Lenny's Podcast: Product | Career | Growth - Building minimum lovable products, stories from WeWork and Airbnb, and thriving as a PM | Jiaona Zhang (Webflow, WeWork, Airbnb, Dropbox)

Episode Date: July 2, 2023

Brought to you by Brave Search API—An independent, global search index you can use to power your search or AI app | Miro—A collaborative visual platform where your best work comes to life | Superhuman—The fastest email experience ever made—Jiaona Zhang (JZ) is a product leader with a strong background in consumer products and extensive hiring and management experience. She is currently SVP of Product at Webflow as well as a lecturer at Stanford, where she teaches a graduate-level course on product management. Before Webflow, JZ was Head of Product for the Homes Platform at Airbnb and has also led product teams at Airbnb, WeWork, and Dropbox. In today’s episode, we discuss:• Building a “minimum lovable product” rather than a minimum viable product• How to create better roadmaps through storytelling• Top lessons from Dropbox, Airbnb, WeWork, and Webflow• The importance of setting ambitious OKRs• JZ’s first 90 days playbook: how to succeed in a new role• Advice for early-career PMs—Find the transcript at: https://www.lennysnewsletter.com/p/building-minimum-lovable-products—Where to find Jiaona Zhang:• Reforge: https://www.reforge.com/managing-your-pm-career• LinkedIn: https://www.linkedin.com/in/jiaona/• Website: https://www.jiaonazhang.com/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• Twitter: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) JZ’s background(04:22) Common mistakes new PMs make(06:44) Why Airbnb Plus didn’t work out, and takeaways from that experience(10:51) Executing big dreams step-by-step(13:45) The right way to push back against founders(16:54) Minimum lovable product vs. minimum viable product(20:53) What makes a product lovable(22:20) Advice on roadmapping and prioritization(28:04) Tips for new PMs to accelerate their career(29:16) JZ’s top skills and how they have evolved over her career(31:37) Designing crisp OKRs(36:09) Lessons from WeWork(43:01) Winning the first 90 days at a new company(48:34) Why trust is crucial(51:48) High-level lessons from Dropbox, Airbnb, WeWork, and Webflow(56:38) The one piece of advice that transformed JZ’s career(58:39) Lightning round—Referenced:• Mike Lewis on LinkedIn: https://www.linkedin.com/in/mikelewis/• “What working at Figma taught me about customer obsession,” VP of Product Sho Kuwamoto: https://www.lennysnewsletter.com/p/what-working-at-figma-taught-me-about• WeWork: https://www.wework.com/• WeCrashed on AppleTV+: https://tv.apple.com/us/show/wecrashed/umc.cmc.6qw605uv2rwbzutk2p2fsgvq9• Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-Solve-Problems-Test-Ideas/dp/150112174X• The Making of a Manager: What to Do When Everyone Looks to You: https://www.amazon.com/Making-Manager-What-Everyone-Looks/dp/0735219567• Tress of the Emerald Sea: A Cosmere Novel: https://www.amazon.com/Tress-Emerald-Sea-Brandon-Sanderson/dp/1250899656/• Arcane on Netflix: https://www.netflix.com/title/81435684• Snoo: https://www.happiestbaby.com/• Midjourney: https://www.midjourney.com/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [e-mail].—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

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, you're making a name for yourself of 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. 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 Jay-Z. Jay-Z 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 Jay-Z for a number of years, and she was also PM at Dropbox and at a gaming company called Pocket Jems. In her conversation, we dig into the most common mistakes early product managers make in their career, plus Jay-Z's biggest product mistake. We cover the concept of minimal lovable products versus minimal viable products. We talk about Jay-Z'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 Jay-Z on the podcast for a while, and I'm really happy that we finally made this happen. With that, I bring you Jay-Z after a short word from our sponsors. 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

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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's all about and how we 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 slash Lenny. With the help of the mirror team, I created a super cool mirror board with two of my own favorite

templates, my one-pageer 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 published in the mirrorverse. 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 slash Lenny. That's MIRO.com slash Lenny. Jay-Z, welcome to the podcast. Thanks for having me. I'm so excited to be here. 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? I think six years. Yeah. Wow. 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, 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. I think 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 can see in your head that you want to build. 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 like untraining that and being like, hey, we're going to go out there. We're 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 like people in the real world and their problems. And the first step is to understand their problems and then understand if there's an opportunity here as opposed to, hey, you want to build X thing for Y person. So that's the biggest mistake that you really have to. unteach and like retrain thinking around. There's a lot of this come from. People want to get into product management because they think like, finally I'll have the power. Finally, I'll be able to tell people what to build. Finally,

my ideas are really going to matter. Is that a lot of it comes from? I think there's a part of that. You know, one of the first things I teach is, you know, you're not a CEO. You're not here.

