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 making a name for yourself a reputation and then you're
giving more responsibility people tend to flock and give responsibility to the people that are known for being excellent at something welcome to Lenny's podcast where I interview world-class product leaders and growth experts to learn from their hard-winning 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 lecturer at Stanford teaching a course on product management before this she was senior director of product management at wework a long time product leader at Airbnb where I got to work with Jay-Z for a number of years
and she's also pm at Dropbox and at a gaming company called pocket gems in our conversation we dig into the most common mistakes early product managers make in their career plus Jay-Z's biggest product mistake we cover the concept of minimal lovable products versus minimal viable products we talk about Jay-Z's
unique Frameworks for Road mapping and fertilization 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 B 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
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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 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 upms make in this experience of kind of helping upms get into the field I think something that is really hard to
untrain but I think every human does it is you jump to Solutions and so one of the biggest things I see not just in my course but also just as a PM and like some of the mistakes that you make as a PM is the idea of you get really attached to a solution a way of implementing something something that
you you can see in your head that you want to build and so that's the first thing I really want to like unteach in in our course and so a lot of people will literally come in they'll be like I want to build X startup or I want to do you know this thing or I I'm in blank school and I've been doing a lot of
research on this particular area and so like untraining that and being like Hey we're gonna go out there we are not 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 does a lot of this come from people want to get into product management because
they think like finally I'll have the power finally I'll be able to tell people what to build finally my ideas are really going to matter because our a lot of it comes from part of that you know one of the 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 rule 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 hear the opportunities and then you're kind of pulling together all the different possibilities and you're really editing so so I do think it comes from desire for a lot of people thinking that's what the product rule 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 beams 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 proud people we're always making mistakes
we're always learning maybe I'll give an example from Airbnb since you and I were both there and 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 we're really trying to do is to be like hey not everyone trusts Airbnb in terms of
you know it's it's a platform it's not like it's managed inventory it's not a hotel how do you go in and really make sure that we're like all the airbnbs are made in the quality bar but I do think we were very solution first and I think we're also competitor afraid at the time right so it was during a time where
there were managed marketplaces there were the the Saunders out there and I think that as a company we're very much like oh goodness like what what are we gonna do in the world of managed marketplaces and so we went really hard down the solution space we essentially were like let's go inspect our inventory
let's actually try to manage our inventory more and really what we should have done is taken a step back and be like what's the real problem the real problem is people want to know what they're getting themselves into we need to represent the homes a lot better and I think the other piece here that's
really important is what as a company is there strategic strength and like what's in your wheelhouse so for example Airbnb we weren't that strong in operations we again where this platform or this marketplace right and so if you don't have that muscle and then you're asking the company the teams to essentially
build it from the ground up that's really really difficult not to mention the unit economics is 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 the 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 we're gonna vet them we're gonna make sure they're awesome there's a minimum bar I think the and I guess this is the question is do you think it was just like this is never possible because there will 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 and was just not executed well I think there wasn't really a clear path I think there's less exactly and it's more just like if you understood again this
is what my point around you in economics there are things where I think you have like magical thinking around unit economics you're like well when we get to the scale of X it's all gonna work out we can make these things happen I think you actually need to really make sure the unit economics were quite at
the beginning so that is definitely one lesson and I think the other thing is again going back to 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 and for a platform like Airbnb the right way to go about doing it is
through our reviews right through our guest reviews which are essentially free as opposed to literally sending out inspectors and I think the other things are if you can get signal on what are the things around quality that people care about is it cleaner the cleaning is it 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 lock box than to deploy an inspector and go look at your property right it is actually cheaper to maybe do a partnership with like a you
know a bunch of cleaners in different local areas and then get that as part of the fee like as opposed to doing this fashion so again it's really about what are you really trying to achieve what is the user problem in each of these areas and can you target that problem with the particular listing that is you know that
you're looking at and so I yeah I personally don't believe the unit economics ever would have really worked out I think we should have known that or like we should have uh dug into that more at the very beginning and then to get very tailored instead of like one blunt instrument to solve it all hey
we're gonna go inspect it's like what is the problem for this listing and what's the best solution to fix that problem there's a couple things that I think are important product Leadership Lessons here one is Airbnb and Brine 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 gonna shoot shoot big and hopefully we figure it out sometimes it works out in this case it didn't work out and what
