Vlad Loktev: Why inquiry beats advocacy in tense rooms

1. 0:00 – 2:54

   Vlad’s background

   1. LRLenny Rachitsky0:00

      (instrumental music) What was it like managing me, Vlad? Most importantly, how painful was it to manage me?

   2. VLVlad Loktev0:03

      Man, how much time do you have?

   3. LRLenny Rachitsky0:05

      (laughs) I used to joke with people that you're kind of this Jedi, where you get crazy stuff done, really hard stuff done, in a really subtle and a really unique way.

   4. VLVlad Loktev0:12

      I've always used inquiry versus advocacy. A lot of people approach a conversation with a point of view and they begin advocating immediately. "We should do this," or, "No, we should not do this," right? Me, I always took the opposite approach. I inquire first. I'm gonna ask a ton of questions because I fundamentally believe maybe there's something I don't know and there's information that I need to understand to make a better decision.

   5. LRLenny Rachitsky0:32

      Is there something you can share about just what you learned from Brian about thinking big?

   6. VLVlad Loktev0:36

      I remember talking to Brian one day and he was like, "Something just feels off right now." And I remember asking him, like, "What do you mean? Our numbers are up and to the right." His response was, "Things are just too calm." Sometimes you want to create chaos in an organization to push the organization to think creatively and to actually, like, make leaps in product development and I've always told myself, "Don't be afraid to poke the bear."

   7. LRLenny Rachitsky1:00

      What are some skills that you believe helped you be as successful as you've been?

   8. VLVlad Loktev1:04

      Impact, impact, impact, impact. That's the only thing that mattered.

   9. LRLenny Rachitsky1:09

      (instrumental music) Today, my guest is Vlad Loktev. This is a very special episode for me because Vlad was my manager at Airbnb for many years and he's the person that I credit most for teaching me how to be an effective product manager and product leader. Within Airbnb, Vlad started as an ICPM, five years later was leading product for the core Airbnb business, the Homes business. A few years later was GM of the core Homes business, reporting directly to Brian Chesky, managing over 1,000 people, including design, engineering and other functions. He's also one of Brian's most trusted partners for most of his time at Airbnb. Before Airbnb, Vlad was a founder. He was also a Senior PM at Zynga where he grew the game Words With Friends to over 14 million daily active users. Even though Vlad recently moved into venture capital as a partner at Index Ventures, he will always be a product manager at heart to me and I'm very excited for more people to get to learn from Vlad. In our conversation, Vlad shares the skills and behaviors and mindsets that most contributed to his success, including a ton of really tactical stuff, also the strategies and tactics that he's found most helpful in building and scaling a fast-growing org, and his thoughts on Airbnb's current ways of working, including their move away from traditional product management and also their approach of thinking very top-down, which I thought was really insightful and so much more. This podcast, I guarantee, will make you a more effective product leader and I am very excited to share it with you. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and helps the podcast tremendously. With that, I bring you Vlad Loktev.

2. 2:54 – 4:28

   Reflecting on transformative years at Airbnb

   1. LRLenny Rachitsky2:54

      Vlad, thank you so much for being here and welcome to the podcast.

   2. VLVlad Loktev2:58

      Thank you. Excited to be here.

   3. LRLenny Rachitsky3:01

      I think this is gonna be an extremely special episode. People will have heard in the intro that we've worked together for many years and even more interestingly, you managed me for many years at Airbnb. I've also told you this before, but those years were probably, not probably, definitely the most transformative years of my career where I learned the most and the years that set me up for the success I ended up having later, and also the crazy work that I do now. So let me just say, I'm just really excited for other people to get a chance to learn from you and to learn from the things that you've learned that ha- helped you be successful and helped me be successful. So thanks again for making time for this.

   4. VLVlad Loktev3:35

      Yeah, of course. Excited to be here. I mean, you were always a rockstar. Um, so you were a rockstar back then, you're a rockstar today, so excited, excited to chat.

   5. LRLenny Rachitsky3:43

      I appreciate it. I don't know if I was a rockstar at the beginning. This is where my first question-

   6. VLVlad Loktev3:46

      Of course.

   7. LRLenny Rachitsky3:46

      ... was gonna go is, what was it like managing me, Vlad? Uh, you were, uh... For- most importantly, how painful was it to manage me?

   8. VLVlad Loktev3:53

      (laughs) Man, how much time do you have?

   9. LRLenny Rachitsky3:55

      (laughs) I don't know. I don't know.

   10. VLVlad Loktev3:56

       It's... No, jo- jokes aside, I- I've loved working with you, man. And I- I have to say, the one thing that I always deeply appreciated was that no matter how hard things were, you, like, always called out the elephant in the room. And so you always told me the stuff I did not want to hear. And, you know, large companies, things are growing, lots of things are happening, as a leader you miss so many things. And so hearing actually what's happening and the reality of- of what you're w- what you're dealing with, it was just so, so helpful. So I- I deeply appreciated that about

3. 4:28 – 11:03

   Skills and mindsets for success

   1. VLVlad Loktev4:28

      you.

   2. LRLenny Rachitsky4:28

      Wow. I think we're just gonna be in love with this, but I feel like I was able to do that 'cause I knew you'd react well and you needed to hear those things. This episode is brought to you by Pendo, the only all-in-one product experience platform for any type of application. Tired of bouncing around multiple tools to uncover what's really happening inside your product? With all the tools you need in one simple-to-use platform, Pendo makes it easy to answer critical questions about how users are engaging with your product and then turn those insights into action. Also, you can get your users to do what you actually want them to do. First, Pendo's built around product analytics, seeing what your users are actually doing in your apps so that you can optimize their experience. Next, Pendo lets you deploy in-app guides that lead users through the actions that matter most. Then Pendo integrates user feedback so that you can capture and analyze what people actually want, and the new thing in Pendo, Session Replays, a very cool way to visualize user sessions. I am not surprised at all that over 10,000 companies use it today. Visit pendo.io/lenny to create your free Pendo account today and start building better experiences across every corner of your product. PS, you want to take your product led know-how a step further? Check out Pendo's lineup of free certification courses led by top product experts and designed to help you grow and advance in your career. Learn more and experience the power of the Pendo platform today at pendo.io/lenny. (singing) Pendo. (instrumental music) This episode is brought to you by Vanta.When it comes to ensuring your company has top-notch security practices, things get complicated fast. Now you can assess risk, secure the trust of your customers, and automate compliance for SOC 2, ISO 27001, HIPAA, and more with a single platform: Vanta. Vanta's market-leading Trust Management Platform helps you continuously monitor compliance alongside reporting and tracking risk. Plus, you can save hours by completing security questionnaires with Vanta AI. Join thousands of global companies that use Vanta to automate evidence collection, unify risk management, and streamline security reviews. Get $1,000 off Vanta when you go to vanta.com/lenny. That's V-A-N-T-A.com/lenny. What I want to start talking about is talking through and spending time on some of the skills that you developed and some of the skills that you're essentially, uh, world-class at, in my experience, that I think might be helpful to a lot of other people. I used to joke with people that you're kind of this Jedi. Th- they have like Jedi powers, where you just get crazy stuff done, really hard stuff done, in a really subtle and a really unique way that I haven't seen other people work. And to show kind of the impact that it's had, your growth trajectory at Airbnb is pretty absurd. When you joined, I think you were ki- we were kind of the same level, maybe, maybe you were a level above, an i- you were an iCPM-

   3. VLVlad Loktev7:27

      Yeah.

   4. LRLenny Rachitsky7:27

      ... at Airbnb. And then five years later, you're head of product basically for the Homes business, which is the core Airbnb business, and then a few years later, you're GM for the entire Airbnb Homes business, managing a thousand people, designers, engineers, research, marketing, and, uh, all these functions. So, I want to spend a little time on some of the things that helped you get to that point. Let me just start with just a broad question.

   5. VLVlad Loktev7:49

      Yeah.

   6. LRLenny Rachitsky7:50

      What are some skills that you believe helped you be as successful as you've been? And they could be skills, maybe behaviors, maybe mindsets that helped you be successful.

   7. VLVlad Loktev8:00

      Um, well first, thank you for that (laughs) introduction.

