Building minimum lovable products, stories from WeWork and Airbnb, and thriving as a PM | Jiaona Zhang (Webflow, WeWork, Airbnb, Dropbox)

21:55And again, you can't, again, pixie dust, everything that that will just at the end of the day, you know, you basically have like 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 loveability. Shifting to a different topic, I know you have strong opinions about road mapping and OCRs and fertilization, and I know that's a big topic, but let me just ask, what's the most common advice you give around how to road map well, do OCRs, fertilize, and or just like, I don't know, common mantras or things you always come back to to be successful in these areas.

22:40Road mapping and fertilization are kind of one bucket for me, and then, you know, OKRs and other. So I'll maybe give you my biggest tip in each one of these buckets. Right. So for road mapping, my biggest thing that I tell my teams is you're telling a story. So what I want from you is I want themes. I want a story like, why are these things, like 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, right, like everything has like an impact or cost, and you know, an effort column filled out, like they think that that is prioritization, and that is a road map, like if you just do that, right, and then you present that to your team, like they're off to the races, but what people, what humans really crave is like, why am I doing this body of work?

23:31And I think it's also really, really important to have that really crisply articulated in your own head, because ultimately, what happens is you'll 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, and therefore, my thinking change, right? So instead of it being this massive spreadsheet, where you're going in, you're tweaking all the values, what is the story that you're telling about your road map, 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 like maybe we have a lot more like non -technical users.

24:07Well, that input changes my road map and changes my themes in a pretty dramatic way.

24:16So, as opposed to going down to like the really granular details of the how. So that's the biggest thing on road mapping, which is like, tell a story, what are your themes, make it so that your team can come up with the actual like how in the projects and all the little details, but really create that scaffolding for them to know what's important. Can I ask a follow -up question on that? Really, yeah. It's easy to visualize the road map of a spreadsheet to help people visualize what you're suggesting there. What does that actual artifact look like? Is it a dock with maybe a ancillary spreadsheet of the actual fertilization?

24:49Is it a stack? How do you actually deliver this to you with like Jay -Z? Here's our proposal for our team. Yeah, I'm a big kind of docs and decks 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 a tarred because you know, decks typically require a voiceover. And so we have been doing a big push even on my teams where I'm like, write it down in document, force yourself to write the pros because when you write the pros, you can actually add the level of granularity. So very much so like the same way I'm like a road map is a story, you're telling themes like you write a story in a notebook, right?

25:25You write a story on pages and so a dock is definitely preferred and even in the dock just being like, here's what we're trying to achieve. Here are the you know, the big areas I want to invest in here are my big themes and then going into each of those themes and be 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 the systems that your team actually uses. So if your team uses Jura, go ahead and link out to Jura because you know, so often docs get out of or like spreadsheets get out of date, right? Because they're they're like a snapshot of whatever it is that you need it at a point in time.

25:57But if you said you link out to the actual things that your teams are working out of, you can always be like, these are the themes. I will edit these if I find major learn major things that 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. Do you have a template or common structure you suggest to teams for think, link out the story or is it just depends on the quarter depends on the year? I'll give a plug for a new thing coming out and re -forage, which is you know, this concept of like artifacts and so we we do have a lot of artifacts out there.

26:29So like what are what's our general platform process? What are our templates for our specs? What are our templates for some of these things that we're talking about a roadmap of like a broader roadmap is that of just like a feature spec. So yes, we have a ton of those artifacts are always evolving. I think every team kind of takes it and like tweets it a little bit, but I do I'm a big believer of like bring 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 greets us the wheels gets all of our teams kind of speaking the same language.

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27:37You can set reminders if you don't hear back so that you can follow up and never drop the ball on an email thread. You can also work faster than ever before with powerful AI features like writing, editing, summarizing and even translating. 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. Moving to a different topic. Yeah. What is your number one piece of advice to new PMs who want to accelerate their career? What do you find most often is the blocker or thing holding them back or something they can change that'll accelerate things?

28:18There's so many parts to it, but I'll pick one and there are many formats even beyond the one, but let's pick one for your question, which is I think it's really important to become really good at and also known for something. 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 shopperating 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.

28:51You can be known for working on things that are like really regulatory complex like find something that you can be really really good at. And the reason I give that advice is because when you do that, you can crush like the projects that you get right like because you're making a name for yourself reputation and then you're giving more responsibility like people tend to flock and give responsibility to the people that are known for being excellent at something. Is there something you were known to be excellent at in the course of your career? I would say early on my career it was actually the fact that I had like a strong analytics background.