you're finding maybe you even knew this early on is just like there's no possible world where this could have worked in this approach I guess is there anything you've learned about just like when to think big and not even like forget it we're gonna figure it out I know this seems impossible but we're
just gonna try it anyway 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 for you
to innovate but it it you got a couple of that really big Vision with thoughtfulness around your execution right and so I think one of the biggest tips I have is how do you just be very how to be clear about 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 like are there signals that we would get that would indicate that the again the communication with host isn't great or you know this type of listing if you if
if it's hosted by a person with multiple property like I think there are factors you can be like hey we can learn this very explicit thing in a given period of time and you can do what I call like unscalable things in that prototyping phase and that early phase to go learn those lessons but you just have to be
very very clear with your team on like what phase you're in hey we're in the learning phase and we explicitly are trying to learn these things versus hey we we have this really big vision and we're just gonna you know kind of go at it like that is not um recommended in my mind it's like
breaking it down into these smaller chunks that that I think gets you the balance of thinking really really big but also being able to be like okay we are still going to be able to say okay this path is not going to work out we ran at it for you know a short period of time we got these learnings now let's go
down this other path yeah there's also like 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 you should articulate what success looks like and the
Milestones you want to hit in the small intervals that I talked about right so you don't get into this world where you're like hey I've gone for two years investing in this thing now we gotta cut it it's like what is the quarter long Milestone okay what's the next quarter long Mazda and every single point it was
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 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 is 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 yeah 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 founders are really into when it makes sense to kind of go along like cool let's do it let's buy and we
gotta you know as a leader you have to be excited and he needs to feel like oh Jay-Z is really excited about this too we gotta try it even though maybe you feel like it's not gonna work out so I guess the question is like when do you think it makes sense to like convince
the founder no 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 still are you personally still learning right I think if you're at the point if you're like I have total conviction then your
job is to say no you you really like if you do not like you're not doing your job and and then 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 consider everybody before to like come and like use Airbnb but the right way to do it is not this very time intensive cost and tested way to you
know inspect all these homes the way to do it is to be much more granular in what we ask people when they upload their home right like and like more checks in in that and that could be automated and 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 of all you know we learn and we're like you know this isn't going to work and I explicitly you know moved off a team and I was like I'm going to work on the review system I'm going to continue to evolve this and
make it better because that is the actual scalable way to do this as opposed to keep going at it in the very manual process and so I think that the biggest thing the biggest tip I would have for for people in this situation is really understand whether it's the founder or your manager or whoever it is
like what is it that you're actually trying to what is it that there trying to accomplish for the user and for the business remind them of that like get get aligned on that and then come back with better options you know very few people I mean we're all a lot of these people they're very smart and they're
very motivated they ultimately 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 proposed a much better path forward and I think to touch on what you've already 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 gonna 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 that 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 uh minimal viable product
so I think that's that's the real point but at the end of the day it does come back to what are the options that a user has and what are they trying to do so there's a world where you know 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 critical 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 Mark 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 it requires a lot of understanding of like again your users and the space that you play in and the tolerance of your given user so for example a designer might have a lot higher of a bar of like this is the kind of workflow I want this is the kind of like bar for my product but you know again someone's
sitting on the Finance team or the IT team right like their their bar might be like Oh I'm used to doing these like 15 things and so your thing is just a lot better I 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 itself is difficult and not to mention like
minimal lovable I'll give a webflow example very recently you know we we so we have been investing in a couple of new features um you know memberships and logic new functionality for our users and what we realized at the end of the day after investing in these areas we were like hey we can get to minimal viable but we
don't know if we can actually get to minimal lovable in a way that our users really really want and so does it make sense for us to continue to go down this path of like keep like continues to ship away to to get to minimal lovable when we are maybe hitting diminishing returns
for a user base or does it actually make sense to release what we have but then encourage our ecosystem to contribute the lovable piece and again it's it's not just like you you put it out there and you hope you have to have a very strong point of view of like are we at minimal viable are we at minimal lovable
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 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 future set
it's it's very much uh 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 a oh this
really meets my need versus trying to do everything and just doing a little bit of everything and so every part of the experience feels a little bit clunky it's not quite there people I think would actually respect this idea of like you've given me minimal lovable in five areas as opposed to minimal viable in 15
areas 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 it or is it what you're saying which is just things are actually good like there's fewer
