yeah, I didn't always understand this. In fact, I moved continents because I had professional FOMO. So I moved from Israel to San Francisco because I believed, and actually a lot of people, you know, had that feeling that, you know, whatever we're doing here in Silicon Valley, they know how to work.

Like, that's the big leagues. And I got to work shoulder to shoulder with people who came from Apple, YouTube, Salesforce, Facebook, Slack, Amazon, Stripe. Like, I got to work with the people who came from these companies I admired so much. And I came over with a conclusion that we're all just making it up as we go along in tech. We're all just improvising as we should. That's the beauty of it. Every situation is different. Every market is different.

Every company is different. What it takes to when is different. And so myself, I've had phases where I've been this zealid of, you know, everything has to be outcomes driven. And then I've gone to like, let's just ship as much as possible and figure it out. And everything needs to be A-B-tested. And, you know, quarterly planning has to work this way and should do scrum or don't do it. And I just realized, like, there is no, it's not that simple. It's about figuring out the problem at hand and optimizing for that and having an open mind.

And just understanding that we're all improvising. That's really powerful. And I think people may hear this and be like, yeah, I think I get it. I guess for people that are just, you know, everyone's reading, reading my newsletter, reading all the newsletters, we're listening to podcasts, listening to how people work. What's your advice? Is it just, like, what should people think in your mind when they read about how another company runs? My personal story, like, one of the things that happened when I landed in San Francisco, I really felt like an imposter. I was like, okay, wow, everybody else here really knows, you know, how to work and I need to like learn from them. and six months later, I found myself giving talks and writing blog posts about how to work.

You know, like blog posts that, you know, were being used in like, reforge courses and all that. And advising people and sharing. And that's when it hit me, like, that's the beauty of this industry is that that can happen because everything is changing so fast. Like, because, like, how did I get there? I was just on a team doing something really difficult and interesting in a very unique way. And that's how you learn. That's like the real way to learn.

My manager, Adam Fisherman at the time, told me, you know, something related to this, which is like the best networking is just to do really good work at a successful company and like everything else will work out. So I think the same goes for like learning, right? The best learning is to just do really good work at a really good company. company with really good people and solve problems that have never been solved before in this way, which will inevitably happen, right? That's what we're all doing. And everything else will work out. Like, you'll be the one writing the blog posts, not just reading them.

Such important advice. So kind of the takeaway here is just if you want to become much better, if you want to be the one sharing advice versus the one reading advice, easier said than done, but the advice is work at a company doing interesting, hard things. driving impact, being growing, being successful, and that's how you level up. Yeah. I love that. That's the best way. Yeah.

And again, easier said than done. Not everyone can join an awesome, you know, high-flying tech startup. Interestingly, you did this like in Israel, right, away from the core of Silicon Valley. So you can find great places outside of Silicon Valley. Absolutely. Great. Okay. So I know that you wanted to spend a bunch of time in failure corner, which I love.

It's this recurring segment on this podcast where folks share times they failed in their career and things they've learned from those experiences. And you wanted me to carve out meaningful time here, which tells me that you've had a lot of these experiences for better or worse. So what I'm thinking is let's just go through a few of these stories that you think might be helpful to people to hear about times you, things didn't go great. And what you learned from those experiences, how does that sound? Yeah. Yeah, it's really important for me to share this. I think during low points in my career, having someone share with me a failure story just really help me understand that that's part of it. And I'm not alone.

And, you know, you browse LinkedIn. You see these incredible profiles with these incredible pedigrees. And what you don't see, it gives you this sense that everybody's just had a smooth sailing and everything's going great. and everybody has had, you know, some, everybody who's been here long enough has had a ton of failure stories and ton of low points and self-doubt. So it's really meaningful for me to just talk about this. Let's do it. Let's get into it. Let's get real.

