Building minimum lovable products, stories from WeWork & Airbnb, and thriving as a PM | Jiaona Zhang

[00:00] I think it's really important to become really good at and also known for something. [00:05] You could be known for shepherding like the most complex launches because you're just so good at quarterbacking, working with go to market teams and cross functional stakeholders. That could be like your thing. You could be known for working on the most technically complex problems. Find something that you can be really, really good at. And the reason I give that advice is because. [00:25] When you do that, you can crush the projects that you get because you're making a name for yourself, a reputation, and then you're giving more responsibility. People tend to flock and give responsibility to the people that are known for being excellent at something. [00:43] Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. [00:52] Today my guest is Jay-Z. Jay-Z is Senior Vice President of Product at Webflow. She's also a lecturer at Stanford, teaching a course on product management. Before this, she was Senior Director of Product Management at WeWork, a longtime product leader at Airbnb where I got to work with Jay-Z for a number of years. And she was also PM at Dropbox and at a gaming company called Pocket Gems. In our conversation, we dig into the most common mistakes early product managers make in their career, plus Jay-Z's biggest product mistake. [01:22] minimal viable products. We talk about Jay-Z's unique frameworks for roadmapping and prioritization and OKRs, and her take on how to structure your first 90 days as a product leader at a new company, plus what she's learned from her wild year at WeWork, also the best advice she's ever gotten around product and leadership, and the story of Airbnb Plus and where it went wrong. I've been hoping to get Jay-Z on the podcast for a while, and I'm really happy that we finally made this happen. With that, I bring you Jay-Z after a short word from our sponsors.

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[03:43] people published in the Miroverse. When you get to the board, you can also leave suggestions for the podcast, answer a question that I have for you, and generally just play around to get a sense of how it all works. Miro is a killer tool for brainstorming with your team, laying out your strategy, sharing user research findings, capturing ideas, giving feedback on wireframes, and generally just collaborating with your colleagues. I actually used Miro to collaborate with the Miro team on [04:13] Check it out at miro.com slash lenny. That's M-I-R-O dot com slash lenny. [04:19] Jay-Z, welcome to the podcast. Thanks for having me. I'm so excited to be here. It's 100% my pleasure. [04:28] Amongst your many accomplishments, you teach product management at Stanford, which sounds very fancy. [04:34] How long have you been doing this at this point? [04:37] I think six years. Yeah. Wow. [04:39] So my question, the real question I want to ask about this is, in that time, you've seen a lot of new PMs. [04:46] And you've seen these PMs succeed. You've seen some fail. [04:49] What are the most common mistakes that you find UPMs make in this experience of kind of [04:54] helping new PMs get into the field? I think something that is really hard to untrain, but I think every human does it, is you jump to solutions. [05:02] And so one of the biggest things I see, not just in my course, but also just as a PM and like some of the mistakes that you make as a PM is the idea of get really attached to a solution, a way of implementing something, something that you can see in your head that you want to build. And so that's the first thing I really want to like un-teach in our course. And so a lot of people will literally come in. They'll be like, I want to build X startup or I want to do this thing or I'm in blank school and I've been doing a lot of research on this particular area.

[05:32] out there, we are not gonna think at all about the thing that you want to build. But instead, we're gonna be focused on [05:38] users and people in the real world and their problems. And the first step is to understand their problems and then understand if there's an opportunity here as opposed to, hey, you want to build X thing for Y person. So that's the biggest mistake that you really have to unteach and like retrain thinking around. [05:55] There's a lot of this come from people want to get into product management because they think like finally I'll have the power. [06:00] Finally, I'll be able to tell people what to build. Finally, my ideas are really going to matter. [06:03] Is that where the library comes from? [06:05] I think there's a part of that. You know, one of the first things I teach is, you know, you're not a CEO. You're not here. You actually have very little true authority because you don't actually manage anyone. It's a lot of it is all through influence. And so that is also a piece where you have to kind of untrain that thinking. I do think a lot of people come into the product role thinking that I get to call the shots. I get to make the decisions. I get to decide what gets built. And really, your job is not that. Your job is to understand here are the opportunities. [06:35] together all the different possibilities, and you're really editing. So I do think it comes from desire for a lot of people thinking that's what the product role is, when it actually isn't. [06:44] So let's kind of go to the other side of this question. [06:47] We talked about what mistakes new beams make. I'm curious [06:51] What's the biggest product mistake that you've made? [06:53] Wow, that's a good one. It's so interesting. I feel like as product people, we're always making mistakes and we're always learning. Maybe I'll give an example from Airbnb, since you and I were both there. Okay. And this one does stand out to me. So,

[07:04] you know, we were working on this concept called Airbnb plus. [07:08] If you took a step back, what you're really trying to do is to be like, "Hey, not everyone trusts Airbnb in terms of, it's a platform. It's not like it's managed inventory. It's not a hotel. How do you go in and really make sure that all the Airbnbs are meeting the quality bar?" But I do think we were very solution first, and I think we're also competitor. [07:26] afraid at the time, right? So it was during a time where there were managed marketplaces, there were the Saunders out there. And I think that as a company, we're very much like, oh, goodness, like, what are we going to do in the world of managed marketplaces? And so we went really hard down the solution space. We essentially were like, let's go inspect. [07:43] our inventory, let's actually try to manage our inventory more. And really what we should have done is taken a step back and be like, what's the real problem? The real problem is people want to know what they're getting themselves into. We need to represent the homes a lot better. And I think the other piece here that's really important is what as a company? [08:00] Is there strategic strength? And like what's in your wheelhouse? So for example, Airbnb, we weren't that strong in operations. We, again, we're this platform with this marketplace, right? And so if you don't have that muscle and then you're asking the company, the teams to essentially build it from the ground up, that's really, really difficult. Not to mention the unit economics. Are the unit economics actually going to work even as you scale? [08:22] Yeah, I feel like Airbnb Plus is an untold story that somebody should tell and [08:27] That could be its own podcast, I guess. You and I can tell it. We could tell this could be Airbnb plus the hidden story. As you said, the problem I was trying to solve was people don't really trust. They don't want to even consider Airbnb because it's like, no, I don't want to stay in someone's home. I don't know what it'll be. It's unpredictable.

[08:42] And so, [08:43] As an outsider, it felt like a really clever approach. We're going to vet them. We're going to make sure they're awesome. There's a minimum bar. [08:50] I think the... [08:51] And I guess this is the question is, [08:53] Do you think it was just like, this is never possible because there will... [08:57] We'll never make money as a business doing this because we don't make that much per booking. [09:01] investing time, resources, [09:03] Sending people pillows. [09:04] All that stuff. [09:05] is ever going to be economical? Or do you think there was a path that was just not executed? [09:09] well. I think there wasn't really a clear path. I think there was less about execution. Exactly. And it's more just like, if you understood, again, this is my point around unit economics, [09:19] There are things where I think you have like magical thinking around unit economics. You're like, well, when we get to the scale of X, [09:25] "It's all gonna work out. "We can make these things happen." I think you actually need to really make sure that unit economics work quite at the beginning. So that is definitely one lesson. And I think the other thing is, and going back to the spirit of what are you trying to achieve, if you're trying to achieve this idea of like, really knowing the quality of the place, [09:41] and for a platform like Airbnb, the right way to go about doing it is through our reviews, right? Through our guest reviews, which are essentially free as opposed to literally sending out inspectors. And I think the other things are if you can get signal on what are the things around quality that people care about? Is it cleaner, cleaning? Is it the, hey, I'm locked out. And I think that there are other solutions besides inspection that then get at that. So for example, [10:07] it is actually cheaper to go send everyone a lockbox than to deploy an inspector and go look at your property right it is actually cheaper to maybe do a partnership with like a you know a bunch of cleaners in different local areas and then get that as part of the fee like as opposed to doing the inspection so again it's really about what are you really trying to achieve what is the user problem in each of these areas and can you target that problem with the particular listing that is you