things but they're each really good there's definitely this idea of like the thing is is just good it has like all I like it is it 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 she feels
small but like that is a piece that creates a lot of love love from user base who are power users and then there's this concept of like pixie dust uh maybe I'll pull out of you know call it like design tool space and we'll talk about some of the other things whether it's Dropbox or Airbnb but you can just
do a little bit of that like extra pixie dust so an example from Airbnb when we're doing a mobile app revamp we're like okay there's like these basic table Stakes but if we actually add it in templates and we 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 us 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 um 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 gonna scatter that pixie dust I'm gonna do a little bit more than what
users are expecting and that creates that lovability shifting to a different topic I know you have strong opinions about Road mapping and okrs and fertilization and I know that's a big topic but let me just ask what's the most common advice you give around how to road map well and
do okrs prioritize and or just like I don't know Common mantras or things you always come back to to be successful in these areas red lightning prioritization or 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 Road mapping my
biggest thing that I tell my teams is you're telling a story so what I want from you is I want themes I want a story like like why are these or things like things the biggest things to invest in these levers the biggest ones to pull and what I really don't want what I think is a very common mistake from Road
mapping is people thinking like a spreadsheet with a bunch of projects all uh you know the rice framework right like everything has like an impact of cost and you know a like an effort column filled out like they think that that is prioritization and that is a map like if you just do that right and then
you present that to your team like they're after 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 my thinking changed right so instead of it being this massive spreadsheet where you're going in you're tweaking all the values what is the story that you're
telling about your roadmap that these inputs can then go and influence it could be like hey I just realized I didn't know before that we have a lot more power users on or like maybe we have a lot more like non-technical users well that input changes my roadmap and changes my themes in a pretty dramatic
way so skating that at that level is really really critical I think for a roadmap as opposed to going down to like the really granular details of the how so that that's the biggest thing on Road mapping which is like tell a story what are your themes make it so that your team can come come up with the actual
like how and the projects and all the little details but really create that scaffolding for them to know what's important can I ask a follow-up question on that really yeah it's easy to visualize the 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 an ancillary spreadsheet of the actual prioritization is it a stack how do you actually deliver this to you with like Jay-Z here's our proposal for our team yeah and kind of Docs 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 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 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 themes like you write a story in a notebook right you write a you write a story on pages and so a doc is definitely preferred and even in the dark just being like here's what we're
trying to achieve here are the you know the big areas I want to invest in here are my big themes and then going into each of those themes and be like these are the big projects and then linking out again not even to a spreadsheet sheet but linking out to the artifacts and and the the systems that your team
actually uses so if your team uses jira go ahead and Link out to jira because you know so often docs get out of or like spreadsheets get out of date right because they're they're like a snapshot of whatever it is that you needed at the point in time but you if you said you link out to the actual things that your
teams are working out of you can always be like these are the themes I will edit these if I find major you know learn major things that would change my themes and then let's go link out to the Jura where you can just see the snapshot of the roadmap at any given point in time
do you have a template or common structure you suggest to teams for think laying out the story or is it just depends on the quarter it depends on the year I'll give a plug for a new thing coming out of reforge which is you know this concept of like artifacts and so we we do have a lot of artifacts out there
so like what are what's our general product development process what are our templates for our specs what are our templates for some of these things that we're talking about a road map like a broader road map instead of just like a feature spec so yes we have a ton of those artifacts they're always evolving
I think every team kind of takes it and like tweaks it a little bit but I do I'm a big believer of like bringing those artifacts back and then sharing them across the team and so product operations is also a function that we've invested in because it just really greases the wheels it gets all of our
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the blocker or 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 um and there are many Frameworks even beyond the one about let's take 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 teens and
cross-functional stakeholders like that could be like your thing you could be known for working on the most like technically complex problems you can be known for working on things that are like really regulatory uh complex like find something that you can be really really good at and the reason I give
that advice is because when you do that you can Crush like the projects that you get right like because you're making a name for yourself a 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 in my career it was actually the fact that I had like a strong analytics background and so when I joined gaming right I came from Consulting I didn't have any CS background and so our 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 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 my joint Dropbox it was like I knew that
I could work with a lot of different teams and and make sure that we like hit a launch deadline and so I would find myself trying to like lean into that superpower and then when delivering upon that getting more responsibility right like hey you just launched this really complex thing had to work across like
this was a project I had to work across like a lot of different platforms we're using brittle apis and it was like a very very small team I had a very very tight deadline so when you're like okay I can do something like this you end up getting more responsibility because people are like oh she 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 it 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 at other places I flex into maybe like a different it's like taking your core strength but then