So I'll say this. I've wasted twice. Twice I've wasted an entire quarter of a growth team's time because of my poor use of user research. first time I can look back after 12 failed A-B tests and then 12 failed A-B tests set us on the right path and got us to revisit our hypothesis

but if I had only spent more time with the customer and this was the kind of A-B testing that people say no you can't do user research you can't ask somebody what they're how a button is going to affect their purchasing but if I had spent time with the customer to just understand who they are what motivates them, how they got there, why they're paying, all that stuff.

I would understand that not every checkout process, you know, is the same psychology as Groupon or, you know, Amazon or booking.com. So the things that work on those sites work, not just because, you know, people are the same everywhere, but they work because people are in the same mindset. You know, for Groupon, for example, Amazon is different. Booking.com is different. And what you're working on, why people are buying, you know,

in this situation that I was in was so different. They had so much motivation over such a long period of time. You know, they had constant reminders naturally in their lives that they were happy to get. And the things that didn't work were all the things that worked, you know, that Groupon and booking and Amazon and all these e-commerce sites did. Those were not relevant. And we tried all those things and they fell flat. The moment we realized that and it clicked for us and all these, you know, all these AB tests that should have printed money did nothing.

Once we realized that, then we really started to, you know, increase conversion and it was a super successful team. But, man, I look back if I had just, you know, I just used more quality. qualitative research, even though it was an area that traditionally you don't use qualitative research, I've got to save so much time. There's also a great reminder of just not assuming wins that work at another company win for you, which I think everyone's like, yeah, I know that, but I think people don't know that. I think they often, oh, look this.

Amazon's killing it with this feature. If we add it, we're going to win so hard. And so this is a great reminder. Don't just take stories from other. There's something Shreos actually talks about a lot is don't take stories from other companies as costable your company. There's so many things that are not the same. Awesome.

What else? What else you got? The second example of that is I was building a referral program and we made a user research plan and we ended up only executing half of it, which means we talked to the people who were already using it successfully. And we decided to skip talking to the people who should use it but didn't. and we're like, yeah, we get it. It's probably the same feedback.

We were in a rush for a lot of other reasons. There was a lot of pressure, just unrelated reasons, and just decided that, okay, we have enough information. We don't need to spend more time. Let's start shipping. And that was a huge mistake as well. Just spent so much time building something that didn't work. And, yeah, I think my lesson there is the reasons that got me to hurry

and make that decision with not as much data were reasons that I just kind of took people's word for stuff. I didn't think as first principles as I should, and I really caved into the time pressure. So, yeah. It's like tall therapy. Just letting it all out. This is great.

And so far, a recurring theme is spend more time and user research, talk to more customers. Again, some we always hear of it. A lot of people are like, ah, user research.

I don't need that. And what we're hearing here is it would have saved your team months in quarters, potential. Yeah. Each of those wasted entire quarter. Oh, geez. All right. Cool. All right. What else? What else we got? I have three times been a hair away from getting fired. And what I mean by that is a senior executive has come to me and said, you are a hair away from getting fired. And one of them, you know, One of them is there were changes that the head of product really wanted to make.

And I felt strongly that it shouldn't be made. And I voiced that directly, candidly, personally, and repeatedly. And then we had that conversation. And a colleague told me, listen, look at it this way. Like, if you trust the leadership team to adapt if something's not working, I said, yeah, I trust them. well, like, what they need from you is just to rely on you that you're going to be with them, even if, you know, the disagree and commit. Like, that's what they need from you.

If you're right, they'll adapt. If you're wrong, then great. You learned something. You know, product work got better. So the most important thing was, you know, there's like a song that, a lyric that goes, you got to give in to win. Like, it wasn't about being right. It was about just like being supportive and letting things fix themselves.

instead of, so that was that moment. It was really, like literally that was the conversation. The second moment, the bigger story, but I was on the group that the, my manager and I, we just weren't a fit. And that happens. It's really important to share it. That happens. It's common.

