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

1. 0:00 – 4:22

   JZ’s background

   1. JZJiaona Zhang0:00

      I think it's really important to become really good at and also known for something. 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 when you do that, you can crush, like, the projects that you get because you're, 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.

   2. LRLenny Rachitsky0:40

      (intro music plays) 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. Today my guest is JZ. JZ 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 JZ 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 JZ's biggest product mistake. We cover the concept of minimal lovable products versus minimal viable products. We talk about JZ's unique frameworks for road mapping 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 JZ on the podcast for a while, and I'm really happy that we finally made this happen. With that, I bring you JZ after a short word from our sponsors. Today's episode is brought to you by Brave Search and their newest product, the Brave Search API, an independent global search index you can use to power your search or AI apps. If your work involves AI, then you know how important new data is to train your LLMs and to power your AI applications. You might be building an incredible AI product, but if you're using the same datasets as your competitors to train your models, you don't have much of an advantage. Brave Search is the fastest growing search engine since Bing, and it's 100% independent from the big tech companies. Its index features billions of pages of high-quality data from real humans, and it's constantly updated thanks to being the default search engine in the Brave browser. If you're building products with search capabilities, you're probably experiencing soaring API costs or a lack of viable global alternatives to Bing or Google. It's only gonna become harder to afford these challenges. The Brave Search API gives you access to its novel web-scale data with competitive features, intuitive structuring, and affordable costs. AI devs will particularly benefit from data containing thorough coverage of recent events. Lenny's Podcast listeners can get started testing the API for free at brave.com/lenny. That's brave.com/lenny. Today's episode is brought to you by Miro, an online collaborative whiteboard that's designed specifically for teams like yours. The best way to see what Miro's all about and how it can help your team collaborate better is not to listen to me talk about it, but to go check it out for yourself. Go to miro.com/lenny. With the help of the Miro team, I created a super cool Miro board with two of my own favorite templates, my one-pager template and my managing up template, that you can plug in play and start using immediately with your team. I've also embedded a handful of my favorite templates that other people have 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 creating my own board, and it was super fun and super easy. Go check it out at miro.com/lenny. That's M-I-R-o.com/lenny.

2. 4:22 – 6:44

   Common mistakes new PMs make

   1. LRLenny Rachitsky4:22

      JZ, welcome to the podcast.

   2. JZJiaona Zhang4:24

      Thanks for having me. I'm so excited to be here.

   3. LRLenny Rachitsky4:26

      It's 100% my pleasure. Amongst your many accomplishments, you teach product management at Stanford, which sounds very fancy. How long have you been doing this at this point?

   4. JZJiaona Zhang4:37

      I think six years. Yeah, wow.

   5. LRLenny Rachitsky4:40

      Okay. So my question, the real question I want to ask about this is, in that time you've seen a lot of new PMs and you've seen these PMs succeed, you've seen some fail. What are the most common mistakes that you find new PMs make in this experience of kind of helping new PMs get into the field?

   6. JZJiaona Zhang4:56

      I think something that is really hard to untrain, but I think every human does it, is you jump to solutions. 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 you get really attached to a solution, a way of implementing something, something that you, you, you can see in your head that you want to build. And so that's the first thing I really want to, like, unteach in, 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, you know, this thing," or, "I, I'm in blank school and I've been doing a lot of research on this particular area." And so, like, untraining that and being like, "Hey, we're gonna go out there. We are not gonna think at all about the thing that you want to build, but instead we're going to be focused on users and pe- Like, people in the real world and their problems." And the first step is to understand their problems and then to 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.

   7. LRLenny Rachitsky5:55

      Does a lot of this come from people want to get into product management because they think, like, "Finally I'll have the power"?... finally I'll be able to tell people what to build. Finally, my ideas are really gonna matter." Is that where a lot of it, a lot of it comes from?

   8. JZJiaona Zhang6:06

      I think there's a part of that. You know, one of the, the first things I teach is, you know, you're not a CEO. You're, 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, 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, and then you're kind of pooling together all the different possibilities, and you're really editing. So, 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.

3. 6:44 – 10:51

   Why Airbnb Plus didn’t work out, and takeaways from that experience

   1. JZJiaona Zhang6:44

   2. LRLenny Rachitsky6:44

      So let's kind of go to the other side of this question. We talked about what mistakes new PMs make. I'm curious, what's the biggest product mistake that you've made?

   3. JZJiaona Zhang6:53

      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, I'll give an example from Airbnb-

   4. LRLenny Rachitsky7:01

      Perfect.

   5. JZJiaona Zhang7:01

      ... since you and I were both there. And, and this one does stand out to me. So, you know, we were working on this concept called Airbnb Plus. You know, if you took a step back, what we were really trying to do is to be like, hey, not everyone trusts Airbnb in terms of... You know, it, it's, 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 we're, like, all the Airbnbs are meeting the quality bar? But I do think we were very solution first, and I think we were a- also competitor afraid at the time, right? So it was during a time where there were managed marketplaces. There were the, the Saunders out there, and I think that as a, as a company, we're very much like, oh goodness, like what's, what are we gonna 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 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 is your 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. Is, is, are the unit economics actually going to work even as you scale?

   6. LRLenny Rachitsky8:22

      Yeah. I feel like Airbnb Plus is an untold story that somebody should tell and that could be its own podcast, I guess.

   7. JZJiaona Zhang8:28

      You and I can tell it. (laughs)

   8. LRLenny Rachitsky8:30

      We could tell, this could be Airbnb Plus, the hidden, the story. As you said, the problem it was trying to solve was people don't really trust. They don't want to even consider Airbnb 'cause 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." And so as an outsider, it felt like a really clever approach. Like we're gonna vet them, we're gonna make sure they're awesome. There's a minimum bar. I think the, and I guess this is the question is do you think it was just like this is never possible because there will... We'll never make money as a business doing this 'cause we don't make that much per booking. And investing time, resources, sending people, pillows, all that stuff is ever gonna be economical? Or do you think there was a path and it was just not executed well?

