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

Jiaona Zhang (00:00:00):
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 the projects that you get because you're making a name for yourself, reputation, and then you are giving more responsibility. People tend to flock and give responsibility to the people that are known for being excellent at something.

Lenny (00:00:43):
Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to learn from their hard won experiences building and growing today's most successful products. Today my guest is JZ. JZ is senior vice president of product at Webflow. She's also a lecture 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's also PM at Dropbox and at a gaming company called Pocket Gems.

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In her 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.

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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.

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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 is 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 and play and start using immediately with your team. I've also embedded a handful of my favorite templates that other people publish in the Miro verse.

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(00:04:22):
JZ, welcome to the podcast.

Jiaona Zhang (00:04:24):
Thanks for having me. I'm so excited to be here.

Lenny (00:04:26):
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?

Jiaona Zhang (00:04:37):
I think six years. Yeah.

Lenny (00:04:40):
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 helping new PMs get into the field?

Jiaona Zhang (00:04:56):
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 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 that you can see in your head that you want to build.

(00:05:16):
And so that's the first thing I really want to unteach in our course. And so a lot of people will literally come in, they'll be like, "I want to build X startup" or "I want to do this thing," or "I'm in blank school and I've been doing a lot of research on this particular area." And so untraining that and being like, "Hey, we're going to go out there. We are not going to think at all about the thing that you want to build, but instead we're going to be focused on users and people in the real world and their problems. And the first step is to understand their problems and then understand if there's an opportunity here as opposed to, 'Hey, you want to build X thing for Y person.'" So that's the biggest mistake that you really have to unteach and retrain thinking around.

Lenny (00:05:55):
Does a lot of this come from people want to get into product management because they think "Finally I'll have the power, finally I'll be able to tell people what to build, finally my ideas really going to matter?" Is that where a lot lobby comes from?

Jiaona Zhang (00:06:06):
I think there's a part of that. One of the first things I teach is 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. A lot of it is all through influence, and so that is also a piece where you have to kind of untrain that thinking. I do think a lot of people come into the product role thinking that I get to call the shots, I get to make the decisions, I get to decide what gets built. And really your job is not that. Your job is to understand here are the opportunities, and then you're kind of pulling together all the different possibilities and you're really editing. So I do think it comes from desire for a lot of people thinking that's what the product role is when it actually isn't.

Lenny (00:06:44):
So let's 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?

Jiaona Zhang (00:06:53):
Wow, that's a good one. It's so interesting. I feel like as product people, we're always making mistakes and we're always learning. Maybe I'll give an example from Airbnb since you and I were both there. And this one does stand out to me, we were working on this concept called Airbnb Plus. 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... It's a platform. It's not like it's managed inventory, it's not a hotel. How do you go in and really make sure that all the Airbnbs are meeting the quality bar?" But I do think we were very solution-first, and I think we're also competitor afraid at the time. So it was during a time where there were managed marketplaces, there were the Sonders out there, and I think that as a company we're very much like "[inaudible 00:07:36] what are we going to do in the world of managed marketplaces?"

(00:07:38):
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 what's in your wheelhouse? So for example, Airbnb, we weren't that strong in operations. Again, we're this platform with this marketplace. And so if you don't have that muscle and then you're asking the company, the teams to essentially build it from the ground up, that's really, really difficult. Not to mention the unit economics, are the unit economics actually going to work even as you scale?

Lenny (00:08:22):
Yeah, I feel like Airbnb Plus is an untold story that somebody should tell and that could be its own podcast, I guess.

Jiaona Zhang (00:08:28):
You and I can tell it.

Lenny (00:08:30):
We could tell this could be Airbnb Plus The Hidden 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 because it's like, "No, I don't want to stay in someone's home. I don't know what it'll be. It's unpredictable." And so as an outsider, it felt like a really clever approach. "We're going to vet them, we're going to make sure they're awesome. There's a minimum bar." And I guess this is the question is do you think it was just like "This is never possible because we'll never make money as a business doing this because we don't make that much per booking and investing time, resources, sending people pillows, all that stuff is ever going to be economical"? Or do you think there was a path that was just not executed well?

Jiaona Zhang (00:09:10):
I think there wasn't really a clear path. I think there was less of-

Lenny (00:09:10):
Yeah, that's my impression.

Jiaona Zhang (00:09:15):
Exactly. And it was more just like if you understood... Again, this is what my point around unit economics, there are things where I think you have magical thinking around unit economics. You're like, "When we get to the scale of X, it's all going to work out. We can make these things happen." I think you actually need to really make sure that unit economics work quite at the beginning. That is definitely one lesson. And I think the other thing is, and going back to spirit of what are you trying to achieve. If you're trying to achieve this idea of really knowing the quality of the place, and for a platform like Airbnb, the right way to go about doing is through our reviews, through our guest reviews, which are essentially free as opposed to literally sending out inspectors.

(00:09:51):
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 cleaning? Is it, "Hey, 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 and go look at your property. It is actually cheaper to maybe do a partnership with a bunch of cleaners in different local areas and then get that as part of the fee, 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 you're looking at?

(00:10:33):
And so I personally don't believe the unit economics ever would've really worked out. I think we should have known that or we should have dug into that more at the very beginning and then to get very tailored instead of one blunt instrument to solve it all, "Hey, we're going to go inspect." It's like what is the problem for this listing and what's the best solution to fix that problem?