And as somebody I respect deeply and has done amazing things and I still respect them. and we just didn't work well together. And the next step was, okay, well, I guess, you know, it's time to let me go. And his manager was like, hey, you know, before we let you go, I want you to stay at this company. And let's find you another group to work in. So I was like, okay, he's like, just finish, you know, the initiatives you're on, don't start new ones. And quarterly planning is coming up, sit in all the meetings, look for opportunities. and things will work out.

And I did that, and I didn't find an opportunity that I was excited about. And my initiatives wound down, and I didn't know, okay, well, what's going to happen? And then there was a group where actually three PMs left at the same time. One went on maternity leave, one got an offer from Fang, and one had to start like an emergency tiger team for their area of expertise. And this director, he filled two of the roles, one internal hire, one external hire, and there was one more role. And I reached out to him, and he's like, yeah, great, you know, come put your desk next to mine. We'll just work on a few projects together, get to know each other.

And I could tell after a few weeks that even though we'd been getting to know each other, he was still interviewing for that third role. And I realized that like something was stuck. And at the same time, the director who had reached out and said, please say at this company, you know, you'll find something, called me with a very different tone. He's like, listen, you can't just float around without a roll. If you don't find something, you know, soon we're going to have to let you go. And he was right. And so I found myself in this situation.

And I actually reached out to a friend Guy Pellid. He's a friend and a mentor. I actually met him through the plenty of community. And yeah, he's here in Israel. We got coffee. and he told me, listen, like, clearly you have nothing to lose. Like, there's probably an elephant in the room. You know, this new director is wondering why did you leave this old group?

He's not opening. He's not broaching the topic. So it's up to you to do it. And I was like, okay, what do I say? He's like, what would you say to him if you didn't have to edit yourself? You didn't have to censor yourself. And I just, I told a guy, well, this is what actually happened. This is what I believe.

This is what I did. Could have done better. This, you know. And he's like, he's like, dude, that's totally. fine to share. You should share that, like word forward, just say that. So the next day, I took the director, you know, aside and I had this conversation. I shared vulnerably just like, here's what I think I messed up. Here's what I think I wasn't under my control. And that conversation, just like the vibe change. I could feel like a weight off

our shoulders. It was like, we really felt like we got closer. And two days later, I was part of the group. I joined the group. I did some really awesome work there. That's such a powerful lesson right there of just opening up and being vulnerable and just sharing what you're actually feeling. And this has come up a couple times in the podcast is what brings people closer. You think being vulnerable and showing weakness makes people think less of you, but almost always they think more of you because they didn't realize what they're doing.

They didn't realize what you're going through. you kind of think they're reading your mind. Yeah, we've all been through that. Like, you know, it doesn't look like it. It doesn't, you see someone you think it's successful that you admire. You look at somebody's LinkedIn profile. You look at their resume. You look at their bio.

Right. It doesn't look like that. But we've all been through all of it, you know. Right. And most times folks don't know that's what you're feeling or going through. And so just sharing, here's what I'm seeing. Here's what I'm feeling. Here's why things maybe aren't working for me.

It was a long way. Amazing. These are awesome stories. What else? Where else have you failed? I've single-handedly tanked new payments for a whole week for a company I worked for. It was a well-meaning change. It was super logical.

It was kind of streamlined. And I violated my own framework for when do you run an AB test. I even wrote like a blog post about this and I violated that. And I was like, oh, there's no downside here. And, you know, we didn't need to measure this. This is just going to make things way smoother. And then I get a call for marketing. They're like, why are none of our.

campaigns converting. Listen to your own advice. Run a veto sometimes. Running Vita sometimes. If you're dealing with really sensitive flows that have big downsides, even if you think logically in your buying, there's no reason there should be a downside here. Great.

If the stakes are really high, yeah. All right. What else? I have some stories. I don't know if they're failure stories, but they're kind of like Wild West. Let's do it. That's what it feels like.

