Building a meaningful career | Jason Shah (Airbnb, Amazon, Microsoft, Alchemy)

Key Takeaways

pushback is you know it i couldn't imagine a word more viscerally that makes you feel like you're sort of physically going against what somebody else wants and it gears people into a mindset of then well how should i push back it starts from a place that i need to disagree i need to say no it's a very negative mindset purely based on the word that has come to label a behavior that alternatively could be about how do i shift the direction on something or how do i help the business actually succeed when i disagree with somebody about something and that's a very different mindset and so the two things that i've seen be most successful would be i think number one is actually understanding what a goal is or what somebody's kind of issue is with something and then actually aligning those things in some way welcome to lenny's podcast i'm lenny and my goal here is to help you get better at the craft of building and growing products i interview world-class product leaders and growth experts to learn from their hard-won experiences building and scaling today's most successful companies today my guest is jason shaw i was lucky to work with jason while i was at airbnb and when i started working on this podcast i knew that i wanted to have jason on he was actually my very first guest on this podcast when i was pre-recording some episodes but as you'll hear in our chat we decided to take another crack at it for reasons you'll soon understand in this episode we cover what it's like to be a pm in web 3 and how that's changed as crypto winter has returned how to lead a team through ups and downs which leaders in web 3 know all too well including how to keep morale up and people focused when so much is changing around you we also get into a ton of killer advice on leadership hiring pushing back on your co working backwards career advancement and a lot more juicy stuff jason is a gem and i am really excited to share this episode with you with that i bring you jason shaw this episode 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outreach and send data to other destinations experimented cdp came out of listening to and observing our customers and supporting growth and learning has always been amplitude's core focus right yeah so amplitude tries to meet customers where they are we just launched starter templates and have a great scholarship program for startups there's never been a more important time for growth absolutely agree thanks for joining us john and head to amplitude.com to get started jason welcome to the podcast thanks so much lenny really excited to chat with you today something listeners don't know that we know is that we actually recorded an episode between you and i back in april it was actually my very first episode that i ever did for this podcast and it was before i launched it was kind of like a pre-launch launch episode and interestingly enough by the time the podcast launched and it was going to go out well let me also add that we talked chatted mostly about web 3 forgot that detail so most of our chat was about web 3 in the state of web 3 and pmg in web3 and by the time the podcast supposed to come out web 3 things have changed in the world of web 3 and so it kind of felt a little stale and out of touch and so we decided let's do let's do it again and so how do you feel about that i appreciate that lenny i'm honored that you would have me back i'm gonna count it as the personal record of two times on lenny's podcast even if the world only knows it as one that's wow good one okay first ever guest and first two-time return guest amazing okay to set a little context for folks on your background your career could you just give us like a 60-second overview of your of your background and your career and how you kind of got to which you are to what you're doing today yeah for sure thanks again for having me lenny so my career has all been about solving important problems in a unique way i think the latter part is the youngest child in me who has to be special and do things different than other people and the former is about making sure that my time is spent well since we're all limited there so i actually got started in a sense in tech when i was 15 i started my first company much like a lot of teenagers it was around test prep and getting people ready for college and it was my first exposure to using technology at scale to help people and i just found it addictive ever since and so i ran that company for seven years through school was lucky to do a small acquisition to a partner of ours that we had worked with throughout and then i was just hooked and i moved to san francisco without a job i was really arrogant i said i'll never work for anybody else and then lo and behold he ever comes along i'm super excited about it i've been working on a product actually in the same space and so that was actually my first formal product management role and i stayed at yammer i stayed through the microsoft acquisition back in 2012. lo and behold i was at the world's largest productivity company at microsoft and most people there in my opinion were wildly unproductive and i wasn't shipping a lot i you know got the itch again so started another company called do.com and ran that for about four years and then eventually you know we found a better fit with amazon they were growing their aws offering sas products so we partnered with them to kind of do a small aqua hire and help build the team out and the product there for a little over a year and then again to be honest i got bored and excited about what airbnb was doing and the mission around belonging that's where i was lucky to meet you and so many other really wonderful product leaders and just human beings in general at their core and then to keep things brief for now you know i got to work on a lot of really exciting products and businesses there but eventually got the edge