you forget about everything else forget about politics forget about promotion or having more with bigger org or whatever if you simply wake up every day trying to have the biggest impact you can or if you're a leader trying to use your team to have the biggest impact you can
in the company how do you do every part of your day that's a really good Guiding Light 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 today my guest is Ian McAllister Ian is the author of one of
the most classic post on product management what separates a top one percent PM from a top 10 pm amongst many other pieces of writing that he shared online Ian has managed over 100 product managers in his career he spent 12 years at Amazon where he built Amazon smile
and led the team responsible for growing Alexa internationally he also worked at Airbnb with me and now he's at Uber leading Global product for the vehicles platform which includes making Uber's Fleet increasingly electric and autonomous in our conversation we focus primarily on two topics what separates a
top one percent PM from everyone else specifically for new PMs and also for senior PMS and we also dig deep into the working backwards process we get into how you can implement the process on your team and how you might be doing it wrong there's also a bunch of links to
templates and guides in the show notes so if you want to follow along definitely check those out with that I bring you Ian McAllister [Laughter] this episode is brought to you by mixpanel offering powerful self-serve product Analytics if you listen to this podcast you know that it's really hard to build great
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having me Lenny I've been looking forward to this me too I'm sure you hear this a lot but when I was a new product manager very Noob PM the post that you wrote on what makes the top one percent product manager was really influential and really helped me figure out what to
focus on and what skills are really important and I find that it continues to live on as this very legendary post for product managers who are trying to figure out what to do and I just reread it in prep for this post and I was just like wow this is like now that I'm on
the other side I'm like this is so right and so I'm really excited to dig into a lot of these things in person sort of virtually in person and yeah with you so thank you again for for doing this yeah man it's awesome I'm excited just to spend some time talking with you about
product and uh we'll see what happens did you expect the impact that this post had when you were writing it when you're just putting this together the impact that the post had in your career and just the PM industry uh definitely not and I said lurk on core at the time and
then I was just kind of having fun reading things and answering some questions and I used to like look for questions in the sort of Goldilocks zone they weren't like too high level of distract like how do you be a good PM but they weren't like sued two like super specific and this one was kind of
right in the middle and so I'd pluck off a couple of those and I think more is a way to structure my own thoughts you know that was kind of what was interesting and fun for me to do that not because I thought I'd have any kind of real reach but obviously it's been
cool to see that and people reference it pretty often and that's been that's been pretty fun we'll link to this in the show notes of folks that are listening don't know what we're talking about we'll link to it and you can check it all out and we're going to be talking about a lot of this stuff
in the actual chat but there's a couple things there that that are worth maybe Drilling in on a little bit one is just the impact that writing on the internet can have on someone's career like this one post I imagine had a lot of impact on the trajectory of your career is
there something you could share there is that true yeah it did and there's another post I think it was before this one someone just asked about Amazon's product development process and so I wrote about the working backwards process which isn't my process I just used it and just described it and just
kind of caught on a little bit there as well and I think those two and then I started to kind of write more about people management and product management and um I think the value for me was so awesome just to like make connections with people in the industry and it felt
like this is I guess the 2010 or something like this where a lot a lot of Amazon people I sort of felt were just like so 100 heads down was a little bit of a secretive culture not meaning like apple but it was pretty private but I was kind of interested in in the startup community and product in
general and so I think I I spent a little time trying to engage with folks and I just made so many kind of great connections and relationships from this you know I remember interacting with you and getting to know jobot and other folks at Airbnb early on even before I
joined obviously I'd credit this work and those relationships for me ultimately going there and so many so many great relationships and people I've met because of it and aside from just like the the little positive feedback I mean people tweet at me periodically be like hey by the way just love this post
and whatever and so it's it's super gratifying you mentioned a little bit about your background that we're about to get into that and I want you to share all the things you've done but the other piece there that I think is interesting that comes up again and again in the power of
writing is it often just starts with you trying to collect your thoughts and putting it out there and then wow so many people find that valuable and it spreads and so that's just like a really simple way of thinking about if you're starting to write online just like
summarize something that you've been thinking about that you want to just crystallize in your own head there's this quote that is probably falsely attributed to Mark Twain and Hemingway often of just like I don't know what I've thought until I've written it down and that's super true with these things