It's like, One time I completely disabaged quarterly planning. My team was told to do one thing, and we just said no. We were going to do something else. It's not as dramatic as it sounds. It was like, hey, we really, really believe that this is an opportunity. And if we delay this, there's going to be like a really nonlinear cost, opportunity cost of this. And we really should do this.

I'm like, no, you should still work on this. We're like, okay, well, what if we made it a really small team and it was just for one quarter and then, you know, like, fine. okay, we have built that capital to be able to do that. But, you know, I remember your W framework post. I love that. And I don't know what letter that would be. But that's how that works. You go off to the side, split it off into it, make it a Y.

But most importantly, did it work? Was that a good idea? Was that a right call? Yeah. It was a right call. It's become a way bigger team today. And, yeah, I still read, you know, press releases and blog posts from the company.

it's clearly that team's work. Amazing. Excellent. I got lucky, though. Yeah. All right. Sounds like. Again, this is just like.

Wild West. You know, Wild West. PM is no less wild than life itself. I have pulled an April Fool's prank on an executive team that resulted in my CEO, seeing me, like, next time you saw me, just looked me in the eye, said, fuck you, tell, and walked away. Can you describe the prank? So the prank was, I'll say, first of all, the best April Fool's pranks are the ones that touch just ever so gently on people's biggest fears at that time.

So in a work context, like, whatever somebody's biggest strategic fear is that quarter or like that March of that year, right, whatever people are talking about, like, you just have to touch it a little bit, they'll do the rest of the work. So this company, there's a really big debate about internationalization and should we do that and there's a big tradeoff to doing it and other things we could be doing with the same resources and the

this was just around everybody's minds especially the leadership team and it was March so my buddy and I also at the company we decided what would be people's biggest fears would be that a really big company would launch the same thing in Europe

up. And we created not just a fake screenshot, like not just fake news, we created a fake domain name, website, publication. It was like really detailed. We really invested a lot of this German website. And it was, we made up a tech arm of their Spiegel. We called the Spiegel tech. We bought the domain. I'm probably incriminating myself by saying this. And then what we did is we knew that if we had, had sent that link on the first of April to the executive team, nobody would believe it. So what we did is every executive on leadership team has that like senior report that they really trust. So we got all of them in on it and the link would come from them. And each of them took it further. The senior engineer, who was really critical to the company, he created a fake

recruiting poaching email. If I recall, I think the legal counsel created a fake cease and desist. Like, we just found it all out. And then, and this was on a Saturday. So we ruined the executive team Saturday. They had like an emergency call. It was a Saturday. We ruined the executive team Saturday. And every time that we decided that, you know, a particular executive had suffered enough, like depending when they woke up and how long they had been, you know, dealing with us, we would let them in on it, let them into the private channel and, you know, ha-ha. So Monday rolls around, CEO sees me, fuck you tall, great. I'm still employed. And I hear later that day that the leadership team had their Monday meeting. And somebody mentioned that, you know,

even though that was a prank, it really got me thinking. And then the CTO of the company goes, wait, what do you mean prank? And he dons on, it dawns on him. And he just gets up, throws down his jacket and walks out of the room. So we forgot to tell him he had to, you know, stew with that the whole weekend. So yeah, sometimes you got a something that goes too far. That is well executed. Oh my God. It actually reminds me at Airbnb when I was I was leading a lot of April Fool's jokes year after year and one of the best ones we did was we launched. It's basically we did the opposite of what you did. We launched AirBRB, which was a desk sharing service. And we made like a whole launch video. We like announced it as like a new product, Airbnb. The idea is like you go get lunch and you can

I'll be right back and then your desk can be rented out for like 20 minutes. For 20 minutes. And we had a whole website and we had like, yeah, amazing video launching it. And basically it was the opposite. All the desk sharing companies got freaked out. Oh, no. Because it's very legit.