You actually have very little true authority because you don't actually manage anyone. It's a lot of it is all through influence. And so that is also a piece where you have to kind of untrain that thinking. I do think, a lot of people come into the product role thinking that I get to call the shots, I get to make the decisions, I get to decide what gets built. And really, your job is not that. Your job is to understand, here's 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. So let's kind of go to the other side of this question. We talked about what mistakes new teams make. I'm curious, what's the biggest product mistake that you've made? 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. So, you know, we're working on this concept called Airbnb Plus. You know, if you took a step back, where you're really trying to do is to be like, hey, not everyone trusts Airbnb in terms of,

you know, 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 Airbnb is 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 saunders out there. And I think that as a company, we're very much like, oh, goodness, like what are we going to do in the world of managed marketplaces? And so we went really hard down the solution space. We essentially were like, let's go inspect our inventory. Let's actually try to manage our inventory more. And really what we should have done is

taking 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 their strategic strength and like what's in your wheelhouse? So for example, Airbnb, we weren't that strong in operations. Again, we're this platform with this marketplace, right? And so if you don't have that muscle and then you're asking the company, the teams to essentially build it from the ground up, that's really, really difficult. Not to mention the unit economics, are the unit economics actually going to work, even as you scale? Yeah, I feel like Airbnb Plus is an untold story that somebody should tell, and that could be

its own podcast, I guess. You and I can tell it. We could tell this could be Airbnb Plus, the hidden story. As you said, the problem is 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. that we're going to vet them. We're going to 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 we'll never make money as a business doing this because we don't make it 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 and was just not executed well? I think there wasn't really a clear path. I think there's less about execution. Exactly. And it's more just like if you understood, again, this is 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 going to work out. We can make these things happen. I think you actually need to really make sure the unit economics work quite at the beginning. So that is definitely one lesson. And I think the other thing is, again, going back to the spirit of what are you trying to achieve? If you're trying to achieve this idea of like really knowing the quality of the place and for a platform like Airbnb, the right way to go about doing is through a review. through our guest reviews, which are essentially free as opposed to literally sending out inspectors. And I think the other things are if you can get signal on what are the things that people care about?

Is it cleaning? Is it the, hey, I'm locked out? And I think that there are other solutions besides inspection that then get at that. So for example, it is actually cheaper to go send everyone a lockbox than to deploy an inspector and go look at your property. right. It is actually cheaper to maybe do a partnership with like a, you know, a bunch of cleaners in different local areas and then get that as part of the feet, like as opposed to doing this session. 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, yeah, I personally don't believe the unit economics ever would have really worked out. I think we should have known that. We should have 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 going to go inspect. It's like, what is the problem for this listing and what's the best solution to fix that problem? 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, shoot big, and hopefully we figured 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 going to figure it out. I know there seems impossible, but we're just going to try it anyway. If you have any kind of framework of when to think big like that and just

go for it versus, oh, let's just work out the math today. Is this ever possible? I think it's really important for every company to be dreaming big. Like, if you don't have a big vision, it's really hard for you to innovate. But you got a 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 do you be clear about the phase that you're in? So I think it's totally fine to be like, hey, we are going to try X for six months, three months, you know, whatever it is. And we're explicitly going to go learn these types of things.

We're going to learn why are people, like, are there signals that we would get that would indicate that, again, the communication with the host isn't great? Or, you know, this type of listing, if it's hosted by a person with multiple property. Like, I think there are factors. We 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 time.

team on like 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, you know, kind of go at it. Like that is not recommended in my mind. It's like breaking it down into these smaller chunks. 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, you know, a short period of time. We got these learning. So let's go down this other path. Yeah. There's also like some cost fallacy that kicks in of just like, oh, we spend so much time and money and resources on this thing. Let's just go a little bit longer. Let's just see if we give it

another quarter, maybe it'll work out. You should articulate what success looks like and the milestones you want to hit in the small interrules that I talked about, right? So you don't get into this world where you're like, hey, I've gone for two years investing in this thing. Now we got to cut it. It's like, what is the quarter long milestone? Okay, what's the next quarter long milestone? And every single point, what does it go and no go? 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. 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 with an 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 like the head of product for one of the new bets. 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 is really into when it makes sense to kind of go along. Like, cool, let's do it. Let's buy. And we got to, you know, as a leader, you have to be excited. And the team needs to feel like, oh, Jay-Z is really excited about this too. We got to try it. Even though maybe you feel like it's not going to work out.

So I guess the question is like, when do you think it makes sense to try to convince the founder to know? this is the bad idea versus like, let's go for it. I think first it comes down to your conviction. Like, do you actually have conviction? This is a bad idea or are you personally still learning? Right. I think if you're at the point, if you're like, I have total conviction, then your job is to say no. You really, like, if you do not, like, you're not doing your job.

And then 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 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 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 that. And that could be

automated through technology as opposed to through humans. It's coming back with like, actual options. It's like saying, you know, and I think we did that a little bit, to be honest, like when we, you know, as a team evolve, you know, we learn and we're like, you know, this isn't going to work. And I explicitly, you know, 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. And so I think that the biggest thing, biggest tip I would have for people in this situation is really understand whether it's the founder or your manager or whoever it is, like,

what is it that you're actually trying to, what is it that they're trying to accomplish for the user and for the business? Remind them of that, like get aligned on that and then come back with better options. You know, very few people. I mean, we're all, a lot of these people, they're very smart and they're very motivated. They ultimately want to just do the right thing for 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 want to go after the solution despite the fact that it's not working. and you've proposed a much better path forward. And I think to touch on what you've 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. Totally. Okay, I'm going to bounce around a little bit. I have a bunch of different questions around different topics. Yeah. You popularize 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? The reason I care so much about minimal level product is because I do think in a world where there are so many different options, it's hard to just be like, hey, use this thing. 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 resonates with your users? And again, especially in a world where there might be a lot of different options, like minimal level products is the new MVP, right? The new minimal viable product.