   9. JZJiaona Zhang9:10

      I, I think there wasn't really a, a clear path. I, I think it was less about execution-

   10. LRLenny Rachitsky9:14

       Yeah. That's my impression.

   11. JZJiaona Zhang9:14

       ... exactly. And it's more just like if you understood... Again, this is what my point around unit economics. 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, it's all gonna work out. We can make these things happen." I think you actually need to really make sure the unit economics work right at the beginning. So that is definitely one lesson. And I think the other thing is aga- and going back to spirit of what are you trying to achieve? If, if you're trying to achieve this idea of like really knowing the quality of the place and, 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 that the other things are if you can get signal on what are the things around quality that people care about? Is it cleaner, uh, cleaning? Is it, is it the, uh, "Hey, I'm, I'm locked out," and I think that there are other solutions besides inspection that then get at that. So for example, it is actually cheaper to go send everyone a lockbox than to deploy an inspector (laughs) 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 know, that you're looking at? And so I, yeah, I, I personally don't believe the unit economics ever would have really worked out. I think we should have known that, or we should have, uh, dug into that more at the very beginning. And then to get very tailored instead of like one blunt instrument to solve it all, "Hey, we're gonna go inspect." It's like, "What is the problem for this listing, and what's the best solution to fix that

4. 10:51 – 13:45

   Executing big dreams step-by-step

   1. JZJiaona Zhang10:51

      problem?"

   2. LRLenny Rachitsky10:51

      There's a couple things that I think are important product leadership lessons here. One is Airbnb and Brian and many great leaders are famous for imagining the ideal situation, imagining the great end result, and then working backwards. And often, that leads to great results when you're being really ambitious, and I don't know how we're gonna get there. We're just gonna shoot, shoot big, and hopefully we figure it out. Sometimes it works out. In this case, it didn't work out. And what you're finding, maybe you even knew this early on, is just like there's no possible world where this could have worked in this approach. I guess is there anything you've learned about just like when to think big and not even like, "Forget it. We're gonna figure it out. I know this seems impossible, but we're just gonna try it anyway." Do you have any kind of framework of when to think big like that and just go for it-

   3. JZJiaona Zhang11:38

      Yeah.

   4. LRLenny Rachitsky11:38

      ... versus, "Oh, let's just work out the math today. Is this ever possible?"

   5. JZJiaona Zhang11:42

      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, for you to innovate. But, eh, you got to couple that really big vision with thoughtfulness around your execution, right? And so I think one of the biggest tips I have is how do you just be very...... how to be clear about th- the phase that you're in. So, I think it's totally fine to be like, "Hey, we are going to try X for six months, three months." You know, whatever it is. And, "We're es- ex- explicitly going to go learn these types of things. We're gonna learn why are people..." Like, like, "Are there signals that we would get that would indicate that the, again, the communication with the host isn't great?" Or, you know, this type of listing, if you, if, if it's hosted by a person with multiple property. Like, I think there are factors where you can 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, in that early phase, to go learn those lessons. But you just have to be very, very clear with your team on, like, what phase you're in. "Hey, we're in the learning phase, and we s- explicitly are trying to learn these things," versus, "Hey, we, we have this really big vision, and we're just gonna, you know, kind of go at it." Like that is not, um, recommended in my mind. It's like breaking it down into these smaller chunks. That, 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 gonna work out." L- we ran at it for, you know, a short period of time, we got these learnings, now let's go down this other path.

   6. LRLenny Rachitsky13:11

      Yeah. There's also, like, some cost fallacy that kicks in of just, like, ugh, we spend so much time and money and resources on this thing-

   7. JZJiaona Zhang13:17

      (laughs) .

   8. LRLenny Rachitsky13:17

      ... let's just go a little bit longer. Let's just see. If we give it another quarter, maybe it'll work out.

   9. JZJiaona Zhang13:21

      You should articulate what success looks like and the milestones you wanna 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 w- we gotta cut it." It's like, what is the quarter-long milestone? Okay, what's the next quarter-long milestone? And every single point, and what is a go and no-go? And I think that really can help a team and a company say, "It's okay I invested a quarter in it, but I didn't invest

5. 13:45 – 16:54

   The right way to push back against founders

   1. JZJiaona Zhang13:45

      two years."

   2. LRLenny Rachitsky13:46

      The other important lesson here is about the importance of, as a product leader, pushing back and convincing leadership that you're wrong and this shouldn't happen. I remember talking to one of our colleagues, Mike Lewis, who was leading a different team within Airbnb, and he was just like, "Oh, I realized I'm the person that should be saying, 'No, we shouldn't do this now.'" 'Cause he was, like, the head of product for one of the new bets.

   3. JZJiaona Zhang14:10

      Yeah.

   4. LRLenny Rachitsky14:10

      And I know maybe in that situation it was impossible, because Brian was very into this and everyone was like, "We need to do this thing." I guess, is there anything you've learned about how to push back on these sorts of things that the founder's really into, when it makes sense to kind of go along and like, "Cool, let's do it. Let's buy in. We gotta..." You know, as a leader, you have to be excited and the team needs to feel like, oh, JZ is really excited about this, too. We gotta try it. Even though maybe you feel like it's not gonna work out. So, I guess the question is, like, when do you think it makes sense to try to, like, convince the founder, "No, this is a bad idea," versus, like, "Let's go for it"?