It's the greatest sphere. Yeah. Yeah, exactly. You don't have to do too much. Yeah. And the good news is we quickly, they quickly realized it was not real, but we probably led to some calls,

some board calls. Okay. This is awesome. Any other stories? I've had thousands of people tag my CEO on Twitter calling on him to fire me. This was by accident, but yeah, I was actually on vacation and I got bored and I was like, I haven't logged into Twitter. I haven't posted anything in Twitter for a while. What's like what's going on on Twitter? And I see that the notifications number is like maxed out. It's like 9-9. 9 plus or whatever. And I was like, wait, what? And I click the notifications tab. And I see the first tweet

is, has at CEO handle fired at Tall Revive yet. And I saw that that has like a ton of retweets. And I just keep scrolling down. I start to piece together the story. And there was a change, the pricing change that earlier I said had an uproar. And the internet was up in arms about this. and somebody found a blog post from a year earlier. Brian Balfour interviewed me about an onboarding experiment that we did. And part of that interview, I shared that, you know, at this company, we'd rather have fewer customers the way we make a bigger impact on their lives

than a lot of customers that we make smaller impact. And kind of explaining the logic and the product principles, that was really core to the mission. of the company. And somebody took a very limited screenshot of that to prove that, you know, Talafeev hates poor people or something. And that screenshot went viral

and that those tweets got embedded on like NPR and Washington Post. And that was a little nerve-wracking. I wasn't fired because I actually wasn't connected to that. I wasn't on that. I really felt bad that the the PR team, marketing team and all that. I reached out to them.

I was like, I'm so sorry. Like, you know, you guys are working overtime because of my big mouth. And they're like, don't worry. Like, this is happening to everybody at the company right now. Everybody's having, you know, people are digging stuff up,

unrelated stuff. But, yeah, that's stuff that happens. What a life you've led, Tal. Maybe just to close out this portion or discussion, is there something that you think people should most take away

from this really important stuff you're sharing of just like things that usually don't go well for people that do well and probably like there are many things that go wrong so the feedback i get from executives about these moments that really i think is transferable and helpful is that they know that no matter how silly i'm being or you know what kind of stuff i get myself into that they know for a fact that i how much i how seriously i take everything like they know how much i i'm taking if i make a funny presentation about something, right? And I put a lot of jokes into it, but they're like, it's still extremely clear how seriously you're taking this. So I have peace of mind. Yeah, I think you have to have both.

You can't just, you know, have these adventures or do these silly things or make these, like, these mistakes. Like, it's important to give the confidence that you know you're making a mistake. You're on top of it before anybody else. That, you know, it's bothering you more than anybody else that you've if you're if you're communicating and you're trying to make you creative and like that first of all you've done all your homework and you you know you've put a ton into it and that gives you the basis like the funny side of this is I have friends who make fun of me that I work really hard to justify like my friends that make fun of me I have friends make fun of me that I work really hard so that I can increase the amount of bullshit that I can

get away without being fired. Depends how you look at it but it's really important to to give that piece of mind. Yeah, build that trust bucket and then just deplete it completely every time. Throw it out the window. Amazing. Tell us, is there anything else that you want to share before we get to our very exciting lightning round? We've covered a ton of stuff.

It feels like there's been three podcasts within one podcast. But just before we move on, is there anything else you want to share or touch on or leave listeners with? Let's do it. Okay. Lighting round, yeah. Well, with that, we reached our very exciting lightning round. I've got five questions. Are you ready? I'm ready. First question. What are two or three books that you've recommended most to other people? The best book on product management that I've read

is called How to Talk so kids will listen and listen so kids will talk. I encountered this book my sister is a speech therapist and she had on her bookshelf at home in her apartment and I was jet lag one night. I was visiting her and I read it and if anybody has read Never Split the Difference by Chris Voss where he talks about how these senior FBI agents in 70s, 80s were realizing that all they were doing

and they're negotiating taxics were just not working and decided to try something different. And that's something is basically nonviolent communication. And he gives these amazing examples of decades of using this with kidnappers and, you know, terrorists and organized crime

to diffuse situations and create productive outcomes. So this book, you know, with all due respect to FBI agents and terrorists and hijackers and kidnappers, right? Like, this is about kids. So this book is, for me, this is what really, the example is how it's communicated. It's like illustrated almost like a comic book, tons of super concrete examples. And for me, I think that's when these principles really sunk in is from that book really, resonated with me the most, more than the book itself for nonviolent communication or the never split the difference, both of which are awesome.