So I think that's the real point. But at the other 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 want to get your product to market as quickly as possible, right? So it doesn't make sense for you to be like, I'm going to 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 perfectly quite honestly, like, lovable. So it requires a lot of understanding of like, again, your users and the space that you play in and the tolerance of your given user. So for example, a design. 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's sitting on the finance team or the IT team, right? Like their bar might be like, oh, I'm used to doing these like 15 things. And so your thing is just a lot better.

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 level product versus MVP? Again, it's very hard. I think every product team, every product person struggles with this idea of like, what is the minimal viable?

Even that concept in itself is difficult and not to mention like minimal lovable. I'll give a what flow example very recently. You know, we, so we have been investing in a couple of new features, you know, memberships and logic, new functionality for our users. And what we realized at the end of the day after investing in these areas, we were like, hey, we can get to minimal viable. but we don't know if we can actually get to minimal lovable 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 continues to ship away to get to minimal lovable when we are maybe hitting diminishing returns for user base?

Or does it actually make sense to release what we have, but then encourage our ecosystem to contribute the lovable piece? And again, it's not just like you put it out there and you hope, but you have to have a very strong point of view of like, are we at minimal viable? are we at minimal lovable? We're kind of where in between are we, right? And so having that point of view and then being able to say, are we going to be able to meet 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 even within the future set, it's very much, how do we do some things well as opposed to do a little bit of everything? I think that is a big piece of minimal lovable, which is, again, you know, to me it's like better to do five things instead of the 15 things and a really, really great. way with a high degree of polish with like, oh, this really meets my need versus trying to do everything and just doing a little bit of everything. And so every part of the experience feels a little bit clunky. It's not quite there. People, I think, would actually respect this idea of like,

you've given me minimal lovable in five areas as opposed to minimal viable in 15 areas. 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 make something lovable? Is it like delightful features. 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. There's definitely this idea of like the thing is just good. It has like all, like it is high quality. It's not janky. It doesn't feel weird. I'll give you like a very small example again, just from Webflow. This idea of like keyboard shortcuts, right? Like that feels small, but like that is a piece that creates a lot of love

from user base who are power users. And then there's this concept of like pixie dust. Maybe I'll pull out of the, you know, call it like design tool space. And we'll talk about some of the, other things, whether it's Dropbox or Airbnb, but you can just do a little bit of that, like, extra pixie dust. So an example from Airbnb, when we're doing the mobile app revamp, we're like, okay, there's like these basic table stakes, but if we actually added in templates, and we made it so that these templates could be maybe pre-populated in certain ways from the content 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 will just, at the end of the day, you know, you basically have like your time, your staffing, right, and the scope of your project and like something has to give. And so, you know, at the end of the day, you can't just like keep investing, keep investing because it's going to push out your launch timeline. But can you pick a few different areas where you're like, I'm going to scatter that pixie dust. I'm going to do a little bit more than what users are expecting. And that creates that level ability. Shifting to a different topic.

I know you have strong opinions about road mapping and OKR's impotization. And I know this is a big topic. 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? Roadmapping prioritization are kind of one bucket for me and then, you know, OKR is another. So I'll maybe give you my biggest tip in each one of these buckets. 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 why are these things the biggest things to invest in, these levers, the biggest ones to pull? And what I really don't want, what I think is a very common mistake from road mapping is people thinking like a spreadsheet with a bunch of projects, all, you know, the rice framework, right? Like everything has like an impact or cost and, you know, an effort column filled out. Like they think that that is prioritization and that is a 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'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 thinking change, right? So instead of it being this massive spreadsheet where you're going in, you're tweaking all the values, what is the story that you're telling about your roadmap, that these inputs can then go and influence. It could be like, hey, I just realized I didn't know before that we have a lot more power users on it.

Or maybe we have a lot more like non-technical users. Well, that input changes my roadmap and changes my themes in a pretty dramatic way. So skating at that level is really, really critical, I think, for a roadmap, as opposed to going down to like the really granular details of the how. So that's the biggest thing on road mapping, which is like, tell a story. what are your themes, make it so that your team can come up with the actual like how and the projects and all the little details, but really create that scaffolding for them to know what's important. Can I ask a follow question on that?