29:25And so when I joined gaming, right, I came from consulting, I didn't have any CS background and so we're designed background. And so it was really like creating reputation around being very analytical around being able to analyze the data sets of my game and then like make decisions. I also learned as I was doing that, I was actually really good 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.

29:58And 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. And so I would find myself trying to lean into that superpower. And then when delivering upon that, getting more responsibility, right, like, hey, you just want this really complex thing at a work cross, like this was a project that had a work cross. I look 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.

30:31You end up getting more responsibility because people are like, oh, she, she's able to do something that was really hard with a small team. And so that's how you get more responsibility. 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 in, finding different ways to bring it to life.

31:09Much of what I just heard is you just worked in Coralby Heart and just got shit done. And so, and I think that's very, very important. And often, I think, I think, you have to get shit done. Yeah, ultimately, you're responsible for the outcome. Just no matter what happens. Yeah, yeah. I like that. Like be known for getting shit done and like working really hard. And that's never going to serve you badly. I think that is just lasting advice for being successful as a pium. I realized that we were talking about your tips on predestination road mapping and then OKRs. And then I shift to topics and you never got to the OKR buckets.

31:45So let me come back to that. Yes. My biggest tip on OKRs is actually get really, really crisp on 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, I don't hit my OKR. I feel like I'm going to have 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 being hesitant to put in numbers until the very last second until they're super, super confident.

32:22And that results in ultimately a failure 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 team. Like, what is the spirit of what you're trying to achieve? And what would make you say, I really, really crushed it this past quarter. Right. And so it's less about like I would rather have all the OKRs be red or yellow and like we missed everything. And we learned around why we missed it than everything to be green. In fact, when everything's green, you're like, we definitely did not set ambitious enough OKRs.

32:58And so it really pushed a lot on like, what does it truly mean to like crush it and be successful? What does it mean for users? What does it mean for business? What does that like for users to feel ex like can you describe that? Can you write that out for our business to see this in terms of, you know, the revenue growth? And I think it's really hard because a lot of times you know, you get your data scientists, you get the PM themselves mean like, oh man, I'm only an input metric and not an output metric. And so like, I definitely can't sign up for that revenue target because I have an input metric and all of those things are true.

33:31But 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 my company and for my users, then a lot of times you end up hitting all your OKRs, but the company and your user at large, you're like, I don't feel anything different. Like your company doesn't look the things that you 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 you're OKRs, you're like, almost like doing OKRs for the sake of OKRs as opposed to letting them be a guide to doing really great product to your end customer.

34:07I like the idea of that. But imagine what often happens is you sign up for an ambitious OKR, you don't wait until the last seconds, I commit to it and then ends up being read and then you go into performance reviews and like, Lenny didn't hit his OKRs. Look at this guy. He's not doing great. How do you think about that as a product leader understanding if the team actually did well and the PM is performing well when they set up sign up for these really ambitious OKRs and their stories 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.

34:45I much harder people take risks than to be safe. So I think that's the first thing. That being said, you know, 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. Like your job is to dream big and also have a plan to go tackle it. And so what I would expect the PM to be able to say is like, this is my North North star. I'm not going to be able to do that in quarter. That just is unreasonable. But here are the five milestones. Yeah, 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.

35:18And 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 shoot for the moon, even for someone to say, like, this is the thing I really want to do. I don't know my path yet. Then to be really, really safe because when you're safe, you're always going to be building something suboptimal. It's going to be some optimal use of your resources as opposed to actually trying to figure out what the best, best swing that you can take is.

35:50So it sounds like it comes back to the story of the roadmap and what they're trying to accomplish and just as long as it feels like the story made sense, there's a path there. The team did their best. I think we knew 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 the PM. Totally. Yeah. Awesome. You mentioned we work and I want to spend a little time on we work. You were at we work for about a year and I think it was like in the middle of a lot of the craziness that went on it, we work. It was, it was a 2019.

36:19I feel like that year, it was either, like headlines were either about Trump or about we work in the news. That's tough. So, okay. So what was that like being a PM leader at a company in that craziness? And is there to take away from that experience that that helps you be a better product manager leader or some? Yeah. I learned a lot from my time there. I think the most important lesson I learned was really around, I think there's like a people leader 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. In fact, you know, what essentially what I was doing was yeah, I built a really, I built a team.