and so that was a really good that's a good example of this yeah and I think with any kind of writing it was probably less structured initially but I would partially because I was trying to share something for an external audience try to just organize it and make it Compact
and and not too wordy or rambling and uh I think business writing it's been a lot of that time doing that at Amazon is so valuable because you've got to be a clear thinker to be a clear communicator and so it's kind of there's two tests in in writing well or communicating well
it's both those things so I found it's it's pretty valuable and kind of sharpening your Acts so these are the two things we're going to focus our chat on is what makes the top one percent product manager and then the Amazon way of working and especially working backwards so these are all good
cues for where we're going but before we get there can you just spend just like a minute giving us a sense of some of the wonderful things you've done in your career and what you're up to now well I can tell you what I have done I'll let others decide what's wonderful or not
um so after doing like finance and economics in school I made The Logical choice and I got a job doing marketing in the beer industry and then the next logical choice I moved to Tokyo and it sort of bootstrapped my way into software development without knowing Japanese or software development did
that for a few years came back to the States working as a developer and a startup and then kind of a mid-sized company and then moved to Microsoft as a program manager or pretty much a product manager the same thing there in that role learn some good stuff and then made
a connection with Amazon and moved there 2006 and that was really the start of of when I think about building my product toolbox and kind of leadership toolbox so a few different things I did over 12 Years a few years in retail and conversion I then moved sort of traffic
and direct traffic loyalty when I created Amazon smile the role in Alexa LED Alexa Internationals to sort of scaling Alexa Echo to six more countries and the last role in delivery experience and operations so I led a number of different programs there and then recently joined Uber we're a senior
director of product and Tech for vehicles so that means everything all the tools that help fleets and and rental companies make their vehicles accessible to Uber drivers so they can earn a sustainability Tech and electrification our vehicle platform and then creating a
path for autonomous vehicles to come out of the platform that's it amazing I I just realized there's one thread through your career is like autonomy and AI a little bit right with Alexa and then with with Uber with these autonomous car stuff you're working on now is that
that's something you realize there's that accident well I mean I guess you could connect those things obviously both are you know machine learning AI I think the way I think about it is that I've done a whole bunch of different lifetimes especially around e-commerce
and so it kind of allows me to cover the gamut plus I guess I forgot to mention the time at Airbnb you know working with joebot and you and Vlad and Dan and Shirley and there was focused on kind of building out the customer support technology platform so that's another
part of the sort of e-commerce platform covers the gamut right I forgot to bring that up too I'm glad you touched on that yeah the most transformative time getting to work together that was awesome that was awesome I learned a lot from YouTube during that time what a time this is a good time to
chat about speaking of Airbnb and and all that to chat about what makes a top one percent product manager so I know your post was really title like what separates at one percent PM from a 10 pm but it feels like it's even broader just like how do you become a top one percent
product manager and I thought maybe a good way to start here is just maybe just like run through the attributes that you've kind of found over the years or like here's the things that a top one percent PM needs to get great at maybe just run through them and then we'll
talk through them in a little more detail yeah I was going to pull up my post here so I could actually refer to it you want me to go through all of them or just kind of pick out a couple to touch on let's maybe just go through them quickly just to like put them out there and then I'll have some follow-up
questions to dig into a few of them all right sounds good well the way I listed it at the time you know think big you know always want to be hunting for bigger impact communicate I think we'll probably touch on that a little bit that's a super important for PMS as a
test of their thinking and their communication simplify you know how you can do more with less and have more impact is simplifying is a great way to do that prioritize that's sort of I think the core skill after communication of a PM and there's so many different lenses to view that
let's see here forecasting and measuring I think that it's really important you know what separates product Managers from Consultants sometimes is you forecast and then you execute and then you measure and validate and that helps you build your build your instincts just
obviously the core execution of just shipping and doing what you said you do understanding technical trade-offs is that you don't have to be a software engineer to be a great PM but the more you learn about technical trade-offs not just product and customer trade-offs that will help you
you know simplify and get more yield out of your resources understanding good design if you're working on anything customer focused that's always going to help you kind of think in the mind of a customer or user uh you don't need a design but the more you understand helps
writing effective copy this goes a long way not to get close so not to like sub out the copy to somebody else but to get good at communicating with a couple words to your customers that's a great skill those were the ones that I wrote at the time you know I guess 10 years
ago and then I refreshed the uh the post recently in my newsletter and I added a couple new ones honestly because as I'd reflected back there was a few that that I think a lot about these days that I missed the first time around earned trust with others that's so important as