for web 3 after being a kind of observer from afar investor and i wanted to be a builder and so in web 3 specifically and to me it's a new vision of a better version of the internet uh and i'm really excited about that so i've been with alchemy which is a blockchain infrastructure company for the last year and really excited about all the opportunities i've gotten to work on products that have been a part of most people's everyday lives and i'm hopeful that we'll get to do that with web3 and alchemy as well amazing i just realized as you're chatting there uh dude.com i'm pretty sure i used that back in the day i think i just realized that i hope so that would be a new i'll add that to my second podcast achievement as if i got lenny to use a product that i worked on especially at startup wow cool okay so we're going to go a little bit backwards through your career and start with web3 we're not going to spend most of the time on web3 but just thought it'd be good to chat about some of these things partly because you guest authored the sixth most popular post on my newsletter of all time currently number six and it was about how to be a pm in web3 basically it's called product manager's guide to web3 and so a few questions there i wanted to touch on one is just like how would you describe the current state of web3 we're recording this at the end of july and so we'll see when this comes out but i'm just curious like from someone working within it kind of going through the boom and the bus not the bus the winter that we're kind of in a little bit right now uh yeah how do you feel about it right now yeah for sure so as much as i'm a techno optimist i'm also a realist and with that being said i genuinely believe web 3 is in the strongest position that it's ever been in i think it's important to remember that the term web 3 has barely existed in kind of popular lexicon for for barely a year we've definitely had crypto for more than a decade now as in technology arguably as a financial instrument of some sort but specifically the number of companies that i'm seeing be formed the number of products that are starting to actually achieve some form of early product market fit some products that are starting to scale there's definitely been obviously a huge drop in price there's definitely been some huge scandals in terms of financial mismanagement and the contagion from that but i think it's been my experience that a lot of new technologies don't move up in a straight line and web3 is especially challenging here because so many things have been financialized from the outset whereas generally speaking you'll see startups or new technologies mature over many years whether it's the internet itself artificial intelligence qr codes all sorts of things that kind of have gone through different periods of adoption and so i think we're seeing things like kind of record ethereum transactions happening new layer two technologies launching all the time that are gonna help scale player 1 blockchains ballana has announced its phone that's going to be the first sort of web 3 native phone out there so there's so many new exciting product developments and users entering the space that as much as prices have come down i'm really optimistic about the state of web3 what i think about a little bit is going through this shift in excitement about web3 as a pm within a company working in this space i imagine it tests some of the core skills of a pm like keeping people focused prioritizing effectively keeping morale up if people are getting like oh man all my crypto is going down i'm curious how you've been able to leverage those skills and what you've learned going through this experience keeping people focused morale prioritizing effectively those sorts of things yeah it's a great question it's really important right because we've seen in this space that there are these cycles and i think that morale and ability to keep building are the determinants of long-term success and if everybody kind of takes the ball and goes home that uncertain future won't necessarily materialize so in my opinion i think that the only way to maintain morale is to make progress i think that no speech no sort of extrinsic you know motivators like we're going to give everybody some free crypto to keep motivated about it or something like that really works i think people get really excited when they see progress so for example we see more developers than we've ever had on the platform today and then we're shipping we just launched solana support people like this is real we're like actually doing things building things we just had our team out at eat cc which is a big conference in paris for the ethereum community and it was wild the number of people that were there products being built like pretty much every crypto conference has a hackathon and so it keeps the spirit of building so alive and so i think it it helped me and just in other situations that i've been in as a leader over time i think it's it's all about a focus on progress and moving forward and you know we saw this at airbnb when the business had a drawdown in revenue you know and i know you covered this with sunshine recently right like it was 85 90 revenue and he didn't know when it was going to turn around right it's not just like oh yeah this will come back in six months and we can just keep plowing forward but i think what worked was making progress and actually focusing on product and your customers and ultimately if you hire the right people who are motivated for the right reasons i think that recipe keeps people highly motivated and highly effective at building for when things do eventually turn around one of the most interesting and maybe surprising points you made in the post that you wrote about being a pm and web 3 is that there's much less need for a pm especially early stage web3 and it feels like the stuff you're talking about it feels like a pm is really helpful along these lines so i'm