   8. LRLenny Rachitsky8:03

      (laughs)

   9. VLVlad Loktev8:03

      Um, I'm a work in progress, so there are many things that I, um, I am constantly working on. I think for me, like when I reflect on my journey at Airbnb, it was more about the mindset rather than any kind of like skill. So, for example, my main mindset was impact above everything else. So like impact, impact, impact, impact, and that's the only thing that mattered, like m- basically my entire career. And so, I woke up every day and asked myself two questions basically. Number one: what are the highest priorities for Airbnb today and over the next like three months? And then two: what can I do to actually make a meaningful dent in those priorities? Like what impact can I have? And I always made sure that whatever I worked on was very aligned with a top priority for the company. And I would say if you're, if you find yourself in a situation where you're not working on a top priority of the company, like you should probably get a different job. Because it's, at the end of the day, you're spending so much of yourself and so much time at your job, you might as well really go for it and work on the hardest thing you can find and somebody's like willing to give you a shot th- you know, to build something crazy. And so for me, like I always thought about what is the hardest thing that I can work on and how can I drive the biggest amount of impact? Now oftentimes, it's, you know, figuring out the priorities is relatively easy for, and th- there, there's typically clarity around what you have to focus on, whether it's expanding a team and really like building out a specific team, whether it's growth rate or focusing on the product quality or like closing deals and closing sales. You can typically figure out what the priorities are. It's oftentimes very hard to figure out how to make impact and like what impact even means. And so for me, like my motto there was always just learn the drivers of the business. So, put like your day job to the side for a second and just immerse yourself in understanding why certain behaviors exist on the product that you're working on, right? Can you influence that behavior? Like what, if you do X, what will happen essentially? And I spent a lot of time actually blocking off, like on my calendar, just time thinking through the drivers with the question of what are the drivers that are gonna have the most impact for the business? And I remember like when we worked on Instant Book together, I think this was like back in probably like 2014, that was not a random project. There was so much thought behind why we should focus on Instant Book and what was the core problem with Airbnb at that moment in time and what impact we thought we could have on the overall trajectory of the company. So that was impact, impact, impact always just my, my motto

4. 11:03 – 13:16

   Impact-driven mindset

   1. VLVlad Loktev11:03

      I guess.

   2. LRLenny Rachitsky11:04

      Let's actually spend more time here 'cause this is such, like not only have I seen you do this well, I've also seen the s- the impact this mindset has had. And I think people listening to this might be like, "Yeah, okay, impact, great."

   3. VLVlad Loktev11:15

      Yeah.

   4. LRLenny Rachitsky11:15

      "Got to work on impacting." But I think there's so much power to this that it's worth us spending a little more time on.

   5. VLVlad Loktev11:20

      Yeah, let's do it.

   6. LRLenny Rachitsky11:21

      What do people do that's not this? Like I imagine many people listening are like, "Oh, I work on things that are impactful. I'm doing great." What is it that you see that's not this?

   7. VLVlad Loktev11:29

      I think when a company matures, I think there is, you know, i- it grows. Many more people join the team. The company gets bigger. At some point, a lot of people are working on similar things. You then, teams start to form, then entire departments start to form. And pretty quickly, I think a lot of people begin to realize that li- you, you yourself are not in control of many things and you actually depend on what other people do, right? And so a lot of people, and I've done this too, have focused a lot of energy day-to-day on the dependencies rather than the things that you yourself can do in, in your day-to-day. So for example-What I've seen as an organization scales, people transition from saying, "I can do X," and they transition to saying, "Can the other team do Y so that I can do X?" And I think that's a very dangerous place to be because at the end of the day, like you just need to let go of some of these dependencies. Like you're not going to move mountains every single day, and you got to focus on the things that a- that are actually within your control. So it, again, it's more of a mindset shift. The other thing I would say is, every single project that we worked on at Airbnb, we did back-of-the-envelope math with assumptions to help us understand the impact that something would have. And you needed to at least... Now those assumptions could be completely crazy and could be very challenging, but you at least needed to think through the mechanics of what you have to believe in order for this project to be a success, and for it to then make a big dent in whatever you're trying to achieve at the company. So every single thing we did had that behind the scenes, and we spent a lot of time on this to make sure that we were focused on the right

5. 13:16 – 17:54

   Saying no and inquiry before advocacy

   1. VLVlad Loktev13:16

      things.

   2. LRLenny Rachitsky13:16

      I remember there was a project we were gonna work on. I'm like, "I think this is a big opportunity. Here's all my thinking on it." And what I didn't have is here's the lift this could potentially drive.

   3. VLVlad Loktev13:26

      Yeah.

   4. LRLenny Rachitsky13:26

      And so what you did is you just created this flowchart of all the levers of the business and then like, okay, you're talking about this sub-lever here, and if you move this 10%, here's the impact on the potential business. And you're right, it is actually a big opportunity, but this is how you want to show it.

   5. VLVlad Loktev13:39

      Yeah, totally. The other thing I'll say is also equally important is saying no to a lot of things. And, and it's actually really hard because, you know, we are basically trained and conditioned to say yes, right? Like, you go to school, you follow the rules. Like, you listen to your parents. You don't want to disappoint people. And so when people ask for help, you help, right? And you want to be a really good teammate. But then at some point you realize that's actually not the job. And if you were to say yes to absolutely everything that you have to do at a company, you would be distracted all the time with like tons of things that will not make impact, right? And so I learned very early on how to say no, and i- i- it was hard emotionally. Like I've gone to many different debates and conversations, but ultimately I think maybe it doesn't win you many friends in the short term, but in the long term people realize that when you say no to something, there's probably a really good reason behind why that thing may not be as impactful today, and maybe we shouldn't even do it in the first place. And so I think doing the back-of-the-envelope math and being really good at prioritization is one thing, but also not getting distracted with all the noise and all the different opinions that everyone's going to have at a big company is another big thing.

   6. LRLenny Rachitsky15:02

      So saying no is hard. So maybe two quick questions here. One is, do you have any tricks for how to say no well where someone's not, like,-

   7. VLVlad Loktev15:08

      Yes.

   8. LRLenny Rachitsky15:08

      ... pissed off? And then the other question I'll just throw in, you can take him however you want, is what's your heuristic on how much people should like you as a PM? Because you touched on like people don't need to necessarily love you.

   9. VLVlad Loktev15:20

      For saying no, first, you can't just be dogmatic and just say no for the sake of saying no and just disagreeing with people. You have to listen. So for me, the framework that I've always used was inquiry versus advocacy. And I w- I don't know if you remember, we've talked about it i- in some context where basically a lot of people approach a conversation with a point of view and they begin advocating immediately, meaning we should do this or no we should not do this, right? Me, I always took the opposite approach and I still do. I inquire first. I dial up inquiry, I tone down my advocacy, meaning I am gonna respect the other opinion. I'm gonna ask a ton of questions because I fundamentally believe maybe there's something I don't know and there's information that I need to understand to make a better decision. So in the beginning, dial up inquiry and then once you... the person who you're talking to feels heard and you actually have absorbed information, and maybe you changed your mind, maybe not though, that's when you begin to advocate. So oftentimes you just come into these conversations where everyone just advocates, advocate, advocate, advocate, and you're talking past each other. You're not even like reflecting on what the other person is saying. And so that's been my... Sometimes when I talk too much, I tell myself, wait, inquire. Dial down advocacy. Just take a breath, take a moment, take a beat and actually ask some questions and, and see why the other person feels so strongly.

   10. LRLenny Rachitsky16:51

       I think that's such a good, uh, specific thing you can do 'cause a lot of... I think a lot of people want to do what you're doing. They're like, "Okay, I'm gonna listen, I'm gonna ask questions," but then they get a reaction. Someone's like, "Hey, we need to change this thing on the landing page." And like, "No, that's a terrible idea," or, "That's gonna take all this time, it's gonna throw off our roadmap." And there's like this bodily like, oh no, I need to stop this thing ASAP. And so your, your advice here is like, pay attention to, am I talking too long? Is that... I guess is that the advice? Am I talking too long? Am I saying too much?-

   11. VLVlad Loktev17:18

       Yeah.

   12. LRLenny Rachitsky17:18

       ... and like start just inquiring instead?

   13. VLVlad Loktev17:20

       Yeah.

   14. LRLenny Rachitsky17:20

       Awesome.

   15. VLVlad Loktev17:21

       Totally. And lead with questions, like basically approach every conversation with curiosity. Like try, like d- don't come in 'cause people usually like when they prepare for a meeting, I've seen many PMs do this and you prepare with like, "Here's my view and here are the bullets that support my view." And that's the wrong way to approach it. I think what you want to go into a conversation are, uh, y- you start the conversation with questions. Prepare the questions that come from a place of curiosity of the things that you want to know more about and you want to learn from the other perspective. And then check yourself to see if you still want to advocate for the same point of view or not.

6. 17:54 – 22:46

   “Poking the bear”

   1. VLVlad Loktev17:54

   2. LRLenny Rachitsky17:54

      Uh, we had an awesome episode with Ami Voros, CPO at Fair, and she is also extremely, uh, good at this and a huge advocate of, of starting with questions and understanding what she's missing.

   3. VLVlad Loktev18:04

      Totally. Well, the other, the other thing I would say is, the other motto that has really helped me drive impact, and, eh, eh, I use the analogy of the bear. And, and I've always told myself...Don't be afraid to poke the bear. And what that means is, don't self-censor. If you have a strong view after you really, er, grounded yourself in the truth and you feel like you've done your homework and you've asked all the questions, if you still disagree, if you still feel like we're going in the wrong direction, don't be afraid to poke the bear, no matter how hard things get. And that's a ... I- it's interesting because I think a lot of, especially as an organization matures, you find yourself in meetings with, with many execs, founders, et cetera. It's often hard to voice your, your real opinion and you usually, like, tone it down a little bit, right? Because you're afraid of being the only one who disagrees, or sounding stupid or things like that. And so I remember, it was probably like 2014 or 2013 where I made a promise to myself, I'm going to always poke the bear no matter how hard things get. 'Cause at the end of the day, like what's the worst thing that's gonna happen? Like, do I get fired? Like, why would I even be afraid of that? But if I do, like I'll find an- another gig, you know? Life is short. And so, you- you've done this really well, where I feel like you also always ... I remember when we were working on the instant book, you definitely poked the bear, where you were like, "You guys are wrong. Like, this is how we have to approach it." And I've always really appreciated that.