flexing it and finding different ways to bring it to life much of what I just heard is you just worked incredibly hard and just got done and uh and so and I think that's very very important and uh often PM's have to get done um yeah ultimately you're responsible for the outcome uh just no matter what
happens yeah yeah I like that like be known for getting done and like working really hard and that's never going to serve you badly I think that is just lasting uh advice for being successful as opium 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 yes my biggest tip on okrs is actually get really really crisp on qualitatively like what would make you say yes we did a great job and the reason I 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 I'm gonna have like a really bad reputation or maybe I won't get promoted or like like you just get all this fear around okrs and so you see people you see people sandbagging you see people you know being hesitant to put in numbers
until like the very last second until they're like super super confident and that results in ultimately like a failure to for a company to like innovate and move quickly and so what I really push on for okrs is like what are you actually what's 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 okrs 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 users what does it mean for a business what is that like for our users to feel X like
can you describe that can you write that out for our business to see this in terms of you know it the revenue growth and I think it's it's really hard because a lot of times you know you get your data scientists you get the PM themselves being like oh man I'm only an input metric and not an output metric
and so like I definitely can't sign up for that Revenue uh Target because I have an input metric and all of 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 and your users at large are like I don't feel anything different like your company doesn't look at the things that you've worked on and they they don't say like this is a smashing success your users are feeling no differently and so
that is the worst outcome in my head where your okrs you're like almost like doing okay hours for the sake of okrs as opposed to letting them be a guide to delivering really great product to your 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 till 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 guys teams 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 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 rather people take risks than to be safe so I think that's the first thing that being said you know you're also not doing a good job as a PM if you're like this is my super super ambitious thing
and you're like I have no idea how to achieve it like your job is to dream big and also have a plan to go tackle it and so what I would expect the PM to be able to say is like this is my North North Star I'm not 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 is the Milestone all the way across and this is the first one and this is why it's so
meaningful so I expect that combination where you're like I know where I'm going it's really really ambitious and then you can then break it down but 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 sub-optimal it's gonna be some absolute 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 road map and what they're
trying to accomplish and just as long as it feels like the story mates ends there's a path there the team did their best I think we knew we knew it was really ambitious we kind of knew maybe they wouldn't get there it sounds like that's kind of the thing you look for in a performance of 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 uh it was it was a it's 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 that helps you be a better product manager leader person yeah I learned a lot from my time there I think the the most important
lesson I learned was really around I think there's a uh like a people lead a management lesson and then there's also just like a how do you build an org period the people lesson I learned is just really around empathy in fact you know what essentially what I was doing was yeah 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 US but you know in in Asia and in Europe and then the second half of my time there was actually being like okay what do we do if 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 that there's so many lessons there around leadership around like how do you how do you think about people how do you think about giving them you know the right transition plans the right like yeah it was it was it was it was a lot of
learning and I think you know probably a lot of people even right now through the macroeconomic downturn they're like learning that lesson in a really hard way and so it was definitely something that I got a crash course on I think before uh you know early and the 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 um how are we really clear about again like these Milestones of like we gotta get get through these Gates we got to be able to show these types of
results and then we unlock hiring in XYZ ways like that hygiene is really really important feels like this connects back to the Airbnb plus story of just let's just be really ambitious where you don't have any idea how we're gonna get there but we're just gonna go for it higher
like crazy scale put a lot of investment in this thing and hopefully we'll figure it out I do think there was a little bit of that in the ethos of how we work with functioning for sure I think that what was really important for us to do was to be like we have this I mean operationally wework is really strong in
fact I went to we work because you know having been at Airbnb I was like I don't feel like we've dialed this operational muscle down but I know from what I've seen the way we work is expanded that they're really really excellent at the operations but I think it was we again we hired beyond our skis on the tech
side it's like we don't need a team of this size to go do the things that are needed for the product to feel really great at the end of the day it's about booking and yes there are definitely technology there's technology that would accelerate that but do we need it to be super platform aware do we need to be
like super futuristic like that's actually not what people care about so this all goes back to what are people's or Desires in whatever product that they're using right whatever thing that your business trying to serve them and so really understanding that will help you have a sense of like hey you can
still be really ambitious like you know again in a hybrid world it's like why have real dedicated office space every company could go through wework as opposed to this dedicated space like that's still a really good idea that's still a really big vision and like a relevant Vision but