Lenny (00:10:51):
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 going to get there, we're just going to 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. Is there anything you've learned about just when to think big and not even like "Forget it. We're going to figure it out. I know this seems impossible, but we're just going to try it anyway"? Do you have any kind of framework of when to think big, then just go for it? Versus, "Oh, let's just work out the math today," is this ever possible?

Jiaona Zhang (00:11:42):
I think it's really important for every company to be dreaming big. If you don't have a big vision, it's really hard for you to innovate, but you got to couple that really big vision with thoughtfulness around your execution. And so I think that one of the biggest tips I have is how do to be clear about the phase that you're in? So I think it's totally fine to be like, "Hey, we are going to try X for six months, three months, whatever it is, and we're explicitly going to go learn these types of things. We're going to learn why are people? Are there signals that we would that would indicate that again, the communication with host isn't great or this type of listing, if it's hosted by a person with multiple property?" I think there are factors we can be like, "Hey, we can learn this very explicit thing in a given period of time."

(00:12:32):
And you can do what I call 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 what phase you're in. "Hey, we're in the learning phase and we explicitly are trying to learn these things" versus, "Hey, we have this really big vision and we're just going to go at it." That is not recommended in my mind. It's breaking it down into these smaller chunks. That I think gets you the balance of thinking really, really big, but also being able to be like, "Okay, we are still going to be able to say, 'Okay, this path is not going to work out. We ran at it for a short period of time. We got these learnings, now let's go down this other path.'"

Lenny (00:13:11):
Yeah, there's also some cost fallacy that kicks in of just like, "Oh, I spend so much time and money and resources on this thing. Let's just go a little bit longer. Let's just see if we give it another quarter, maybe it'll work out."

Jiaona Zhang (00:13:21):
You should articulate what success looks like and the milestones you want to hit in the small intervals that I talked about. So you don't get into this world where you're like, "Hey, I've gone for two years investing in this thing. Now we got to cut it." It's like, what is the quarter long milestone? Okay, what's the next quarter long milestone? And every single point, 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 two years."

Lenny (00:13:46):
The other important lesson here is about the importance of as a product leader pushing back and convincing leadership that you are wrong and this shouldn't happen. I remember talking to one of our colleagues, Mike Lewis, who was leading a different team with Airbnb, and he was just like, "Oh, I realized I'm the person that should be saying, 'No, we shouldn't do this now'" because he was the head of product for one of the new [inaudible 00:14:09]. 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."

(00:14:18):
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 go along? Like "Cool, let's do it. Let's buy in." As a leader, you have to be excited and he needs to feel like, "Oh, JZ is really excited about this too. We got to try it." Even though maybe you feel like it's not going to work out. So I guess the question is when do you think it makes sense to try convince the founder, "No, this is the bad idea" versus like "Let's go for it"?

Jiaona Zhang (00:14:42):
I think first it comes down to your conviction. Do you actually have conviction that this is a bad idea or are you personally still learning? Right. I think if you're at the point, if you're like, "I have total conviction," then your job is to say, no, you really... If you do not, you're not doing your job. And then the question is 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. Being able to go back with, "Hey, I understand the spirit. The spirit is that we're trying to get people who previously didn't consider Airbnb before to come and use Airbnb, but the right way to do it is not this very time-intensive, cost-intensive way to inspect all these homes. The way to do it is to be much more granular in what we ask people when they upload their home and more checks in that. And that could be automated and through technology as opposed to through humans."

(00:15:37):
It's coming back with actual options. It's like saying... And I think we did that a little bit to be honest, when we as a team evolve, we learn and we're like, "This isn't going to work." And I explicitly moved off the team and I was like, "I'm going to work on the review system. I'm going to continue to evolve this and make it better because that is the actual scalable way to do this as opposed to keep going at it in the very manual process."

(00:15:59):
And so I think that the biggest tip I would have for people in this situation is really understand whether it's the founder or your manager or whoever it is, what is it that they're trying to accomplish for the user and for the business? Remind them of that, get aligned on that. And then come back with better options. A lot of these people, they're very smart and they're very motivated. They ultimately want to 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's very rare that someone will be like, "I still want to go after this solution despite the fact that it's not working and you proposed a much better path forward."

Lenny (00:16:37):
And I think to touch on what you've already said is also make sure it's actually... There's a world where this could work. Do some math to figure out if this is a business that will actually make some money in the future.

Jiaona Zhang (00:16:49):
Totally.

Lenny (00:16:50):
Okay. I'm going to bounce around a little bit. I have a bunch of different questions around different topics. 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 go in that direction versus a traditional MVP?

Jiaona Zhang (00:17:10):
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 feel like, "Hey, use this thing. It barely meets a quality bar." And so I think this idea of actually deeply understanding for the thing that you're working on, what is a lovable experience? What is the quality bar that resonates with your users? And again, especially in a world where there might be a lot of different options. Minimal lovable products is the new MVP. The new minimal viable product.

(00:17:40):
So I think that's the real point, but at the end of the day, it does come back to what are the options that a user has and what are they trying to do? So there's a world where your quality bar, your "Quality bar," or let's call it your polished bar, can be a little bit lower because the reality is the thing that you're "Competing against" or you're replacing is literally a manual workflow. It's like spreadsheets. It's doing something in a super terrible way.