[10:32] that you're looking at. And so, yeah, I personally don't believe the unit economics [10:36] ever would have really worked out. I think we should have known that, or we should have dug into that more at the very beginning and then to get very tailored instead of like one blunt instrument [10:45] To solve it all, hey, we're going to go inspect. It's like, what is the problem for this listing? And what's the best solution to fix that problem? [10:51] There's a couple of things that I think are important product leadership lessons here. One is [10:56] Airbnb and Brian [10:58] and many [10:59] Great leaders are famous for imagining the ideal situation, imagining the [11:04] great end result and then working backwards. [11:07] And often that leads to great results when [11:09] You're being really ambitious, and I don't know how we're going to get there. We're just going to shoot. [11:14] shoot big and hopefully we figure it out. [11:16] Sometimes it works out. In this case, it didn't work out. [11:19] What you're finding, maybe you even knew this early on, is just like, there's no possible world where this could have worked. [11:24] in this approach. [11:25] I guess, is there anything you've learned about just when to... [11:28] Think big and not even like forget it. We're going to figure it out. I know there seems impossible. [11:33] but we're just going to try it anyway. Do you have any kind of framework of when to [11:36] Think big like that and just go for it. [11:38] Versus, oh, let's just work out the math today. [11:40] is this ever possible? [11:41] I think it's really important for every company to be dreaming big. Like if you don't have a big vision, it's really hard for you to... [11:48] Innovate. [11:49] But [11:51] you got a couple of that really big vision with [11:54] thoughtfulness around your execution, right? And so I think that one of the biggest tips I have is how do you just be very [12:00] how do you be clear about the phase that you're in? So I think it's totally fine to be like, hey, we are going to try,

[12:07] X for six months, three months, you know, whatever it is. And we're explicitly going to go learn these types of things. We're going to learn why are people like, like, are there signals that we would get that would indicate that the, again, the communication with hosts isn't great or, you know, this type of listing, if you, if it's hosted by a person with multiple property, like, I think there are factors and be like, hey, we can learn this very explicit thing in a given period of time. And you can do what I call like unscalable things in that prototyping phase and that early [12:37] to go learn those lessons. But you just have to be very, very clear with your team on what phase you're in. Hey, we're in the learning phase, and we explicitly are trying to learn these things, versus, hey, we have this really big vision, and we're just gonna, [12:50] you know, kind of go at it. Like that is not recommended in my mind. It's like breaking it down into these smaller chunks. [12:58] That I think gets you the balance of thinking really, really big, but also being able to be like, okay, we are still going to be able to say, okay, this path is not going to work out. We ran at it for a short period of time. We got these learnings. Now let's go down this other path. [13:11] Yeah, there's also like some cost fallacy that kicks in of just like, oh, [13:14] We spend so much time and money and resources on this thing. Let's just go a little bit longer. Let's just see if we give it another quarter. Maybe it'll work out. [13:21] you should articulate what success looks like and the milestones you want to hit in the small intervals that I talked about. Right. So you don't get into this world where you're like, hey, I've gone for two years investing in this thing. Now we got to cut it. It's like, what is the quarter long milestone? OK, what's the next quarter long milestone? And every single point, what is a go and no go? I think that really can help a team and a company say, hey,

[13:42] It's OK. I invested a quarter in it, but I didn't invest two years. [13:46] The other important lesson here is about the importance of, as a product leader, [13:51] pushing back and convincing leadership that, [13:54] you're wrong and this shouldn't happen. [13:56] I remember talking to one of our colleagues, Mike Lewis, who was leading a different team within Airbnb. [14:01] And he was just like, [14:03] Oh, I realized I'm the person that should be saying, no, we shouldn't do this now, because he was like the head of product for one of the new bets. [14:10] Yeah. And, [14:11] I know maybe in that situation it was impossible because... [14:15] Brian was very into this and everyone was like, we need to do this thing. [14:18] I guess, is there anything you've learned about [14:20] how to push back on these sorts of things that the founder is really into. [14:24] when it makes sense to kind of go along like cool let's do it let's buy and we gotta [14:28] As a leader, you have to be excited, and the team needs to feel like, oh, Jay-Z is really excited about this too. We've got to try it. [14:32] even though maybe you feel like it's not going to work out. So I guess the question is, when do you think it makes sense to try to convince the founder, no, this is a bad idea? [14:40] Versus like, let's go for it. [14:42] I think first it comes down to your conviction. Like, do you actually have conviction that this is a bad idea or are you personally still learning? Right? I think if you're at the point, if you're like, I have total conviction, then your job is to say no. You really, like, if you do not, like you're not doing your job. And then the question is like, what are the tips in how to convince someone who's very bought into an idea that that's not the right idea? And there, what I would say is it's understanding the spirit of what they're trying to achieve, right? [15:09] being able to go back with, hey, I understand the spirit. The spirit is that we're trying to get people who previously considered Airbnb before to come and use Airbnb. But the right way to do it is not this very time intensive, cost intensive way to inspect all these homes. The way to do it is to be much more granular in what we ask people when they upload their home, right? And more checks in that. And that could be automated through technology as opposed to through humans. It's

[15:39] It's like saying, you know, and I think we did that a little bit, to be honest, like when we, you know, as a team evolved, you know, we learned and we're like, you know, this isn't going to work. And I explicitly, you know, moved off a team and I was like, I'm going to work on the review system. I'm going to continue to evolve this and make it better because that is the actual scalable way to do this as opposed to keep going at it in the very manual. [15:58] process. And so I think that the biggest thing, biggest tip I would have for people in this situation is really understand whether it's the founder or your manager or whoever it is, like, what is it that you're actually trying to, what is it that they're trying to accomplish for the user and for the business? Remind them of that, like get aligned on that and then come back with better options. You know, very few people, I mean, we're all, a lot of these people, they're very smart and they're very motivated. They ultimately want to just do the right thing for [16:28] the thinking behind it, it's very rare that someone will be like, "Well, I still want to go after this solution despite the fact that it's not working and you proposed a much better path forward." [16:38] And I think to touch on what you've already said is also make sure it's actually... [16:43] There's a world where this could work. Do some math. [16:45] to figure out if this is a business that will actually make some money in the future. [16:49] Totally. [16:50] Okay, I'm going to bounce around a little bit. I have a bunch of different questions around different topics. [16:54] Yeah. You popularized this concept of minimal lovable product. [16:58] versus this idea that everyone always comes back to, which is minimal viable product. [17:03] Can you just talk about what is a minimal lovable product and then when does it make sense to kind of [17:07] go in that direction versus a traditional MVP? The reason I care so much about minimal level product is because I do think in a world where there are so many different options, it's hard to just be like, "Hey, use this thing and barely meets a quality bar." And so I think this idea of like actually deeply understanding for the thing that you're working on, what is a lovable experience? What is the quality bar that resonates with your users? And again, especially in a world where there