curious are things changing at all there have you changed your perspective on pms in web3 and then i don't know where do you see the evolution of product management and web3 i actually am seeing things change a lot and you know one thing in web3 if one learns nothing is the ability to admit when they're wrong or when things change and so i think that that's exactly what i'm seeing so basically i'm specifically noticing a lot of teams hiring product leaders more product managers those product managers are actually now working kind of in increasingly in sort of a more traditional product management fashion in addition to some of the differences that we discussed in the post around community management and a role in marketing and things like this but specifically uniswop just made a big hire out of meta i saw that gemini also did the same uh we're seeing openc i hire a lot of talent along these lines too even through the ups and downs that their business has seen so and at all levels whether it's kind of product manager senior product manager director vp or cpo you're seeing it across the board and so i think that's partially happening because you're seeing a maturation of products right and so maybe you can start early with a few engineers a community manager get the ball rolling but eventually the product is more mature the complexity has grown the role of a product manager is far more useful and they can differentiate i also think the market is getting increasingly competitive so there's many nft marketplaces there's many layer one and layer two blockchains as a result i think product is always a competitive advantage right if it's working it improves strategy it improves execution and improves team collaboration and so maybe that was less of a difference maker before where these teams didn't need that competitive advantage as much because maybe they launched a token and the token was moving and so a bunch of people were adopting the product but that only lasts so long and first principles still come come into focus whether it's one day or one month from now and so so i'm definitely seeing it shift it's definitely making a huge positive difference in the cases that i've observed and my punch is we're only going to continue to observe this because with more user adoption comes new challenges and for all these players that are growing and getting some form of adoption the product complexity is only going to grow and having somebody to help lead teams help prioritize between all the different products that they could build or strategies they could pursue is going to only increase in importance i know we're like we're pm people talking about the value of pm but something i find is that people that are kind of anti having a pm or don't see why they need a pm in my experience just haven't worked with a great product manager because my experience you find a great pm they just make everything better and so it's not surprising to hear what you're sharing which is people are kind of discovering the value of bringing on a product manager even if it's mostly engineering work and so that's that's promising and i wonder if that's just a natural evolution of a new a new space where people are oh and only pms in this one and they're like oh okay i see all these things aren't happening i need someone to help who can do that for us maybe it's a pm yeah that's a great observation i think that combination of having a direct need for something that emerges as well as if somebody's had either a bad experience or not even had any experience with somebody who can play this role which is quite common in web 3 especially because a lot of folks are relatively early in their career given the kind of accessibility of the space and the i think frankly the more adept understanding of the space naturally that a lot of people have when they're earlier in their career and less set in their ways and so that's a great point and as a result the better ps4c and web3 hopefully the the value will prove itself out over time and hopefully they do well so people don't keep keep getting burned out by bad fans we're rooting for all the all pms but definitely web 3pms too yeah what surprised you most about working in web 3 as a pm i mean i think that the biggest surprise to me despite what we were just talking about was how big some products have gotten without kind of the traditional either product manager role or without the playbooks that were so used to from the last 20 years of the internet and so for example you know uniswap has done more daily volume on certain days than coinbase and your swap is about 100 people versus five thousand plus at coinbase right so that's astounding to me i think a lot of these nft collections and communities that have grown um you know i met with a lot of these at nft nyc recently and a lot of them aside from the price speculation and things like this have actually built you know the board api club is actually building a metaverse project that does look better than some of the digital games that i've used in the past of second life and things like this like obviously a lot of time has passed and so there's a greater foundation of technology to build off of and they're working with a partner on that product as well but there's a ton of progress being made without some of the traditional product structure or individuals so again i think pms play a really strong role but it's been incredibly surprising to see how far products can get without the product playbooks and resources that somebody who's worked in the internet space from the last 10 or 20 years is so used to awesome okay we're gonna move on from a three and chat a bit about some of your other career accomplishments and companies you worked at so you worked at you mentioned yammer microsoft amazon airbnb i'm curious which which of those companies is most informed the way you approach product and build product and run teams because they're all so different and how