(00:18:05):
So you want to get your product to market as quickly as possible, so it doesn't make sense for you to be like, "I'm going to build these 15 additional features." Because compared to what people are doing right now, your product without those 15 additional features is perfectly fine, perfectly usable, and perfectly quite honestly lovable. So it requires a lot of understanding of, again, your users and the space that you play in and the tolerance of your given user. So for example, a designer might have a lot higher of a bar of like "This is the kind of workflow I want, this is the kind of bar for my product." But again, someone sitting on the finance team or the IT team, their bar might be like, "Oh, I'm used to doing these 15 things and so your thing is just a lot better."

Lenny (00:18:53):
I'd love to go even one level deeper. Is there an example of something you've worked on that was minimal lovable product that you think about? Or is there something out there that's an example of here's maybe an example of a minimal lovable product versus MVP?

Jiaona Zhang (00:19:08):
Again, it's very hard. I think every product team, every product person struggles with this idea of what is the minimal viable. Even that concept itself is difficult and not to mention minimal lovable. I'll give a Webflow example. Very recently, so have been investing in a couple of new features, 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 continues to chip away 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?"

(00:19:56):
And again, it's not just like you put it out there and you hope, you have to have a very strong point of view of are we at minimal viable, are we at minimal lovable? Where in between are we? And so having that point of view and then being able to say, "Are we going to be able to meet it as a company? Are we going to rely on our ecosystem to help us meet it? What are we actually going to do?" And then even within the feature set, it's very much 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... To me it's better to do five things instead of the 15 things in a really, really great way with a high degree of polish with 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.

(00:20:45):
People I think would actually respect this idea of "You've given me minimal lovable in five areas as opposed to minimal viable in 15 areas."

Lenny (00:20:53):
Is there anything you've seen of just that makes something lovable? I don't know. I know it's not easy to define, but what are things you've seen that makes something lovable? Is it delightful features? Or is it what you're saying, which is just things are actually good, there's fewer things, but they're each really good?

Jiaona Zhang (00:21:08):
There's definitely this idea of the thing is just good. It has all. High quality, it's not janky, it doesn't feel weird. I'll give you a very small example again, just from Webflow, this idea of keyboard shortcuts, feels small, but that is a piece that creates a lot of love from user base who are power users. And then there's this concept of pixie dusts, and maybe I'll pull out of call it like design tool space and we'll talk about some of the other things, whether it's Dropbox or Airbnb, but you can just do a little bit of that extra pixie dusts. So an example from Airbnb when we're doing the mobile app revamp where like "There's like these basic table stakes, but if we actually added in templates and we made it so that these templates could be maybe pre-populated in certain ways from the content they already have," that is lovable, that is that extra little bit of pixie dust and spending the time to do that.

(00:21:55):
Again, you can't pixie dust everything. At the end of the day, you basically have your time, your staffing and the scope of your project and something has to give. And so at the end of the day, you can't just keep investing, keep investing because it's going to push out your launch timeline, but can you pick a few different areas where you're like, "I'm going to scatter that pixie dust, I'm going to do a little bit more than what users are expecting"? And that creates that lovability.

Lenny (00:22:20):
Shifting to a different topic, I know you have strong opinions about road mapping and OKRs, improvisation, 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 OKRs, prioritize and/or just, I don't know, common mantras or things you always come back to be successful in these areas?

Jiaona Zhang (00:22:40):
Road mapping prioritization are one bucket for me. And then OKRs is another. So I'll maybe give you my biggest tip in each one of these buckets.

(00:22:46):
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. Why are these things the biggest things to invest in these levers, the biggest ones to pull?" And what I really don't want, what I think is a very common mistake from road mapping is people thinking a spreadsheet with a bunch of projects, the RICE framework, everything has an impact, a cost and an effort column filled out. They think that is prioritization and that is a roadmap. If you just do that right and then you present that to your team, they're off to the races.

(00:23:26):
But what people, what humans really crave is like, "Why am I doing this body of work?" And I think it's also really, really important to have that really crisply articulated in your own head because ultimately what happens is you'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 changed." 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 influence?

(00:23:59):
It could be like, "Hey, I just realized I didn't know before that we have a lot more power users on our," or "Maybe we have a lot more non-technical users." That input changes my roadmap and changes my themes in a pretty dramatic way. So skating at that level is really, really critical, I think for a roadmap as opposed to going down to the really granular details of the how. 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 how and the projects and all the little details, but really create that scaffolding for them to know what's important.

Lenny (00:24:33):
Can I ask a follow-up question on that?

Jiaona Zhang (00:24:35):
Totally, yeah.

Lenny (00:24:36):
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"?

Jiaona Zhang (00:24:55):
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 lots of us are in hybrid remote cultures it's hard because 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 add that level of granularity." So very much so the same way like "I'm a roadmap is a story. You're telling themes, you write a story in a notebook, you write 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 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."

(00:25:40):
And then linking out, again, not even to a spreadsheet, but linking out to the artifacts and the systems that your team actually uses. So if your team uses Jira, go ahead and link out to Jira because so often docs get out of... Or spreadsheets get out of date, because they're like a snapshot of whatever it is that you needed at that point in time. But 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 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."

Lenny (00:26:12):
Do you have a template or common structure you suggest to teams for laying out this story or is it just depends on the quarter, it depends on the year?