   4. LRLenny Rachitsky19:35

      Thanks, man. Is there an example of maybe working with Brian where you poked Brian and the like never-

   5. VLVlad Loktev19:40

      Yeah. Absolutely.

   6. LRLenny Rachitsky19:40

      ... effect.

   7. VLVlad Loktev19:40

      I mean, I've poked the bear many times. And by the way, I've been humbled many times. It's not like I poked the bear and I like rightfully poked the bear. Sometimes I learn stuff and I realize, I was wrong. A couple of examples that come to mind, like one, I remember having these debates with all, like basically senior leaders at Airbnb i- just about every couple of years actually, um, around how much supply should we have on the platform and what kind of supply should be on the platform? And there was one school of thought where we needed basically ... That school of thought represented the view that we needed all supply out there to be on our platform, regardless of if it was a, a person hosting, it was a vacation rental, it was a hotel. We just needed all supply on the platform, right? I came at it from a very different perspective where I felt like that wasn't actually our mission from the very beginning, and although I understood that in the short term, the numbers like probably would go up and you would get ... you would choose growth. But at the same time, like that wouldn't, in the long run, be a point of differentiation for us, right? And so I had a very different point of view, and it was very hard in that conversation, you know? Everyone's excited. Everyone seems to be aligning around the point of view, to be the voice that's like poking and it's like, "Nope. Let me, let me share why I think maybe we should go in a different direction." And it's when I rem- remember, like, telling myself that I am here to surface and share information that will help the group make a decision. That's what gave me peace of mind to actually like poke the bear and be able to, to surface the things, the things that I've seen. I mean, the other thing is when we, um, were working on the instant book, change from request a book to instant book, right? For the entire marketplace. That was very challenging, and I remember getting up on stage in front of the entire company and explaining why, like, this is actually good for humanity. Like, literally those words. Many people disagreed, and it was not an easy ... It was not an easy thing to do, but had to be done.

   8. LRLenny Rachitsky21:53

      And one thread that I've noticed across all these things that ... And noticed working with you, is it's not like just making a case for something you disagree with. It's showing the data that will convince them they are wrong or here's what they're missing. It's, it's not like a ... We're ... It's not like a speech. It's a here's the data, and ask- asking them, "What data would you want to see to convince you this might be not as you think?"

   9. VLVlad Loktev22:13

      Totally. Totally. I think I remember like doing a Q&A with the whole company on, on the instant book topic. I've ... This was a very long time ago, but I still remember where instead of, again, advocating for a point of view, I just asked all the people that were concerned like what their main questions were, and then we just tackled them one by one, and we would talk about them. And it's ... There's just something very disarming when you embrace the questions, you embrace the negativity, and you have an open mind, that maybe there's some things that you missed and some things that you didn't consider.

7. 22:46 – 30:08

   Psychological tools for leadership

   1. VLVlad Loktev22:46

   2. LRLenny Rachitsky22:46

      I love that. Okay. There's so many little nuggets already through this that I just want to come back to and make sure people take away, uh, of how to be more successful as ... And this is not just as a product leader. This is just as a leader in any company. So the first is advice around, uh, thinking about impact above all else, and the very simple heuristic that I wrote down as you're talking is, ask yourself, what are the priorities for the company? How can I impact these priorities? And to do that, think about the levers that drive the business and where do I think I can make an impact to drive these priorities and drive the business?

   3. VLVlad Loktev23:23

      Yep.

   4. LRLenny Rachitsky23:23

      Uh, two is inquiry first. When you're trying ... When you disagree with something or when you want to say no, start with understanding, asking questions, dialing up inquiry versus advocacy, versus like, "Here's what I think." Poking the bear, which is really fun, just like this idea of don't be afraid to disagree with someone in power. And your advice here is to disagree with, "Here's data you may not be aware of. Here, have you done ... Have you seen this? Hey, check this out. Or what is it that would convince you you're wrong?"

   5. VLVlad Loktev23:50

      Yeah.

   6. LRLenny Rachitsky23:51

      And then is there anything else I missed? Otherwise, we'll go on to more.

   7. VLVlad Loktev23:54

      I think that's great. I mean-

   8. LRLenny Rachitsky23:55

      Okay, cool.

   9. VLVlad Loktev23:55

      ... don't poke the bear for, for the sake of poking.

   10. LRLenny Rachitsky23:57

       Mm-hmm.

   11. VLVlad Loktev23:58

       Share. Share the information that you think will be helpful to make a decision.

   12. LRLenny Rachitsky24:02

       Cool. Anything else? Any other things you've found to be really effective in helping you succeed?

   13. VLVlad Loktev24:08

       Oftentimes, it's about also, like, being able to be impactful at a company that is in hyperscale and is growing quickly. A lot of it is actually just psychological. So it's not like there are these, like, core skills that ... Sure, like, you got to have some baseline skills, right?But a lot of it is day-to-day regulating your mind. And it's so easy to get lost in the sea of projects, the sea of priorities, the sea of opinions, um, and like I said before, dwell on the dependencies, right, that exist between teams without actually asking yourself, like what you can do in the moment to, to make a, to make an impact. And for me, like I've actually used two tools, uh, which some of them you may remember that have helped me. The first tool to re- this is again purely psychological, to help my mind. It's the serenity prayer. So I... So, so the serenity prayer goes something like this. Grant me the serenity to accept the things that I cannot change, the courage to change the things that I can, and the wisdom to know the difference. So I actually... That prayer was so powerful for me that I actually wrote it out on a piece of paper and like on Post-It notes and I would read that thing, like every other day. And it would help me just take a step back from the day-to-day and, and just like put into context what's actually important and again, what is in my control today and the things that I can actually do. Um, so that-

   14. LRLenny Rachitsky25:43

       Wow.

   15. VLVlad Loktev25:43

       ... highly recommend.

   16. LRLenny Rachitsky25:44

       Did not know that.

   17. VLVlad Loktev25:45

       The, the other one which you may remember is the shit bucket.

   18. LRLenny Rachitsky25:48

       Mm-hmm. I do remember that. (laughs)

   19. VLVlad Loktev25:50

       So, so the shit bucket was a visual analogy where I would take a piece of paper, and some of it actually wasn't as visual, it was like real. I would take a piece of paper, I would write down something that wasn't going well, perhaps a dependency, perhaps a project, perhaps a meeting that I was gonna have that I knew I was gonna be frustrated or maybe like we didn't even decide to go the way that I deeply felt passionate about, right? I would write it down. I would crumple the piece of paper and I would throw it in my, like shit bucket basically. And the rule was once I threw something in the shit bucket, I couldn't take anything out of the shit bucket. So I would not dwell on the things that I just needed to let go of, you know? So this was a very powerful tool that I... Like, I'm a perfectionist. Like I just deeply care about many different things and I, I have a hard time letting go. And so for me it was just a reminder that I need to let some things go and focus on the things that matter.

   20. LRLenny Rachitsky26:50

       Mm-hmm.

   21. VLVlad Loktev26:50

       And I actually, I remember, um, even going into one-on-ones with my direct where I would sometimes leave... Like I could tell, you know, the PM is, is like a bit frustrated about how things are going and one of my first questions would be, "What are we throwing in the shit bucket today?" You know? It's, it's actually like a very liberating thing that, that, that you can do.

   22. LRLenny Rachitsky27:13

       And did you have like a special trash can that was your shit bucket or is it the regular trash can?

   23. VLVlad Loktev27:17

       No. (laughs) Every meeting room always had a trash can and I would always, like throw stuff into the trash can whenever I got like upset about something.

   24. LRLenny Rachitsky27:23

       That's like a different dimension trash can.

   25. VLVlad Loktev27:26

       Yeah.

   26. LRLenny Rachitsky27:26

       Shit bucket. Is there something you remember throwing in that shit bucket that would be a interesting example or story to share?

   27. VLVlad Loktev27:31

       I remember there was one person who I deeply wanted to hire who I felt was just phenomenal and would be such an amazing addition to the team. And I just, I tried and tried and tried for a very long time and I just failed. I just could not get that person to join. And at some point it became like counterproductive and I had to, like let go and, and literally just like wrote like, okay, getting this person into the company. I'm like, this is not gonna happen. I gotta move on at this point. Just threw it in.

   28. LRLenny Rachitsky28:03

       I love these two pieces of advice and it touches on how mentally challenging it is to be a s- a leader at a hyper growth company.

   29. VLVlad Loktev28:11

       Yeah.

   30. LRLenny Rachitsky28:13

       Is there anything you can share there about just like that part of the world? Like people see your career like, "Holy shit, look at him. He's running Airbnb's business, what an amazing life." It's... There's a lot of pain behind it. Is there anything there that would be useful to people you think?
8. 30:08 – 36:12

   Building and scaling teams

   1. LRLenny Rachitsky30:08

   2. VLVlad Loktev30:08

      (laughs)

   3. LRLenny Rachitsky30:08

      I want to spend time talking about things you've learned about scaling Airbnb and the org, but before we get to that, is there anything else that you think might be... That you think contributed to your success as a, as a per- individually as a leader? Any other behaviors or mindsets?