what's the key piece of that Vision the key piece of the vision is around inventory and then you make that Inventory management easier you make all of these things easier but that's not a technology play in the same way as it is an operational play right so just really understanding again like you can still
dream really big but you don't have to dream big and higher big and all the things in order to have a very ambitious Vision that you deliver to the market if you think back to 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 joined wework they were like we could do a lot here like the idea of really kind of like the physical space infusing technology I just feel like the people that we work were were dreamers and like the best possible way so that that definitely I feel like for every company
that I've been at it's really about like you know you join you I personally joined for the product but I say 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 uh memory I think the 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 uh 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 you know gonna stay do I I do that or do I actually I think there are 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
gonna have so many days to be able to go find their new role and so the hardest moment I actually I remember this very vividly like am I gonna take this new role or am I going to put myself on the layoff list essentially and and give the role to someone else on the team who
when I really think about it like yes I was pregnant but I would have more time and and more freedom to go find my next thing versus someone who I brought to the company who was on a Visa so that to me just really stood out and then goes back to this concept around like leadership is so much about like empathy
and like people it's it's as much that as is it about as it's about like understanding you know your Market your your customers and the strategy of your product damn what uh convinced you eventually to take off and try something different well I made the call in that particular
case I'd give the role uh to someone else and and then once I made that call I was like well I gotta go find something like I you know I know that this is my last day uh so I'm gonna have to go find something and it was really interesting because I actually well I went through an interview process um
well I was uh in my second trimester and then ultimately I chose to join uh 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 that's a great segue to the question I was gonna ask is around your 90-day plan
that I know you have you put a lot of thought into how to think about the first 90 days but before we get there the movie on we work with Jared Leto how similar to reality was that brought I actually have not watched it okay parent life you like don't have any time and I do think there's you know it's like I
feel like if you ask you know people at Uber if they've watched some of them right they're like uh it's like I don't know 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 a 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 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 yeah I do think the first 90 days depending on your role is very different but I well maybe I'll just talk a little bit about the first 90 days as like a header product right because you're like whoa or even just as a leader like how
do you go in how do you really absorb all the information get all the contacts you need and then affect change and I think what was unique about my first tiny 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 yeah like I just
don't have the luxury of the time and so because you're gonna go and Matt leave right after because yeah essentially I was gonna go on that way that's right and so the biggest things that you know I thought a lot about from my first 90 days was at the end of the day yes you
have to re like 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 well how do I quickly build contacts probably like 5 faster than I would be given the luxury you know any other time in my life and so I thought a lot about
who do I speak to at the company how do I create like a like a even just like a calendar of like speaking to people yes my leadership team but also like across a bunch of functions and then across a bunch of levels so it's really important for me to like even start talking to some of the engineers from the team some
of the engineers who had been there for the longest time to really understand well what's hard about our Tech stack like what what's going on like what's hard about your day-to-day and so I actually took time to really think about okay I want to speak to all of these types of people at the company and I
packed my first like a couple weeks with like a lot of those meetings and so I think that was one piece which is like how do you build context as quickly as possible and my tip there is like again it's not just with your peers it's not even just with your team but to really think across all the different functions
and then think about where you're going to get the most amount of information in that particular function I think that was one piece of it the other piece was like I was like well I'm going to be out I was only out for two months but I was like that's still a long period of time
in the life of a startup and so what I it was really important to me was like I did not go out having just listened and like great like I have the context I'll see you in two months but it was really important for me to actually have a plan in place before I went out for my team and so there were pieces where I was
like okay I want to first again get that lay of the land I want to have enough of like a strategic hey these things make sense keep going keep executing these things like don't make sense let's get the like let's identify what those things are and let's actually start to do research around these things so that
when I do come back we we have a body of work that we can look at and be like okay this information this data is is making us choose to go down the path or this is a no go or no-go decision we can make that decision now where we couldn't make that decision number four 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 things that we gotta do a lot a lot more research on and then like assigning people like okay you're gonna do this research and then
we're gonna come back and talk about it in you know the two months that I was out and I also you know took the time 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 right to
like step in and be accountable those were 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 uh well definitely everyone on my direct team and definitely everyone in uh like on the leadership team so call it but those two combined were maybe I don't know like 20 or so people um 25 people but then it was it was really about like finding the people in