   5. JZJiaona Zhang14:42

      I think first it comes down to your conviction. Like, do you actually have conviction that this is a bad idea, or are you still, 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, you really, like, if you do not, like, you're not doing your job. And, and then, it, that, 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? Being able to go back with, "Hey, I understand the spirit. The spirit is that we're trying to get people, you know, who previously didn't con- consider Airbnb before to, like, come and, like, use Airbnb. But the right way to do it is not this very time-intensive, cost-intensive way to, to, you know, 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? Like, and like, more checks in, in that. And, and that could be automated and through technology as opposed to through humans. It's coming back with, like, actual options. It's like saying, I, 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 gonna work." And I explicitly, you know, moved off the team, and I was like, "I am going to work on the review system. I'm gonna 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 process." And so, I think the, the biggest thing, the biggest tip I would have for, 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... W- what is it that they're trying to accomplish for the user and for the business? Remind them of that. Like, get, 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 wanna just do the right thing for their users. When you come back with a much better solution and you have the data and you have the thinking behind it, it's very rare that someone will be like, "Well, I still wanna go after this solution despite the fact (laughs) that it's not working, and you've proposed a much better path forward."

   6. LRLenny Rachitsky16:38

      And I think to touch on what you've alre- already said is also make sure it's, like, actually there's a world where this could work. Like, do some math to figure out if this is a business that will actually make some money in the future.

   7. JZJiaona Zhang16:49

      Totally.

   8. LRLenny Rachitsky16:50

      Okay, I'm gonna bounce around a little bit. I have a bunch of different questions around different topics.

6. 16:54 – 20:53

   Minimum lovable product vs. minimum viable product

   1. LRLenny Rachitsky16:54

   2. JZJiaona Zhang16:54

      Yeah.

   3. LRLenny Rachitsky16:54

      You popularized this concept of minimal lovable product versus this idea that everyone always comes back to, which is minimal viable product. Can you just talk about what is a minimal lovable product, and then when does it make sense to kind of go in that direction versus a traditional MVP?

   4. JZJiaona Zhang17:10

      The reason I care so much about minimal lovable 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. It 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, that, that resonates with your users? A- and again, especially in a world where there might be a lot of different options, like, minimal lovable product is the new (laughs) MVP, right? The new, uh, minimal viable product. So I think that's, that's the, 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, you're replacing, is literally, like, a manual workflow. It's, like, spreadsheets, it's doing something in a super terrible way, so you wanna get your product to market as quickly as possible, right? So it doesn't make sense for you to be like, "I'm gonna build these, like, 15 additional features," because compared to what-... you know, people are doing right now. Your product without those 15 additional features is perfectly fine, perfectly usable and, and, and perfectly, quite honestly, like, lovable. So it, it requires a lot of understanding of like, again, your users and th- the space that you play in, and the tolerance of, 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. But you know, again, someone sitting on the finance team or the IT team, right? Like their, their, their bar might be like, "Oh, I'm used to doing these like 15 things." And so your thing is just a lot better.

   5. LRLenny Rachitsky18:53

      I'd love to go even one level deeper. Is there an example of something you've worked on that was a minimal lovable product that you think about? Or is there something out there that's an example of like, here's maybe an example of a minimal lovable product versus MVP?

   6. JZJiaona Zhang19:07

      A- 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, is difficult, and not to mention-

   7. LRLenny Rachitsky19:17

      Yeah.

   8. JZJiaona Zhang19:17

      ... like minimal lovable. I'll give a Webflow example. Uh, very recently, you know, we, we... So we have been investing in a couple of new features, um, 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 in a way that our users really, really want." And so does it make sense for us to continue to go down this path of like keep... Like continuously ship away to, to, to get to minimal lovable when we are maybe hitting diminishing returns for our 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, it's not just like you, 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? Or kind of where in between are we, right? And so having that point of view and then being able to say, "Are we gonna be able to meet as a company or are we going to rely on our ecosystem to help us meet it? What are we actually going to do?" And then, and then even within the feature set, it's, it's very much a- a 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 again, you know, 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, in 15 areas.

7. 20:53 – 22:20

   What makes a product lovable

   1. JZJiaona Zhang20:53

   2. LRLenny Rachitsky20:53

      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 what are things you've seen that makes something lovable? Is it like delightful features? It... 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.

   3. JZJiaona Zhang21:08

      There's definitely this idea of like the thing is, is just good. It has like all... Like it is, uh, high quality, it's not janky, 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 s- feels small, but like that is a piece that creates a lot of love, love from user base who are power users. And then there's this concept of like pixie dust, uh, that maybe I'll pull out of, you know, call it like design tool space and we'll, we'll talk about some of the other things, w- whether it's Dropbox or Airbnb. But you can just do a little bit of that like extra pixie dust. And so an example from Airbnb when we were doing the mobile app revamp, we were like, okay, there's like these basic table stakes, but if we actually added in templates and we, and we made it so that these templates could be maybe pre- pre-populated in certain ways from the content they 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... Again, you can't pixie dust everything. That, that will just... At the end of the day, um, you know, you basically have like your, 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 gonna push out your launch timeline. But can you pick a few different areas where you're like, "I'm gonna scatter that pixie dust. I'm gonna do a little bit more than what users are expecting," and that creates that lovability.

8. 22:20 – 28:04

   Advice on roadmapping and prioritization

   1. JZJiaona Zhang22:20

   2. LRLenny Rachitsky22:20

      Shifting to a different topic. 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, what's the most common advice you give around how to roadmap well, do OKR prioritize, and/or just like, I don't know, common mantras or things you always come back to to be successful in these areas?

   3. JZJiaona Zhang22:40

      Roadmapping and prioritization are kind of one bucket for me, and then, you know, OKR is another. So I'll, I'll maybe give you my biggest tip in each one of these buckets.

   4. LRLenny Rachitsky22:46

      Great.