   4. VLVlad Loktev30:22

      I mean, I, I think it's building teams and realizing that...Sometimes when you build a team, and this is actually often misunderstood. I think when people build teams, they try to make sure every person on the team is good at just about everything. Like, you typically go through this process of like, "Here are my strengths, here are my development areas." And typically the development areas are like the... You basically develop, you try to develop just about every single thing so that you can be good at e- almost every single skill that exists, right? And I just think that's the wrong mindset. Instead, what I've learned over time is instead of trying to find people that are good at everything, you need to look for people who spike on specific things and then add them to a team with different spikes. So there's no single person that is like spikes on absolutely everything. That's very rare, but they spike on something that's very crucial to the team. And if you assemble different spikes on a given team, that team is going to do great things as long as everybody inquires and everybody starts asking questions, actually listens to other people versus just, you know, c- c- coming about that.

   5. LRLenny Rachitsky31:41

      Mm-hmm.

   6. VLVlad Loktev31:41

      So even now, like as an investor, when I look for... When I talk to founders, the first question like in my head is like, what does this founder spike on and how is that spike relevant to the problem that they're tackling today? And how well does this founder hire to bring other spikes to the team? Like, that's literally like what I think about these days.

   7. LRLenny Rachitsky32:02

      What are some examples of spikes just to make it even more real, like things that people might be good at, like strategy, influence? What are some things you commonly see that are spike skills?

   8. VLVlad Loktev32:10

      Yeah, I mean, I think there's the- the very natural spike sometimes is you get a domain expert. So there's a specific field, l- let's take marketplaces, and there's someone who just understands the mechanics of how things work and it's e- and, and just really spikes on understanding how you can take certain drivers, what you can do with those drivers and how you translate those drivers to measurable results. There are people who spike on, on sales and who spike on like just being able to, to package something in a way that other people cannot package it, right?

   9. LRLenny Rachitsky32:47

      Mm-hmm.

   10. VLVlad Loktev32:48

       There are people who spike in process. Like there are people who will literally every day think about how to get people to work together really well, and that i- like they just know how to get to the essence of that, how to connect the dots between different teams working together. Some people are really great at product design. Like there are... I've seen quite a few founders actually who can tell you immediately about what kind of interface is going to resonate with people and what kind won't and why, you know? So there's just some examples, but there are many dimensions here.

   11. LRLenny Rachitsky33:20

       Awesome. Okay. As a last question along these lines-

   12. VLVlad Loktev33:23

       Yeah.

   13. LRLenny Rachitsky33:24

       ... I'm going to share a few other skills that I noticed you're incredibly good at. And how about just pick one that's resonates with you and share some thoughts on how to get better at that and why that's important?

   14. VLVlad Loktev33:34

       Mm-hmm.

   15. LRLenny Rachitsky33:35

       One is influence. You're an incredibly strong influencer. You get a lot of stuff done that I think people will be like, "How did he do that? I have no idea what he just did." Uh, another is you're very good at keeping a very high bar. That's one of the things I learned from you is just the importance of keeping a very high bar and spending more time on stuff. That's something I remember from you. Just like spend a little more time on this doc, make it a little bit better, refine it a little bit more. That's to you. Another is just getting stuff done in focus while also avoiding the limelight. You're not like... You try to not be in- in front and center, like you haven't done any other podcasts. I don't think you've written a Medium post. I don't know if you've tweeted. Like you try to just get stuff done behind the scenes and not, not be f- uh, not get attention from everyone. So maybe those are a few. Is there any one of those you want to spend a little time on?

   16. VLVlad Loktev34:17

       Yeah, I mean, uh, first of all, thank you for saying that. Uh, some of those resonate for sure. I, I think the getting stuff done and being hyperfocused on the job is, it, it, it's something that's really important. I mean, at Index here we also say keep the main thing the main thing. And just like in investing, same thing in operating, you know? You got to focus on the actual job versus like all the other things that you could potentially be doing. So to me, I remember when I was actually hiring product leaders and there's some product leaders would do lots of different engagements outside of the company, whether it's investing, advising, speaking, attending conference, all those things. And they were huge red flags to me because it was clear that this person, there was just something missing in their day-to-day. They didn't try to put them, like all of them into the thing that they were doing. And so for me, like it, it's really important when I, when I hired people to hire people who were incredibly mission-driven and would dedicate every ounce of energy to keeping the main thing the main thing.

   17. LRLenny Rachitsky35:27

       Yeah. The... I talk about this on Twitter and LinkedIn, this idea that people see people like me and other PMs tweeting, sharing wisdom and they're like, "Oh, these are the best PMs. They know so much." But in reality, the best folks, you as an example, like spend zero time on Twitter or LinkedIn. They're just doing the job, trying to show great impact, trying to make business successful, trying to build great products. And I think it's important to remember you don't need to be tweeting and writing Medium articles.

   18. VLVlad Loktev35:53

       Yeah, I mean, I think there are, you know, people who find joy in, in solving hard problems and like the joy you get from working on a hard problem is fulfilling and you don't need to seek like external validation for, for the things you do every single day, you know? So yeah, I love hiring people like

9. 36:12 – 47:34

   Letting fires burn

   1. VLVlad Loktev36:12

      that.

   2. LRLenny Rachitsky36:12

      Let me zoom out a little bit. So we've been talking a lot about the skills that you built and the mindset that you built to be successful individually, but also you managed large teams. You helped scale Airbnb massively through hypergrowth and there's a few skills I noticed you're really good at that specifically apply to scaling an org, building an org, building teams and things like that. And so I want to spend a little time there. You touched on this one a little bit, but I think there's more here around setting priorities. You're incredibly good at setting priorities, making sure everyone's aligned, making sure the, the main, the main thing is the main thing. Can you just talk about what else you've seen be important here as a leader of a larger growing org around setting priorities?

   3. VLVlad Loktev36:54

      I have a lot of strong opinions here wi- with setting priorities. I would say the first one is, and this was my motto for the longest time and it still is, you got to let fires burn. And what that means is, you can't do it all. Like you just need to let go of things that are not important because if you have 20 different things that you're equally engaged on, it just means you don't actually know what is most important. And so my motto has always been, let fires burn. You got to be okay with some things not going well so that you can dedicate most of your energy on like the few things that actually matter and the things that are most important. Um, and it's, it's hard to do. Um, it doesn't feel good. Again, many people, especially PMs, are perfectionists, and so it like, it just, it, it hurts when things aren't going well and you just got to learn how to let things go. Um, the, what I always did was I kicked off every Monday with a leadership meeting where we would talk about our priorities for the week. We would not talk about longer term priorities. It was literally like, "For this week, what are we trying to get done?" And it, it could only be one to three things. And we would jointly agree on the fires that we would let burn. And so then when like my, my partner, my engineering counterpart or my design counterpart would like see a fire burning, they would know like, yep, we agreed that we're going to keep letting the fire burn for now. And it was just really important to be aligned as a team on that. Now, the other thing that I've learned is you got to let other people burn fires too. And it's very actually empowering. And oftentimes I remember, especially when you're leading a very large organization, there could be teams and sub-teams and many different leaders who you're working with. Oftentimes people come to you and are basically like, "Hey, we got to do this new thing to drive goal one, and I just don't have enough resources. And I, w- we need to, we need to hire more people or we need to like expand the resources of this team." My first question always was, "Well, what, what are your actual priorities and what can we let burn?" Meaning, do you actually have to expand and do more things or can we maybe reprioritize certain things and focus on fewer things and put a lot more energy behind them, you know? But to have those conversations, you, as a leader, you also have to recognize that people on your team are eventually in a really good position to gauge what fires should be burning and which one not to be burning. Now the one thing I'll say though is with this, it, it could be dangerous, and there are some things that you should never let burn because if you let them burn for too long, bad stuff's going to happen, right? So I have a few of those examples for me that I have like over the years learned to not let burn. First, timelines, major timelines. This is like huge product launches. Once timelines slip, you basically establish precedent that timelines are not as important and timelines can always slip. So you never want to set the precedent that timelines slip. So that to me was when there was a major project and the timeline was significantly slipping, I never let that fire burn. Immediately jumped in. The second is when there is disagreement on a strategic decision or maybe even part of the vision. If you feel like that exists, like for example, i- if not everybody like buys into Instant Book or like there's just some disagreement about what supplies should be on the platform, you got to squash that immediately. You cannot let that fire burn because it can spread. I guess if I follow the analogy, like it could become a wildfire and then suddenly you have a team of people who are, who don't believe in what they're doing and they're losing meaning, they lose meaning in their work, right? Which is just really bad. So you have to bring people together immediately when you feel like people, whether it's many or a few people, do not believe in the direction that the company's headed. You got to squash that immediately. Then the third one for me, and this was a bit painful to learn, but you never let a senior hire process burn. Meaning like you will always, and this is what I felt during my 10 years at Airbnb, I always felt underwater and I always felt like we just needed to bring on more people who had experience in certain things that we were doing. And any time I delayed or I was like not fully engaged with the hiring process, especially a very senior person, it just, it bit me for such a long time and it set the whole team back. And so those are the three things that I would never let burn but you got to let a whole bunch of other stuff burn, for sure.