a PM but especially if you're going to grow as a product leader becomes even more important and I think trust is the currency of a product manager and a product leader especially if you're going to grow in your career digging for data it's out there and you got to develop the tools to go find it
not to to depend on your analyst or your or what's in the reports today so that's a really important skill for anyone in products and probably the more Junior you are the more important it is as you're really in the weeds they're building product pushing back effectively this is an art and a skill
but I think your ability to do this is pretty correlated with your ability to grow and succeed as a leader because if you say yes to everything you're gonna go nowhere adapting to change how you react to change will obviously impact one year mood and your morale as well as
how effectively you can kind of rally yourself your team and then driven by impact not promotion ultimately that's what you want to wake up every day thinking about how to have an impact for your business and that will be an indicator on your likelihood of promotion so do that instead of just
focusing on how to get promoted and having that guide your day awesome so it's a long list there's a lot that a PM needs to be good at which I think if you're a PM you already know it's like a wild crazy impossible job to have everything nailed down and at the
end of this post even mentioned like you've never met a one percent PM that does all these things and I think that's important like no one's going to be the best at all these things and so just to drill down a little bit and get a little more focused say you're a new product manager
of these I forget how many there are maybe 10 12. what are like the top three that you think new PM should get most good at and focus on probably communicate you know prioritize and execute I think those are just the core building blocks other ones will be more important as you grow and become more
senior but those ones no matter where you are in your product career I think are super important being a better Communicator is something I've been working on my entire product career and I'll be working until the day I stop I remember years ago I was at Microsoft I
first kind of effectively product manager role in my product unit manager Thomas came by the office and I think he asked me like when is this going to ship and I was like well this thing is taking a little bit longer here and this other thing and yada yada and I sort of gave a
bunch of background but I didn't really answer the question and I got a little feedback from him like that's not really the you know ultimately he's like he's waiting for a date and so that you know I just sort of reflected on that and that was kind of as I remember my my
journey to try to be a better Communicator over time and I'm still on it when I went to Amazon I worked for Kim rackmuller it was our I think it's time SVP for worldwide Discovery and I think she was Amazon's first TPM and and she was tough but super smart and so that was also kind of an early
experience to kind of learn from her and sometimes you get some feedback when you didn't uh really answer the question and my first boss Russell I kind of organized and started to gather this thing called The Book of Kim and so we would we would gather these best practices that we learned from her
elsewhere you know avoid weasel Words Answer First and then explain own your problems and started building this and then I sort of extended that over time and added a bunch more and and wrote a post called the operator's manual I sort of tried to gather all these things
together but it's such an important thing and the stakes get higher as you work with more and more senior people but if you can get in the habit early of you know answering it a when question with a date knowing how to use numbers to answer questions and honestly just
learning from feedback and kind of grade yourself after you get feedback on a doc or after a meeting or after answering a question in an elevator and if you if you try to say gosh how could I have done that better and then try to get better you can and you can go far if you
just focus on that and all the other 150 skills of a product manager but if you don't have that it's unlikely that you're going to really go too far in your product career so that was communicate I guess prioritize is the next one and so I think this is like the number one key tool of a product manager
is prioritization because so many things come from from you know being a good at prioritizing and it's not just like what what project do you do next or do you do this project or that project there's so many different dimensions to prioritization there's sort of which
themes are you going to prioritize in a road map and which projects within a theme and how are you going to sequence those projects how much of a project you're going to build and also just time management is also a prioritization function it's like what are you going to
choose to spend your time on you know which things are you going to really go all out to make great which things are you going to kind of starve for attention or just not do given the same amount of skill intelligence and resources a product manager with a great innate ability to prioritize is going to
generate 5x the impact of someone without that skill my early if you could call it success at Amazon I think was like completely dependent it wasn't because I worked smarter or was I was smarter I worked longer hours or I was more technical than other people I think
it was just because I was like one super hungry for impact you know and if there was a number a metric that measured success at the business I was running I wanted that to go up into the right not to hit a goal but just to go as far and as fast up to the right as possible
and and I said I think it was just like working with the team to hone in on the projects that would do that with the greatest leverage and just marshaling all the team's resources so if that was a good start that was a fit with Amazon in terms of working backwards from a