Jiaona Zhang (00:26:21):
I'll give a plug for a new thing coming out of Reforge, which is this concept of artifacts. And so we do have a lot of artifacts out there, so what's our general product development process? What are our templates for our specs? What are our templates for some of these things that we're talking about, a roadmap, like a broader roadmap instead of just a feature spec. So yes, we have a ton of those artifacts, are always evolving. I think every team takes it and tweaks it a little bit, but I'm a big believer of 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, gets all of our teams speaking the same language.

Lenny (00:26:57):
Awesome.

(00:26:59):
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(00:28:02):
Moving to a different topic, 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?

Jiaona Zhang (00:28:18):
There's so many parts to it, but I'll pick one. 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 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 your thing. You could be known for working on the most technically complex problems. You could be known for working on things that are really regulatory complex. 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 the projects that you get. Because you're making a name for yourself, reputation, and then you are giving more responsibility. People tend to flock and give responsibility to the people that are known for being excellent at something.

Lenny (00:29:16):
Is there something you were known to be excellent at in the course of your career?

Jiaona Zhang (00:29:20):
I would say early on in my career, it was actually the fact that I had a strong analytics background. And so when I joined gaming, I came from consulting, I didn't have any CS background or design background, and so it was really creating a reputation around being very analytical, around being able to analyze the datasets of my game and then make decisions. I also learned as I was doing that I was actually really good at execution, and so being able to keep a lot of plates spinning and working on 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 working in the role.

(00:29:58):
And so that was something I brought to Dropbox. When I joined Dropbox. It was like I knew that I could work with a lot of different teams and make sure that we 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, "Hey, you just launched this really complex thing, this was a project that had to work across a lot of different platforms. We're using Griddle APIs." And it was a very, very small team and it had a very, very tight deadline.

(00:30:29):
So when you're like, "I can do something like this," you end up getting more responsibility because people were like, "Oh, she was able to do something that was really hard with a small team," and so that's how you get more responsibility. But it has evolved in my career. I think that at the beginning of your career, you do want to lean into some of these pieces. It makes sense, but also even when you start to manage, it shifts dramatically. Being known as the best executor is not necessarily the thing that gives you and your team the most responsibility. So as I've grown my career, whether it's at Airbnb or WeWork or other places I flex into maybe a different... It's like taking your core strength but then flexing it and finding different ways to bring it to life.

Lenny (00:31:09):
Much of what I just heard is you just worked incredibly hard and just got shit done. And I think that's very, very important and often leads to a lot of success.

Jiaona Zhang (00:31:20):
PMs have to get shit done. Yeah, ultimately you're responsible for the outcome just no matter what happens.

Lenny (00:31:26):
Yeah. I like that. Be known for getting shit done and working really hard, and that's never going to serve you badly. I think that is just lasting advice for being successful as a PM. I realized 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.

Jiaona Zhang (00:31:47):
Yes. My biggest tip on OKRs is actually get really, really crisp on qualitatively. What would make you say "Yes, we did a great job"? And the reason I pushed so hard on that is because I see so many teams get really mucked down by OKRs. They're like, "Oh man, if I don't hit my OKR, I feel like I'm going to have a really bad reputation, or maybe I won't get promoted." 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. And that results in ultimately a failure for your company to innovate and move quickly.

(00:32:29):
And so what I really push on for OKRs is are you actually... What's the spirit... I think I asked this question maybe too much to my team, but 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'? And so it's less about I would rather have all the OKRs be red or yellow and 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 really pushed a lot on what does it truly mean to crush it and be successful? What does it mean for our users? What does it mean for our business? What does that... For our users to feel X, can you describe that? Can you write that out? For our business to see this in terms of the revenue growth?

(00:33:17):
And I think it's really hard because a lot of times, you get your data scientists, you get the PM themselves being like, "Oh man, I'm owning an input metric, not an output metric. And so I definitely can't sign up for that revenue target because I have an input metric." And all of those things are true, but if you don't do the homework of really drawing that line of being like, "This is the ultimate thing I want to do for the company and for my users," then a lot of times you end up hitting all your OKRs, but the company and your users at large are like, "I don't feel anything different." Your company doesn't look at the things that you've worked on and they don't say like "This is a smashing success." Your users are feeling no differently. And so that is the worst outcome in my head where your OKRs, you're almost like doing OKRs for the sake of OKRs, as opposed to letting them be a guide to delivering really great product to your end customer.

Lenny (00:34:09):
I like the idea of that, but 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 ends up being red, and then you go into performance reviews and like, "Oh, Lenny didn't hit his OKRs. Look at this guy. His team is not doing great." 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 sign up for these really ambitious OKRs and their story's great and they're doing the right thing, but they fail?

Jiaona Zhang (00:34:37):
First of all, I think it's creating a culture where you are not punished for that. Because I definitely don't want a culture where it's like you took a risk and you failed and therefore your performance is impacted. I'd much rather people take risks than to be safe. So I think that's the first thing. That being said, you're also not doing a good job as a PM if you're like, "This is my super, super ambitious thing," and you're like, "I have no idea how to achieve it." Your job is to dream big and also have a plan to go tackle it. And so what I would expect the PM to be able to say is, "This is my North Star. I'm not going to be able to do that in a quarter, that just is unreasonable, but here are the five milestones," whatever number, some number of milestones "That it's going to take me to do quarter over quarter to achieve this really, really ambitious thing. And let me draw you that path. Here's the milestone all the way across, and this is the first one. This is why it's so meaningful."