   5. JZJiaona Zhang22:46

      So for roadmapping, 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, like why are these are thing, 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 roadmapping is people thinking like a spreadsheet with a bunch of projects, all, uh, you know, the RICE framework, right? Like everything has like an impact, a cost, and you know, a, a... like an effort column filled out. Like they think that, that is prioritization and that is a roadmap. 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?" And I think it- 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, and therefore my, my, my thinking changed," 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 roadmap that these inputs can then go and im- im- influence? It could be like, "Hey, I just realized I didn't know before that we have a lot more power users on our..." Or like, "Maybe we have a lot more like non-technical users." Well, that input changes my roadmap and changes my themes in a pretty dramatic way. So skating that at that level is really, really critical I think for a roadmap as opposed to going down to like the really granular details of the how. So that, that's the biggest thing on, on roadmapping, which is like tell a story, what are your themes? Make it so that your team can come, come up with the actual like how and the projects and all of the little details, but really create that scaffolding for them to know what's important.

   6. LRLenny Rachitsky24:33

      Can I ask a follow-up question on that?

   7. JZJiaona Zhang24:35

      Totally, yeah.

   8. LRLenny Rachitsky24:36

      It's easy to visualize the roadmap of a spreadsheet. To help people visualize what you're suggesting there, what does that actual artifact look like? Is it a doc with maybe an ancillary spreadsheet of the actual prioritization? Is it a deck? How do you actually deliver this to you with like, "JZ, here's our proposal for our team?"

   9. JZJiaona Zhang24:55

      Yeah. I'm a big fan 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, uh, cultures, it's- it's hard, 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 and document. Force yourself to write the pros, because when you write the pros, you can actually l- 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 a notebook, right? You write a sn- you write s- a story on pages. And so a doc is definitely preferred. And even in the doc 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 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, and the, the systems that your team actually uses. So if your team uses Jira, go ahead and link out to Jira, 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 needed at that point in time. But e- if instead 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 s- if I major, you know, learn major things that would change my themes." And then let's go link out to the Jira where you can just see the snapshot of the roadmap at any given point in time.

   10. LRLenny Rachitsky26:12

       Do you have a template or common structure you suggest to teams for f- think laying out the story? Or is it just depends on the quarter, depends on the year?

   11. JZJiaona Zhang26:21

       I'll give a plug for a, a new thing coming out of Reforge, which is, you know, this concept of like artifacts. And so we- we do have a lot of artifacts out there, so like what are- 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, uh, like a broader roadmap instead of just like a feature spec. So yes, we have a ton of those artifacts, they'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 and gets all of our teams kind of speaking the same language.

   12. LRLenny Rachitsky26:58

       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. Superhuman is blazingly 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 saved 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 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/lenny. That's superhuman.com/lenny. Moving to a different topic.

9. 28:04 – 29:16

   Tips for new PMs to accelerate their career

   1. LRLenny Rachitsky28:04

   2. JZJiaona Zhang28:04

      Yeah.

   3. LRLenny Rachitsky28:05

      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?

   4. JZJiaona Zhang28:18

      There's so many parts to it, but I'll pick one, um, and there are many frameworks 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 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 regulatorily, uh, 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- you're making a name for yourself, a reputation, and then you're given more responsibility. Like people tend to flock and give responsibility to the people that are known for being excellent at something.

10. 29:16 – 31:37

    JZ’s top skills and how they have evolved over her career

    1. LRLenny Rachitsky29:16

       Is there something you were known to be excellent at in the course of your career?

    2. JZJiaona Zhang29:20

       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, uh, and so... Or- or design background, and so it was really like creating reputation around being very analytical, around being able to analyze the datasets of my game and then like make decisions. 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- 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- and make sure that we, like, hit a launch deadline, and so I would find myself trying to, like, lean into that superpower, and then when delivering upon that, getting more responsibility, right? Like, "Hey, you just launched this really complex thing, had to work across like..." This was, uh, a project that had to work across like a lot of different platforms, we were using brittle APIs, and it was like a very, very small team and 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- she was 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 grown my career, wh- whether it's at Airbnb or WeWork or other places, I've flexed into maybe, like, a diff- It's like taking your core strength but then flexing it and finding different ways to bring it to life.

    3. LRLenny Rachitsky31:09

       Much of what I just heard is you just worked incredibly hard and just got shit done, and, uh, and so... and I think that's very, very important and, uh, often leads to a lot of success.

    4. JZJiaona Zhang31:19

       I think, yeah, PMs have to get shit done. Um, yeah, ultimately you're responsible for the outcome, uh, just... no matter what happens. (laughs)

    5. LRLenny Rachitsky31:26

       Yeah, yeah, I like that. Like, be known for getting shit done and, like, working really hard, and that's never gonna serve you badly. I think that is just lasting, uh, advice for being successful as a PM.

    6. JZJiaona Zhang31:36

       (laughs)

11. 31:37 – 36:09

    Designing crisp OKRs

    1. JZJiaona Zhang31:37

    2. LRLenny Rachitsky31:37

       I realize that we were talking about your tips on prioritization road mapping and then OKRs, and then I shifted topics, and you never got to the OKR bucket, so let me come back to that.