fitness function or a metric and so did that with the first team I was there and then again later manage the gifting business and so it just was one skill that I think helped me as well as make up for maybe some deficiencies I had I don't have the biggest brain in the world and I don't have the the biggest
working memory and I wasn't the most technical but by trying to really get good at that prioritization I think that I think that's helped me and it still does I think execute is the third one which is no surprise that like every pm has to execute and I think it's you know
assuming you prioritize well then execution means sort of molding what you want to build and do a simple compact package that has the highest impact possible and then he also it's execution is a big function of the team you're working with so it's your designers and your data science folks and especially
your engineers so anything to do with how well they're doing their jobs or how well they're resourced or whether they're getting better and better at every Sprint like you have some amount of ownership in helping make that happen because that directly impacts your
team's ability to execute and and ultimately your reputation as well for being able to execute you know sort of the drive that goes into execution product managers of the the Motive Power behind execution and impact and and if if you stall out or you don't do your job the Project's
probably going to stall out as well and so you're the ones like with especially with a TPM if you're lucky enough to have one in the back of the ship kind of beating the drum and driving everyone forward but again lots of people have wrote a lot of stuff about execution and
there's there's a lot to it but I think those are probably the three I'd focus on awesome and what's what's interesting about these threes if you look at the rest of the list like think big understand technical trade-offs understand good design I think what I would take away from this is those are
things you don't need to focus on that much when you're in EPM focus on as you're set communication prioritizing executing Focus Less on these other things because later they'll become more and more important and obviously you know learn as much as you can but it's
it's almost easier to think about the things you don't need to stress about when you're starting out yeah I think that makes sense if there's a core right or like think about in year one is a PM focusing on those things and you can develop other skills over time but yeah I think you're you're spot on
there if we were to go back through these three just maybe as a last question and you may not have an answer to this but if you think about communicating prioritizing and executing is there like one tactical thing you could suggest that a PM listening to this can do to get
better at one of these things they're like a trick you've learned of like wow this is one way you can level up communicating executing prioritizing or not the the closest thing to like a checklist right the post I mentioned the operator's manual that was that was the
closest thing to like if you do these things these specific actions I think it'll go a long way because a lot of them are guided around not doing the easy pitfalls and communication mistakes like rambling if you're asked a question and you explain and then maybe you get
to the answer it's if you just think answer and then explain or sometimes answer and then shut up that actually is a tactical thing you can do to get better at communicating and there's some other tips in there as well so that's that was my attempt to try to encode to to take some of the ones that we
gathered early at Amazon add some more the others are yeah there's there's no just simple trick unfortunately to prioritize other than I mean I think working backwards is a good technique to have impact to guide your prioritization and that is something where it's not a simple tip
but there's a set of practices and behaviors that you can do that will that will ultimately lead you to prioritize better awesome we'll talk about all that and then I think communication the simple tip was just like grade yourself after you communicate and try to just
take a moment in it after a while you'll just do it naturally to think about gosh how would I have answered that question better and so the next time you can try to answer that question better and it's just a continuous improvement process or maybe even ask your manager hey what
could I have done better in terms of how I communicated in that last meeting or that last email yeah absolutely absolutely okay so then coming at it from the other direction say you're a senior PM what are three of these attributes that you would suggest folks focus on to get better and level up in
their career gosh it's still communicate to be honest like I think that's the one at every level of of product it's just the stakes are higher I think think big is one for sure there was a phrase I think Warren Buffett in the Berkshire Hathaway letter used at some point was
like at our scale we got to hunt for bigger elephants and so I think at any scale as a PM whatever your idea is or whatever your solution or the problem you're solving take a minute at the beginning to say could this be bigger could this be a bigger thing and more impactful than the
initial idea even if the initial idea sounds big so that's a sort of a tool to and that's often where I'd start when when my PMS were sort of sharing an idea is I try to expand it to the degree it might be expanded think about it from that perspective and then maybe you want
to still start small but with a bigger vision in mind earn trust is a huge one and that's kind of why I added it more recently and it becomes even more important as you get into senior roles because that's I think it's truly like the currency of of a product leader or
probably any leader in any function because if you want to ask for more resources to do something bigger if if your leadership doesn't trust you to use those resources well or do what you said you're going to do you're probably not going to get them but if you've built
trust that you're a good Steward of resources and you make a lot of impacts with a given team that's directly going to correlate with your ability to gain more resources you know trust is just built by repeatedly setting and meeting expectations and I think that's a good