36:59I spent the first six months of my time there actually like growing my team a lot and not just, you know, in the US, but you know, in Asia and in Europe. And then the second half of my time there was actually be like, okay, what do we do? If this is what's happening with we work, what are we actually going to do with all of these people who have like come to we work to work? And there's so many lessons there around leadership around like how do you how do you think about people? How do you think about giving them, you know, the right transition plans, the right like, yeah, it was it was it was a little 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.

37:38And so I was definitely something that I got a crash course on I think before, you know, early. And the the second lesson really was around not overhiring. And so I think that was huge. And I think I personally met lessons 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, it's not something you want to do. And so being really thoughtful around like how do we not over hire? How do we 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.

38:16And then we unlock hiring in xyz ways, like that hygiene is really, really important. Feels like this connects back to the Airbnb plus story of just let's just be really ambitious, where you don't have any idea we're going to get there, but we're just going to go for it. I hear like crazy scale put a lot of investment in this thing and hopefully we'll figure it out. I do think there was a little bit of that in the ethos of how we work with functioning for sure. I think that what was really important for us to do was to be like we have this, I mean, operationally, we work is really strong. In fact, I went to we work because you know, having been at every of these, I was like, I don't feel like we've dialed this operational muscle down, but I know from what I've seen the way we work is expanded that they're really, really excellent at the operations.

38:56But I think it was we 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 are definitely technology that would accelerate that. But do we need it to be super platform aware? Do we need it to be like super futuristic? Like that's actually no, but people care about it. So this all goes back to what are people's core desires and whatever product that they're using, right? Whatever thing that your business trying to serve them.

39:28And 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 could go through we work as opposed to this dedicated space. Like that's still a really good idea. That's still a really big vision and like a relevant vision. But what's the key piece of that vision? The key piece of the vision is around inventory. 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?

40:01So just really understanding again, like you just still dream really big, but you don't have to dream big and higher big and all the things in order to have a very ambitious vision that you deliver to the market. If you think back to we work, what was your favorite memory? And what was your hardest, least happy memory if anything comes to mind? I mean, I think this idea like during really big, like I think everyone who joined we work, they were like, we could do a lot here. Like the idea of really kind of like the physical space and fusing technology. I just feel like the people that we were dreamers and like the best possible way.

40:40So that definitely, I feel like for every company that I've been at, it's really about like, you know, you join, I personally joined for the product, but I say for the people, right? Like you joined because you're like, I want to work on this mission. This product is really motivating. And then you really say for the people. And you know, the people we work were really great. So 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. And I basically was faced with a choice.

41:10It was like, Hey, do I say at we work, I would be guaranteeing 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, and I think there just a last piece of like the thing I was resting 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 don't feel right.

41:42Again, 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 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 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 empathy and like people.

42:17It's as much of that as it is about as it's about like understanding, you know, your market, your customer is in the strategy of your product. Damn. What convinced you eventually to take off and try some different? Well, I made the call in that particular case and give the role to someone else. And and then once I made that call, I was like, well, I got to go find something like I, you know, I know that this is my last day. So I'm going to have to go find something. And it was really interesting because I actually, well, I went through an interview process. Well, I was in my second trimester. And then ultimately chose to join a web flow.

42:53And 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. 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, the movie on we work with Jared Leto, how similar to reality was that brought? I actually have not watched it. Okay. parent life you like don't have any time. And I do think there was, you know, it's like I feel like if you ask, you know, people at Uber, they've watched some of the time where they're like, uh, it's like, I don't, it's not for me.

43:29Same way of like why haven't watched Silicon Valley? You like, it's a little too close to home. Yeah. Well, it was, it was quite a great movie. And I really enjoyed it. Okay. I'm curious. I'm curious how close it was to realize. Okay. So then back to the 90 day question. So I know you spent a lot of time thinking about your first 90 days of Webflow, your pregnant as you described. Any of a perspective on just how to think about the first 90 days when you join a company. Can you just share what you've learned there? What you recommend there? Yeah. I do think the first 90 days, depending on your role is very different.

43:58But I, well, maybe I'll just talk a little bit about the first 90 days is 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, like, I just don't have the luxury of the time. And so because you're going to go out and mat leave right after. Because yeah, essentially, I was going to go out and mat leave.