So I really recommend that book. Man, I want to do a whole podcast on what you learned there, but I'm going to force myself to move on. Yeah. That's awesome. This is going to be really helpful to me as a new parent. There's a book that another, I'm just going to throw out a book recommendation, reverse lighting around on this topic that Joe Hudson, recent podcast guest recommended offline that I've found to be incredibly helpful. It's called Listen. It's an orange book.

So there's a few on Amazon, and we'll link to it in the show notes, but it's just called Listen. And it's about why listening is the most powerful way to help your kids get through stuff that is challenging to them. That's a powerful title. Just listen.

That's it. And there's all these different ways of listening. So anyway, okay, we'll keep going. Do you have a favorite recent movie or TV show you've really enjoyed? I recently rediscovered Ted Lassow. The first time I was, watched it. I got tons of recommendations. It's hilarious. I didn't connect to it. I just didn't connect to the humor. I was like, oh, okay, fine. You know, I stopped watching it. And then I heard

a podcast where somebody recommended watching it from a point of view of like leadership lessons. And they just couldn't stop recommending. They just so passionately recommended it. And I was like, okay, let me revisit this. And when you watch it from that point of view, it's mind blowing. If you think about, I'm sure, you know, a ton of people listening to this have a lot of watch the show. You think about the premise of the show, it's this guy who's been given an impossible task, and he's surrounded by the worst human beings in the world in terms of, you know, they're, yeah, just the worst human beings and behaviors. And the way he gets through that, right, is, it's hard to describe. You have to watch it. I think any attempt to summarize it. The show, like,

just watching it how this character behaves and gets through this stuff is incredible when you watch it from that point of view. And for me, when I, it definitely affected how I work, definitely influenced me, but not just work, like, just also how I deal with, you know, aggressive Middle Eastern urban life situations, how I deal with, I've applied this, dealing with really tough locals at surf breaks, you know, in South America. Like, it's incredible. I'll give a story of the surf break. I was in Chile and I was surfing and it was an hour of the day where a lot of people who were local would be surfing and a bunch came out and they started giving me these like looks, you know, this happens everywhere in the world, every surf break.

And it's just like really uncomfortable and one of the guys especially. And after a while, I was realizing, like, I'm not going to get the surf if I, if this keeps up. And, you know, I'm not, there's no conflict way to get out of this. And I swam up to him. And I asked him, I was like, hey, are you from like, Pichilemo? Are you from here? And he's like, yeah, why? I was like, you are one of the luckiest people in the world.

And he didn't, you know, he was totally caught off guard. he started smiling. And like, you know, that just changed the whole vibe. It got to a point where, you know, he was telling other people, like, you know, let me have this wave. And that's not my experience, you know, in a lot of surf breaks. And, you know, my friend calls it Ted Lassow, the Ted Lassow somebody, which is also very genuine.

Like, you really have to believe it. Okay. Next question. Do you have a favorite product you've recently discovered that you really love? So this morning, I spent half the day surfing, and I think the products I've really come to appreciate. There's not a lot of products used in surfing. It's like a wetsuit, like war shorts, you know, maybe a hat. But you can really feel like I surf with O'Neill wetsuit, Hyperfreek web suit,

but that doesn't matter. It's like when a piece of gear is like really well constructed, you can feel that the person, behind this also surfs or spends a lot of time with surfers and really gets you probably gets you more than you understand on face value and you start to notice all these details over time. It takes a long time to notice all these details and you can really feel that there's a person behind this product that gets you. And that's like, it's kind of like art almost. You know, when you feel, you know, a piece of art or music really resonates with you, you