they operate and i'm always curious what companies like the formative experience for you that's like here's how i like to build product most and i know it's always a combination but how do you think about that yeah it's definitely a combination but i would say if i had to pick amazon even though i was only there for about a year after the acquisition i i say that because of this blend between product and business thinking that is especially present there and so people say google is an engineering culture people said facebook is a product culture airbnb or pinterest maybe sometimes a design culture or things like this and i think that amazon was a place where you couldn't divorce business and product you couldn't be a product manager without thinking about revenue growth without thinking about go to market and i really liked that because as a startup founder doing product in a bigger company it gave me the chance to exercise a lot of those skills and it's very similar actually to how i feel at alchemy now where i remember my first month there i was like people ask me how's it going i'm like i feel like an athlete feel live again i can do m a one day i can be doing product another minute i could be figuring out oh we need to hire our first lawyer write onboarding plans for employees the next minute and it wasn't as siloed as sometimes a product rule can be so i i think amazon i went there to learn and understand that was my biggest goal was this is an incredible company that's gone into you know the whole foods acquisition happened when i was there and i was wondering how does the same company kind of within retail win with aws go create studios and i think the amazon culture ultimately more than anything else around ownership being vocally self-critical is right a lot is one of the leadership principles all these things combined i think created a really unique culture so i would say amazon's had the biggest impact on me and there have been certain lessons that i've taken from like you said all these places but amazon was by far the place that i think left the biggest mark on my view on product and leadership that's quite amazing that you were there for a year and that's the one that's most informed and impacted you do you feel like people should try to go work at amazon as a training ground as a pm like is that something you encourage pms to try to do in general like i certainly had a positive experience but i think that as you know and as i'm sure you've advised countless people it's so context dependent is it are you learning the zero to one are you learning the one to scale what's your aspiration you know somebody trying to start a company eventually or are they trying to work the ranks of of the product leadership trajectory and so i definitely enjoyed it a lot and i think to your point there's often a non-linear sort of correlation between factors that we traditionally think are linked right so my time there was one of the shortest but my learnings were some of the greatest because i was really intentional and maybe because of the sort of moment in time and what i wanted to get out of it the same way for what it's worth while we're talking about this disconnect when i went to yammer i also interviewed with kind of this was the era of like taskrabbit i talked to square and i remember people always say well what stage do you want to join seed series a source b and the crazy thing is that yammer was it was already past 100 people at route 500 by the time the acquisition and it felt almost like the culture was so tight-knit it felt like a seed stage company at some points even though eventually it kind of felt like uh well once it was quite from microsoft let's just say it didn't feel like a seed stage company anymore but it felt smaller than a lot of the actual smaller companies that i was at so i think that's something i've noticed a lot is that a lot of the proxies don't necessarily match the internal realities in certain cases you mentioned you picked up a bunch of tactics and kind of like lessons from some of these companies what's like one concrete process or tactic that you took it away from either amazon or one of these other companies that's that stuck with you that you'd like to kind of share with folks yeah definitely i mean i think one that amazon is well known for is the working backwards process and for those that don't know the idea is you try to define effectively an ideal end state which funny enough is very similar to some of what we both experienced at airbnb and took away and usually the mechanism for doing this is what's called a prfaq and that's a press release in frequently asked questions and it forces a certain degree of clarity to have to actually write a press release about the product that you're going to eventually launched you every employee goes through actually like a business writing class after they started amazon they give you a little card with five tips that you're supposed to keep on your desk about concession and specificity in the words you use for example you should never write the word great in an amazon press release you should write user friendly in xyz way and will save customers time 20 minutes each day through this it it's intended to be very concrete in a way that avoids some of the fluffiness that frankly is funny when people try to move from slides to dots they really just import the same mindsets that they use in slides but just with more words and so i think the working backwards process of establishing the long-term goal using a mechanism like a press release where and the faq is where every word matters and even the faqs for what it's worth there's a section for external faqs that you would include for example as an appendix but also internal faqs that are meant to de-risk launch or or raise you know the elephant in the room or dog's not barking as amazon likes to call it often so that was a really helpful process that felt very true to me as as a way i