   4. LRLenny Rachitsky41:52

      Such counterintuitive and amazing advice. I, um, you shared a bunch of examples of things that you don't want to let burn. Are there any examples you could share of things you let burn, things that surprise people or a story that comes to mind of like, yeah, that's fine?

   5. VLVlad Loktev42:04

      You know, sometimes you would have examples where certain products, product launches didn't go well and let's say it just, you know, you weren't seeing the numbers, the users weren't happy. Like, okay, that's sometimes you just need more time to understand what's actually wrong. You don't need to like jump on it immediately, right? Um, so that's maybe like one example of, of a fire that I, I let burn quite a bit. And quite frankly at some point I had so many teams that I was working with that I just needed to prioritize even between the teams, where like-This team is the number one priority, and I know that I need to be in designer reviews with, with this other team. I just... I can't, because I have to be thoughtful about how I'm spending my time in this given moment. And so, I actually have to de-prioritize projects. And so there are certain projects that were important, but I let burn for a while because I just had to spend my energy elsewhere, you know? And then, of course, I would... To myself I was thinking, like, "Are we doing too many things?" Like, "Is this the right way to operate?"

   6. LRLenny Rachitsky43:12

      I think this is, uh, really useful for someone that, say, is an ICPM on a team that's wondering, "Why the hell... Our team is just wasting our time. We're building all this stuff. It's not working. Why, why isn't anyone doing anything? Why aren't they giving us more resources? Why aren't they reprioritizing?" It's because they know there's many other problems they're dealing with and they're letting this burn for now.

   7. VLVlad Loktev43:30

      Yeah. And this was actually a learning for me in an area where I, I would say I failed over time, is just general communication to, to the broader organization. You... Uh, when you rise really quickly, you tend to under-appreciate, or I did, just how important it is to communicate what, as a leader, you're spending your time on, and the areas that you, you think are the highest priority right now. And so eventually, I started doing a lot of all-hands, and I started sending, like, the weekly thoughts from Vlad or just, like, my random musings on what's in my head. And I, I realized that sharing that context with people is just so important. People actually want to hear from you. And then it's good to over-communicate, and it can help people understand certain things about their day-to-day.

   8. LRLenny Rachitsky44:15

      I know that didn't come naturally to you. I mentioned that you kind of liked to be behind the scenes, under the radar, not in the limelight. So, I could see why that wasn't something you were doing initially.

   9. VLVlad Loktev44:24

      Yeah.

   10. LRLenny Rachitsky44:24

       Is there anything more you can share there about what you've learned, what you learned about why that's important? Like, why are people... Why, why spend time there? What happens if you don't?

   11. VLVlad Loktev44:32

       Everybody wants to find meaning in their work, and everybody typically wants to understand the reasons behind a decision. And it's important to share, to, to take like... I've done this myself, where you just, like, make a decision, and you, like, move on and you go on to the next decision. And it's actually so, so helpful if you take, like, 10% more energy and time to now bring everyone along around why a certain thing was decided, 'cause it's gonna help them just, themselves, make better decisions, because then now they have a lot more context about how this decision was made and they can learn from that moment.

   12. LRLenny Rachitsky45:11

       Mm-hmm.

   13. VLVlad Loktev45:11

       So, that's partly why it's important. I mean, for me, it didn't come naturally to me. I'm like a pretty... I don't know. I'm a deep introvert. Like, I shy away from many different things. And it, like... It had to be a learned thing.

   14. LRLenny Rachitsky45:25

       I think you're also a really good example of something I talk about here and there, is, you can be really successful in very different ways. I'm also introverted. I think we're similar on the spectrum of colors or whatever the thing, personality test we used.

   15. VLVlad Loktev45:39

       Yeah.

   16. LRLenny Rachitsky45:39

       And you've been really successful. You could also be incredibly s- incredibly successful as a very extroverted person or someone that's very analytical. And I think you're a great example of someone that's less... That's more reserved and doesn't want to... And is introverted, as you said.

   17. VLVlad Loktev45:52

       Yeah.

   18. LRLenny Rachitsky45:53

       And I think it's important people know you can be incredibly successful as a PM, as a huge leader-

   19. VLVlad Loktev45:57

       Totally.

   20. LRLenny Rachitsky45:58

       ... from that place. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features. And Eppo 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. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. Okay, so just to summarize the lesson we just talked about mostly is let fires burn. Basically, don't feel like you need to solve every problem as you rise in the ranks. And I think this applies even if you're not the, the top of the org, even if you're manager of managers, even if you're manager of

10. 47:34 – 54:40

    Embracing chaos

    1. LRLenny Rachitsky47:34

       nobody.

    2. VLVlad Loktev47:35

       Yeah. Maybe the other thing I'll mention-

    3. LRLenny Rachitsky47:36

       Uh-huh.

    4. VLVlad Loktev47:36

       ... and, like, as I reflect on-

    5. LRLenny Rachitsky47:38

       Yeah.

    6. VLVlad Loktev47:38

       ... on setting priorities and just, like, working.

    7. LRLenny Rachitsky47:41

       Yeah.

    8. VLVlad Loktev47:43

       I think a big lesson for me is that chaos is good. Chaos is actually great. And sometimes you want to create chaos in an organization to push the organization to think creatively and to actually, like, make leaps in, in product development. And so, I mean, I, I kind of... You know, as I reflect on my life, I, uh, I like cleaning up messes. I like when things are very organized. I liked when there's just, like, very cl- There's a lot of clarity on, on how things are put together, right? And it's very... Uh, chaos is scary, right? And I think that that's just very natural for a lot of people, for chaos to be scary. But I've seen examples when just a bit of chaos is so, so helpful. Just, uh, to give you an example, I remember me talking to Brian one day, and he was like, "Hey, I just don't feel good. Like, something just feels off right now."And, and I remember asking him like, "Wh- what do you mean? Like, ev- like, our numbers are up and to the right. Like, we're, we're chipping quickly. Everything's great. What do you mean? Like, what are you unhappy with?" And his response was, "Things are just too calm. I don't like it." And I was (laughs) was like, "Okay. Wh- what do you mean? Like, calm is great, right? Like, I operate in calm." And, um, he then picked a project that he thought was important. I think it was actually host onboarding at the time. And of course in this project, we had like three or four ... I remember we had this like perfectly crafted timeline. We're gonna design this for the next four weeks, and then we're gonna start building and we're gonna deploy in certain pockets of users. We're gonna learn, we're gonna iterate, et cetera. Very, like, rational, like, timeline, right? (laughs) And he said, "Yeah, I don't care about any of that. We're gonna design this in 24 hours." (laughs) And I was just like, mind blown, right? Like, one, how? Two, the ripples that's gonna send through the organization, 'cause I knew, like, all of the people that were involved on building this and we had, like this, a whole, like, neat flow. And we did design it actually in 24 hours. Well, it was, took a little bit longer, but (laughs) we designed it very quickly. And what I learned in that moment is that the chaos that ... That was actually an example of chaos that he inserted into, like, this very calm building process. And that chaos forced us with our artificial time constraint to dial up our intuition, and to think a bit more creatively than maybe we would have in the past. Now, that didn't always work, 'cause there were examples of this where you're just like, I, I don't know what the answer is. Like, I need more time to design this and to think about this problem, right? There were definitely examples of that. But there were many examples where it was actually a great forcing function to go with your gut and actually, like, innovate.

    9. LRLenny Rachitsky50:43

       That's an amazing story. And it reminds me of something else, just to take a quick tangent here, is Brian's incredible at just asking people always, "Okay, that's a great goal you have there. What would it take to 10X that goal?"

    10. VLVlad Loktev50:53

        Yeah.

    11. LRLenny Rachitsky50:54

        He'd like get to the FP&A projection and he's like, "Great. Okay, how do we 10X this?" And I found that to be really scary but also really effective in helping people think a lot bigger. Is there something there you can share about just what you learned from Brian about thinking that big?

    12. VLVlad Loktev51:08

        I think it's less about hitting the goal. I think a lot of people when they see really big goals they get ... they immediately, like, afraid of, of the goals because they think, "Oh my God, I don't know how to hit this. If we don't hit it, what happens?" And you start thinking about all the downstream consequences. The reality is, it's not about hitting the goal, it's about thinking how to hit the goal and going through the journey of ... That creative journey of, like, what does the world need to look like for this to be true, this like crazy goal to be true? Like, how should we think about it? And oftentimes, it pushes you to test extremes, right? When the whole world is gonna operate this way or nobody in the world is gonna operate this way versus like something in the in between. And usually it's when you start testing the extremes is you begin to, like, realize, like, oh, you know, th- th- th- this, this is the path that we should actually take.

    13. LRLenny Rachitsky52:00

        Yeah. I f- I found exactly the same thing. Just thinking from, backwards from what is the best possible thing we could do versus incrementally forward ends up unlocking a lot of big ideas. Something I imagine is in people's minds as they hear some of this stuff, like designing something in 24 hours or thinking 10X bigger is like, "I don't wanna work that way. That sounds incredibly stressful. That sounds like ... What do, what ... I, I don't wanna, why do I ... That sounds really hard." You mentioned this, that this isn't necessarily for everyone. Not everyone needs to work at this company or work this way. There's ... Part of it is hiring, is finding people that want to g- lean in, to work really hard. Other people don't. Is there anything there of just like, this is actually really hard and it's not for everyone, but it also ends up being successful and you end up having a good time a lot of times afterwards?