the other functions and to me for any given function is really like getting a read from again that leader but also someone closer to the actual work and so you kind of like look at the the functions whether it's product marketing or engineering you know whatever it was back then I didn't have designs like
design and really getting a couple of data points for each one of those functions so if you add that up that probably you know was like 45 40 to 50 like conversations but but again if you 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 in part of this of how you thought about it or do you feel like as a product leader coming in that's less essential versus like say nupm joining
it my team a team is that I see trust is so important I mean I trust is is everything right you know as a PM you're the trust that your cross-functional partners have in you the trust that the you know the CEO has a new it like it's 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 gotta you know go go we gotta go I was almost pushing too hard I was pushing too hard for change I think that's that's the tricky part that every product leader especially if they're
coming into a new role has to figure like how do I gain trust and then take that trust and then push for change as opposed to push for change too quickly before I have that trust and so again it was it was a personal learning and I think you know I think part of it was really driven by the time-bound nature
of it but if you if you hopefully not everyone has only 90 days so if you take that learning into mine it's like really thinking about your trust as like a bank right it's like you're putting money into your bank and then at some point you're gonna take money out you're going to use that Social Capital you're gonna
use that trust to go push for Things Push for change but you have to be you have to be thoughtful about how full your piggy bank is and you don't want to be spending you know when you don't have the Trust In The Bank what were signs maybe looking back that you didn't necessarily have the trust
that you thought you did or you should have had I think something like you know a product like waffle is a very complex product and there are so many pieces to it so it you know it's it's very difficult to learn the product and you know the first 90 days especially if I was also prioritizing all these
conversations with the team and so I think that again without the time constraint what I would recommend right is to be like hey every product leader has to take the time to really go deep on the product given the complexity of webflow and given the time-bounder nature of what I had to go out and given
the fact that I really also wanted to build that like social context around like what is working and not working from like a functions working together not not just like what the product is what I wasn't able to do is spend enough time with my with the product to be able to have all
of that in my back pocket to be able to be like oh okay well like I know how this this and this works because I I've like literally used it like a bunch so like you had to choose and in my head I was like I I would much rather understand how the the team is is functioning together and and the reality
is like the team 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 Lenny like everything's a trade-off and so it's a trade-off and so you know you kind of had to make the call of what you want to trade off and the thing I traded
off the most was that that product context in my first 90 days and again it got me some things because I was able to have the time to go deep on the things I mentioned but it didn't give me enough trust in the piggy bank around the actual like product fundamentals or like product like the actual thing we're
building as opposed to like the discipline so at this point you've worked it for legendary companies Dropbox Airbnb wework 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 gonna actually give you my biggest thing across all four on the product side and then on the people side there are so many nuances also and you know we could spend another two hours talking about each one of these but I think just in part like 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 everything around that and and so I'll walk you through the different companies so specifically for for Dropbox I think we
did waste Cycles where we would be like oh we see you know X happening in the market like slack is really taking off why don't we build you know a like a like a slack competitor or like why don't we build chat and I think that it really missed this idea of like well why do people love Dropbox and what do we
need to do to keep investing in that so that that remains true people love Dropbox for 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 the competitive space
and I think going back to chasing the competitive space is this idea of like what is your Alpha like again why do people come to you you know people come to Dropbox again for all the things I mentioned but also ultimately like we have your files right like so if you're going and building a chat product that's
fine but really the 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 you know we spend some time talking about Airbnb plus when you are thinking like I gotta go in I gotta manage the inventory how to inspect it
you're you're almost like taking away from the thing that is like what makes everything be special as opposed to leaning into it right we also spend a lot of time on experiences we dabbled in transportation we spent a bunch of times on other things but if you really sat back and you're like well what makes
Airbnb special how do you double down on your strength it's like spending the time to make that that experience of like really understanding what's in a home so people don't go and get surprised like making that you know onboarding Journey for the host and then Discovery journey and like you know like
you know guest booking Journey really really great so I think that that same lesson would apply to Airbnb would have in my head like change the way we 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 same again same principle applies so 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 wework
experience special right and so again if you knew that you wouldn't spend all that time being like I'm gonna really deeply invest in the tech team I'm gonna do all these interesting things you'd be like I just need to make inventory management 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 it's just not the core and then finally like even at webflow we are learning this lesson you know all the time we're like at the end of the day like people really love our
designer they love the fact that they can use it it does so much for them it's so powerful and then you add our CMS and it's really powerful you can 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 like you're not like a single Product Company you're not like a one-trick pony you are going to invest in these multi-products but when you invest in a