like to live my life as well and then also very applicable the tidbit about not using the word great is so interesting is there anything else there that you could share but just basically just like how to write effectively and communicate and launch is there any other tidbits along those lines yeah it's a good question um in addition to not using the word great and words like it that are either subjective and what they mean or unclear and what they actually mean definitely using numbers you know more than adjectives strict concision you know i would go over these documents like countless times and uh there's a phrase i can't remember it's either mark twain or or another famous writer who said kill your darlings right cut cut cut and just remove and so i think i found that really useful in emails i write or documents i write to this day is just going over because not because you're saving ink by cutting words but because it forces clarity of thought fewer words means every word is you know 10 pounds in weight instead of one and that means that the decisions you're making the trade-offs are far more intentional and in the case of great if you say something is great because we're going to deliver something in two hours versus amazon's great because the selection is very wide the implications on strategy are completely different and so that's one of the benefits of being very specific and very concrete in language i didn't intend to go too deep into this topic but it's no one's ever covered this working backwards process on this podcast so it's kind of interesting to talk about it a little bit more maybe how does it actually work so you you sit there and you actually like write out a press release that would go out when you launch this thing is there there's like a template used is there anything you could share for folks that want to try this out and or point them to a resource that will help them down this road yeah definitely that's a great question so there definitely is a template and so it's a combination of an internal training where you have to write one of these documents you review kind of good bad medium versions of this it's generally used if there's let's say a proposal for a new product or even a proposal to buy a company this helps you know really simulate what it's going to be like with respect to a template what i recall is it was often sort of an introduction where you get kind of right to the point you say what you're announcing then usually you describe the problem in one paragraph and in very clear language again all the writing is this way then the solution you briefly describe the product after that there's always a customer quote and this is an example of this customer obsession that amazon is so famous for that many companies like to say or emulate but i think it really kind of may not be true if you evaluate the mechanisms that they use for example product specs that either don't have customer data or don't have quotes from customers things like this and so there's a customer pool you have to literally put yourself you know into the shoes of let's say you were launching prime you know you put yourself in the shoes of you know lenny from san francisco what exactly is he going to say when he has access to this and how is it different than his life today and what are the words that he's going to use you can't use great use i mean if gray is one of your favorite words maybe you could stretch it but i would i think if you were in a room with your your peers at amazon they might you know put some red pen through any grates that are used there so i found that really helpful and it also helps force out of this box that product managers frog leaders tend to get into of thinking that they are always the customer and being a little sort of intellectually lazy where i'm like yeah i would like prime so let me write the quote what i would like but maybe i'm only you know a small segment within our total customer addressable market right so anyhow there's a customer quote then there's one leadership quote similarly that this achieves a complimentary goal like how does this fit into our strategy you know in a way that you would express to the public but is still true to what the internal sensitivities and mechanisms would be and then a call to action towards the end and not just download here right but you know this will be available to customers next month they can go you know access these portals within these whole foods stores at this state and it it again forces clarity of thought with respect to not only the rollout plan but taking a step back and when you read it do you feel like you would actually well this product would you use it so i found that really helpful as a structure can you just summarize those again real quick for sure so the structure of the prfa2 docs was generally an introduction where you announced the product problem solution customer quote leadership quote and a call to action so interesting how similar that is to like a one-pager potentially the other thought i had while you're chatting so the airbnb approaches work back from the ideal like brian talks about it like the 11 star experience versus the amazon approach which it doesn't need to be the ideal it just needs to be like an awesome launch so that's an interesting difference both both effective and different ways i think people tend to when they hear that both companies have some sort of working backwards process of thought let's say working backwards on one hand and then eleven star experience on the other listening to how you describe it i will almost frame it as working backwards from sort of like a moment in time or launch like you said with amazon versus working backwards from a quality standard in some sense of an 11-star experience going in a slightly different direction one of the one of the things i wanted to chat about is you worked at all these different companies and they have different types of leadership and