[17:37] MVP, right? The new minimal viable product. So I think that's the real point. But at the end of the day, it does come back to what are the options that a user has and what are they trying to do? So there's a world where, you know, your quality bar, your quote unquote quality bar, or your, let's call it your polish bar, can be a little bit lower because the reality is the thing that you're quote unquote competing against or like replacing is literally like a manual workflow. It's like spreadsheets. It's doing something in a super terrible way. So you want to get your [18:07] possible, right? So it doesn't make sense for you to be like, I'm going to build these like 15 additional features because [18:12] Compared to what people are doing right now, your product without those 15 additional features is perfectly fine, perfectly usable and perfectly, quite honestly, like lovable. [18:23] So, it requires a lot of understanding of like, again, your users and the space that you play in and the tolerance of your given user. So, for example, a designer might have a lot higher of a bar of like, this is the kind of workflow I want. This is the kind of like bar for my product. [18:42] Again, someone sitting on the... [18:44] finance team or the IT team, right? Like their bar might be like, oh, I'm used to doing these like 15 things. And so your thing is just a lot better. [18:52] I'd love to go even one level deeper. Is there an example of... [18:56] something you've worked on that was the minimal lovable product? [19:00] that you think about [19:01] Or is there something out there that's an example of like, here's maybe... [19:04] an example of a minimal level product versus MVP.

[19:07] Again, it's very hard. I think every product team, every product person struggles with this idea of like, what is the minimal viable? Even that concept in itself is difficult and not to mention like minimal lovable. I'll give a Webflow example. Very recently, you know, we so we have been investing in a couple of new features, you know, memberships and logic, new functionality for our users. And what we realized at the end of the day, after investing in these areas, we were like, hey, we can get to minimal viable, but we don't know if we can actually get to minimal lovable. [19:37] a way that our users really, really want. [19:41] Does it make sense for us to continue to go down this path of like keep like continues to ship away to get to minimal lovable when we are maybe hitting diminishing returns for user base? Or does it actually make sense to release what we have, but then encourage our ecosystem to contribute the lovable piece? And again, it's not just like you put it out there and you hope you have to have a very strong point of view of like, are we at minimal viable? Are we at minimal lovable? Kind of where in between are we right? And so having that point of view and then being able to say, are we going to be able to meet as a company? [20:11] rely on our ecosystem to help us meet it, what are we actually going to do? And then even within the feature set, it's very much how do we do some things well as opposed to do a little bit of everything? I think that is a big piece of minimal lovable, which is, [20:25] Again, you know, [20:27] To me, it's like better to do five things instead of the 15 things in a really, really great way with a high degree of polish with like a, "Oh, this really meets my need," versus trying to do everything and just doing a little bit of everything. And so every part of the experience feels a little bit clunky. It's not quite there. People I think would actually respect this idea of like, "You've given me minimal lovable in five areas as opposed to minimal viable in 15 areas."

[20:53] Is there anything you've seen of just like that makes something lovable? I don't know. I know it's not like easy to define, but like, [20:59] What are things you've seen that make something lovable? Is it delightful features? [21:03] Or is it what you're saying, which is just things are actually good? Like there's fewer things, but they're each really good. [21:08] There's definitely this idea of like the thing is just good. It has like all like it is high quality. It's not janky. It doesn't feel weird. I'll give you like a very small example again just from Webflow. This idea of like keyboard shortcuts, right? Like that feels small, but like that is a piece that creates a lot of love from user base who are power users. And then there's this concept of like pixie dust. Maybe I'll pull out of, you know, call it like design tool space and we'll talk about some of the other things, whether it's Dropbox or Airbnb. But you can just do a little bit of that like extra pixie dust. [21:38] example from Airbnb, when we're doing the mobile app revamp, [21:41] We're like, okay, there's like these basic table stakes, but if we actually added in templates, and we made it so that these templates could be maybe pre-populated in certain ways from the content that you already have, that is lovable. That is that extra little bit of pixie dust, and spending the time to do that, and again, you can't pixie dust everything. That will just... [21:58] At the end of the day, you basically have like, [22:01] your time, your staffing, right, and the scope of your project and like something has to give. And so, you know, at the end of the day, you can't just like keep investing, keep investing because it's going to push out your launch timeline. But can you pick a few different areas where you're like, I'm going to scatter that pixie dust. I'm going to do a little bit more than what users are expecting. And that creates that lovability. [22:20] Shifting to a different topic, [22:22] I know you have strong opinions about roadmapping and OKRs and prioritization, and I know that's a big topic, but let me just ask,

[22:28] What's the most common advice? [22:30] you give around how to roadmap well, do OKR, spiritize, [22:33] and/or just like, I don't know, common mantras or things you always come back to to be successful in these areas. [22:39] Road mapping and prioritization are kind of one bucket for me, and then OKR is another, so I'll maybe give you my biggest tip in each one of these buckets. So for road mapping, my biggest thing that I tell my teams is you're telling a story. [22:52] So what I want from you is I want themes, [22:55] I want a story, like why are these things, the biggest things to invest in, these levers, the biggest ones to pull? And what I really don't want, what I think is a very common mistake from road mapping, is people thinking like a spreadsheet with a bunch of projects, all the RICE framework, like everything has an impact or cost. [23:16] an effort column filled out. They think that that is prioritization and that is a roadmap. If you just do that right and then you present that to your team, they're off to the races. But what people, what humans really crave is like, why am I doing this body of work? And I think it's also really, really important to have that really crisply articulated in your own head because ultimately what happens is you will learn things as a product person. You'll be like, oh, I assumed this in the narrative in my head about my users or about my product area. And then I learned why. [23:46] therefore my thinking changed, right? So instead of it being this massive spreadsheet, where you're going in, you're tweaking all the values, [23:52] What is the story that you're telling about your roadmap that these inputs can then go and influence? It could be like, hey, I just realized I didn't know before that we have a lot more power users on it. Or maybe we have a lot more non-technical users. Well, that input changes my roadmap and changes my themes in a pretty dramatic way. So skating at that level is really, really critical, I think, for a roadmap, as opposed to going down to the really granular details of the how.

[24:22] Tell a story, what are your themes, make it so that your team can come up with the actual like how and the projects and all the little details, but really create that scaffolding for them to know what's important. [24:33] Can I ask a follow-up question on that? Totally, yeah. [24:36] It's easy to visualize the roadmap of a spreadsheet. [24:39] to help people visualize what you're suggesting there. What does that actual artifact look like? Is it a dock? [24:45] with maybe an ancillary spreadsheet of the actual prioritization, [24:49] Is it a stack? How do you actually deliver this to you with like Jay-Z? Here's our [24:54] proposal for our team. [24:55] Yeah, I'm a big fan of docs. Dex are obviously helpful if you're talking live, but I do think in a remote first culture or like lots of us are in hybrid remote cultures. It's hard because, you know, that's typically require a voiceover. And so we have been doing a big push even on my teams where I'm like, write it down and document. Force yourself to write the prose because when you write the prose, you can actually add that level of granularity. So very much so like the same way I'm like a roadmap is a story. You're you're telling themes like you write a story in. [25:24] notebook right you write a story on pages and so a doc is definitely preferred and even in the doc just being like [25:31] here's what we're trying to achieve. Here are the big areas I want to invest in. Here are my big themes. And then going into each of those themes and being like, these are the big projects. And then linking out, again, not even to a spreadsheet sheet, but linking out to the artifacts and the systems that your team actually uses. So if your team uses Jira, go ahead and link out to Jira because so often docs get out or like spreadsheets get out of date, right? Because they're like a snapshot of whatever it is that you needed at that point in time. But if you said you link out to the