Totally. Yeah. 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 dock with maybe ancillary spreadsheet of the actual prioritization? Is it a deck? How do you actually deliver this to you with like Jay-Z, here's our proposal for our team. 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 cultures, 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 in a 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 like the same way I'm like, a roadmap is a story. You're telling theme. Like you write a story in a notebook, right? 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. 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, you know, so often docs get out of, or like, spreadsheets. get out of date, right? Because they're like a snapshot of whatever it is that you need it at

a point in time. But 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 find major, you know, learn major things that would change my themes. And then let's go link out to the juror where you can just see the snapshot of the roadmap at any given point in time. Do you have a template or common structure you suggest to teams for laying out the story? Or is it just depends on the quarter, it depends on the year? I'll give a plug for a, uh, a need. thing coming out in 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, like a broader roadmap instead of just like a feature spec. So yes, we have a ton of those artifacts are always evolving. I think every team kind of takes it and like tweaks it a little bit. But I do, I'm a big believer of like bring those artifacts back and then sharing them across the team. And so product operations is also a function that we've invested in because it just really greases the wheels and gets all of our teams kind of speaking the same language. Awesome.

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thing holding them back or something they can change that'll accelerate things? There's so many parts to it, but I'll pick one. And there are many frameworks even beyond 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. That could be like your thing. You could be known for working on the most like technically complex problems. You can be known for

working on things that are like really regulatory complex. Like find something that you can be really, really good at. And the reason I give that advice is because when you do that, you can crush like the projects that you get, right? Like because you're making a name for yourself reputation. And then you're giving more responsibility. Like people tend to flock and give responsibility to the people that are known for being excellent at something.

Is there something you were known to be excellent at in the course of your career? I would say early on my career. it was actually the fact that I had like a strong analytics background. And so when I joined gaming, right, I came from consulting. I didn't have any CS background or design background. And so it was really like creating reputation around being very analytical around being able to analyze the data sets of my game and then like make decisions. I also learned as I was doing that, I was actually really good at execution.

And so, you know, being able to keep a lot of plates kind of spinning and working on kind of like the largest studio and managing all the complex pieces. of that, that was what I discovered. I didn't know this, but I discovered as I started like working in the role. And so that was something I brought to Dropbox, you know, when I joined Dropbox. It was like, I knew that I could work with a lot of different teams and make sure that we like hit a launch deadline. 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 launch this really complex thing. I had to work across like, this was a project that had to work across a

like a lot of different platforms. We're using brittle APIs. And it was like a very, very small team. I had a very, very tight deadline. So when you're like, okay, I can do something like this, you end up getting more responsibility because people are like, oh, she was able to do something that was really hard with a small team. And so that's how you get more responsibility. 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 makes sense. But also, even when you start to manage, it shifts dramatically. You know, being known as like the best executor is not necessarily the thing that gives you and your team the most responsibility.

So, you know, as I've run my career, whether it's at Airbnb or we work or other places, I flexed into maybe like a different, it's like taking your core strength, but then flexing it and finding different ways to bring it to life. Much of what I just heard is you just worked incredibly hard and just got shit done. And so, and I think that's very, very important. And often leads a lot of success. I think PMs have to get shit done. And, yeah, ultimately, you're responsible for the outcome. Just no matter what happens. Yeah, yeah, I like that.

Like, be known for getting shit done and, like, working really hard. And that's never going to serve you badly. I think that is just lasting advice for being successful as a PM. I realized that we were talking about your tips on prioritization roadmaping and then OKRs and then I shifted topics and you never got to the OKR bucket. So let me come back to that. Yes. My biggest tip on OKRs is actually get.

really, really crisp un-quality. What would make you say, yes, we did a great job. And the reason I push so hard on that is because I see so many teams get really mucked down by OKRs. They're like, oh, man, if I don't hit my OKR, I feel like I'm going to have like a really bad reputation, or maybe I won't get promoted. Or like, you just get all this fear around OKRs. And so you see people, you see people sandbagging. You see people, you know, being hesitant to put in numbers until like the very last second until they're like super, super confident. And that results in ultimately, like a failure to, for your company to like innovate and move quickly. And so what I really push on for OKRs is like, what are you actually, what's a spirit? I think I asked this question, maybe too much to my teens,

but like what is the spirit of what you're trying to achieve? And what would make you say, I really, really crushed it this past quarter, right? And so it's less about like, I would rather have all the OKRs be red or yellow and like we missed everything. And we learned around why we missed it, then everything to be green. In fact, when everything's green, you're like, we definitely did not set ambitious enough OK, ours. And so it really pushed a lot on, like, what does it truly mean to, like, crush it and be successful?

What does it mean for 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, the revenue growth. And I think it's really hard because a lot of times, you know, you get your data scientists, you get the PM themselves 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 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, for my, 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, you're like, I don't feel anything different. Like your company doesn't look at the things that you've worked on, and they don't say, like, this is a smashing success. Your users are feeling no differently. And so that is the worst outcome in my head where your OKRs, you're like almost like doing OKRs for the sake of OKRs, as opposed to letting them be a guide

to delivering really great product to your end customer. I like the idea of that. But I imagine what often happens is you sign up for an ambitious OKR, you don't wait until the last second to commit to it. And then ends up being read. 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 set up, sign up for these really ambitious OKRs and their story is great and, you know, they're doing the right thing in that, but they fail. 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 harder people take risks than to be safe. So I think that's the first thing. That being, said, you know, you're also not doing a good job as a PM if you're like, this is my super, super ambitious thing. And you're like, I have no idea how to achieve it. Like, your job is to dream big and also have a plan to go tackle it. And so what I would expect the PM to be able to say is like, this is my North North Star. I'm not going to be able to do that in a quarter. That just is unreasonable. But here are the five milestones, you know, whatever number, some number of milestones that it's going to take me to do quarter over quarter to achieve this really, really ambitious