kind of Mantra to think about as a PM like you know my meeting the expectations that I set and not just doing good things but like calling your shots forecasting setting a goal and then and then hitting it and if you do that repeatedly you're going to be in pretty good shape
and there's like so many practices as a product manager a product leader that build trust you know you tell the truth without fail and you launch when you say you'd launch and you launch what you said you launch and you own your mistakes and and then the the other practices just lose trust you know if
you lie or if you're evasive if you don't ship what you said you're gonna do if you ignore your mistakes or you repeat them and so I think you know just simply having high standards for yourself and think of trust is that like currency that's going to correlate well as a PM as a GPM or
director of product in any level you know that's the that's the thing that you want to build so thinking big building trust was there a third I think maybe the last one which is is is certainly relevant for a PM but is really true as well as like driven by
impact and that if you if you forget about everything else forget about politics forget about promotion or having more bigger org or whatever if you simply wake up every day trying to have the biggest impact you can or if you're a leader trying to use your team to have the biggest impact you can
in the company which will influence how you build your roadmap and how you how you do every part of your day that's a really good Guiding Light and you know I remember in my first 10 years at Amazon just naturally uh not because I thought about it I was just hungry to have an
impact take my business grow it as fast as possible I wasn't maybe Loosely thinking about promotion but I wasn't thinking about it I didn't never talk to my manager about it and I wasn't bringing it up I was just focused on taking my book of business and making it
bigger and then the the net result was I I was promoted several times and I did grow in my role but that wasn't what drove me it was just the impact would you say that driving impact is more important for new PM or senior PM like it feels like impact is like the soup within which all PMS swim and
that's like constantly important but it's interesting that you mostly put that into the latter part of a career do you feel like with new PMS on your team you're less expecting them to like think about impact and focus on impact well I mean I think for junior PMS right
if you're if you're a brand new PM then yeah you want to have an impact but you're really just like you have a project or a feature to ship or something like that and you're often kind of not necessarily told what to uh you know given a lot of latitude to build your own road map but you're
you're asked to sort of ship this do you want to spec it you want to execute and do it but increasingly as you grow there are opportunities to to sense out and try to have a bigger impact maybe and then start to influence prioritization or road maps it's just that the
expectations it goes from being a nice to have as a junior or a first time pm to as you get a little more senior hopefully if things work the way they should work that's really how you're evaluated yes you want to treat your team well and you want to do a whole bunch of other things but take two
people one has a massive impact on the business and one who doesn't then the right way to work should be that first person should be the one that grows and develops and is is tasked and and with bigger challenges just because if you're impactful at a bigger challenge that's
even more important for the business so I think that's a good kind of way to think about the flywheel of product leadership yeah it feels like a lot of times you get lucky as an upm you work on a project that ends up having a lot of impact that you didn't necessarily drive you just happen to work on
something that wow this was a huge deal and that feels like an important thing to optimize for a little in your early careers like work on something that's likely to have a lot of impact even if you're not responsible for setting the strategy and prioritizing well I think
that's true if you have a choice in where you work in product if you you know if you have a choice to work on something that's part of like offense you know something that drives the business and and like you know it's true that Executives wake up if something drives dollars or customers or offense
things and you know it just it maybe shouldn't be this way but a little less interested in things that maybe less than a risk that just the risk never happens it comes to pass or a cost center that operates a little more efficiently so that it's one lens where that might relate to your success I
think also who you work for you know and I think most of us don't get to choose that especially early in our career and either works out in your favor which is great and that was the case for for me especially to Amazon some of the leaders I work with but sometimes it doesn't but
I think the more that you can suss out who you work for because then the better they are at these skills and prioritizing one they're just going to be a better teacher and a better role model to learn from so I think that's a that's an important thing to think about
in any kind of job change to close the loop on this piece of for more senior PMS the skills to focus on you said thinking big building trust and driving impact I'll give you I'll put you on the spot I'm gonna give you two options two directions to go with this one is if you
want to get better at each of these three things do you have any one thing someone could do or what does great look like for thinking big or building trust or driving impact those are two options that was like six questions there Lenny let me see here what I'm what I'm answering um
well I think the the think big one is interesting and one way to think about thinking big especially as you grow in your career is is most people are like operate within a box you know there's a box of there's product management and there's these are the things that product managers do and