[26:01] be like, these are the themes, I will edit these, if I learn major things, I would change my themes, and then let's go link out to the Jura where you can just see the snapshot of the roadmap at any given point in time. [26:12] Do you have a template or common structure you suggest to teams for laying out the story? Or is it just depends on the quarter and depends on the year? I'll give a plug for a new thing coming out of Reforge, which is this concept of artifacts. And so we do have a lot of artifacts out there. So what's our general product development process? What are our templates for our specs? What are our templates for some of these things that we're talking about? A roadmap, like a broader roadmap instead of just a feature spec. [26:42] We're always evolving. I think every team kind of takes it and like tweaks it a little bit. But I do. I'm a big believer of like bringing those artifacts back and then sharing them across the team. And so product operations is also a function that we've invested in because it just really greases the wheels. It gets all of our teams kind of speaking the same language. Awesome. This episode is brought to you by Superhuman. How much time do you spend in email each day? How about your team? You may not realize this, but your email tools are wasting your time. [27:12] fast email for high performing teams. Built to work with Gmail and Outlook, teams who use Superhuman spend half the time in their inboxes, respond to twice the number of emails, and save over four hours a week. That's over a month of save time per year. With Superhuman, you can split your inbox into streams for VIPs, team members, and emails from your favorite products to reduce context switching and make sure you never miss an important email. You can set reminders if you don't hear

[27:42] thread. You can also work faster than ever before with powerful AI features like writing, editing, summarizing, and even translating. [27:49] Join the ranks of the most productive teams and unleash the power of superhuman. Try one month free at superhuman.com slash Lenny. That's superhuman.com slash Lenny. [28:02] Moving to a different topic. [28:04] Yeah. What is your number one piece of advice to... [28:07] new PMs who want to accelerate their career, [28:10] What do you find most often is the blocker or thing holding them back. [28:15] or something they can change that'll accelerate things? - There's so many parts to it, but I'll pick one. And there are many firm works even beyond the one, but I'll just pick one for your question, which is, I think it's really important to become really good at and also known for something. [28:30] And what I mean by that is when you're known in your company for a particular thing, I'll give you a couple examples. You could be known for shepherding like the most complex launches because you're just so good at quarterbacking, working with, you know, go to market teams and cross-functional stakeholders. Like that could be like your thing. You could be known for working on the most like technically complex problems. You can be known for working on things that are like really regulatory complex. Like find something that you can be really, really good at. [29:00] When you do that, you can crush the projects that you get, right? Because you're making a name for yourself, reputation. And then you're giving more responsibility. People tend to flock and give responsibility to the people that are known for being excellent at something.

[29:16] Is there something you were known to be excellent at in the course of your career? [29:20] I would say early on in my career, it was actually the fact that I had like a strong analytics background. And so when I joined gaming, right, I came from consulting. I didn't have any CS background or design background. And so it was really like creating a reputation around being very analytical, around being able to analyze the data sets of my game and then like make decisions. [29:40] I also learned as I was doing that, I was actually really good at execution. And so, you know, being able to keep a lot of plates kind of spinning and working on kind of like the largest studio and managing all the complex pieces of that. That was what I discovered. I didn't know this, but I discovered as I started like working in the role. And so that was something I brought to Dropbox. You know, when I joined Dropbox, it was like, I knew that I could work with a lot of different teams and make sure that we like hit a launch deadline. [30:10] trying to lean into that superpower and then [30:13] when delivering upon that, getting more responsibility, right? Like, hey, you just launched this really complex thing, had to work across, like, this was a project that had to work across, like, a lot of different platforms, we're using brittle APIs, and it was like a very, very small team, I had a very, very tight deadline. So when you're like, okay, I can do something like this, you end up getting more responsibility, because people are like, oh, she was able to do something that was really hard with a small team. And so that's how you get more responsibility. [30:40] But it has evolved in my career, right? Like I think that, you know, at the beginning of your career, you do want to lean into some of these pieces that make sense. But also, even when you start to manage, it shifts dramatically. You know, being known as like the best executor is not necessarily the thing that gives you and your team the most responsibility. So, you know, as I've run my career, whether it's at Airbnb or we work at other places, I flex into maybe like a different, it's like taking your core strength, but then flexing it and finding different ways to bring it to life.

[31:09] Much of what I just heard is you just worked incredibly hard and just got shit done. [31:14] I think that's very, very important and often leads to a lot of success. I think PMs have to get shit done. [31:21] Ultimately, you're responsible for the outcome, no matter what happens. Yeah, I like that. Be known for getting shit done and working really hard. That's never going to serve you badly. [31:32] I think that is just lasting... [31:34] advice for being successful as a PM. I realized that we were talking about your tips on prioritization roadmapping and then OKRs, and then I shifted topics and you never got to the OKR bucket. So let me come back to that. [31:47] Yes, my biggest tip on OKRs is actually get really, really crisp on [31:53] qualitatively, like what would make you say, yes, we did a great job. And the reason I push so hard on that is because I see so many teams get really mucked down by OKRs. They're like, oh man, if I don't hit my OKR, I feel like I'm going to have like a really bad reputation or maybe I won't get promoted or like you just get all this fear around OKRs. And so you see people, you see people sandbagging, you see people, you know, being hesitant to put in numbers until like the very [32:23] results in ultimately a failure to [32:26] for your company to innovate and move quickly. And so what I really push on for OKRs is like, what are you actually, what's the spirit? I think I asked this question maybe too much to my teens, but like, what is the spirit of what you're trying to achieve and what would make you say, I really, really crushed it.

[32:41] this past quarter. [32:42] And so it's less about, I would rather have all the OKRs be red or yellow, and we missed everything. [32:50] "and we learned around why we missed it, "then everything to be green." In fact, when everything's green, you're like, "We definitely did not set ambitious enough OKRs." And so it really pushed a lot on like, what does it truly mean to like, [33:02] crush it and be successful? What does it mean for our users? What does it mean for our business? What does that like [33:08] for users to feel X, like can you describe that, can you write that out, for our business to see this in terms of the revenue growth. And I think it's really hard because a lot of times you get your data scientists, you get the PM themselves being like, "Oh man, I'm only an input metric, not an output metric. And so I definitely can't sign up for that revenue target because I have an input metric." And all of those things are true. [33:31] But if you don't do the homework of really drawing that line of being like, this is the ultimate thing I want to do for the company and for my users, then a lot of times you end up hitting all your OKRs. But the company and your users at large are like, I don't feel anything different. [33:48] Like your company doesn't look at the things that you've worked on and they don't say like this is a smashing success. Your users are feeling no differently. And so that is the worst outcome in my head where your OKRs, you're like almost like doing OKRs for the sake of OKRs as opposed to letting them be a guide to delivering really great product to your to your end customer. [34:07] I like the idea of that. [34:08] But imagine what often happens is