    3. JZJiaona Zhang31:47

       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. If I don't hit my OKR, I feel like I, I'm gonna have, like, a really bad reputation or maybe I won't get promoted or, like..." 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 last second, until they're, like, super, super confident, and that results in ultimately, like, a failure to- i- for a company to, like, innovate and move quickly. And so what I really push on for OKRs is, like, what are you actually... what's the spirit? And I think I ask this question maybe too much in my teams, but, like, what is the spirit of what you're trying to achieve and w- what would make you say, "I really, really crushed it this past quarter," right? And so it's less about... Like, I, 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." And so it, it... I really push a lot on, like, what does it truly mean to, like, crush it and be successful? What does it mean for our users? What does it mean for our business? What does that... Like, for our users to feel X, like, can you describe that? Can you write that out for our business to see this in terms of, you know, it... the, the revenue growth? And I think it's, it's really hard because a lot of times, you know, you get your data scientists, you get the PM themselves being 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, uh, target because I have an input metric." And all of th- those things are true, 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, for my co- my- the company and for my users, then a lot of times you end up hitting all your OKRs but the company st- and, and, and your users at large are like, "I don't feel anything different." Like, your company doesn't look at the things that you've worked on and they, 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.

    4. LRLenny Rachitsky34:07

       I like the idea of that, but I imagine what often happens is you sign up for an ambitious OKR, you don't wait till the last second to commit to it, 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's... is 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 story is great and, you know, they're doing the right thing and then... but they fail?

    5. JZJiaona Zhang34:37

       First of all, I think it's creating a culture where, like, 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 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 gonna be able to do that in a quarter. That just is unreasonable. But here are the five milestones," you know, whatever number, w- some number of milestones that it's gonna 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 and 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 I... 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," than to be really, really safe. Because when you're safe, you're always gonna be building something suboptimal. It's gonna be suboptimal use of your resources as opposed to actually trying to figure out what the best, best swing that you can take is.

    6. LRLenny Rachitsky35:50

       So, it sounds like it comes back to the story of the road map and what they're trying to accomplish and just... as long as it feels like the story made sense, there is a path there, the team did their best, and that 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 a PM.

    7. JZJiaona Zhang36:07

       Totally, yeah.

    8. LRLenny Rachitsky36:08

       Awesome.

12. 36:09 – 43:01

    Lessons from WeWork

    1. LRLenny Rachitsky36:09

       You mentioned WeWork, and I want to spend a little time on WeWork.

    2. JZJiaona Zhang36:12

       (laughs)

    3. LRLenny Rachitsky36:12

       So, 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. Uh-

    4. JZJiaona Zhang36:18

       It was. It was t- 2019.

    5. LRLenny Rachitsky36:20

       Okay.

    6. JZJiaona Zhang36:20

       I feel like that year, it was either... like, headlines were either about Trump or about WeWork in the news. (laughs)

    7. LRLenny Rachitsky36:26

       That's tough. 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 you... that helps you be a better product manager or leader or someone?

    8. JZJiaona Zhang36:37

       Yeah. I learned a lot, uh, from my time there. I think the, the most important lesson I learned was really around...I think there's, uh, uh, like a people lead, uh, management lesson, and then there's also just like a how do you build an org, period. The p- the people lesson I learned was just really around empathy. In fact, you know, what, essentially what I was doing was, you know, I built a really, I built a team. I 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, uh, you know, in, in Asia, and in Europe. And then the second half of my time there was actually being like, "Okay, what do we do if, if this is what's happening with WeWork, what are we actually gonna do with all of these people who have, like, come to WeWork to, to work?" And that, there's just 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 just, it was, it was, 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, um, it was definitely something that I got a, a crash course on, I think, before (laughs) , uh, you know, early. And the, the second lesson, uh, really was 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, uh, 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 that you wanna do. And so being really thoughtful around, like, how do we not over-hire? How do we, um, how are we really clear about, again, like these milestones of, like, we gotta get, get through these gates. We gotta 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.

    9. LRLenny Rachitsky38:22

       Feels like this connects back to the AirbnbPlus story of just, let's just be really ambitious. We don't have any idea if we're gonna get there, but we're just gonna go for it. Hire like crazy scale, put a lot of investment in this thing, and hopefully we'll figure it out.

    10. JZJiaona Zhang38:34

        I do think there was a little bit of that in the ethos of, 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." I mean, operationally, WeWork is really strong. In fact, I, I went to WeWork because, you know, 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 the- and the way WeWork has expanded, that they're really, really excellent at the operations. But I think it was, we, again, we hired beyond our skis on the tech side. It's like, we don't need a, 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 technolo- there's 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 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 can still be really ambitious. Like, you know, again, in a, in a hybrid world, it's like, why have real dedicated office space? Every company could go through WeWork as opposed to this dedicated space. Like, that's still a really good idea. That's still a really big vision, and like a, a relevant vision. But what's the key piece of that vision? The key piece of that 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? So just really understanding, again, like you can still dream really big, but you don't have to dream big and hire big in all the things in order to have a very ambitious vision that you deliver to the market.

    11. LRLenny Rachitsky40:13

        If you think back to WeWork, what was your favorite memory, and what was your hardest, least happy memory, if anything comes to mind?

    12. JZJiaona Zhang40:23

        I mean, I think this idea of, like, dreaming really big. Like, I think 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, were dreamers in like the best possible way. So that, that definitely, I feel like for every company that I've been at, it's- it's really about like, you know, you join, you, you... I personally joined for the product, but I stayed for the people, right? Like, you join because you're like, "I wanna work on this mission. This product is really motivating." And then you really stay for the people. And, you know, the people at W- WeWork were really great. So that was definitely my favorite, uh, memory. I think the, the hardest memory was, and this gets a little bit personal, but I was actually in my first trimester when we were going through all of these layoffs, and-

    13. LRLenny Rachitsky41:07

        Oh.