    14. VLVlad Loktev52:43

        I find that those sprints were like, design this in 24 hours, were ... Brought a lot of connection to the team actually. And they were like m- my most fun moments actually, because you kinda like ... You're forced to let go of a lot of constraints. All these, like, organizational dependencies disappear, all, like, the stuff that's kinda noise, and you can just start building, right? So for me, especially when you're not doing this by yourself and you're doing this with a team of people, it was deeply rewarding because you were all working together just, like, shooting the shit and, like, throwing a whole bunch of ideas out there. No idea was, like, too crazy, right? Now, it's not for everybody. And so I actually, in the interview process when I would hire PMs, I was always ... Not always. In the early days, I guess, I, I had to learn this. But in the later days, I always set expectations about how we work. And so I think some leaders do this. It's like the anti-sell sell where I will share the worst day or what I think you will think as a candidate what the worst day would be at Airbnb and then still ask you if you wanna join the team. And I would basically tell people, "We're gonna work day and night. We're gonna work weekends. Direction's gonna change. The strategy, like, out the window every three months. The projects you're working on today, we're gonna kill three weeks later. The roadmap that you are right now auditing as you're deciding your offer when you actually join after you took some break from your other job is gonna completely change." And so (laughs) getting people are being ... I think the, the common thread there is everything is changing all the time. You gotta be cool with that if you wanna join this team. And n- uh, totally fine, like, if that's not for you.

    15. LRLenny Rachitsky54:30

        I love that. It reminds me, thinking of something when a colleague used to say at Airbnbs, "If you haven't changed teams or your, or your desk in six months, something's about to happen. Something's about to change." (laughs)

    16. VLVlad Loktev54:39

        Totally.

11. 54:40 – 1:02:01

    The unsell email strategy

    1. VLVlad Loktev54:40

    2. LRLenny Rachitsky54:40

       This un-sell idea, uh ... There's a, a recent podcast episode where someone did something similar. He called it the un-sell email.... where he sends the candidate, "Here's all the thing..." Based on all the things he heard from the candidate during the interview process, "Here's all the things you probably won't love about working here."

    3. VLVlad Loktev54:54

       Yeah.

    4. LRLenny Rachitsky54:54

       And the recruiter was always really mad at him for like, "Don't send that. My numbers are really going down because of this email." But, uh, long term it ends up being really successful for them.

    5. VLVlad Loktev55:02

       Yeah, I mean, you're gonna probably, like, hire fewer people that way, but you will hire the right people. So I think then you, you're gonna actually have a team that you can rely on for years and years and years as things change.

    6. LRLenny Rachitsky55:11

       Yeah. Just have to align incentives with recruiting on that-

    7. VLVlad Loktev55:14

       Yes.

    8. LRLenny Rachitsky55:14

       ... piece of it. Um, okay, so one other area I wanted to spend time on is basically org design and hiring and people.

    9. VLVlad Loktev55:22

       Yeah.

    10. LRLenny Rachitsky55:22

        So you are very good at building really effective teams, prioritizing them, bringing in amazing talent. What can you share about things you've learned about, as the company's growing and org is scaling, about org design hiring?

    11. VLVlad Loktev55:34

        Yeah, so for me, like, one of the hardest things about building teams and going through hypergrowth was the fact that you're gonna lose a lot of friends on that journey. Like, you just have to be prepared to say goodbye to your friends. Meaning, when you start, you build really deep relationships with people, like when you're a smaller startup, right? Like, you typically have one-on-one interaction and you know everybody, right? And you have that connection with people. And the reality is, most people, if the company is truly going through hypergrowth, most people are not going to scale. It is very rare for somebody to scale with the company. And I mean, we actually... So at Index, we wrote a book, Scaling Through Chaos, and there's this crazy stat, um, where basically when you look at many, many companies that reached 1,000 people and were successful, when you look back to the first 10 employees, you realize that only two to three of those 10 first employees stayed with the company when the company reached 1,000 people, right? And that's just so, like, indicative of what will actually happen in practice. Like, there are certain skills that you have that are good for... in this specific domain for a period of time. And that time is not, like, universal forever, right? Like, at some point, everybody taps out. And so it's... Just having that realization is, it- it- it's tough. It's tough emotionally. It was, like, one of the hardest things for me, like, as a leader. And I would say the way to break out of that is to ask for help and to, to try to learn as much as you can about what the next role for you is going to look like. So that's one thing that I've learned. I would say another thing is that all org charts suck. Like, there is no good org chart. Every single org chart has problems. So you can be organized around business units, you can be functionally organized, you can be organized around problems, and the reality is, like, every single one of those constructs suck, right? There are pros and cons to each approach. Like, if you are a... If you organize yourself into business units, the problem you typically run into is silos and people start basically advocating for their business unit with little regard for other business units, right? If you're functionally organized, sometimes you create too many dependencies across the organization and it becomes this, like, matrix way of working, which is, could be challenging, and as a result, could be slower to ship product, right? Those are just examples. These are not universal issues, but those are examples where regardless of how you organize, there are going to be problems. So for me, one learning was if you're having a problem and you're trying to solve this problem, reorganizing and, like, a new org chart is rarely the solution. Like, it's not about the boxes and how you configure the boxes, right? It's about the people in those boxes and it's about how those people work together because you, you just need to understand the cons of working a certain way and then how do you design a process around your org structure to make sure that people connect and work really well together. So my advice there also to founders who I talk to now, focus a lot less energy on the actual org design, study the different types and just pick one, and once you pick one, focus on the people, the culture and how people work together.

    12. LRLenny Rachitsky59:16

        That's really interesting. So basically you think people are overthinking org design.

    13. VLVlad Loktev59:20

        Yes.

    14. LRLenny Rachitsky59:21

        How do you think about incentives and goals and how that kind of impacts all that stuff, 'cause there's people and then there's like, "Here's your goal. Here's how you're measured," and that's what they're going to work on in this, in this thought.

    15. VLVlad Loktev59:30

        I mean, I think incentives come down to culture and it's-

    16. LRLenny Rachitsky59:33

        Mm-hmm.

    17. VLVlad Loktev59:33

        It's what you set as, like, the fiber of your organization. So again, like, I- I- I think you can align incentives and people will be excited to make impact on an organization regardless of how an organization is actually organized.

    18. LRLenny Rachitsky59:47

        Mm-hmm. That's a really interesting takeaway because I think a lot of people think about, "Okay, if we just org this and put this person here and create business units, things are going to start moving," and not, you're not saying don't think about that and don't necessarily do that, but you're probably putting too much, uh, weight on that actually solving your problems.

    19. VLVlad Loktev1:00:03

        Yeah, I mean, I- I think you want to certainly study different ways of organizing and the pros and cons, but just know that no matter which choice you make, it's going to suck and there are going to be organizational problems, right? And you just need to go into it with wide open eyes and then create process to make sure that the... whatever the cons are, like if- if people are in silos, well then you got to have a really good way of bringing people together and creating the right incentives to make sure people collaborate, right? So there's all these things, other things that I would say are much more important to focus your energy on.

    20. LRLenny Rachitsky1:00:40

        Awesome. Anything else along these lines around org design or hiring that you think is really important or has been really effective for you?

    21. VLVlad Loktev1:00:46

        Hiring, I, you know, I... The- the one thing that is universal for me and always has been is mission over domain expertise.... basically, mission over

    22. LRLenny Rachitsky1:00:56

        Yeah.

    23. VLVlad Loktev1:00:56

        ... domain expertise, mission over skills. I think that if you have, like, a raw, like, that raw horsepower and you're deeply, like, you just love the mission so much, you can build whatever skills are necessary for the job.

    24. LRLenny Rachitsky1:01:14

        Hm.

    25. VLVlad Loktev1:01:14

        And so I actually love taking, like, as an operator, I've loved taking bets on people who are maybe earlier in their career who have energy, who have drive, and who are deeply thoughtful and deeply resonant with the mission that we're working on. Because at the end of the day, like, strategy changes, orgs change, teams change, everything changes all the time and the one constant, I think, is actually the mission. And when shit gets really, really hard, when your company almost collapses like we did, uh, during COVID, the thing that gets you through those hard times is the mission. If you don't have mission, if you don't believe in the mission, you lose meaning in your day-to-day and you start to disengage from the company.

    26. LRLenny Rachitsky1:01:58

        Hm.

    27. VLVlad Loktev1:01:59

        So, I think that's actually the most important thing.

12. 1:02:01 – 1:05:38

    Finding your place in an organization

    1. VLVlad Loktev1:02:01

    2. LRLenny Rachitsky1:02:02

       So, what I'm hearing there is potentially, if you're just, like, hating it at your job or you think it's just not going anywhere, it might be that you don't actually care that much about what the company's trying to do and the mission? And maybe there's not a lot that can change for you to actually be happy there because you don't actually care.

    3. VLVlad Loktev1:02:16

       Yeah.