different approaches to leadership and some curious what have you learned about effective leadership watching all these awesome operators work and what kind of separates them in your experience from folks that maybe aren't as effective yeah it's a great question and to briefly recap right i've gotten to see somebody like david sachs who've been ceo of paypal and then the founder of yammer and gone to do many more things since then i've gotten to see sort of jeff bezos at a distance i was never that close to him obviously and never got to work with him but got to observe his impact on the organization obviously i've gotten to witness brian chesky and his leadership in sort of the pre-ipo days as well as through the ups and downs of covid and then also now at alchemy our co-founders joe and nikhil are leaders that have really had an impact on me as well and i wouldn't count myself but i've also seen myself as a bad leader in the start of typewriting and learn from that and so i i think you know i think it's a really important thing to reflect on and i think for me there are three things that have stood out the most i think number one nothing is above them i've seen you know whether it's brian caring about the the full bleed image on the home page whether it's jeff bezos who famously you know would receive customer emails read many of them forward them and he's famous for question mark emails where for his time sake he would just forward an email to a leader with a question mark and you just have to figure it out and then report back in 24 hours with the resolution thereof but nothing's above them right and a lot of founders or a lot of ceos or even cpos and leaders think you get to a certain point and then i'm above a product spec i'm above looking at the data or running a sql query and i think that that is a mistake in a lot of ways especially from a standpoint of who people come to respect as well as efficacy at one's job and then the other two things would be i think they're in the details so it's less about being above something but this is kind of amazon's famous for auditing the details for example and leaders are you know for example if one we're going to launch prime order a bunch of prime things and see see what happens and really test things out and write up a long feedback email on you know saturday or something like that and make sure that things are moving forward so i think you know in my opinion some of the best leaders david sacks would do this too he he actually ran the product reviews it was the ceo of the company doing product reviews not some kind of middle tier of uh director of product who was just running them they were forced involved and there were things to delegate and activate around but um sax was in all of those details and ran those properties himself and would talk to the product managers directly and i think that was really impactful and it also i think from an accountability and culture perspective when you're a pm and you talk to the ceo and you feel like you're presenting something at product review it's totally different and it creates a certain amount of responsibility and quality frankly that i think is really important and it's a way to coach obviously as well for those leaders to really make a mark on the organization and then lastly i think they adapt right i think that a lot of leaders who are like i've worked 20 years to become a leader in this way and i have a playbook either based on past experience or based on some sort of philosophy that they've developed over time that they feel committed to in some way and i think coming back to some of these examples of you know watching brian lead through covet or watching joe nikhill now through this particular crypto winter shift gears and figure out exactly like we're still building the core business but how else can we lean into this and adapt to the unique opportunities that are in front of us i think that's really powerful so what i've seen is nothing is above them they're in the details and they adapt to new information and new situations that's what i've seen the most that i've appreciated and the best leaders that i've gotten to either observe or work closely with awesome that was that's super interesting the first two are kind of connected which is really interesting and it just reminds me of brian and how detail-oriented he was about everything like he used to review every product launch and every screen of every new product like we had to show him here's what we're launching this week and just kind of went through and either blew that up or or let it pass and then i just remember the founders when they were designing the office space just looking at pictures of listings they wanted to because airbnb the office conference rooms were modeled after airbnb listings and jim just looking through hundreds of listings that the team brought him and he just like picked the ones that he was wanted to turn into conference rooms and also obviously steve jobs like this is a really interesting through line of great leaders it's just this huge attention to detail and there's probably something about once they let go of that thing start to kind of diminish without you yeah that's such a great point and yeah you mentioned the jobs example and there's a great book that you've probably read or in your community i believe it's called creative selection by ken cocienda about the early days of the iphone and i think project purple or something like that and you're absolutely right there were no there wasn't no slides right no no this they brought in the prototypes for each of those reviews and things like how to do typing on a tiny screen right and those early keyboards and how to do autocomplete and jobs was totally in those details from you know ken's telling in this book so i i couldn't agree with you more and it's something that people miss because most of their exposure to leaders is on a youtube video or at all hands and so they