    14. JZJiaona Zhang41:07

        ... I basically, uh, was faced with a choice. It was like, "Hey, do I stay at WeWork?" I would be guaranteed maternity leave. I was gonna be moved onto this other team that was definitely, you know, gonna stay. Is, do I do that, or do I actually, uh... And, and I think there, just a l- last piece of like, uh, 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 don't feel right." Again, like, you know, laying someone off, like that's only gonna have so many days to be able to go find their new role. And so the hardest moment, I actually (laughs) remember this very vividly, like, am I gonna take this new role, or am I going to put myself on the layoff list essentially and, and give the role to s- 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, and more freedom to go find my next thing versus someone who I brought to the company who was on a visa. So th- that to me just really stood out and, and goes back to this concept around like leadership is so much about like empathy and like people. It's- it's as much that as it- as it about, as it's about like understanding, you know, your market, your c- your customers, and the strategy of your product.

    15. LRLenny Rachitsky42:24

        Damn. What, uh, convinced you eventually to take off and try something different?

    16. JZJiaona Zhang42:30

        Well, I made the call of, in, in that particular case, I'd give the role, uh, to someone else.

    17. LRLenny Rachitsky42:34

        Mm-hmm.

    18. JZJiaona Zhang42:35

        And, and then once I made that call, I was like, "Well, I gotta go find something." (laughs) Like, "I, you know, I, I know that this is my last day, uh, so I'm gonna have to go find something." And it was really interesting because I actually... Well, I went through an interview process, um, while-I, I was, uh, in my second trimester and then ultimately chose to join, uh, Webflow and I joined when I was literally at the beginning of my third tre- trimester. So I had exactly 90 days before (laughs) my first son was born.

13. 43:01 – 48:34

    Winning the first 90 days at a new company

    1. JZJiaona Zhang43:01

    2. LRLenny Rachitsky43:01

       That's a great segue to the question I was gonna 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 WeWork with Jared Leto, how similar to reality was that brought?

    3. JZJiaona Zhang43:16

       I actually have not watched it.

    4. LRLenny Rachitsky43:17

       Okay. (laughs)

    5. JZJiaona Zhang43:18

       Parent life, you, like, don't have any time and I do think there's, you know, it's, like, I feel like if you ask, you know, people at Uber if they've watched some of the documentary-

    6. LRLenny Rachitsky43:26

       Super Fun.

    7. JZJiaona Zhang43:26

       ... they're like, ah, it's like, I don't, it's not for me. (laughs) Same way of like why I haven't watched Silicon Valley. You're like, "It's a little too close to home."

    8. LRLenny Rachitsky43:33

       Yeah.

    9. JZJiaona Zhang43:33

       Yeah.

    10. LRLenny Rachitsky43:33

        Well, it was, it was a, quite a great movie and I really enjoyed it.

    11. JZJiaona Zhang43:37

        Okay.

    12. LRLenny Rachitsky43:37

        I'm curious, curious how close it was to real life. Okay, so then back to the 90-day question. So I know you spent a lot of time thinking about your first 90 days at Webflow, you're pregnant as you described, and you have 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 and what you recommend there?

    13. JZJiaona Zhang43:54

        Yeah. I do think the first 90 days, depending on your role, is very different. But I, well, maybe I'll just talk a little bit about the first 90 days as, like, a header product, right? 'Cause you're like, "Whoa." Or even just as a leader, like, how do you go in, how do you really absorb all the information and get all the context you need and then effect change? And I think what was unique about my first 90 days is there, 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, yeah, like, I just don't have the luxury of the time." And so-

    14. LRLenny Rachitsky44:21

        Because you were gonna go on mat leave right after.

    15. JZJiaona Zhang44:23

        Because, yeah, essentially I was gonna go on mat leave, that's right.

    16. LRLenny Rachitsky44:25

        Mm-hmm. Got it.

    17. JZJiaona Zhang44:26

        And so the biggest things that, you know, I thought a lot about from my first 90 days was at the end of the day, yes, you have to real... Like, 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, like, faster than I would be given the luxury, you know, any, 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 functions and then across a bunch of levels. So 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, what's going on? Like, what's hard about your day-to-day? And so I actually 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 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 w- where you're gonna get the most amount of information in that particular function. And that was one piece of it. The other piece was, like, I was like, well, I'm gonna be out, uh, I was only out for two months, but I was like, that's still a long period of time in, 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 (laughs) and like, "Great, like, I have the context. I'll see you in two months."

    18. LRLenny Rachitsky45:58

        Mm-hmm.

    19. JZJiaona Zhang45:58

        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 wanna 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, we have a body of work that we can look at and be like, 'Okay, this information, this data is, 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, 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, a lot more research on." And then, like, assigning people, like, "Hey, you're gonna do this research and then we're gonna come back and talk about it," in, you know, the two months that I was out. And I also, you know, took the time, a- 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. I don't want it to just, like, be with one founder. I want the whole f- 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 se- I, you know, 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." And so ex- explicitly calling those things out and creating awareness around them and then asking other executives, right, to, like, step in and be accountable, those were big pieces of what I wanted to achieve in my first 90 days.

    20. LRLenny Rachitsky47:34

        So I took 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? 'Cause you could do this infinitely, meet everyone eventually. How many people did you end up maybe scheduling meetings with?

    21. JZJiaona Zhang47:47

        Uh, well, definitely everyone on my direct team and definitely everyone in, uh, like, on the leadership team. So call it betw- those two combined were maybe, I don't know, like, 20 or so people, um, 25 people. But then it was, it was really about, like, finding the, the people in the other functions. And to me, for any given function, it was 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, the functions, whether it's product marketing or engineering, you know, whatever it was, back then I didn't have design, so 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, but again, if you a- 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.

14. 48:34 – 51:48

    Why trust is crucial

    1. JZJiaona Zhang48:34

    2. LRLenny Rachitsky48:34

       And then the second bucket was identify things that need to be shifted, changed, flagged. Imagine there's also an element of trust and building trust. 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, a team, a team as in IC?