44:25Okay. And so the biggest things that, you know, I thought a lot about for my first 90 days was at the end of the day, yes, you have to read like the most important thing for anyone's first 90 days is to build context and to build context well. But when I had to think about a lot was, well, how do I quickly build context, probably like faster than I would be given the luxury, you know, any other time in my life. And so I thought a lot about who do I speak to at the company? 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 function and then across a bunch of levels.

45:02So it was 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 time to really understand, well, what's hard about our tech stack? Like what's going on? Like what's hard about your day to day? And so I actually took time to really think about, okay, I want to speak to all of these types of people at the company. And I packed my first, like a couple 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.

45:32It'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 information in that particular function. And that was one piece of it. 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.

46:03And so there are 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, hey, these things make sense. Keep going, keep executing. These things like don't make sense. Let's get the like, 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 the 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.

46:34So that was another big piece, which is like getting all the strategic pieces in place, having a plan laid out and explicitly articulating in that plan, keep moving. These are things that we got to do a lot more research on. And then like assigning people like, okay, you're going to do this research. And then we're going to come back and talk about it in, you know, the two months that I was out. And I also, you know, took the time. I 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, you know, for the things that I'm seeing, for the gaps that I'm seeing, I want everyone to be aware.

47:06I don't want it to just like 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 like, for example, engineering hiring was really really important. And I was, you know, I was communicating, hey, we are just not staff in a way where we can deliver some of the ambitious things that we want to do. And so it explicitly calling those things out and creating awareness around them and then asking other executives, right, to like step in and be accountable. Those are big pieces of what I wanted to achieve in my first 90 days.

47:34So I take notes on this. So the first is just get context, figure out who you need to talk to. Is there a tip there of just like how many people because you could do this infinitely meet everyone eventually? How many people did you end up maybe scheduling meetings with? Well, definitely everyone on my direct team and definitely everyone in like on the leadership team, so call it, but 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 and 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.

48:08And 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 really getting a couple of data points for each one of those functions. So if you add that up, that probably, you know, was like 45 40 to 50 like conversations. But again, if you're 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. And then the second book was identify things that need to be shifted, changed, flagged. I imagine there's also an element of trust and building trust.

48:43Was 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, I knew PM joining it. I team a team as an IC. Trust is so important. I mean, trust is is everything, right? You know, as a PM, you're the trust that your cross -functional partners have in you. The trust that the, you know, the CEO has in you, like it's it's huge. Trust is everything. And I maybe hear all even talk about some of the mistakes I made in the first 90 days. I think I was so much like, okay, only have 90 days. I got to, you know, go, go, go, we got to go.

49:15I was almost pushing too hard. I was pushing too hard for change. I think that's that's the tricky part that every product leader, especially if they're coming into a new role, has to figure like, how do I gain trust? 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, it was it was a personal learning. And I think, you know, I think part of it was really driven by this time -bound nature of it. But if you, if you, you know, 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, right?

49:49It'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, you have to be thoughtful about how full your piggy bank is. And you don't want to be spending, you know, when you don't have the trust in the bank. What were signs maybe looking back that you didn't necessarily have the trust that you thought you did or you should have had? I think something like, you know, a product like Waffle is a very complex product. And there are so many pieces to it.

50:18So it's, you know, it's very difficult to learn the product in, you know, for sunny 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 is to be like, hey, every product leader has to take the time to really go deep on the product, given the complexity of Waffle and given the time bound in nature of what I had to go out. And given the fact I really also wanted to build that like social context around like what is working and not working from like functions working together, not just like what the product is.

50:52What I wasn't able to do is spend enough time with the product to be able to have 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 a bunch. So like 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 like the team was comprised of a lot of people with a lot of deep product context. So ultimately, you know, as all things in product, you know, this line, like everything's a trade off. And so it's a trade off. And so you know, you kind of had to make the call of what you wanted to trade off.

51:27And the thing I traded off, the most was that that product context in my first 90 days. 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. So at this point, you've worked it for legendary companies, Dropbox, Airbnb, WeWork, WePlow. If we were to just go through each one, what's just one lesson that you take away from each of these companies in terms of how it's informed either how you build product or lead people anything along those lines?

52:06I'm going to actually give you 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 to impart like my biggest high level learning on the product side, it's really about really understanding why people love you. But not forgetting to invest deeply in that 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.