    4. LRLenny Rachitsky1:02:17

       Fascinating. Something that I wanted to come back to real quick, you, a lot of your advice comes back to impact. Like, impact above all else. Drive impact, focus is, comes back to what is the most important thing to do. Something that I think about a lot is how do you be successful within a company and one of the levers is go to a place in a team that is driving impact. Do you have any advice there around just, like, where you're best suited to be successful within an org? Kinda coming at it from where impact is most happening.

    5. VLVlad Loktev1:02:47

       I mean, I always thought about it as, like, the, the combination, or almost like this Venn diagram of, like, there, there's one circle which is, like, all the different priorities that are important. Then the other circle are your strengths and where you spike. And the intersection of the two is the place where you should be, right? And sometimes, you're not quite there at the intersection and you're kinda gravitating towards that intersection. You're building a specific skill that you're already, like, naturally, like, pretty decent at, but you, you definitely want to double down on it as you're learning more about the priorities and there's a match there. The worst thing I think you can do is just, like, sit in a job where you're not being impactful, you're not working on a top priority, and, like, you're just kinda wasting your life. You know? Like, our time is short on Earth, like, you might as well wake up every day and work on the hardest thing you can where you can truly, based on who you are and the spikes you have, make a dent in whatever is going to happen, right?

    6. LRLenny Rachitsky1:03:13

       Love that, and also have the serenity prayer ready to go when things get really hard.

    7. VLVlad Loktev1:03:13

       Yeah.

    8. LRLenny Rachitsky1:03:13

       (laughs) Fascinating. Something that I wanted to come back to real quick, you, a lot of your advice comes back to impact. Like, impact above all else. Drive impact. Focus is, comes back to what is the most important thing to do? Something that I think about a lot is how do you be successful within a company and one of the levers is go to a place in a team that is driving impact. Do you have any advice there around just, like, where you're best suited to be successful within an org? Kinda coming at it from where impact is most happening.

    9. VLVlad Loktev1:03:14

       I mean, I always thought about it as, like, the, the combination or almost like this Venn diagram of, like, there, there's one circle which is, like, all the different priorities that are important. Then the other circle are your strengths and where you spike. And the intersection of the two is the place where you should be, right? And sometimes, you're not quite there at the intersection and you're kinda gravitating towards that intersection. You're building a specific skill that you're already, like, naturally, like, pretty decent at, but you, you definitely want to double down on it as you're learning more about the priorities and there's a match there. The worst thing I think you can do is just, like, sit in a job where you're not being impactful, you're not working on a top priority, and, like, you're just kinda wasting your life, you know? Like, our time is short on Earth, like, you might as well wake up every day and work on the hardest thing you can where you can truly, based on who you are and the spikes you have, make a dent in whatever is going to happen, right?

    10. LRLenny Rachitsky1:03:45

        Love that. And also have the serenity prayer ready to go when things get really hard.

    11. VLVlad Loktev1:03:49

        Yeah.

    12. LRLenny Rachitsky1:03:49

        (laughs) Okay, so what I want to do right now is summarize many of the things that you've shared before we get to talking about Airbnb today and Brian Chesky's approach to product. Uh, I guess before I try to summarize stuff, is there anything else you think is important skill-wise or behavior-wise that we haven't touched on?

    13. VLVlad Loktev1:04:05

        No, I- I think we-

    14. LRLenny Rachitsky1:04:06

        Okay.

    15. VLVlad Loktev1:04:06

        ... we, yeah.

    16. LRLenny Rachitsky1:04:07

        We've done a lot. Okay, cool.

    17. VLVlad Loktev1:04:08

        Yeah.

    18. LRLenny Rachitsky1:04:08

        So, I'm gonna just, this is, like, almost a Vlad's guide to being a successful product leader.

    19. VLVlad Loktev1:04:11

        (laughs)

    20. LRLenny Rachitsky1:04:11

        I don't have it all summarized here yet. I just have a bunch of notes, but I thought it'd be fun just to try. So, one is, and the way I would think about this as you're listening to this is how do I be more, what can I do to be more successful as a leader in a company? And this is all kinds of stuff that I 100% agree with is effective. So, one is impact above all else. Think about what is the company prioritizing? What is important to the business? How can I drive impact there? And to do that, think about the levers in the business that move that and then find ways to work on those things. Uh, this idea of inquiry first. When you disagree with something, shift your mindset to asking questions. And then along those lines, kind of when you disagree, this idea of poking the bear. Sharing, hey, here's why this might not be right, here's why you might be wrong about this, here's data that I found, or what data would help you understand maybe you're wrong here. Okay, what else? Uh, saying no. Being really good at s- saying no. Just... And this comes back to impact and focus. Let fires burn. Really powerful idea. Don't feel like everything has to be solved. Uh, I am similar to you where I feel like I need things in order and clean and organized, and so this would be very h- very hard for me. (laughs) Uh, but such a powerful lesson of just it's okay if things aren't going great. And I love your advice of align with your team on, "We will let these things burn for now."

    21. VLVlad Loktev1:05:31

        Yeah.

    22. LRLenny Rachitsky1:05:31

        Uh, anything you want to add, by the way, as I'm going through this?

    23. VLVlad Loktev1:05:34

        No, got to let-

    24. LRLenny Rachitsky1:05:35

        Okay.

    25. VLVlad Loktev1:05:35

        ... everyone be a pyromaniac. Lead- leads to great things.

13. 1:05:38 – 1:13:16

    The importance of company culture

    1. VLVlad Loktev1:05:38

    2. LRLenny Rachitsky1:05:38

       Awesome. So, along those lines, uh, embrace chaos. Let things be chaotic sometimes, 'cause some of the best things come out of that. And as you shared, Brian sometimes just introduces a little chaos-

    3. VLVlad Loktev1:05:47

       Yep.

    4. LRLenny Rachitsky1:05:47

       ... to get people out of their little, their safe world a little bit. Uh, this idea of a shit bucket. If things are just like, "I hate this thing and it's not going well, I'm just gonna throw it in the shit bucket for now and that's just how it's gonna be and I'm gonna move on so I can focus on impact and important things." Amazing. Okay, what else do we have here? So many little notes here. Uh, be prepared. So, as you're organizing fr- uh, teams, be prepared to lose friends that you had at the company as you rise and as you have to do things that maybe they're not aligned with or happy about, that aren't h- helping their career. Uh, all org charts suck. Nothing's gonna be amazing. Don't over-focus on the org chart. Focus on the people and the culture. Oh, yeah, the mission above all else. Just, like, if things are not going well, it might be people aren't aligned with the mission of the company.

    5. VLVlad Loktev1:06:31

       Yeah.

    6. LRLenny Rachitsky1:06:31

       Okay. Is there anything else (laughs) off the top of your head?

    7. VLVlad Loktev1:06:33

       I mean, I, it- it's so interesting, like, when I think back to my 10 years, like, the things that I actually remember the most are these moments with other people and not the, some project or some product launch that's, like, going super well or, you know, us doing really well with metrics. It was th- the things that really made, I think, Airbnb special andI really, now that I think back through to- to those 10 years of my experience, I- I deeply just resonate with are those little moments. And like one example, and this is why culture is just so important, because the- these things don't just happen, like organically, like you have to be thoughtful about building culture and then I think you create a place where these little things can happen. So for me, I don't know if you remember your experience when you first joined the company, my most memorable experience at Airbnb is the human tunnel. And it was just this thing where, I remember it was my first day and I was standing behind like this giant wall and there was silence in, I think it was the cafeteria, it was like this huge, huge room, right? And then somebody, like this engineer who runs up to me and says, "Hey, go around the- to the other side of the wall." And I turn and suddenly the room just explodes in cheering and clapping and everyone yelling my name and everyone is like basically doing a human tunnel with their hands. Literally every single person at the company, at HQ, including the founders. And then I run through under everyone's cheering and I jump into this beanbag while everyone's like chanting my name. That was my first day. And here I am like, I don't know, 12 years later, 13 years later, I still remember that as one of the most amazing moments of the entire journey. And it like, I immediately felt accepted, and I wanted to contribute to the team. You know? And a lot of the reasons why, there were many moments like that throughout my 10 years, and it was a result of how we hired people for certain core values and were very intentional about just helping people integrate into this crazy company that was growing super fast.

    8. LRLenny Rachitsky1:08:50

       That was an amazing story, I feel exactly the same way, I went through a similar experience when I joined.

    9. VLVlad Loktev1:08:54

       Yeah.

    10. LRLenny Rachitsky1:08:54

        And obviously the human tunnel eventually didn't scale and people, uh, started doing it like per team versus the entire company. We could do a whole episode on Airbnb culture and learnings from that.

    11. VLVlad Loktev1:09:03

        Yeah.

    12. LRLenny Rachitsky1:09:03

        Interestingly that with the human tunnel, it's like, it started I think with the founders, but it ended up being they had no involvement in these tunnels, like it was just employees knew that this is the thing we're going to do for every new employee. And so I think it's interesting, um, I guess just spending a little time on culture and learnings from Airbnb about the value and power of culture. Is there anything there you take away with two other companies you work with now of just like how to set up a great culture, how to do this well?