    3. JZJiaona Zhang48:53

       Trust is so important. I mean, trust is, is everything, right? You know, as a PM, your, the trust that your cross-functional partners have in you, the trust that the f- you know, the CEO has in you, it, like, it's, it's huge. Trust is everything. And maybe here I'll, 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 gotta, you know, go, go, go. We gotta go." I was almost pushing too hard. I was pushing too hard for change, and I think that's, that's a tricky part that every product leader, especially if they're coming into a, a new role, has to figure out. 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 a- again, it was, it was a personal learning, and I think, you know, I, I think part of it was really driven by this, like, time-bound nature of it. But if you, if you, you know, hopefully not everyone has only (laughs) 90 days. So if you take that learning into mind, it's like really thinking about your trust as like a bank, right? It's like you're putting money into your bank, and then at some point you're gonna take money out. You're gonna use that social capital, you're gonna 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.

    4. LRLenny Rachitsky50:06

       What were signs, maybe looking back, that you didn't necessarily have the trust that you thought you did or you should've had?

    5. JZJiaona Zhang50:13

       I think something, like, you know, a product like Webflow is a very complex product, and there are so many pieces to it. So it, you know, it, it's very difficult to learn the product in, you know, the first 90 days, especially if I was also prioritizing all these conversations with the team. And so I, 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 a product. Given the complexity of Webflow and given the time-bound nature of when 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 function working together, not, not just like what the product is. What I, I wasn't able to do was spend enough time with my, 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, I've, I've, like, literally used it, like, a bunch. So like, you had to choose, and in my head I was like, I, I would much rather understand how the, the team is, is functioning together. And, and the reality is, like, the team is 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, Lenny, like everything's a trade-off. And so it's a trade-off, and so y- you know, you kind of had to make the call of what you wanted to trade off. And 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 other, 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, the discipline.

15. 51:48 – 56:38

    High-level lessons from Dropbox, Airbnb, WeWork, and Webflow

    1. JZJiaona Zhang51:48

    2. LRLenny Rachitsky51:48

       So at this point you've worked at four legendary companies, Dropbox, Airbnb, WeWork, Webflow. 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.

    3. JZJiaona Zhang52:06

       I'm gonna actually give you a, 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, it's really about really understanding why people love you, that, and like not forgetting to invest deeply in that core concept and then building everything around that. And, and so I'll g- I'll walk you through the different companies. So specifically for, for Dropbox, I think we did waste cycles where we would be like, "Oh, we see, you know, X happening in the market, like Slack is really taking off. Why don't we build a, you know, a, a, like a, 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 that remains true? People love Dropbox for its simplicity, for how delightful it is, how easy it is to use, right? So you know, I, I think we actually went for a period of time where we didn't in- invest enough in like, just like performance of our client. 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've shifted your investments into like doing that performance work as opposed to kind of like chasing the, the competitive space. And 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 the things I mentioned, but also ultimately like, we have your files, right? Like so if you're going and building like a chat product, that's fine, but really the, the, the best chat experience or, or like collaboration experience is gonna 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, it's very true for Airbnb, right? So at the end of the day, Airbnb is known for like all the homes, the fact that, that these are homes that real people put on the platform. And l- you know, we spent some time talking about Airbnb Plus. When you are thinking like, "I gotta go in, I gotta manage the inventory, gotta inspect it," you're, you're almost like taking away of, 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?" and had to 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. So I think that that same lesson, when applied to Airbnb, would've, it in my head, like changed the way we, we invested and I think we would've gotten more returns as opposed to spreading ourselves and then like having things that like sort of worked but then didn't quite work. And then same, again, same principle applies to, to WeWork.What is the thing that makes you really special? It's the inventory. It, 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 WeWork experience special, right? And so r- 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 great." Like, I need, 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 where like, uh, 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 can design with data. So like investing deeply there as opposed to spreading ourselves too thin is also a lesson. So I think that the, 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, 'cause 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 gonna 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 in delive- delivering a really great product experience for our users in X adjacent area or X add-on.

    4. LRLenny Rachitsky56:34

       Final question before we get to our very exciting lightning round.

    5. JZJiaona Zhang56:37

       Okay.

16. 56:38 – 58:39

    The one piece of advice that transformed JZ’s career

    1. JZJiaona Zhang56:38

       (laughs)

    2. LRLenny Rachitsky56:38

       What is the best advice that you've gotten that has transformed or impacted the way you build product or hire or lead? Does anything come to mind?

    3. JZJiaona Zhang56:48

       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, is this idea of like asking for help. And I, 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 buck stops with me. I need to have my, like act together, you know? Like I, I can't be asking for help. If I'm asking for help, like do ev- is everyone gonna 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 to, for you to give them advice. But if you don't ask for help, there's so many times where you're just gonna 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 to go ask for help. You have to go ask for help from your, your partners, your peers, even your team, even being like, "Team, I, I don't know. Like, I really don't know. Like, here's the guidelines, like here's how you might wanna think about it, but like, I don't know 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, I hold as like a, a core principle, and, and just helps me build better products.

    4. LRLenny Rachitsky58:03

       What's something that you've asked for help about recently as an example?

    5. JZJiaona Zhang58:06

       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 service providers and to support all our users who come into Webflow and, you know, have a hard time sometimes learning how to use our product. And so I'm not an AI 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, what's possible in the world is changing. And so constantly asking for help to iterate on the strategy is a huge part of, um, that's happening every day for my, for me in my

17. 58:39 – 1:06:00

    Lightning round

    1. JZJiaona Zhang58:39

       job.

    2. LRLenny Rachitsky58:40

       JZ, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?

    3. JZJiaona Zhang58:44

       All right, let's do it.

    4. LRLenny Rachitsky58:46

       What are two or three books that you've most recommended to other people?