52:45Like Slack is really taking off. Why don't we build like a Slack competitor or like why don't we build chat? And I think that it really missed this idea of like, well, why do people love Dropbox? And what do we need to do to keep investing in that? So that remains true. People love Dropbox for simplicity 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. Like how long it takes for the thing to sink 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.

53:31And I think going back to chasing the competitive space is this idea of like, what is your alpha? Like again, why do people come to you? You know, people come to Dropbox again for all things I mentioned, but also ultimately like we have your files, right? Like so if you're going and building a chat product, that's fine, but really that the best chat experience or like collaboration experience is going to be more around your files as opposed to around just the conversation, right? So I think really understanding that is like a huge, huge learning. And I think that same lesson can be, you know, it's very true for Airbnb, right?

54:05So at the end of the day, Airbnb is known for like all the homes, the fact that these are homes that real people put on the platform. And we spend some time talking about Airbnb plus when you are thinking like, I got to go in, I got to manage the inventory, I'd inspect it, you're you're almost like taking away from the thing that is like what makes Airbnb special as opposed to re -earning 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 and how do you double down on your strength, it's like spending the time to make that that experience of like really understanding what's in a home so people don't go and get surprised, like making that, you know, onboarding journey for the host and then discovery journey and like, you know, like, you know, guest booking journey, really, really great.

54:51So I think that that same lesson when I applied to Airbnb would have in my head like changed the way we invested. And 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 say again, same principle applies so to we work. What is the thing that makes you really special, it's the inventory, it like 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, like that's not what makes the the we work experience special, right?

55:23And so again, if you knew that, you wouldn't spend all that time being like, I'm going to really deeply invest in the tech team and I'm going to do all these interesting things. You'd be like, I just need to make inventory management great. Like I need I need to make it so that like the sales team, that 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. It's just not the core. And then finally, like even at webflow, we are learning this lesson, you know, all the time, where we're like, at the end of the day, like, people really love our designer.

55:51They love the fact that they can use it. It does so much for them. It's so powerful. And then you can add our CMS. And it's really powerful. You can design with data. So like investing deeply there as opposed to spreading ourselves to thin is also a lesson. So I think that that 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, 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.

56:19But 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 deliver delivering a really great product experience for our users in X adjacent area or X add on. Final question before we get to our very exciting lightning round. Okay. What is the best advice that you've gotten that is transformed or impacted the way you build product or hire or lead? Is anything come to mind? I can't remember where I explicitly got this advice, but I feel like I got in multiple forms. And I just really sat with me as this idea of like asking for help.

56:56And 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 clock stops in the I need to have I like act together. You know, like I can't be asking for help if I'm asking for help. Like do everyone that 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 not intuitive to go ask for help when everyone is looking to 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.

57:28And there's like whatever you have in your mind is just not the global best thing. And you have to go ask for help. You have to go ask for help from your partners, your peers, even your team, even being like team, I don't know. Like I really don't know. Like here's the guidelines. Like here's how you might want to think about it. But like I don't the answer, you know the answer. Going out and getting mentorship. Like I think this idea of like really being able to say like, 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 hold as like a core principle and just helps me build better products.

58:02What'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 resource fighters 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 the founders, from external folks, from engineers to be like, well, what's happening? Like every single week, I feel like LMs are changing. But it's possible in the world is changing. And so constantly asking for help to iterate on the strategy is a huge part of the happening every day for me and my job.

58:39Jay Z, we've reached our very exciting lightning round. I've got six questions for you. Are you ready? All right, let's do it. What are two or three books that you've most recommended to other people? I love the design sprint by Google. I also really like Julie's book around managing people. How to be like a good manager. That one's really great. And so those are those are my, I guess like more like business side of the house books. And then you know, we can also talk about like fantasy stuff if you want. But yeah, give us some give us some wrecks there. I'm a big fan of Brandon Sanderson. He completed the Wheel of Time series on behalf of the Prius author.

59:14He, you know, he has the Missborn series. And so he's a great one. He actually has this during the pandemic. He like hold up and like wrote a bunch of books. And this was like, I have a question to make or I wrote, I wrote like four extra books. And the latest one is that trust by the emerald sea that I really love. I saw the video of him sharing that news. And he's just like, I wrote a book during COVID. And then, okay, I wrote a second book. And then, oh, I wrote a third book also. Just keep 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 ghost writer because you're so prolific?