feel that the artist is like communicating with you directly and letting you feel something that they were feeling, it's almost like that. So I think like, for me, it's outdoor equipment that you can feel that the person behind this is like using it along there with you. First time a wetsuit's been recommended on the podcast. A great milestone. Two more questions. Do your favorite life motto that you often come back to find useful in work or life,

share with friends or family? I think I can, but I'm doing three surf stories in a row, but my, this is, the life motto is just like stuck in my head for almost a day yeah for more than a decade now which it comes from a piece of plywood outside of surf shop in mexico um that was painted on it you can't stop the waves but you can learn how to surf and uh yeah like there's a lot to that that you know over time that i've really tried to apply that in a lot of ways uh emotionally um organizationally at every level you think about that. Along those lines, final question.

So at the beginning of this podcast, you mentioned that this podcast has been a long time coming. And the reason that's the case is we had this scheduled for some time in early October. You live in Israel. War broke out. You've been living through that being in Israel this entire time. I saw this Venn diagram that you put out that I think summarizes your life right now, which is, I forget one side of it, but just like... Apocalypse.

Apocalypse. One circle, the other is got to get to work. Got to wake up and make it. Israel's in the middle. That's what, yeah. And you've been in the middle of that for the past year. So I'd love to just briefly just hear how that's been for you in the past year. How are you doing? How's life for you? Here at Riverside, we've had a bunch of people out for reserve duty. I think all all of them are back now. I have a team lead. Well, people are still going in and out of reserve duty while working here. I have a team lead who leaves, some days around, you know, 4 p.m. goes to the base. I won't say what he what he has to do, but it's super intense and shows up the next morning. A little tired, but back at work.

And in general, we have, it's not just in Israel, we have teammates in Ukraine all along at the same time. Yeah, like one of my teams is almost entirely in Ukraine. So you'll have, we've had moments where, you know, we'll all be on a call. And then there'll be, you know, missile siren here in Israel, here in Tel Aviv. And we'll say, hey, sorry, we got to go, go down to the shelter, hear the explosions overhead, come back, sit back down. Later that day, we'll have another meeting. And on the Ukraine side, you know, you'll hear like, hey, that beeping, isn't not the, the missile alert, you know, on your end. And Andre, like, isn't that the critical alert on your iPhone?

He looks at his phone and he'll be like, yeah, but I got 10 minutes. Like, let's just finish the meeting, right? Like, all these like surreal moments where you just, at the same time where everything's not normal, people have this really strong desire for normalcy. It's, you know, work and everything around us and our routines, like, become more important than ever. And it's just these you know you have oh you know where's blood oh you know the power grid was attacked in this town so he's working on getting the generator back up okay um but you know I don't know if it's like a no excuse his mindset or badass for you so much as I know in my end it's just a like I think for Ukrainian team definitely for my end it's just like really

really crave the routine and the sense of normalcy when you can get those moments and um like I said But I think doing this podcast, working on this course, all these things, I'm not doing them because things are normal. I'm doing them because they're not. So, yeah. And I'll use this opportunity to say that, you know, biggest thing in all of our minds is there's 107 hostages that have been held for 328 days by Hamas.

Yeah. You need to bring them home now. Yeah. Let's help hostages come home. Let's help things end. soon. I'm really impressed with how much you've been able to get done in the middle of all of that. And thanks for making time for this. I know that this isn't the most important thing in the world right now. But I think this conversation is going to help a lot of people and you have so much

wisdom to share. Thanks for being here, to all. Thank you. On the course real quick, just to make sure people check it out. How do people find it? Just throw that out there as a final step. it's on maven.com in the product catalog and I'll have it. I'll probably post links to my LinkedIn as well. You can find it there. And yeah, it'll launch in mid-October. That'll be the first cohort. Amazing. And we'll link to it in the show notes. Tell. Thank you so much for being here. Funny. Thank you. Thank you. 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 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 lenny'spodcast.com. See you in the next episode.