(00:35:24):
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" than to be really, really safe. Because when you're safe, you're always going to be building something suboptimal. It's going to be suboptimal use of your resources as opposed to actually trying to figure out what the best swing that you can take is.

Lenny (00:35:50):
So 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 know 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.

Jiaona Zhang (00:36:07):
Totally. Yeah.

Lenny (00:36:10):
Awesome. I mentioned WeWork and I want to spend a little time on WeWork. You were at WeWork for about a year, and I think it was in the middle of a lot of the craziness that went on at WeWork.

Jiaona Zhang (00:36:18):
It was. It was 2019, I feel like that year it was either headlines were either about Trump or about WeWork in the news.

Lenny (00:36:26):
That's tough. So what was that like being a PM leader at a company in that craziness? And is there a takeaway from that experience that helps you be a better product manager, a leader, person?

Jiaona Zhang (00:36:37):
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, essentially what I was doing was I built a team. I spent the first six months of my time there actually growing my team a lot, and not just in the US but in Asia and in Europe. And then the second half of my time there was actually being like, "What do we do? If this is what's happening with WeWork, what are we actually going to do with all of these people who have come to WeWork to work?"

(00:37:19):
And there was so many lessons there around leadership, around how do you think about people? How do you think about giving them the right transition plans? It was a lot of learning. And I think probably a lot of people, even right now through the macroeconomic downturn, they're learning that lesson in a really hard way. And so it was definitely something that I got a crash course on, I think early.

(00:37:44):
And the second lesson 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 at any company that I go to. Just because laying off half your team is a terrible feeling. 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 how do we not over-hire? How are we really clear about, again, these milestones of we got to get through these gates, we got to be able to show these types of results, and then we unlock hiring in X, Y, Z ways? That hygiene is really, really important.

Lenny (00:38:22):
Feels like this connects back to the Airbnb Plus story of "Let's just be really ambitious. We don't have any idea how we're going to get there, but we're just going to go for it, hire like crazy, scale, put a lot of investment in this thing and hopefully we'll figure it out."

Jiaona Zhang (00:38:34):
I do think there was a little bit of that in the ethos of how WeWork was functioning, for sure. I think that what was really important for us to do was to be like, "We have this." Operationally, WeWork is really strong. In fact, I went to WeWork because having been at Airbnb, I was like, "I don't feel like we've dialed this operational muscle down," but I know from what I've seen and the way WeWork has expanded, that they're really, really excellent at the operations. But I think it was, again, we hired beyond our skis on the tech side. It's like we don't need a team of this size to go do the things that are needed for the product to feel really great. At the end of the day, it's about booking. And yes, there's technology that would accelerate that, but do we need it to be super platform aware? Do we need it to be super futuristic? That's actually not what people care about.

(00:39:19):
So this all goes back to what are people's core desires in whatever product that they're using, whatever thing that your business is trying to serve them? And so really understanding that will help you have a sense of, "Hey, you can still be really ambitious." Again, 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. That's still a really good idea, that's still a really big vision and 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. So just really understanding, again, 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.

Lenny (00:40:13):
If you think back to WeWork, what was your favorite memory and what was your hardest, least happy memory if anything comes to mind?

Jiaona Zhang (00:40:23):
I think this idea dream really big. I think everyone who had joined WeWork, they were like, "We could do a lot here." The idea of really the physical space infusing technology. I just feel like the people at WeWork were dreamers in the best possible way. So that definitely... I feel like for every company that I've been at, it's really about, you join... I personally joined for the product, but I stayed for the people you joined because you're like, "I want to work on this mission. This product is really motivating." And then you really stay for the people. And the people at We WeWork were really great. So that was definitely my favorite memory.

(00:40:58):
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. It was like, "Hey, do I stay at WeWork? I would be guaranteed maternity leave." I was going to be moved onto 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... The thing I was wrestling with is I hired a lot of these people and I felt really responsible for the fact that I convinced them to come to this company that now was going through a lot of change.

(00:41:33):
And I specifically remember someone when I hired them, we had a long conversation about their visa and in my head I was like, "I just don't feel right. Again, laying someone off. 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, "Am I going to take this new role or am I going to put myself on a layoff list essentially and give the role to someone else on the team?" When I really think about it, 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.

(00:42:09):
That to me just really stood out and goes back to this concept around leadership is so much about empathy and people as much as it's about understanding your market, your customers, and the strategy of your product.

Lenny (00:42:24):
Damn. What convinced you eventually to take off and try something different?

Jiaona Zhang (00:42:31):
I made the call of, in that particular case, I'd give the role to someone else. And then once I made that call, I was like, "I got to go find something. I know that this is my last day, so I have to go find something." And it was really interesting because I actually... I went through an interview process. I was in my second trimester and then ultimately I chose to join Webflow and I joined when I was literally at the beginning of my third trimester. So I had exactly 90 days before my first son was born.

Lenny (00:43:01):
That's a great segue to the question I was going to ask is around your 90-day plan that I know you 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?

Jiaona Zhang (00:43:16):
I actually have not watched it. Parent life, you don't have any time. And I do think there's... I feel like if you ask people at Uber, if they've watched some of the [inaudible 00:43:26] they're like, "It's not for me." Same way why I haven't watched Silicon Valley. You're like, "It's a little too close to home."

Lenny (00:43:35):
It was quite a great movie and I really enjoyed it. I'm curious how close it was to real life. Okay, so then back to the 90-day questions. 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, what you recommend there?