    5. JZJiaona Zhang58:50

       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 ca- we can also talk about like fantasy stuff if, if you want, but...

    6. LRLenny Rachitsky59:06

       Yeah, give us some, give us some recs there.

    7. JZJiaona Zhang59:09

       I'm a big fan of Brandon Sanderson. He completed The Wheel of Time series on behalf of the previous author. He, you know, he has the Mistborn series. And so he, he's a great one. He actually has, uh, this, during the pandemic he like holed up and like wrote a bunch of books and, (laughs) and basically was like, "I have a confession to make. Oh, I w- I wrote, uh, I wrote like four extra books." And the latest one is Trust by the Emerald City that I really love.

    8. LRLenny Rachitsky59:32

       I saw a 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." (laughs) And then it just keeps going.

    9. JZJiaona Zhang59:43

       I think he was like, "I have a secret," or, "I have a confession to make." And everyone was like, "Oh no, are you gonna say that you have like a ghost writer because you're so prolific?" And he's like, "Nope, I just wrote four more books."

    10. LRLenny Rachitsky59:51

        What a beast. Next question on that topic a little bit, what's a favorite recent movie or TV show that you watch? And I know you said you don't really get to watch much, but anything come to mind?

    11. JZJiaona Zhang1:00:01

        I feel like every night I'm watching Sesame Street, like s- like video, uh, like songs. We don't, we don't do TV, but we do do YouTube songs. (laughs)

    12. LRLenny Rachitsky1:00:09

        (laughs)

    13. JZJiaona Zhang1:00:09

        So I honestly don't have an answer to that other than like we watch like the Elmo song and the ABC song with my three-year-old.

    14. LRLenny Rachitsky1:00:17

        There's been a lot of parenting advice on this podcast with my child coming soon, and so this is very on brand.

    15. JZJiaona Zhang1:00:23

        (laughs)

    16. LRLenny Rachitsky1:00:24

        Uh, before we started this, you mentioned the painting behind you is referenced in, like Arcane is a, is, it's connected to the show Arcane, which I imagine you enjoy.

    17. JZJiaona Zhang1:00:32

        Yes. I, I'm a big, yeah, I'm a big fan. So painted this a long time ago before Jinx and Vi were a thing. And, uh, you know, when Arcane was made, both my husband and I were like, "What? How did we predict this?" This is amazing. So it, it's a good one.

    18. LRLenny Rachitsky1:00:45

        There we go. Uh, some adult content. What is a favorite interview question that you like to ask candidates?

    19. JZJiaona Zhang1:00:53

        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, 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 gonna encounter. So asking a lot of behavioral questions around, around that.

    20. LRLenny Rachitsky1:01:14

        And is there anything specific you look for in their answer that tells you, this is a good answer or not a good answer?

    21. JZJiaona Zhang1:01:20

        Yeah. Uh, good answers are people who put structure and- 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, "Yep, 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 learned 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 t- say, "Hey, is this working? Is this not working?" And then make you either make a different decision. Seeing people do that really well, uh, is- is a big thing I look for.

    22. LRLenny Rachitsky1:02:12

        Awesome. What is a favorite product you recently discovered that you love?

    23. JZJiaona Zhang1:02:17

        I love... And this is not recent, but I do love the SNOO, and it's very top of mind, because I just graduated my second son from the SNOO, and it was- it was a little bit like, "Oh my gosh, like no more rocking (laughs) of the baby." But I do think i- i- it, it does a good job of like actually doing the thing, and also giving parents peace of mind. The other thing I- I'm big fan of, uh, again, you'll see where my head's at, lots of child sh- like, uh, related things, uh, Midjourney for your toddler is actually great, because instead of it being like absolute instant gratification of like, "I wanna see a firetruck, and here you go, here's my phone," it's like, "Let's wait for Midjourney to create the firetruck." And specifically, you can even tell Midjourney what you want. You can be like, "I would like it to be Baloo," he's obsessed with Jungle Book, "wearing a fire hat, next to a firetruck." Right? And so you can actually like create... And I- and I do believe in the future so much of what we are gonna be doing as- as humans is literally like, 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... I..." Like, "This is the idea that I want to bring to life." And so I just think like training that is- is huge.

    24. LRLenny Rachitsky1:03:24

        Feels like you've just defined your three-year strategy for Webflow right there.

    25. JZJiaona Zhang1:03:27

        (laughs)

    26. LRLenny Rachitsky1:03:28

        With AI. Next question, what is something that you've changed in the way you build product, that might be relatively minor, that had a big impact on your team's ability to execute?

    27. JZJiaona Zhang1:03:40

        There's so many different things that we've done, uh, at e- all the different companies. It's- it really depends on the company. And- and 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, right? You're like, "I- 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- 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 gonna 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- this doesn't make sense'?" So I feel like that that's like a- 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- 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 kick-off meeting. That might be the thing that just like changes the d- dynamic of like how you work with teams. So i- it's really... I don't know if there's like one thing, but I- it's almost like every day, I'm- I'm thinking about small tweaks in process to make all of us more efficient.

    28. LRLenny Rachitsky1:04:44

        Final question, what is your number one pro tip for using Webflow and being successful with Webflow?

    29. JZJiaona Zhang1:04:49

        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 ha- 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 gonna bring the magic of Webflow University, the magic of AI, all together so that you can just use and learn Webflow so much faster. Learn Webflow in the context of what you're doing, as opposed to going into a different tab and like looking for like the Webflow University stuff. It's gonna be in context to the product. Being able to actually like take action directly, w- like prompting Webflow to be able to do things for you. Like, it's just gonna 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.

    30. LRLenny Rachitsky1:05:42

        Okay. No specific dates yet yet you could share? This sounds like breaking news of cool stuff coming.

Episode duration: 1:07:31