[34:11] You... [34:12] Sign up for an ambitious OKR. You don't wait till the last second to commit to it. [34:16] And then it ends up being red. And then you go into performance reviews and like, oh, Lenny didn't hit his OKRs. Look at this guy. His team is not doing great. [34:24] How do you think about that as a product leader, understanding if the team actually did well and the PM is performing well when... [34:31] they sign up for these really ambitious OKRs and their story is great and they're doing the right thing, but they fail. First of all, I think it's creating a culture where you are not punished for that, because I definitely don't want a culture where it's like you took a risk and you failed and therefore your performance is impacted. I'd much rather people take risks than to be safe. So I think that's the first thing. That being said, you're also not doing a good job as a PM if you're like, this is my super, super ambitious thing. And you're like, I have no idea how to achieve it. Your job is to dream big and also have a plan to go tackle it. [35:01] expect the PM to be able to say is like, this is my North North Star. [35:06] I'm not going to be able to do that in a quarter. That just is unreasonable. But here are the five milestones, you know, whatever number, some number of milestones that it's going to take me to do quarter over quarter to achieve this really, really ambitious thing. And let me draw you that path. Like here's the milestone all the way across. And this is the first one. This is why it's so meaningful. So I expect that combination where you're like, I know where I'm going. It's really, really ambitious. And then you can then break it down. But again, I would much rather have someone

[35:36] do, I don't know my path yet, than to be really, really safe because when you're safe, you [35:40] you're always going to be building something suboptimal. It's going to be some ultimate use of your resources as opposed to actually trying to figure out what the best, best swing that you can take is. [35:50] So it sounds like it comes back to the story of the roadmap and what they're trying to accomplish and just [35:54] as long as it feels like the story made sense, [35:57] There's a path there. [35:58] The team did their best. I think we knew it was really ambitious. We kind of knew maybe they wouldn't get there. It sounds like that's kind of the thing you look for in a performance of a PM. [36:07] Totally. Yeah. Awesome. [36:09] You mentioned WeWork, and I want to spend a little time on WeWork. You were at WeWork for about a year, and I think it was like in the middle of a lot of the craziness that went on at WeWork. [36:17] - It was, it was 2019, I feel like that year, it was either, like headlines were either about Trump, [36:23] Or about WeWork in the news. [36:26] That's tough. [36:27] So, okay, so what was that like being a PM leader at a company in that craziness? And is there a takeaway from that experience that helps you be a better product manager leader? [36:36] - Yeah, I learned a lot from my time there. I think the most important lesson is [36:41] I learned was really around [36:44] I think there's like a people management lesson. And then there's also just like a, how do you build an org period? The people lesson I learned was just really around empathy. [36:54] In fact, essentially what I was doing was, I built a team. I spent the first six months of my time there actually growing my team a lot, and not just in the US, but in Asia and in Europe. And then the second half of my time there was actually being like, "Okay, what do we do? If this is what's happening with WeWork,

[37:14] what are we actually gonna do with all of these [37:16] people who have like come to WeWork to work. And there's so many lessons there around leadership, around like, how do you think about people? How do you think about giving them, you know, the right transition plans, the right, like, it was a lot of learning. And I think, you know, probably a lot of people even right now through the macroeconomic downturn, they're like learning that lesson in a really hard way. And so it was definitely something that I got a crash course on, [37:46] around not over hiring. And so I think that was huge. And I think I personally learned that lesson through my time there. And it's something that I'm very conscious of, like at any company that I go to. And so just because like laying off half your team is a terrible feeling, right? Like literally having hired people and then having to let them go, [38:04] it's not something you want to do. And so being really thoughtful around like, how do we not overhire? How do we, um, [38:10] How are we really clear about, again, like these milestones of like we got to get through these gates. We got to be able to show these types of results. And then we unlock hiring in X, Y, Z ways. Like that hygiene is really, really important. [38:22] Feels like this connects back to the Airbnb Plus story of just [38:25] Let's just be really ambitious. We don't have any idea we're going to get there. [38:28] But we're just going to go for it, hire like crazy scale, put a lot of investment in this thing, and hopefully we'll figure it out. [38:34] I do think there was a little bit of that in the ethos of how WeWork was functioning, for sure. I think that what was really important for us to do was to be like, we have this [38:42] I mean, operationally, [38:43] WeWork is really strong. In fact, I went to WeWork because having been at Airbnb, I was like, I don't feel like we've dialed this operational muscle down. But I know from what I've seen, and the way WeWork has expanded, that they're really, really excellent at the operations. But I think it was, again, we hired beyond our skis on the tech side. It's like, we don't need a team of this size to go do the things that are needed for the product to feel really great. At the end of the day, it's about booking. And yes, there's technology that would accelerate that,

[39:13] be super platform aware? Do we need it to be like super futuristic? Like that's actually not what people care about. So this all goes back to what are people's core desires in whatever product that they're using, right? Whatever thing that your business is trying to serve them. And so really understanding that will help you have a sense of like, hey, you still be really ambitious. Like, you know, again, in a hybrid world, it's like, why have real dedicated office space? Every company [39:43] that's still a really big vision and like a relevant vision but [39:49] What's the... [39:50] key piece of that vision. The key piece of the vision is around inventory. [39:53] And then you make that inventory management easier. You make all of these things easier, but that's not a technology play in the same way as it is an operational play. Right. So just really understanding again, like you still dream really big, but you don't have to dream big and hire big and all the things in order to have a very ambitious. [40:10] vision that you deliver to the market. [40:13] If you think back to WeWork, what was your... [40:15] Favorite memory? [40:16] And what was your... [40:18] hardest, least happy memory. [40:21] if anything comes to mind. [40:23] I mean, I think this idea of like dreaming really big, like I think, [40:26] everyone who had joined WeWork, they were like, we could do a lot here. Like the idea of really kind of like the physical space infusing technology. I just feel like the people at WeWork were dreamers in like the best possible way. So that definitely, I feel like for every company that I've been at, it's really about like,

[40:44] You know, you join [40:46] I personally joined for the product, but I stayed for the people. You joined because you're like, "I want to work on this mission. This product is really motivating," and then you really stayed for the people. The people at WeWork were really great. That was definitely my favorite memory. I think the hardest memory was, this gets a little bit personal, but I was actually in my first trimester when we were going through all of these layoffs. [41:08] was faced with a choice. It was like, "Hey, do I stay at WeWork? I would be guaranteed maternity leave. I was going to be moved on to this other team that was definitely going to stay. Do I do that or do I actually [41:21] And I think there is just a last piece of like, [41:24] the thing I was wrestling with is I hired a lot of these people. And I felt really responsible for the fact that, you know, I convinced them to come to this company that now was going through a lot of change. And I specifically remember someone when I hired them, you know, we had a long conversation about like their visa. And in my head, I was like, I just, [41:41] don't feel right. Again, like, you know, laying someone off, like that's only going to have so many days to be able to go find their new role. And so, [41:48] The hardest moment, I actually remember this very vividly, like, am I going to take this new role or am I going to put myself on the layoff list, essentially, and give the role to someone else on the team who, when I really think about it, like, yes, I was pregnant, but I would have more time. [42:04] and more freedom to go find my next thing versus someone who I brought to the company who was on a visa. So that to me just really stood out and goes back to this concept around like leadership is so much about like,

[42:15] empathy and like people it's it's as much that as is it about as it's about like understanding you know your market your your customers and the strategy of your product. [42:24] Damn. [42:25] What convinced you eventually to take off and try something different? [42:30] Well, I made the call in that critical case and give the role to someone else and I [42:35] And then once I made that call, I was like, "Well, I gotta go find something. I know that this is my last day, so I'm gonna have to go find something." And it was really interesting because I actually, well, I went through an interview process while I was in my second trimester, and then ultimately, I chose to join Webflow, and I joined when I was literally at the beginning of my third trimester. So I had exactly 90 days before my first son was born. [43:01] That's a great segue to the question I was going to ask is around your 90 day plan that I know you have. You put a lot of thought into how to think about the first 90 days. But before we get there. [43:09] The movie on WeWork with Jared Leto [43:12] how [43:13] Similar to reality was that brought... [43:15] I actually have not watched it. Okay. Parent Life, you like don't have any time. And I do think there's, you know, it's like... [43:22] I feel like if you ask people at Uber if they've watched some of the documentary, they're like, "It's not for me." Same way of like, "Why haven't you watched Silicon Valley?" You're like, "It's a little too close to home." [43:34] Quite a great movie, and I really enjoyed it. [43:36] I'm curious how close it was to realize it. [43:40] Okay, so then back to the 90-day question. So I know you... [43:43] Spent a lot of time thinking about your first 90 days of Webflow. You're pregnant, as you described.