thing. And let me draw you that path. Like here's the milestone all the way across. And this is the first one. This is why it's so meaningful. So I expect that combination where you're like, I know where I'm going. It's really, really ambitious. And then you can then break it down. But again, I would much rather have someone 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, best swing that you can take is. 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 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. Totally. Yeah. Awesome. You mentioned WeWork and I want to spend a little time on WeWork. You were at WeWork for about a year, and I think it was like in the middle of a lot of the craziness that went on at WeWork. It was 2019. I feel like that year, it was either, like headlines were either about Trump or about WeWork in the news. That's tough.

So, okay, so what was that like being a PM leader at a company in that craziness? And is there a takeaway from that experience that helps you be a better product manager, a leader person? Yeah, I learned a lot for my time there. I think the most important lesson I learned was really around, I think there's like a people management lesson. And then there's also just like a how do you build an org period? The people lesson I learned was just really around empathy. 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. They're actually like growing my team a lot and not just, you know, in the U.S., but, you know, in Asia and in Europe. And then the second half of my time there was actually being like, okay, what do we do? If this is what's happening with WeWork? What are we actually going to do with all of these people who have like come to WeWork to work? And there's so many lessons there around leadership around like how do you how do you think about people?

How do you think about giving them, you know, the right transition plans, the right? Like it was a lot of learning. And I think, you know, probably a lot of people even right now through the macroeconomic downturn. And 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, before, you know, early. 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, like, at any company that I go to. And so just because, like, laying off half your team is a terrible feeling, right? Like literally having hired people and then having to let them go, it's not something you want to do. And so being really thoughtful around like, how do we not over hire? How do we, how are we really clear about, again, like these milestones of like we got to get through these gates. We got to be able to show these types of results. And then we unlock hiring in X, Y, Z ways. Like, that hygiene is really, really important.

Feels like this connects back to the Airbnb Plus story of just, let's just be really ambitious. We don't have any idea 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. I do think there was a little bit of that in the ether. of how we work 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, we work is really strong.

In fact, I went to WeWorks 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, and the way We Work 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 process, to feel really great. At the end of the day, it's about booking. And yes, there are definitely technology that would accelerate that. But do we need it to be super platform aware? Do we need it to be super futuristic? Like, that's actually not what people care about. So this all goes back to what are people's core desires in whatever product that they're using, right? Whatever thing that your business is trying to serve them. And so really understanding that will help you have a sense of like, hey, you still be really ambitious. Like, you know, again, in a hybrid world, It's like, why have real dedicated office space?

Every company 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 like a relevant vision. But what's the key piece of that vision? The key piece of the vision is around inventory. And then you make that inventory management easier. You make all of these things easier. But that's not a technology play in the same way as it is an operational play.

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. If you think back to WeWork, what was your favorite memory? And what was your hardest, least happy memory, if anything comes to mind? I mean, I think this idea like 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 and fusion.

using technology. I just feel like the people at we work were dreamers in like the best possible way. So that definitely, I feel like for every company that I've been at, it's really about like, you know, you join. I personally join for the product, but I stay for the people, right? Like, you join 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, you know, the people we work were really great. So that was definitely my favorite memory. I think the hardest memory was this gets a little bit personal, but I was actually in my first trimester when we were going through all of these layoffs. And I basically was faced with a choice. It was like, hey, do I stay at WeWork? I would be

guaranteed maternity leave. I was going to be moved on to this other team that was definitely going to stay. Do I do that? Or do I actually, and I think there's just a last piece of like, 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 going to have so many days to be able to go find their new role. And so the hardest moment, I actually remember this very vividly, like, am I going to take this new role or am I going to put myself on the layoff list essentially and give the role to someone else on the team who, when I really think about it, like, yes, I was pregnant, but I would have more time and more freedom to go find my next thing versus someone who I brought to the company who was on a visa. So that, to me, just really stood out and goes back to this concept around, like, leadership is so much about, like, empathy and, like, people. It's as much that as it's about, as it's about, like, understanding, you know, your market, your customers and the strategy of your product. Damn. What convinced you eventually to take off and try some different?

Well, I made the call in that particular case. I gave the role to someone else. And then once I made that call, I was like, well, I got to go find something. Like I, you know, I know that this is my last day. So I mean, I have to go find something. And it was really interesting because I actually, well, I went through an interview process. Well, I was in my second trimester. And then ultimately, I chose to join Webflow. And I joined. 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. That's a great segue. The question I was going to ask is around your 90-day plan that I know you have, you put a lot of thought into how to think about the first 90 days. But before we get there, the movie on WeWork with Jared Leto, how similar to reality was that brought?

I actually have not watched it. Okay. Parent life, you like don't have any time. And I do think there's, you know, it's like, I feel like if you ask, you know, people at Uber, if they've watched some of the time, right? They're like, it's like, it's not for me. Same way of like, why haven't watched Silicon Valley. You're like, it's a little too close to home. Yeah. Well, it was, it was quite a great movie and I really enjoyed it. Okay.