don't really get to see that side of leaders i think and it's also not what i think from an ego perspective is kind of what people want it to be about they want to be about making big decisions or you know commanding a large group of people and i think it's hard to do that without these pieces one other thing i just wanted to briefly touch on to your point on how they're connected it's a really good point and at the surface it almost seems like they could potentially be the same thing one thing worth calling out though i think is the idea of something not being above somebody i think is uh or a person not being above things i think the biggest thing i take away from that is humility right is that nothing is not my job right anything you know could be picking up paper off the floor that's and putting in the trash or it could be you know reviewing a product spec whatever it is and then begin the details in my opinion is about craft right and really understanding things at a low level such that you're able to reason about it and make good decisions like brian with the home page for bezos in some cases with customer processes that he got in the weeds on i think the two together humility and being excellent at craft i think is a very potent combination especially when you throw in the last thing of being able to adapt to any situation that's really interesting what also makes me think about is the reason things are less good often if there isn't a person at the top that's being very detail-oriented and i find this with a newsletter and this podcast and other stuff is no one's going to care as much about it no one's going to be like oh my god i really need to get this right so much because i'm just like i'm personally feeling like responsible for the quality of this stuff and it's like it's on my shoulders to make this awesome and so i think that's probably why a lot of the best stuff is led by a singular leader or singular opinion or a singular person a lot of the best startups are just like someone's vision it's like here this is what we're gonna do and then the more becomes a community driven thing the less often it ends up being successful this episode is brought to you by maven i've been an investor and advisor and a customer of maven from day one i even taught my product management course through maven maven is a cohort based learning platform where you learn alongside peers with a direct connection to your instructor maven's got a ton of courses for product managers founders and executives to help them level up in all kinds of ways over 10 000 people from airbnb to coinbase to google to tesla have taken courses from real experts and operators that have spent decades honing their craft as part of their fall season which maven just launched there are over 100 new courses starting in the next few weeks many of the people i've had on this podcast are teaching courses like jackie bavaro on product strategy ariel jackson on startup branding emily kramer on b2b marketing plus annie duke on decision making near at all on behavioral design and how to break into product management with merely nika check out all of my favorite courses and learn more at maven.com lenny i feel like you're totally right especially i mean this is the natural progression but it doesn't have to be that way right and i think to your point i think a lot of leaders focus on accountability in an organization once they get large and so you see things like performance reviews and things like this it's a very top-down approach to trying to drive results but as opposed to a sense of accountability if you drove a sense of responsibility if people felt like this is this is my company too this is my product this is my office floor i don't want trash on the floor i'm going to pick it up and throw it there even if we have somebody whose job it supposedly is to clean that up it's like i take pride of ownership in this and i'm connected to it and i think that makes all the difference in terms of you know at airbnb i think people who felt that way were willing to push back on certain things or they were willing to propose new ideas because they felt invested in the company i see it at alchemy all the time you see an engineer hop in and fix something at 3am because they feel committed to the code base and it's not a thousand person engineering organization where my only job is to make the ios app you know two percent more effective at engaging users so you touched on kind of the skill of pushing back on on a founder ceo and i know that's something you're really good at i've seen you do this i'm curious what you've learned about how to effectively do that as a pm at a company pushing back on the ceo or founder when you disagree i mean i think this is one of the i actually think it's one of the most misunderstood terms in a sense because i think language like we were talking about earlier is so important and yet what you call something ends up defining i think 90 of what people understand about a concept right and so pushback is you know it i couldn't imagine a word more viscerally that makes you feel like you're sort of physically going against what somebody else wants and it gears people into a mindset of then well how should i push back it starts from a place that i need to disagree i need to say no it's a very negative mindset purely based on the word that has come to label a behavior that alternatively could be about how do i shift the direction on something or how do i help the business actually succeed when i disagree with somebody about something and that's a very different mindset and so the two things that i've seen be most successful would be i think number one is actually understanding what a goal is or what somebody's kind of issue is with something and then actually aligning those things in some way so coming back to airbnb i remember airbnb had bought a company luxury retreats there was a goal to integrate that business and that product into