[43:47] And you have a [43:48] perspective on just how to think about the first 90 days when you join a company. [43:51] Can you just share what you've learned there, what you recommend there? [43:54] Yeah, I do think the first 90 days, depending on your role, is very different. But maybe I'll just talk a little bit about the first 90 days as like a header product, right? Because you're like, whoa. Or even just as a leader, like how do you go in? How do you really absorb all the information, get all the contacts you need, and then affect change? And I think what was unique about my first 90 days is it was time bound. It was literally something where you're like, sure, I'd love to absorb information for many months, but I don't... [44:19] I just don't have the luxury of the time. Because you're going to go on mat leave right after. Because, yeah, essentially I was going to go on mat leave. Got it. That's right. And so the biggest things that I thought a lot about for my first 90 days was at the end of the day, yes, you have to really, the most important thing for anyone's first 90 days is to build context and to build context well. But what I had to think about a lot was, well, how do I quickly build context? Probably faster than I would be given the luxury any other time in my life. [44:49] Who do I speak to at the company? [44:52] how do I create like a like a even just like a calendar of like speaking to people yes my leadership team but also like across a bunch of functions and then across a bunch of levels so it's really important for me to like even start talking to some of the engineers from the team some of the engineers who had been there for the longest [45:09] time to really understand, well, what's hard about our tech stack? What's going on? What's hard about your day to day? And so I actually

[45:16] took time to really think about, okay, well, I want to speak to all of these types of people at the company. And I packed my first, like a couple of weeks with like a lot of those meetings. And so I think that was one piece, which is like, how do you build context as quickly as possible? And my tip there is like, again, it's not just with your peers. It's not even just with your team, but to really think across all the different functions and then think about where you're going to get the most amount of information in that particular function. And that was one piece of it. [45:43] The other piece was like, I was like, well, I'm going to be out. I was only out for two months, but I was like, that's still a long period of time in the life of a startup. And so what I, it was really important to me was like, I did not go out having just listened and like, great, like I have the context, I'll see you in two months. But it was really important for me to actually have a plan in place before I went out for my team. And so there were pieces where I was like, okay, I want to first, again, get that lay of the land. I want to have enough of like a strategic [46:10] "Hey, these things make sense, keep going, keep executing. These things don't make sense. Let's identify what those things are and let's actually start to do research around these things so that when I do come back, we have a body of work that we can look at and be like, "Okay, this information, this data is making us choose to go down a path or this is a no-go or no-go decision. We can make that decision now where we couldn't make that decision before." So that was another big piece, which is getting all the strategic pieces in place, [46:37] having a plan laid out and explicitly articulating in that plan keep moving these are things that we got to do a lot a lot more research on and then like assigning people like

[46:46] "Hey, you're gonna do this research, and then we're gonna come back and talk about it in the two months that I was out." And I also took the time, actually, funny story, I think I literally had a board meeting the day before I went in for a checkup, and then in the checkup, they're like, "You're in labor." And it was really important for me to do that, because I was like, I want, for the things that I'm seeing, for the gaps that I'm seeing, I want everyone to be aware. I don't want to just be with one founder. I want the whole leadership team, I want all the founders, I want the board, I want everyone to be aware that, for example, engineering hiring was really, really important. [47:16] I was communicating, "Hey, we are just not staffed in a way where we can deliver some of the ambitious things that we want to do." So explicitly calling those things out and creating awareness around them and then asking other executives to step in and be accountable, those were big pieces of what I wanted to achieve in my first 90 days. [47:34] So I took notes on this. So the first is just get context, figure out who [47:37] you need to talk to. [47:38] Is there a tip there of just like how many people? Because you could do this infinitely, meet everyone eventually. [47:43] How many people did you end up maybe scheduling meetings with? [47:46] Well, definitely everyone on my direct team and definitely everyone in like on the leadership team. So call it those two combined were maybe, I don't know, like 20 or so people, 25 people. But then it was it was really about like finding the people in the other functions. And to me, for any given function is really like getting a read from, again, that leader, but also someone closer to the actual work. And so you kind of like look at the functions, whether it's product marketing or engineering, you know, whatever it was. Back then, I didn't have designs like design and read.

[48:16] getting a couple of data points for each one of those functions. So if you add that up, [48:22] was like 45, 40 to 50 conversations. But again, if you're doing them back to back, and you're really synthesizing, you're actually getting a really good picture of what's going on. [48:34] And then the second bucket was identify things that need to be [48:38] Shifted, changed. [48:39] flagged. [48:40] I imagine there's also an element of trust and building trust. [48:44] Was that a part of this, of how you thought about it? Or do you feel like as a product leader coming in, that's less essential versus like, say, a new PM joining a team as an IC? [48:53] Trust is so important. I mean, trust is everything, right? You know, as a PM, the trust that your cross-functional partners have in you, the trust that the CEO has in you, like, it's huge. Trust is everything. And maybe here I'll even talk about some of the mistakes I made in the first 90 days. I think I was so much like, okay, I only have 90 days. I got to [49:13] "Go, go, go, we gotta go." I was almost pushing too hard. I was pushing too hard for change. I think that's the tricky part, that every product leader, especially if they're coming into a new role, has to figure out, like, how do I gain trust [49:27] and then take that trust and then push for change as opposed to push for change too quickly before i have that trust and so again [49:34] It was a personal learning, and I think [49:37] I think part of it was really driven by the time-bound nature of it. Hopefully, not everyone has only 90 days. So if you take that learning into mind, it's like really thinking about your trust as like a bank. It's like you're putting money into your bank, and then at some point, you're going to take money out. You're going to use that social capital. You're going to use that trust to go push for things, push for change. But you have to be...