Jiaona Zhang (00:43:55):
Yeah, I do think the first 90 days, depending on your role is very different. But maybe I'll just talk a little bit about the first 90 days as a head of product. Because you're like, "Whoa." Or even just as a leader, how do you go in, how do you really absorb all the information and get all the context 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 just don't have the luxury of the time" and so-

Lenny (00:44:21):
Because you're going to go on mat leave right after?

Jiaona Zhang (00:44:23):
Because yeah, essentially I was going to go on mat leave.

Lenny (00:44:25):
Got it.

Jiaona Zhang (00:44:25):
That's right. And so the biggest things that I thought a lot about for my first 90 days was at the end of the day, yes, you have to really... The most important thing for anyone's for assigning days is to build context and to build context well. But what I had to think about a lot was, "How do I quickly build context probably faster than I would be given the luxury 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 even just a calendar of speaking to people? Yes, my leadership team, but also across a bunch of functions and then across a bunch of levels. So it was really important for me to 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, what's hard about our tech stack? What's going on? What's hard about your day to day?

(00:45:15):
And so I actually took time to really think about, "I want to speak to all of these types of people at the company." And I packed my first couple weeks with 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 again, it's not just with your peers, it's not even just with your team, but to really think across all the different functions and then think about where you're going to get the most amount of information in that particular function. I think that was one piece of it.

(00:45:43):
The other piece was I was like, "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 it was really important to me was like, I did not go out having just listened and like "Great, 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.

(00:46:03):
And so there were pieces where I was like, "I want to first, again, get that lay of the land. I want to have enough of a strategic, 'Hey, these things make sense. Keep going, keep executing.' 'These things don't make sense, let's identify what those things are and let's actually start to do research around these things so that when I do come back, we have a body of work that we can look at and be like, "Okay, this information, this data is making us choose to go down the path." Or "This is a go or no-go decision. We can make that decision now where we couldn't make that decision before."'"

(00:46:34):
So that was another big piece, which is 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 assigning people like, "Hey, you're going to do this research and then we're going to come back and talk about it in the two months that I was out." And I also 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, "For the things that I'm seeing, for the gaps that I'm seeing. I want everyone to be aware. I don't want to just be with one founder. I want the whole leadership team. I want all the founders, I want the board. I want everyone to be aware that."

(00:47:14):
For example, engineering hiring was really, really important. And 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 explicitly calling those things out and creating awareness around them and then asking other executives to step in and be accountable, those were big pieces of what I wanted to achieve in my first 90 days.

Lenny (00:47:34):
So 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 how many people? Because you could do this infinitely, meet everyone eventually. How many people did you end up maybe scheduling meetings with?

Jiaona Zhang (00:47:47):
Definitely everyone on my direct team and definitely everyone on the leadership team, so call it those two combined were maybe, I don't know, like 20 or so people, 25 people. But then it was really about finding the people in the other functions. And to me, for any given function, it was really getting a read from, again, that leader, but also someone closer to the actual work. And so you look at the functions, whether it's product marketing or engineering, 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 was like 40 to 50 conversations. But again, if you're doing them back to back and you're really synthesizing, you're actually getting a really good picture of what's going on.

Lenny (00:48:35):
And then the second bucket was identify things that need to be shifted, changed, flagged. I 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 say an new PM joining it? A team as an IC?

Jiaona Zhang (00:48:53):
Trust is so important. Trust is everything. As a PM, the trust that your cross-functional partners have in you, the trust that the CEO has is you... It's huge. Trust is everything. And maybe here, I'll even talk about some of the mistakes I made in the first 90 days. I think I was so much like, "I only have 90 days. I got to go, go, go. We got to go." I was almost pushing too hard. I was pushing too hard for change. I think that's the tricky part that every product leader, especially if they're coming into a new role, has to figure out 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?

(00:49:33):
So again, it was a personal learning and I think part of it was really driven by the time-bound nature of it, but hopefully not everyone has only 90 days. So if you take that learning into mind, it's really thinking about your trust as a bank. It's like you're putting money into your bank and then at some point you're going to take money out, you're going to use that social capital, you're going to use that trust to go push for things, push for change, but you have to be thoughtful about how full your piggy bank is and you don't want to be spending when you don't have the trust in the bank.

Lenny (00:50:06):
What were signs maybe looking back that you didn't necessarily have the trust that you thought you did or you should have had?

Jiaona Zhang (00:50:13):
I think something, a product like Webflow is a very complex product and there are so many pieces to it. It's very difficult to learn the product in the first 90 days, especially if I was also prioritizing all these conversations with the team. And so I think that again, without the time constraint, what I would recommend is to be like, "Hey, every product leader has to take the time to really go deep on the product." Given the complexity of Webflow and given the time-bound nature of when I had to go out, and given the fact I really also wanted to build that social context around what is working and not working from a function working together? Not just what the product is. What I wasn't able to do was 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, I know how this, this and this works because I've literally used it a bunch."

(00:51:06):
So you had to choose. And in my head I was like, "I would much rather understand how the team is functioning together." And the reality is the team was comprised of a lot of people with a lot of deep product context. So ultimately as all things in product, you know this Lenny, everything's a trade off. And so it's a trade off. And so you had to make the call of what you wanted to trade off. And the thing I traded off the most was 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 product fundamentals or product, the actual thing we're building as opposed to the discipline.