Curious, curious how close it was to realize. Okay, so then back to the 90-day question. So I know you spent a lot of time thinking about your first 90 days of what flow, you're pregnant as you described, and you have a perspective and 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? Yeah. I do think the first 90 days, depending on your role, is very different. But maybe I'll just talk a little bit about the first 90 days as like a head of product, right? Because you're like, whoa, or even just as a leader. Like, how do you go in? How do you really absorb all the information and get all the contacts you need and then affect change? And I think what was unique about my first 90 days is it was time bound. It was literally something where you're like, sure, I'd love to absorb information for many months, but I don't, you know, like, I just don't have the luxury of the time. And so. Because you're going to go and Matt leave right after. Because, yeah, essentially, I was going on Matt leave. That's great. And so the biggest things that, you know, I thought a lot about for my first 90 days was at the end of the day, yes, you have to really, 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 a luxury, you know, any other time in my life. And so I thought a lot about who do I speak to at the company. how do I create like a like a even just like a calendar of like speaking to people yes my leadership team but also like across a bunch of functions and across a bunch of levels so it's really important for me to like even start talking to some of the engineers from the team some of the engineers who had been there for the longest time to really understand well what's hard about our tech stack like what's going on like what's hard about your day to day and so I actually took time to really think about okay I want to speak to all of these types of people at the company and I packed

my first, like a couple of weeks with like a lot of those meetings. And so I think that was one piece, which is like, how do you build context as quickly as possible? And my tip there is like, again, it's not just with your peers. It's not even just with your team, but to really think across all the different functions and then think about where you're going to get the most amount of information in that particular function. And that was one piece of it. The other piece was like, I was like, well, I'm going to be out. I was only out for two months. But I was like, that's still a long period of time in the life of a startup. And so what I was, it was was really important to me was like, I did not go out having just listened and like, great,

like I have the context. I'll see you in two months. But it was really important for me to actually have a plan in place before I went out for my team. And so there are pieces where I was like, okay, I want to first, again, get that lay of the land. I want to have enough of like a strategic, hey, these things make sense. Keep going. Keep executing. These things like don't make sense. Let's get the, like, let's identify what those things are. And let's actually start to do research around these things so that when I do come back, we have a body of work that we can look at and be like, okay, this information, this data is making us choose to go down the path. Or this is a 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 more research on and then like assigning people, like, hey, you're going to do this research. and then we're going to come back and talk about it in, you know, the two months that I was out. And I also, you know, took the time. I actually, funny story, I think I literally had a board meeting the day before I went in for a

checkup. And then in the checkup, they're like, you're in labor. And it was really important for me to do that because I was like, I want, you know, for the things that I'm seeing, for the gaps that I'm seeing, I want everyone to be aware. I don't want to just like be with one founder. I want the whole leadership team. I want all the founders. I want the board.

I want everyone to be aware that, like, for example, engineering hiring was really, really important. And I was saying, 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 explicitly calling those things out and creating awareness around them and then asking other executives to like step in and be accountable. Those are big pieces of what I wanted to achieve in my first 90 days. 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?

Because you could do this infinitely meet everyone eventually. How many people did you end up maybe scheduling meetings with? Well, definitely everyone on my direct team and definitely everyone in like on the leadership team. So call it, those two combined were maybe, I don't know, like 20 or so people, 25 people. But then it was it was really about like finding the people and the other functions. And to me, for any given function, 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 functions, whether it's product marketing or engineering, you know, whatever 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 45, 40 to 50, like 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. 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 part of this of how you thought about it? Or do you feel like as a product leader company and that's less essential versus like, say, an UPM joining a team, a team as an I see?

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

I was almost pushing too hard. I was pushing too hard for change. I think that's a tricky part that every product leader, especially if they're coming into a new role, has to figure, like, how do I gain trust and then take that trust and then push for change as opposed to push for change too quickly before I have that trust? And so, again, it was a personal learning. And I think, you know, I think part of it was really driven by the timebound nature of it. But if you, hopefully not everyone has only 90 days. So if you take that learning into mind, it's like really thinking about your trust as like a bank, right? 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 use that trust to go push for things, push for change. But you have to be, you have to be thoughtful about how full your piggy bank is. And you don't want to be spending, you know, when you don't have the trust in the bank. What were signs maybe looking back that you didn't necessarily have the trust that you thought you did or you should have had. I think something like, you know, a product like Webflow is a very complex product and there are so many pieces to it. So, you know, 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 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 about the nature of when I had to go out and given the fact I really also wanted to build that like social context around like what is working and not working from like a function working together, not just like what the product is. What 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've like literally used it like a bunch. So like you had to choose. And in my head, I was like, I would much rather understand how the team is functioning together. And the reality is like the team was comprised of a lot of people with a lot of deep product context. So ultimately, you know, as all things in product, you know this money, like everything's a tradeoff. And so it's a trade off. And so, you know, you kind of had to make the call of what you wanted to trade off. 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 like product fundamentals or like product, like the actual thing we're building as opposed to like the discipline. So at this point you've worked 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? I'm going to actually give you my biggest thing across all four on the product side and then on the people's 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 really about really understanding why people love you. And like not forgetting to invest deeply in that core concept and then building a lot of. 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. Like Slack is really taking off. Why don't we build, you know, 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 simplicity, for how delightful it is, how easy it is to use, right?