[49:58] You have to be thoughtful about how full your piggy bank is. And you don't want to be spending [50:03] you know, when you don't have the trust in the bank. [50:06] What were signs maybe looking back? [50:08] that you didn't necessarily have the trust that you thought you did or you should have had. [50:12] I think something like a product like Webflow is a very complex product and there are so many pieces to it. So it's very difficult to learn the product in a way. [50:22] you know, the first 90 days, especially if I was also prioritizing all these conversations with the team. And so I think that, again, without the time constraint, what I would recommend, right, is to be like, "Hey, every product leader has to take the time to really go deep on the product." Given the complexity of Webflow and given the time-bound nature of what I had to go out, and given the fact that I really also wanted to build that, like, social context around, like, what is working and not working from, like, a... [50:48] functions working together, not just like what the product is. What I wasn't able to do is spend enough time with the product to be able to have the [50:57] all of that in my back pocket to be able to be like, oh, okay, well, like I know how this, this and this works because I've like literally used it. Like, [51:05] a bunch. So you had to choose. And in my head, I was like, I would much rather understand how the team is functioning together. And the reality is the team is comprised of a lot of people with a lot of deep product context. So ultimately, as all things in product, you know this Lenny, like everything's a trade off. And so it's a trade off. And so you kind of have to make the call of what you want to trade off. And the thing I traded off the most was that product context in my first 90 days,

[51:32] And again, it got me some things because I was able to have the time to go deep on the things I mentioned, but it didn't give me enough trust in the piggy bank around the actual like product fundamentals or like product, like the actual thing we're building as opposed to like the discipline. [51:47] So at this point, you've worked at four legendary companies, Dropbox, [51:51] Airbnb, WeWork. [51:53] Webflow. [51:54] If we were to just go through each one, what's just one lesson? [51:58] that you take away from each of these companies in terms of how it's informed either how you build product [52:03] or lead people, anything along those lines. I'm going to actually give you [52:08] - My biggest thing across all four, on the product side, and then on the people side. There are so many nuances also, and you know, we could spend another two hours talking about each one of these, but I think just in part, like my biggest [52:20] high-level learning. On the product side, [52:24] It's really about really understanding why people love you. [52:30] and not forgetting to invest deeply in that, [52:33] core concept and then building everything around that. And so I'll walk you through the different companies. So specifically for Dropbox, I think we did waste cycles where we would be like, oh, we see X happening in the market. Slack is really taking off. Why don't we build a Slack competitor or why don't we build chat? And I think that it really missed this idea of, well, why do people love Dropbox? And what do we need to do to keep investing in that so that that remains true?

[53:03] for how delightful it is, how easy it is to use, right? So, you know, I think we actually went for a period of time where we didn't invest enough in like, just like performance of our client. [53:14] Like how long it takes for the thing to sync is a big part of the experience of using Dropbox, right? And so I think that is like a big, big learning where it's like really understanding that would have shifted your investments into like doing that performance work as opposed to kind of like chasing the competitive space. I think going back to chasing the competitive space, it's this idea of like, [53:34] what is your alpha? Like, again, why do people come to you? You know, people come to Dropbox again, for all the things I mentioned, but also ultimately, like, [53:41] we have your files, right? Like, so if you're going and building a chat product, [53:46] that's fine, but really the best chat experience or like collaboration experience is going to be more around your files as opposed to around just [53:56] the conversation. Right. So I think really understanding that is like a huge, huge learning. [54:01] And I think that same lesson can be, you know, it's very true for Airbnb, right? So at the end of the day, Airbnb is known for, [54:08] like all the homes, the fact that these are homes that real people put on the platform. And we spent some time talking about Airbnb plus when you are thinking like, I got to go in and I got to manage the inventory and inspect it. You're almost like taking away from the thing that is like what makes Airbnb special as opposed to leaning into it. Right. We also spend a lot of time on experiences. We dabbled in transportation. We spent a bunch of times on other things. But if you really sat back and you're like, well, what makes Airbnb special? How do you double down on your strength?

[54:38] the time to make that [54:39] that experience of like really understanding what's in a home so people don't go and get surprised, like making that onboarding journey for the host and then discovery journey and like, you know, like, you know, guest booking journey really, really great. So I think that that same lesson would apply to Airbnb would have in my head like changed the way we invested. I think we would have gotten more returns as opposed to spreading ourselves and then like having things that like sort of work, but then didn't quite work. And then again, same principle applies to WeWork, [55:08] what is the thing that makes you really special? It's the inventory. It's not actually like, oh, it's so amazing that I get to use this key card, and this key card does like 10 different things. That's not what makes the WeWork experience special, right? And so, again, if you knew that, you wouldn't spend all that time being like, I'm gonna really deeply invest in the tech team, I'm gonna do all these interesting things. You'd be like, I just need to make inventory management [55:33] great like i need to make it so that like the sales team the operations team like they have the tools they need to go out and get the inventory on the platform you wouldn't do all this other stuff that's just not the core and then finally like even at webflow we are learning this lesson you know all the time we're like at the end of the day like people really love our designer they love the fact that they can use it it does so much for them it's so powerful and then you add our cms and it's really powerful you design with data so like investing deeply there as opposed to [56:03] I think that that, [56:04] I think across so many companies, this lesson around like, understand why people love you, double down on that. And then whatever else you build around it, because again, you don't want to also be like, you're not like a single product company. You're not like a one trick pony. You are going to invest in these multi products. But when you invest in a new product, really go back to, again, what's the core of our advantage? And how can that be something we leverage and delivering a really great product experience for our users in X adjacent area or X add on?

[56:34] Final question before we get to our very exciting lightning round. [56:37] Okay. What is the best advice that you've gotten? [56:40] that has transformed or impacted the way you [56:43] Build product, or hire, or lead? Does anything come to mind? [56:48] I can't remember where I explicitly got this advice, but I feel like I got it in multiple forms. And it just really sat with me. It's this idea of like asking for help. [56:56] And I do think about that a lot because I think there are so many times when you're like, oh, I'm the leader of X thing. Like everyone's looking to me, like the puck stops to me. [57:05] I need to... [57:06] have I like act together? You know, like I can't be asking for help if I'm asking for help. Like is everyone going to feel like, you know, I don't know what I'm doing. And ever since I've been people managing, I've been pushing myself to be like, I know it feels non-intuitive to go ask for help when everyone is looking for you to give them advice. But if you don't ask for help, there are so many times where you're just going to be sitting there with your problems. And there's like whatever you have in your mind is just not the global best thing. And you have [57:36] partners, your peers, even your team, even being like team, I don't know. I really don't know. [57:41] here's the guidelines, here's how you might wanna think about it, but I don't know the answer, you know the answer. Going out and getting mentorship, I think this idea of really being able to say, [57:50] be honest about what you know and what you don't know and ask for help when you don't know something that's probably the biggest thing that i i hold as like a core principle and and just helps me build better products [58:02] What's something that you've asked for help about recently as an example? So I'm working on our product strategy for the next three years. I'm thinking a lot about how do we really leverage AI to support all of our source writers and support all our users who come into Webflow and have a hard time sometimes learning how to use our product. And so I'm not an expert. So asking for help from

[58:23] the founders, from external folks, from engineers to be like, well, what's happening? Like every single week I feel like LLMs are changing. What's possible in the world is changing. And so constantly asking for help to iterate on the strategy is a huge part of it's happening every day for me and my job. [58:39] Jay-Z, we've reached our very exciting lightning round. I've got six questions for you. Are you ready? [58:44] All right, let's do it. [58:45] What are two or three books that you've most recommended to other people? [58:50] I love the design sprint by Google. I also really like Julie's book around managing people. [58:56] "How to Be a Good Manager," that one's really great. And so those are my, I guess, more business side of the house books. And then we can also talk about fantasy stuff if you want. Yeah, give us some recs there. I'm a big fan of Brandon Sanderson. He completed the Wheel of Time series on behalf of the Prius author. He has the Mistborn series, and so he's a great one. He actually has a... [59:18] During the pandemic, he holed up and wrote a bunch of books. And basically, I have a confession to make. I wrote four extra books. And the latest one is Trust by the Emerald Sea that I really love. [59:32] I saw a video of him sharing that news and he's just like, [59:35] I wrote a book during COVID and then... [59:38] Okay, I wrote a second book and then, oh, I wrote a third book also and it just keeps going. I think he was like, "I have a secret or I have a confession to make." And everyone was like, "Oh, no, are you going to say that you have like a ghostwriter because you're so prolific?" And he's like, "Nope, I just wrote former books." What a beast. [59:53] Next question on that topic a little bit. What's a favorite recent movie or TV show that you watched? I know you said you don't get to watch much, but anything come to mind.