Lenny (00:51:48):
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?

Jiaona Zhang (00:52:06):
I'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 we could spend another two hours talking about each one of these. But I think just to impart my biggest high level learning. On the product side, it's about really understanding why people love you and 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. Slack is really taking off. Why don't we build a Slack competitor? Or why don't we build chat?" And I think that it really missed this idea of, "Why do people love Dropbox and what do we need to do to continue investing in that so that remains true?" People love Dropbox for simplicity, for how delightful it is, how easy it is to use.

(00:53:08):
I think we actually went for a period of time where we didn't invest enough in just performance of our client. How long it takes for the thing to sync is a big part of the experience of using Dropbox. And so I think that is a big, big learning where it's really understanding that would've shifted your investments into doing that performance work as opposed to chasing the competitive space. And I think going back to chasing the competitive space, it's this idea of what is your alpha? Again, why do people come to you? People come to Dropbox again for all the things I mentioned, but also ultimately we have your files. So if you're going and building a chat product, that's fine, but really the best chat experience or collaboration experience is going to be more around your files as opposed to around just the conversation. So I think really understanding that is a huge, huge learning.

(00:54:01):
And I think that same lesson can be... It's very true for Airbnb. So at the end of the day, Airbnb is known for all the homes, the fact that these are homes that real people put on the platform. We spent some time talking about Airbnb Plus. When you are thinking "I got to go in and I got to manage the inventory and inspect it," you're almost like taking away from the thing that is what makes Air Airbnb special as opposed to leaning into it. 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, "What makes Air Airbnb special and how do you double down on your strength?" It's spending the time to make that experience of really understanding what's in a home so people don't go and get surprised. Making that onboarding journey for the host and then discovery journey and guest booking journey really, really great.

(00:54:52):
So I think that that same lesson when applied to Airbnb, would've in my head changed the way we invested and I think we would've gotten more returns, as opposed to spreading ourselves and then having things that sort of work but then didn't quite work. And then again, same principle applies to WeWork, what is the thing that makes you really special? It's the inventory it. It's not actually like, "Oh, it's so amazing that I get to use this key card and this key card does 10 different things." That's not what makes the WeWork experience special. And 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, I'm going to do all these interesting things." You'd be like, "I just need to make inventory management great. I need to make it so that the sales team, the operations team, 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.

(00:55:44):
And then finally, even at Webflow, we are learning this lesson all the time where at the end of the day, 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 investing deeply there as opposed to spreading ourselves too thin is also a lesson. I think across so many companies this lesson around understand why people love you, double down on that and then whatever else you build around it... Because again, you don't want to also be like... You're not like a single product company, you're not like a one trick pony. You are going to invest in these multi products, but when you invest in a new product, really go back to, again, what's the core of our advantage and how can that be something we leverage in delivering a really great product experience for our users in X adjacent area or x add-on?

Lenny (00:56:34):
Final question before we get to a very exciting lightning round.

Jiaona Zhang (00:56:38):
Okay.

Lenny (00:56:38):
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?

Jiaona Zhang (00:56:48):
I can't remember where I explicitly got this advice, but I feel like I got it in multiple forms and it just really sat with me. It's this idea of asking for help. 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, everyone's looking to me like the [inaudible 00:57:04] stops in me. I need to have my act together. I can't be asking for help. If I'm asking for help, is everyone feel like I don't know what I'm doing?"

(00:57:13):
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 going to be sitting there with your problems. 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 my team, I don't know. I really don't know. Here's the guidelines, here's how you might want to think about it, but I don't know the answer, you know the answer." Going out and getting mentorship. I think this idea of really being able to say, "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 a core principle and just helps me build better products.

Lenny (00:58:03):
What's something that you've asked for help about recently as an example?

Jiaona Zhang (00:58:06):
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 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 AI expert, so asking for help from the founders, from external folks, from engineers to be like, "What's happening?" Every single week I feel like LLMs are changing. What's possible in the world is changing. And so constantly asking for help to iterate on the strategy is a huge part of... It's happening every day for me and my job.

Lenny (00:58:40):
JZ, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?

Jiaona Zhang (00:58:44):
All right, let's do it.

Lenny (00:58:46):
What are two or three books that you've most recommended to other people?

Jiaona Zhang (00:58:50):
I love the Design Sprint by Google. I also really Julie's book around managing people how to be a good manager. That one's really great. And so those are my more business side of the house books. And then we can also talk about fantasy stuff if you want. But-

Lenny (00:59:07):
Yeah, give us some recs there.

Jiaona Zhang (00:59:09):
I'm a big fan of Brandon Sanderson. He completed the Wheel of Time series on behalf of the [inaudible 00:59:14] author. He has the Mistborn series and so he's a great one. He actually has this... During the pandemic, he holed up and wrote a bunch of books and Vince was like, "I have a confession to make. I wrote four extra books." And the latest one is Tress by the Emerald Sea that I really love.

Lenny (00:59:32):
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" and it just keeps going.

Jiaona Zhang (00:59:43):
I think he was like, "I have a secret or I have a confession to make." And everyone was like, "Oh no, are you going to say that you have a ghost writer because you're so prolific?" And he's like, "Nope, I just wrote four more books."

Lenny (00:59:51):
What a beast. Next question on that topic a little bit. What's a favorite recent movie or a TV show that you watched? And I know you said you don't get to watch much, but anything come to mind?