So, you know, I think we actually went for a period of time where we didn't invest enough in, like, just like performance of our client. Like how long it takes for the thing to sync is a big part of the experience of using Dropbox, right? And so I think that is like a big, big learning where it's like really understanding that would have shifted your investments

into like doing that performance work as opposed to kind of like chasing the competitive space. And I think going back to chasing the competitive space, it's 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 a chat product,

that's fine, but really that the best chat experience or like collaboration experience is going to be more around your files as opposed to around just the conversation, right? So I think really understanding that is like a huge, huge learning. And I think that same lesson. can be, you know, it's very true for Airbnb, right? So at the end of the day, Airbnb is known for like all the homes, the fact that these are homes that real people put on the platform. And we spent some time talking about Airbnb Plus. When you are thinking, like, I got to go in,

I got to manage the inventory, I'd inspect it, you're almost like taking away from the thing that is like what makes Airbnb special as opposed to leaning into it, right? We also spent a lot of time on experiences. We dabbled in transportation. We spent a bunch of times on other things. But if you really sat back and you're like, well, what makes Airbnb special? How do you double down on your strength? It's like spending the time to make 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 have in my head like changed the way we invested. I think we would have gotten more returns as opposed to spreading ourselves and then like having things that like sort of work but then didn't quite work. And then again, same principle applies. So we work. What is the thing that makes you really special? It's the inventory. It like it's not actually like, oh, it's so amazing that I get to use this key card and this key card does like 10 different things. Like that's not what makes the we work experience special. Right. 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. 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. We're like, at the end of the day, like people really love our designer. They love the fact that they can use it. It does so much for them. It's so powerful. And then you add our CMS and it's really powerful when you design with data. So like investing deeply there as opposed to spreading ourselves too thin is also a lesson. So I think that that I think across so many companies, this lesson around like understand why people love you, double down on that.

And then whatever else you build around it, because again, you don't want to also be, you're not like a single product company. You're not like a one-trick pony. You are going to invest in these multi-products. But when you invest in a new product, really go back to, again, what's the core of our advantage? And how can that be something we leverage and deliver delivering a really really great product experience for our users in X adjacent area or X add-on. Final question before we get to our very exciting lightning round. Okay. What is the best advice that you've gotten that has transformed or impacted the way you

build product or hire or lead? Does anything come to mind? I can't remember where I explicitly got this advice, but I feel like I got it in multiple forms and it just really sat with me. It's this idea of like asking for help. And I do think about that a lot because I think that. There are so many times when you're like, oh, I'm the leader of X thing. Like, everyone's looking to me. Like, the puck stops to me. I need to have I, like, act together.

You know, like, I can't be asking for help. If I'm asking for help, like, do ever, is everyone to feel like, you know, I don't know what I'm doing? And ever since I've been people managing, I've been pushing myself to be like, I know it feels non-intuitive to go ask for help when everyone is looking for you to give them advice. But if you don't ask for help, there are so many times where you're just going to be sitting there with your problems.

and there's like whatever you have in your mind is just not the global best thing. And you have to go ask for help. You have to go ask for help from your partners, your peers, even your team, even being like team. I don't know. Like I really don't know. Like here's the guidelines. Like here's how you might want to think about it. But like I don't 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 hold as like a core principle and just helps me build better products. What's something that you've asked for help about recently as an example? So I'm working on our product strategy for the next three years. I'm thinking a lot about how do we really leverage AI to support all our source writers and support all our users who

come into Webflow and have a hard time sometimes learning how to use our product. And so I'm not an 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 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. Jay-Z, we've reached our very exciting lightning round.

I've got six questions for you. Are you ready? All right. Let's do it. What are two or three books that you've most recommended to other people? I love the design sprint by Google. I also really like Julie's book around managing people. people, how to be like a good manager. That one's really great. And so those are, those are my,

I guess, like, more like business side of the house books. And then, you know, we can also talk about like fantasy stuff if you want. But yeah, give us some, give us some wrecks there. I'm a big fan of Brandon Sanderson. He completed the Wheel of Time series on behalf of the Prius author. He, you know, he has the missborne series. And so he, he's a great one. He actually has, uh, this during the pandemic, he like, hold up and like wrote a bunch of books. And basically I have a confession to make. Oh, I wrote, I wrote like four extra books. And the latest one is trust by the Emerald Sea that I really love.

I saw the video of him sharing that news. And he's just like, I wrote a book during COVID. And then, okay, I wrote a second book. And then, oh, I wrote a third book also. And it just keeps going. I think he was like, I have a secret or I have a confession to make. And everyone was like, oh, no, are you going to say that you have like a ghost writer because you're so prolific?