59:49And he's like, no, I just wrote former books. What a beast. Next question on that topic a little bit. What's a favorite recent movie or TV show that you watch? I know you said you don't want to get to watch much, but anything comes to mind. I feel like every night I'm watching Sesame Street like video like songs. We don't do it down to TV, but we do do YouTube songs. So I honestly don't have a answer to that other than like we watched like the Elmo song and the ABC song with three year old. There's been a lot of parenting advice on this podcast with my child coming soon. And so this is very on brand.

1:00:24Before we started this, you mentioned the painting behind you's reference in like arcane is a, it's connected to the sharkane, which I imagine. Yes. I am a big, yeah, I'm a big fan. So painted this a long time ago before Jigs and Vi were a thing. And you know, when arcane was made, both my husband and I were like, what? How did we predict this? It's amazing. So it's a good one. There we go. Some adult content. What is a favorite interview question that you like to ask candidates? I do like to do behavioral questions is really understanding like when they've been in challenging situations when they've been in ambiguous situations.

1:01:00Like 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. And is there anything specific you look for in their answer that tells you this is a good answer or not a good answer? 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.

1:01:33I 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 doing is like the right path from the first time that you do it so rare. And so I want to see someone be able to like get those inputs, be able to like say, like, this is the path. This is how I like 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 podcast is like, what are the little milestones that make you say, hey, it's just working.

1:02:05Is this not working? And then make you either make a different decision, seeing people do that really well. It's a big thing I look for. Awesome. What is a favorite product you recently discovered that you love? I love, I mean, it's not recent, but I do love the snow. And it's very top of mind because I just graduated my second son from the snow. And it was, it was a little bit like, oh my gosh, like no more rocking of the baby. But I do think it, it doesn't good job of like actually doing the thing. And I'm also giving parents peace of mind. The other thing, a big fan of again, you'll see where my heads at, lots of child chill, like related things.

1:02:41I'm mid -journey for your toddler is actually great because instead of it being like absolute instant gratification of like, I want to see a fire truck. And here you go. Here's my phone. It's like, let's wait for mid -journey to create the fire truck and specifically can even tell mid -journey what you want. It could be like, I would like it to be blue. He's obsessed with jungle book wearing a fire hat 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, what is the creative process?

1:03:10What'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. It feels like you've just defined your three -year strategy for what flow right there. With AI. Next question, what is something that you've changed in the way you built product that might be relatively minor that had a big impact in your team's ability to execute? There's so many different things that we've done. All the different companies, it really depends on the company.

1:03:47And what I mean by that is like at a company like Webflow where the tech stack is complex and where a given feature has so many different interactions where you're like, I, 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.

1:04:15That's like a tweak in the process that has really made a big difference at a company like Webflow. But 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 press 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.

1:04:44Final question. What is your number one pro tip for using Webflow and being successful with Webflow? 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, it 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 so much faster.

1:05:20Learn Webflow in the context of what you're doing is going into a different tab and like looking for like the Webflow University stuff to be in context to the product, being able to actually like 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. We're working on it and it will be out in the future. Okay, no specific dates yet. Yeah, you could share. And this sounds like breaking news of cool stuff coming. Something's are in, you know, 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?

1:05:55Is this thing that's going to get you over the activation hump that you've struggled with in the past? Jay Z, I think we've made a maximally lovable podcast episode. Thank you so much for being here. Two final questions. How can listeners find you online if they want to reach out? And how can listeners be useful to you? Well, I always love feedback. So there's feedback on the podcast, send it my way. Or like you were even just like, what would you want to learn? Send it my way. And the reason I asked that is because I'm actually working on a course. Another course through ReForage, which is around managing your PM career.

1:06:25And so really just, you know, I've talked to so many people 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 as I am creating this course, which is going to launch in a couple months. And so I'm excited to find me there if you want to chat more and send the problems that you're struggling with when it comes to your career. And that would help me refine my course. And that's just ReForage .com. There's no you're all yet specifically for that course. Not yet, but it will come soon. And what maybe I'll do is I'll put it on my website, which is built in Webflow.

1:06:56So my full name .com. Got it. Jay Z, thank you so much for being here. And thanks again. Thanks for having me. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple podcasts, Spotify or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's Podcast .com. See you in the next episode.