[1:00:01] I feel like every night I'm watching Sesame Street, like, like video, like songs. We don't do, we don't do TV, but we do do YouTube songs. So. [1:00:10] I honestly don't have an answer to that other than like we watched like the Elmo song and the ABC song with three year old. [1:00:17] There's been a lot of parenting advice on this podcast with my child coming soon. [1:00:21] And so this is very on brand. [1:00:23] Before we started this, you mentioned the painting behind you is [1:00:27] referenced in like arcane as it is it's connected to the shark cane which i imagine yes [1:00:32] I'm a big fan. So painted this a long time ago before Jinx and Vi were a thing. And when Arkane was made, both my husband and I were like, what? How did we predict this? This is amazing. So it's a good one. [1:00:45] There we go. Some adult content. [1:00:48] What is a favorite interview question that you like to ask candidates? [1:00:53] I do like to do behavioral questions, just really understanding like when they've been in challenging situations, when they've been in ambiguous situations, like how do they navigate ambiguity is a big one for me. Because at the end of the day, like the PM job is really ambiguous. Like it's really hard to describe on a piece of paper all the things that you're going to encounter. So asking a lot of behavioral questions around around that. [1:01:14] And is there anything specific you look for in their answer that tells you, [1:01:17] this is a good answer or not a good answer. [1:01:20] Yeah, good answers are people who put structure and a way forward through the ambiguity. Like, that's what you look for. Like, you want your PM to not just be like, "Oh no, we're swimming in ambiguity," but like actually put a path forward. I think also looking for people who are like seeking help, seeking those inputs as opposed to being like, "This is the way, this is very clear." Because again, the chances of whatever path you chart out for any product, for anything that you're

[1:01:50] rare and so i want to see someone be able to like get those inputs be able to like say like this is [1:01:55] Learn why you know I put this path together and then going back to a lot of the stuff. I think we touched upon in this this podcast is like What are the little milestones that make you say hey, is this working? Is this not working? And then make you either make a different decision? Seeing people do that really well is a big thing I look for awesome and [1:02:13] What is a favorite product you recently discovered that you love? [1:02:17] I love and it's not recent, but I do love the SNU and it's very top of mind because I just graduated my second son from the SNU and it was [1:02:24] It was a little bit like, oh my gosh, like no more rocking of the baby. But I do think it does a good job of actually doing the thing and also giving parents peace of mind. The other thing I'm a big fan of, again, [1:02:37] you'll see where my head's at, lots of child-related things. Mid-journey for your [1:02:43] toddler is actually great because instead of it being like absolute instant gratification of like I want to see a firetruck and here you go Here's my phone. It's like let's wait for me during to create the firetruck and specifically can even tell me journey what you want It could be like I would like it to be blue and [1:02:57] he's obsessed with jungle book, wearing a fire hat, [1:03:00] next to a fire truck, right? And so you can actually like create and I do believe in the future so much of what we are going to be doing as humans is literally like, [1:03:09] What is the creative process? What's the idea? It's less about like executing all the pieces of it. But it's so important to still be able to be like, I want like this is the idea that I want to bring to life. And so I just think like training that is as huge.

[1:03:24] Feels like you've just defined your three-year strategy for Webflow right there. [1:03:28] with AI. [1:03:29] Next question. [1:03:31] what is something that you've changed in the way you build product that might be relatively minor [1:03:36] that had a big impact on your team's ability to execute. [1:03:40] There's so many different things that we've done at all the different companies. [1:03:45] it really depends on the company. And what I mean by that is like at a company like Webflow where the tech stack is, [1:03:52] complex and where a given feature has so many different interactions, right? You're like, you know, people depend on this workflow. This thing interacts with this thing. It's a whole platform. One of the biggest things we've been tweaking is like, how do we do more of a tech spike at the beginning to be like, do we have a good sense of like how difficult this is going to be? The unknowns, can we get a little bit more detail on them so that we don't go down a path and be like, oh, this doesn't make sense. So I feel like that's like a tweak in the process that has really made a big difference at a company like Webflow. But [1:04:21] When I look back to other companies, again, that might not be your biggest problem. Another problem could be like, hey, it's just like so difficult to work with cross-functional partners and doing a little tweak in the process where you bring them in in a kickoff meeting. That might be the thing that just like changes the dynamic of like how you work with teams. So it's really, I don't know if there's like one thing, but it's almost like every day I'm thinking about small tweaks and process to make all of us more efficient. [1:04:44] Final question, what is your number one pro tip for using Webflow and being successful with Webflow? [1:04:49] My number one pro tip is, you know, there's a lot of stuff coming out that I'm very excited about. I do think, you know, Webflow has traditionally had a high learning curve. And it's because we're a pro tool. We're a professional tool. We can do really amazing stuff. So much power that we deliver you. But with that power, you know, has come with like, it's like hard to learn. And so one of the things that I'm really excited about, pro tip for using Webflow in the future is, you know, we're really going to bring the magic of Webflow University, the magic of AI all together so that you can just use and learn Webflow.

[1:05:19] so much faster. Learn Webflow in the context of what you're doing as opposed to going into a different tab and looking for the Webflow University stuff. It's gonna be in context to the product. Being able to actually, [1:05:30] take action directly, like prompting Webflow to be able to do things for you. Like it's just going to be so much easier in the future to use the product. So that's what I'm excited about. [1:05:38] We're working on it and it will be out in the future. [1:05:41] Okay, no specific dates yet yet you could share. This sounds like breaking news of cool stuff coming. [1:05:46] Some things are in alpha and beta, but we do want to be developing it with our users and really learning, like, is this the power that you're looking for? Is this thing that's going to get you over the activation hump that you've struggled with in the past? [1:06:00] Jay-Z, I think we've made a maximally lovable podcast episode. Thank you so much for being here. Two final questions. [1:06:06] How can listeners find you online if they want to reach out? And how can listeners be useful to you? [1:06:11] Well, I always love feedback, so if there's feedback on the podcast, send it my way. Or even just like, what would you want to learn? Send it my way. And the reason I ask that is because I'm actually working on a course, another course through Reforge, which is around managing your PM career. And so really just, you know, I've talked to so many people. [1:06:28] advice around their career, but if you want to reach out and be like, these are the problems that I'm facing, it would actually really help me [1:06:35] as I am creating this course, which is going to launch in a couple of months. And so I'm excited to find me there if you want to chat more and send the problems you're struggling with when it comes to your career. And that would help me refine my course. [1:06:47] And that's just reforge.com. There's no URL yet specifically for that course.

[1:06:51] Not yet, but it will come soon. And maybe what I'll do is I'll post it on my website, which is built in Webflow. So my full name dot com. [1:06:58] Got it. Jay-Z, thank you so much for being here. And, uh, [1:07:02] Thanks again. [1:07:03] Thanks for having me. [1:07:04] Bye, everyone.