    13. VLVlad Loktev1:09:28

        I would say there- there's no like single playbook. I- I would say the- the one thing that comes to mind is just being really intentional and thoughtful about it and actually dedicating energy to it. Just as much as you spend time building product, hiring people is, you got to spend just as much energy actually thinking about culture and your core values. And so core values are very, I would say, indicative of what the culture will be. So those two are very linked, right? And once you have, once you think about core values, I remember what worked really well was you don't just like write your core values in a document somewhere and then no one ever opens it. You need to... The- the key is, regardless of what the core values are, you want to make sure that those core values are prominent in just about every single thing that you do, right? So when you hire people, you hire for certain core values. And at Airbnb we had core value interviewers up until, I mean, my entire tenure basically, even when we had thousands of people already at the company when we were hiring people, everybody had to pass core values interviews. So it was very ingrained in how we hired and what we looked for. Then even performance reviews and promotions, no matter how much impact you- you made, right? No matter what you did, if you were not also exemplifying core values, you didn't get promoted, right? You didn't get to the next level. And so even in our performance conversations, those core values were very present in the day-to-day. And then of course they were also printed everywhere. They were just like physically everywhere all the time. So like I felt like every single person around me always knew what the core values were. And so that's my biggest advice, it's like don't copy some other company's core values, instead just be intentional about what matters to- to your organization. And then make sure that those core values are freaking everywhere, part of every single process. Otherwise like no one's gonna care.

    14. LRLenny Rachitsky1:11:21

        Just to reinforce what you're saying, I've been gone from Airbnb for five, six years now and, uh, I still 100% remember the core values. Uh, I'll go through them real quick.

    15. VLVlad Loktev1:11:30

        (laughs)

    16. LRLenny Rachitsky1:11:31

        Uh, be a host, uh, be a serial entrepreneur, which is uh, serial as in the cereal store at Airbnb.

    17. VLVlad Loktev1:11:37

        Yeah.

    18. LRLenny Rachitsky1:11:37

        Champion the mission, and uh-

    19. VLVlad Loktev1:11:39

        Simplify.

    20. LRLenny Rachitsky1:11:40

        ... simplify w- although they tweaked that one or they cut it, right?

    21. VLVlad Loktev1:11:43

        And then embrace the adventure.

    22. LRLenny Rachitsky1:11:44

        Embrace the adventure is my favorite.

    23. VLVlad Loktev1:11:46

        Mm-hmm.

    24. LRLenny Rachitsky1:11:47

        Uh, I love that one the most.

    25. VLVlad Loktev1:11:49

        See years later like you still remember.

    26. LRLenny Rachitsky1:11:52

        There's also every... Eh, exactly. Every frame matters was the other one they decided-

    27. VLVlad Loktev1:11:54

        Yes.

    28. LRLenny Rachitsky1:11:54

        ... to cut out because they realized... Something they learned about effect- core values that I thought is really interesting is they shouldn't be aspirational, they should be who you actually are.

    29. VLVlad Loktev1:12:03

        Yeah.

    30. LRLenny Rachitsky1:12:03

        And so there's a period where the founders are like, "We're not actually amazing at this thing, so let's just remove it from the core values-"
14. 1:13:16 – 1:26:41

    Airbnb’s unique approach to product management

    1. VLVlad Loktev1:13:16

    2. LRLenny Rachitsky1:13:16

       Amazing. Okay, so we again, we could spend an entire hour on the qu- the culture of Airbnb and all the things we've learned there. It's actually a good segue to the last area, the last part I want to talk to you about, which I think a lot of people are probably wondering about as we have been chatting, which is about Airbnb's current ways of working. So we had Brian Chesky on the podcast, the most popular episode of the podcast, it turns out. And he shared his approach to product, which, uh, a lot of people were like, "Huh, that's, that's unique and different and I don't necessarily want to work that way." Other people were like, "This is amazing. This is exactly how I want to operate and so I'm going to make my company work this way." The way he described Airbnb is it kind of moved from bottom up, experimentation driven to very top down, we're gonna have one roadmap, I'm gonna be involved in everything. Product managers are now product marketing managers and all these things that I think people are like, "Wow, that's really new and, and interesting." You actually worked through a lot of that. You went through that transition. I think technically you were a product marketing manager when you left Airbnb?

    3. VLVlad Loktev1:14:12

       Yeah.

    4. LRLenny Rachitsky1:14:12

       Okay, so you're a really good example of that. You reported to Brian during this time.

    5. VLVlad Loktev1:14:16

       Yeah.

    6. LRLenny Rachitsky1:14:17

       Thoughts now that you're removed from Airbnb on that way of working? Pros and cons, right for everyone, maybe not right for everyone? How do you think about this stuff?

    7. VLVlad Loktev1:14:24

       Yeah, so first I guess let me zoom out of like from, from Airbnb for a second and then we'll go into the concrete details of what Brian said. I don't think you should copy another company's ways of working. Like the reality is, it is, how a company operates is so unique to the founders, to the leadership team, to all the employees, and the domain potentially, the moment in time because like how companies operate also evolve sometimes over time and just certain, like different ways of operating might, might be needed, right? So I wouldn't just copy someone else's way of operating. Even like at Airbnb, it wa- it was just very interesting. For us, it took us a long time to figure out how to operate, right? And we were actually, we didn't for a long time explain and give clarity to people of how we should even operate in the first place because so we hired people from Facebook and Amazon and Google and like Netflix and every, Apple, like every company, right? And every person would come in with their own preconceived notions of how they wanted to work, and oftentimes, those no- those opinions differed and so because we never actually stated like the Airbnb way for a very long time, it, sometimes it would be chaotic, right? And like people would just, wouldn't know how to operate and then you go from team to team, teams would just operate very, very differently, and that was a problem. So I think here the lesson for me was not necessarily like there is one way to like, every, every company should operate like this way. And it's much more about picking o- an explicit way to operate and then voicing it to every single person so that everyone has clarity on how to do their job. I think the worst thing is like people just don't have clarity on how to do things day-to-day. They don't know how to drive impact and then they're just like, "What am I doing with my life?" You know? So that was kind of one lesson. Now specifically like going, double clicking into Airbnb and like where we moved, so I, I think one of the things, um, that Brian mentioned was being, uh, top down, right? I actually think top down is this construct that has negative connotations associated with it quite a bit and is often, at least in the context of Airbnb, I, I think misunderstood. Like what people think top down, and, and I've had many by the way, many of these conversations with folks, right? So most people think, oh, there's a leader here in an ivory tower sitting somewhere divorced from the team making a whole bunch of decisions, right? And everyone else is like powerless and can't do anything. That's not actually a reality, right, of top down. Now, in that room where we made many of the hard decisions with Brian, the reality was he asked a shit ton of questions, right? It wa- again, he didn't advocate in the beginning. He would come in with tons and tons of questions and he would listen. And of course sometimes like he would disregard certain things that he heard because he had very strong conviction in a different direction, but he listened. And oftentimes he would also change his mind, right? And so as a leader, like at Airbnb for so long, I never felt like I wasn't listened to or like he was just making these random decisions. I always had an ability to influence and an ability to voice where I felt like the company should go. So like yes, he made a lot of decisions, but he made sure he was informed in those decisions and then many of us were contributing to all the information he needed to make a decision, which is then also why he wanted every leader to be in the details. Why did he like stress that for himself and every single leader on the team? It's because when you get into that room, right, and you start discussing many different directions you can go, if the leaders in that room can't tell you what's actually happening with the business, then why are there in the first place, right? Like you can't then make a th- a good decision with that group of people so then suddenly like you're a team of like 10, you have to blow up to a team of 30 and if those people are not in the details, then you got to like what, bring in like 50 people? And so at some point you, you need to make sure that leadership is actually in the details to understand what's happening and can help bring to light information that's going to help somebody make the right decision, right? So that's why I like top down and being in the details, to me they were actually very connected and it made a whole lot of sense. Now the one thing I'll say is like at some point-When you're working on many things, like it is challenging to be in, in all the details, right? And if you mandate that like product cannot ship without like, you know, certain people being in every single detail, sometimes you could slow it down, right? And that could be a con of that way of working. I would argue for us and for at Airbnb, the quality like of what we were releasing kind of suffered because we were just push, push, push, ship, ship, ship and people were shipping across the board. And I did feel as a leader, like I wasn't proud of some of the things we were shipping, you know? And so I appreciated the intentional slowdown at the expense of our goals to get to a higher quality bar and then amp up velocity again after everyone had a better understanding of what quality actually was. So we kind of had to slow down for a bit to then speed up later. And, and I think a lot of it is Bryan always wanted to make sure that every leader would be able to make decisions and have really good judgment, and he wanted to teach what that meant. And I r- actually really appreciated that over the years. Now, you know, like if you were to go back to semantics and say, "Hey, were we top-down, bottom-up?" Those are just semantics. Like I would say, we were actually n- like if you really think about it, we were neither because bottom-up, you could always, through certain channels, voice information. Again, if you didn't self-censor and you were not afraid to poke the bear, you had an ability to voice information. So from that sense, there's lots of information that came bottom-up. But then at the same time, there was also like a lot of conviction and intuition and context that came top-down. And because for a lot of these decisions, there was so much conversation, the reality is, I think that the way we operated was actually somewhere more towards the middle on, on a day-to-day basis which is why for me, like I, I thought it was great.

Episode duration: 1:37:18