And he's like, nope, I just wrote former books. What a beast. Next question on that topic. bit, what's a favorite recent movie or TV show that you watched? I know you said you don't get to watch much, but anything up to mind. I feel like every night I'm watching Sesame Street, like videos, like songs. We don't do, we don't do TV, but we do YouTube songs. So I honestly don't have an answer to that other than like we watched like the Elmo song and the ABC song with three-year-old. 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. we started this, you mentioned the painting behind you is referenced in, like, Arcane is a, it's connected to, or the show Arcane, which I imagine. Yes, I'm a big, yeah, I'm a big fan. So painted this a long time ago before Jigs and I were a thing. And, you know, 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. There we go. Some adult content. What is a favorite interview question that you like to ask candidates. I do like to do behavioral questions, just really understanding, like, when they've been in challenging situations, when they've been in ambiguous situations, like, how do they navigate

ambiguity is a big one for me? Because at the end of the day, like, the PM job is really ambiguous. Like, it's really hard to describe on a piece of paper all the things that you're going to encounter. So asking a lot of behavioral questions around around that. And is there anything specific you look for in their answer that tells you this is a good answer or not a good answer? Yeah. Good answers are people who put structure and a way forward through the ambiguity. Like that's what you look for. 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 be like, this is the way. This is very clear. Because again, the chances of whatever path you chart out for any product, for anything that you're doing is like the right path from the first time that you do it.

So rare. And so I want to see someone be able to, like, get those inputs, be able to like say, like, this is the path. This is how I like learn why, you know, I put this path together. And then going back to a lot of the stuff, I think we touched upon in this podcast is like, what are the little milestones that make you say, hey, is this working? Is this not working? And then make you either make a different decision, seeing people do that really well is a big thing I look for. Awesome. What is a favorite product you've recently discovered that you love? I love, I mean, it's not recent, but I do love the snoo and it's very top of mine 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 of the baby but I do think

it does a good job of like actually doing the thing and I'm also giving parents peace of mind the other thing I'm a big fan of again you'll see where my head's at lots of child like related things mid journey for your toddler is actually great because instead of it being like absolute instant gratification of like I want to see a fire truck and here you go here you go here my phone. It's like, let's wait for Midduring to create the fire truck. And specifically, you can even tell the majority what you want. It could be like, I would like it to be Blue, he's obsessed to Jungle Book, wearing a fire hat next to a fire truck. Right. And so you can actually like create and I do believe in the future so much of what we are going to be doing as humans is literally like,

what is the creative process? What's the idea? It's less about like executing all the pieces of it, but it's so important to still be able to be like, I want, like this is the idea that I want. to bring to life. And so I just think like training that is huge. Feels like you've just defined your three year strategy for Webflow right there 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 in your team's ability to execute? 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 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, you know, people depend on this workflow. This thing interacts with this thing. It's a whole platform. One of the biggest things we've been tweaking is like, how do we do more of a tech spike at the beginning to be like, do we have a good sense of like how difficult this is going to be the unknowns? Can we get a little bit more detail on them so that we don't go down a path and be like, oh, this doesn't make sense? So I feel like that that's like a tweak in the process that has really made a big difference at a company like Webflow. But when I look back to other companies, again, that might not be your biggest problem. Another problem could be like, hey, it's just

like so difficult to work with press functional partners and doing a little tweak in the process where you bring them in in a kickoff meeting. That might be the thing that just like changes the dynamic of like how you work with teams. So it's really, I don't know if there's like one thing, but it's almost like every day I'm thinking about small tweaks and process to make all of us more efficient. Final question. What is your number one pro tip for using Webflow and being successful with Webflow? My number one pro tip is, you know, there's a lot of stuff coming out that I'm very excited about. I do think, you know, Webflow has traditionally had a high learning curve. And it's because we're a pro tool, we're a professional tool. We can do really amazing stuff. So much power

that would deliver you. But with that power, you know, has come with like, it's like hard to learn. And so one of the things that I'm really excited about pro tip for using Webflow in the future is, you know, we're really going to bring the magic of Webflow University, the magic of AI, all together, so that you can just use and learn Webflow 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, like 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. So that's what I'm excited about. We're working on it, and it will be out in the future. Okay, no specific dates yet. Yeah, you could share. This sounds like breaking news of cool stuff coming. Some things are in, you know, Alpha and Product of Beta, but we do want to be developing it with our users and really learning. Like, is this the power that you're looking for? Is this thing that's going to get you over the activation hump that you've struggled with in the past? Jay-Z, I think we've made a maximally lovable podcast episode. Thank you so much for being here. Two final questions. How can listeners find you online if they want to reach out? And how can listeners be useful to you? Well, I always love feedback. So there's feedback on the podcast, send it my way. Or like, you're even just like, what would you want to learn? Send it my way. And the reason I ask

that is because I'm actually working on a course, another course through Reforge, which is around managing your PM career. And so really just, you know, I've talked to so many people, 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, you know, find. me there if you want to chat more and send send the problems that you're struggling with when it comes to your career and that would help me refine my course. And that's just reforge.com. There's no URL yet specifically for that course. Not yet, but it will come soon. And what maybe what I'll

do is I'll post it on my website, which is built in Webflow. So my full name.com. Got it. Jay-Z, thank you so much for being here. And thanks again. Thanks for having me. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny'spodcast.com. See you in the next episode.