you basically have built a road map and you prioritize features and you work with engines and so that might be the typical kind of product scope in Tech most of my roles were ones where I was kind of a GM but a really product focused GM and so I naturally found
myself taking a much wider view of what product is across disciplines and I was lucky enough that I had engineering teams and marketers and you know analysts and other folks and so that helped me but I think as a PM you can still do that even if those functions don't report to you
is take that really wide view of what success for your product is and not have the blinders on its product or Tech it's anything it's anything that influences the success and your your your customers success or anything else and it just means you know you don't own marketing
or you don't own this other function but you own it until you find somebody else to own it and so that's not necessarily thinking big in terms of scale or whatever but in terms of how you think about your role as a PM and what your ownership responsibility is and so I think just the more that you you know
you don't want to get over your skis is a PM and then you're trying to like change your cfo's mind about something necessarily but the more you grow that you have to increasingly do that and find the constraints or barriers to your success or your your product success and
knock them down no matter what they are so yeah it makes me think about just the advice of like think like an owner think Beyond just like your one little bubble think about the broader business out outside of the one little product you might be working on so that's great advice
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backwards piece which I'm excited to get into is there anything else you want to share on this thread I might just talk about earn trust because this is one that I don't think I really I didn't put in there initially and I honestly don't think that I recognize the importance of
it early on in my career or even in the middle of my career and it's it's been in the last couple years that I really understood the importance of it you know my wife my wife Sarah is a is a product manager at AWS and so I've kind of as I've mentored her a little bit in her
career and I've seen how this is really a superpower for her it really made me reflect I'm like one of the things I could have done better in different roles to earn trust more and and it's you know it's not just the basic things like to be honest and tell two different
people the same thing versus different things I think it's you know trying to really understand work backwards from that person and what are their goals and and what are their organizations goals and honestly spend the time and the energy to try to get to the to alignment
in the same place and be willing not just bullheaded which I might have been earlier in my career maybe still to many people but charging forth what do I think is right but taking some more time to try to forge an alliance with someone because if you do that you're ultimately
going to be more successful so that was just one that I was probably slow to recognize the importance of uh and I'm trying to catch up now is there a story that comes to mind where you look back and I should have earned trust there or I broke some trust here that you'd be willing to share you
know when I was working working with you and the team at Airbnb I think this is one where jobot brought me on to help sort of build out the customer support technology platform maybe more how Amazon would do it like to to maintain a high level of quality but to become like
more efficient as well and to reduce the cost so that Airbnb wouldn't have to scale customer support to the same degree the business was scaling and so you know coming kind of trying to build a new team and develop and and I was pretty heads down doing it the way I thought it should be done and like
working with the team there in terms of like let's get a strong analytics framework anyway let's measure let's measure all these things and really understand what's going on at the data level and then let's use the same prioritization muscles that had had kind of made me successful at Amazon to
prioritize things that were best work backwards and I think that what I didn't do as much as I should have is obviously really partnering with the you know the customer support you know leadership team as well is that was something where you know I think in some ways it felt
like we were in alignment and getting on stage together and stuff but it turned out I maybe hadn't spent as much time and effort on that as I thought to get that to build that true support there such that that leader would rally the organization around it as well and we'd
be marching in the same beat and so that was something that I would reflect now I think the team did amazing things and you know Shirley really carrying the torch there in the entire team and so accomplished a lot but that was the learning about like going back I probably would have spent more time and
really tried to do even more on that thanks for sharing that I never knew that story and it sounds like the takeaway there is maybe don't take for granted the leadership team the team that'll actually be using the product is that is that kind of a roughly way to
think about it well I would say that if you have a certain approach you maybe I believe it's the right one and it may be the right one but if you don't build the support and the relationships you know that they're going to help carry that out execute on that strategy it may not
it may not get executed as well as you think it should be and so that's an important part of success it's a risk that you have to to kind of mitigate and trying to to earn trust and to to do it that way as a way to mitigate that risk that the the right product in the right
direction and the right strategy it may not land if you don't have that support that you need and so that that I think was my learning what better way to learn a lesson than get some wrong and then you never forget it again you could call it getting raw you just think of like something I could