new product really go back to again what's the core of our advantage and how can that be something we leverage and delivering a really great product experience for our users in ex 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 device but I feel like I got 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 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 and they 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 dude is everyone gonna feel
like you know I don't know what I'm doing and ever since I've been people managing I've been pushing myself to be like I know it feels not intuitive to go ask for help when everyone is looking to for you to give them advice but if you don't ask for help there's so many times
where you're just gonna be sitting there with your problems and there's like whatever you have in your mind is just not the global best thing and you have to go ask for help you have to go ask for help from your your partners your peers even your team even being like team I I don't know like I really don't
know like here is 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 I hold as like a core principal and 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 of our source writers and to support all our users who come into webflow and you know have a hard time sometimes learning how to use our product and so I'm not an AI expert so asking for help from the founders from external folks from Engineers to be like well what's
happening like every single week I feel like LMS are changing but it's possible in the world is changing and so constantly asking for help to iterate on the strategy is a huge part of um it's happening every day for my 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 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 mistborn series and so he
he's a great one he actually has uh this during the pandemic he like holed up and like wrote a bunch of books and and visibly have a confession to make or I wrote I wrote like four extra books and the latest one is the trust by the emerald C that I really love I saw a video of him sharing that news
and he's just like I wrote a book during covid and then okay I wrote a second book and then oh I wrote a third book also 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 gonna stay there you have like a ghost writer because you're so
prolific and he's like no I just wrote former books what a beast next question on that topic a little bit what's a favorite recent movie or TV show that you watched I know you said you don't get to watch much but anything comes to mind I feel like every night I'm watching Sesame Street like like
video uh like songs we don't we don't do TV but we do 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 uh before we started this you mentioned the painting behind you is referenced in like Arcane is a is it's connected to the show Arcane which I imagine I I'm a big yeah I'm a big fan so painted this a long time ago before Jinx and VI were a thing and uh you know when Arcane was made both my husband and I
were like what how did we predict this is amazing so it's a good one there we go and some adult content what is a favorite interview question that you like to ask candidates I do like to do behavioral questions it's 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 gonna 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 not a good answer yeah uh good answers are people who put structure and a way forward through the ambiguity like that's what you look for like you want your pm to not just be
like oh no we're swimming in ambiguity but like actually put a path forward I think also looking for people who are like seeking help seeking those inputs as opposed to being like this is the way this is very clear because again the chances of whatever path you chart out for any product for anything that you're
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 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 this new and it's very top of mind because I just graduated my second son from the snoo and it was it was a little bit like oh my gosh like no more rocking of the baby but I do think it it does a good job of like actually doing the thing and 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 she'll like uh related things a mid-journey for your toddler is actually great because instead of it being like absolute instant gratification of like I want to see a fire truck and here you go
here's my phone it's like let's wait for my durian to create the fire truck and specifically you can even tell my journey what you want it could be like I would like it to be blue he's obsessed with Jungle Book wearing a fire hat next to a fire truck right and so you can actually like create and I do
believe in the future so much of what we are going to be doing as 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 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's it really depends on the company and and what I mean by that is like at a company like webflow where the tech stack is complex and where a given feature has so many different interactions right you're like I 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 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 cross-functional partners and doing a little tweak in the process where you bring them in in a kickoff meeting that might be the thing that just like changes the dynamic of like how you work with teams so it's really I don't know if there's like one thing but it's
almost like every day I'm thinking about small tweaks and process to make all of us more efficient 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 it's because we're a pro tool we're a professional tool we can do really amazing stuff so much power that we deliver you but with that power hat 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 wetful University the magic of AI all together so that you can just use and learn webflow so much faster learn webflow in the context of what you're doing as opposed to going into a
different Tab and like looking for like the Buffalo University stuff it's gonna be in context to the product being able to actually like take action directly like prompting what flood to be able to do things for you like it's just gonna be so much easier in the future to use
the product so that's what I'm excited about we're working on it and it will be out in the future okay no specific dates yet yeah you could share the sounds like breaking news of cool stuff coming some things are in uh you know Alpha and probably 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 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 if there's feedback on the podcast send them my way uh 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 for 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 uh 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 the problems 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 maybe what I'll do is I'll post it on my website which is built in webflow so my fullname.com got it Jay-Z Thank you so much for being here and uh thanks again thanks for having me bye everyone thank you so much for listening if you
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