Jiaona Zhang (01:00:01):
I feel like every night I'm watching Sesame Street like songs. We don't do TV, but we do do YouTube songs. I honestly don't have an answer to that other than we watch the Elmo song and the ABC song with my three year old.

Lenny (01:00:18):
There's been a lot of parenting advice on this podcast with my child coming soon. And so this is very on brand. Before we started this, you mentioned the painting behind you is referenced in like Arcane, it's connected to or the show Arcane, which I imagine-

Jiaona Zhang (01:00:31):
Yes. I'm a big fan. So painted this a long time ago before Jinx and Vi were a thing, and when Arcane was made, both my husband and I were like, "What? How did we predict this? This is amazing." So it's a good one.

Lenny (01:00:45):
There we go. Some adult content. What is a favorite interview question that you like to ask candidates?

Jiaona Zhang (01:00:53):
I do like to do behavioral questions, just really understanding when they've been in challenging situations, when they've been in ambiguous situations, how do they navigate ambiguity? Is a big one for me because at the end of the day, the PM job is really ambiguous. 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 that.

Lenny (01:01:14):
And is there anything specific you look for in their answer that tells you this is a good answer or not a good answer?

Jiaona Zhang (01:01:20):
Yeah. Good answers are people who put structure and a way forward through the ambiguity. That's what you look for. You want your PM to not just be like, "Oh no, we're swimming in ambiguity," but actually put a path forward. I think also looking for people who are 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 the right path from the first time that you do it, so rare. And so I want to see someone be able to get those inputs, be able to say, "This is the path, this is how I learned why 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, is this working? Is this not working?" And then make you either make a different decision. Seeing people do that really well is a big thing I look for.

Lenny (01:02:12):
Awesome. What is a favorite product you've recently discovered that you love?

Jiaona Zhang (01:02:17):
I love... It's 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 a little bit like, "Oh my gosh, no more rocking of the baby." But I do think it does a good job of actually doing the thing and I'm also giving parents peace of mind.

(01:02:34):
The other thing I'm a big fan of, again, you'll see where my head's at, lots of child related things. Midjourney for your toddler is actually great because instead of it being absolute instant gratification of "I want to 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. It could be like, "I would like it to be blue." He's obsessed with Jungle Book, "Wearing a fire hat next to a firetruck." And so you can actually create, and I do believe in the future, so much of what we are going to be doing as humans is literally what is the creative process? What's the idea? It's less about executing all the pieces of it, but it's so important to still be able to be like "This is the idea that I want to bring to life." And so I just think training that is huge.

Lenny (01:03:24):
Feels like you've just defined your three-year strategy for Webflow right there with AI.

(01:03:30):
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 in your team's ability to execute?

Jiaona Zhang (01:03:40):
There's so many different things that we've done at all the different companies. It really depends on the company. And what I mean by that is at a company like Webflow, where the tech stack is complex and where a given feature has so many different interactions, you're like "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 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 that's a tweak in the process that has really made a big difference at a company like Webflow.

(01:04:20):
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 so difficult to work with cross-functional partners and doing a little tweak in the process where you bring them in a kickoff meeting." That might be the thing that just changes that dynamic of how you work with teams. So it's really... I don't know if there's one thing, but it's almost like every day I'm thinking about small tweaks and process to make all of us more efficient.

Lenny (01:04:44):
Final question, what is your number one pro-tip for using Webflow and being successful with Webflow?

Jiaona Zhang (01:04:49):
My number one pro-tip is there's a lot of stuff coming out that I'm very excited about. I do think Webflow has traditionally had a high learning curve, and it's because we're a pro tool, we're a professional tool. We do really amazing stuff, so much power that we deliver you, but with that power has come with it's hard to learn. And so one of the things that I'm really excited about pro-tip for using Webflow in the future is 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, learn webflow in the context of what you're doing as opposed to going into a different tab and looking for the Webflow University stuff. It's going to be in context to the product, being able to actually take action directly, prompting Webflow to be able to do things for you. It's just going to be so much easier in the future to use the product. That's what I'm excited about. We're working on it and it will be out in the future.

Lenny (01:05:42):
Okay. No specific dates yet. Yeah, you could share, this sounds like breaking news of cool stuff coming.

Jiaona Zhang (01:05:47):
Some things are in alpha and [inaudible 01:05:49] beta, but we do want to be developing it with our users and really learning is this the power that you're looking for? Is this thing that's going to get you over the activation hump that you've struggled with in the past?

Lenny (01:06:00):
JZ, 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?

Jiaona Zhang (01:06:11):
I always love feedback, so if there's feedback on the podcast, send it my way. Or even just what would you want to learn? Send it my way. And the reason I ask that is because I'm actually working on a course, another course through Reforge, which is around managing your PM career. And so really just... 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 of 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.

Lenny (01:06:47):
And that's just reforge.com? There's no URL yet specifically for that course?

Jiaona Zhang (01:06:51):
Not yet, but it will come soon. And maybe what I'll do is I'll post it on my website, which is built in Webflow, so my full name dotcom.

Lenny (01:06:59):
Got it. JZ, thank you so much for being here, and thanks again.

Jiaona Zhang (01:07:03):
Thanks for having me.

Lenny (01:07:05):
Bye, everyone.

(01:07:08):
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 lennyspodcast.com.

(01:07:27):
See you in the next episode.