the full airbnb suite and there was a lot of potential with that but i remember that there was part of the product experience that was oriented around chatting with somebody and the idea that the business that had a very large team of of wonderful people who helped you as concierge is basically for your trip and so this was a team that i was on that to be honest had fairly low morale it's always difficult to integrate you know an acquisition with a company especially when we were based in different places etc and i remember hearing from a leader who had been at airbnb for a while who's very effective at persuading senior leadership and they understood why this was a problem because this chap product was growing in complexity you'd have to build all these features into it and nobody could successfully shift the direction and as a result it was just this sort of it was a mess as a result and there was a very low morale because everybody we were taking on too much scope people weren't sure was the right product it was being built up as one giant launch as opposed to an iterative thing and what was really interesting was that this leader was very effective at understanding that the goal wasn't about building a bunch of features it was about as often discussed at airbnb a magical experience and so when we took a step back it was reimagined as trip designers not concierges and their goal is to design your trip and part of that meant a very elegant simple chat experience so that you could have a efficient fast positive experience with that trip designer and move on and it shifted the pushback of like we can't build this thing it's too many features we don't have enough time we don't have enough resources to oh we all want a really elegant really smooth slick experience for our customers how do we do that let's a trip design or a new concept that is actually going to elevate things we're not telling you we want to pair back scope we're not saying we want to settle for less we're actually just not only going to call it something different but also envision a simpler experience which is more elegant it's more on brand with luxury boom all of a sudden everybody gets what they want it's a better customer experience less scope and it wasn't about saying no it was about understanding what we're all actually sharing as a goal which was a great simple customer experience and then actually building that so i saw that to be really effective and i think that's something i try to bring into into my career a couple other examples if it's useful but that was a big one that i learned from airbnb yeah another example would be great one thought there though is do you think it was mostly like the name and the concept or was it that it was a bigger idea what do you think it was about reframing it that way that got people oh wow okay now i'm really excited about it again that's a great point i think it was a big idea right with a good reframing and i think it's like many things where there's the substance of something and then there's the communication of it and so this is true often if for example if a company is changing strategy oftentimes people might walk away feeling like yeah i guess i kind of agree with the strategy but the way it was communicated was really poor or vice versa like yeah they told us in advance and they set us down all hands i really disagree with this strategy and i'm gonna be dug in on my heels and not disagree and commit now so in this case i think you're totally right like if it was just window dressing of you know founders are too smart especially at all these companies we've talked about to be fooled with a simple renaming of something but i think the combination of a bigger idea more exciting idea that was at the heart of what we were all going after together combined with a simple way of communicating it because i've also seen big ideas that are poorly communicated fall flat on their face and not achieve the intended outcome those two together i think we're really potent combination awesome i'd love to hear another example yeah for sure so you know a recent example at altme actually right we're growing we're hiring but there are a lot of roles that especially being in web 3 that are not yet created for example we've created a you know there's traditionally growth product growth marketing we've created new york around growth operations which i'd be happy to talk about if we want to get into it but it's a really interesting interesting area and we were going back and forth like should we hire for this role it's not even a real thing maybe you know we've looked at some candidates we're not so sure about them and when i realized with our founders who are incredibly smart very talented have built the company over so many years now they want to win that's what they care about at the end of the day they are so driven to win at the end of the day and so ultimately it wasn't like let me make some rational argument about the role of growth operations or let me you know defend some issues with this person's resume that maybe you're spotting when we make this hiring decision but oh you want to win we want to grow faster awesome this is the way to do it and that's how we're going to actually become the generational company we want to be again a reframing in this case around yeah we might disagree or squabble about certain things at a detail level but i understand what we all came here to do and let's focus on that and how this is a part of that versus just focusing on maybe the means to an end versus the end itself and the end always brings a lot of clarity in my experience what's cool about both these examples and another guest touched on this when you're trying to influence the ceo or the founder coming back to your working backwards concept you almost want to work backwards from what are they excited about how do they see the world what's important to them and then pitch it that way so in the first example i imagin