have done better you know and just that same continuous Improvement mindset you know it's it's to everything every role every experience every project every communication and if you build that muscle to try to like do it better the next time and also just the try to be a
little self-aware about what could have gone better then I think it's a really good muscle to build so it's a good segue to the second area of where our chat is gonna go which is Amazon and things you've learned about just the working backwards process how many years did you say you worked at Amazon total
12 years 12 years it feels like everyone that worked at Amazon is like 10 years or more it's these like large numbers so they must be doing something right and I don't know what do you think that is actually why are people stay there so long it's amazing what's interesting
about Amazon and it's changed over time is that I think you know pretty quickly whether you're a fit for it or not you know and it can be kind of a crucible and uh you know a little little Spartan and it just clicked with me though because I'm kind of a structured thinker and right brain
and so this idea that like hey I could have this business and then figure out one metric or a fitness function that determines success and then my job is to make that number go up and to the right that that kind of fit with me and then you know I rewired my brain probably
over the first 10 years around this concept and I just I just felt like I was learning I was not only working with smart people that were driven which was true at Microsoft as well but there was kind of this DNA in the organization and in this wiring that I thought was really
effective and it just kind of clicked with me and so I kind of molded myself to the to the environment and you know at every step of the way I felt like I was learning and growing and I was you know one of the benefits for me is you get a chance to learn from so many other
people in these different settings you get a chance to read documents that make you you know learn more so than probably a slide deck you get a chance to be in weekly business reviews with really smart people and learn from that not just learn from your own experience but
from everyone else in that room so I was just a sponge and so much learning happening that I think propelled my career and so that's that was why especially the first 10 years that it was so fantastic of just like growing and you know feeling yourself kind of build these new muscles and develop
these new tools and I loved it so that was why why I stayed so long and obviously Airbnb then it was the time to try something new which was a great experience you know kind of a test you know I was in Seattle and the company was in San Francisco Cisco and spending
three days on a road each week was a good learning and ultimately uh you know a reason to come back and be Seattle based but then I chose Amazon again because it was still a great place and and I thought I could continue to learn so awesome I was going to mention they
drew you back in so yeah that's pretty rare what did you learn from folks like Jeff Bezos and Jeff Wilkie about Building Product leadership company building what's kind of stuck with you working with folks like that obviously two very different people but like complimented themselves so well you know
I didn't have you know hundreds of meetings with with Jeff Bezos while I was there but I did have a chance especially in kind of the development of Amazon smile and then early when I started the social team to have some some of those meetings where I wrote the doc and it was Jeff and you know 10
other people reviewing the the process of kind of doing even before hitting on Amazon smile it was really kind of a Innovation process I guess you could call it where we had a goal in mind to increase customers kind of loyalty to Amazon their direct traffic loyalty not
in the way Prime did which is a paid program but to try to come up with another program or way in which customers might start their shopping on Amazon instead of Elsewhere and so I kind of I was running the gifting business I just moved over to the traffic org to try to come up with a new
program with no team or anything and then I would meet with Jeff and and you know Bezos and Wilkie and others every couple months and just kind of I would profile a couple different options and use the working backwards process and we'd review some facts and so there was
a bunch of of kind of learnings throughout that process one I found Jeff to be super encouraging and you know each time we leave one of those meetings we maybe didn't find the thing in that meeting we talk about it and brainstorm a little bit but he would always leave and and be encouraging and you know with
a quote you know one time he was like you know remember this process doesn't have to be efficient because the prerequisite for efficiency is knowing where you're going and then he leave the room and whatever so I just I found like the the rhetoric around Jeff or blowing
up or whatever I didn't find any of that and I found him to be super encouraging and he found all these times to sort of help train me in the working backwards process like there was a time when I came with a press release for a concept and it didn't have a problem paragraph
I'd skip that and you know we reviewed it and so forth and he was like you know what maybe if you don't have a problem paragraph there's not really a problem and so it was kind of a little lesson to me like yeah maybe that is why I did it I wasn't really working backwards I kind of had
the solution in mind and so I'd skipped over that part so that was one just very specific learning about the process from Jeff so Jeff Wilkie I probably learned more from from Wilkie just because I had more exposure over my time there you know at one point it was my skip level
and I have such tremendous respect for for Wilkie or jaw as he was called internally because he was sort of the consummate like operator this muscle that I think you learned working at Amazon about being an operator whether you're you're not in operations but any
part of the business that I think came from him and I think it was due to him that Amazon developed that muscle and I think it's one way that separates some Amazon PMS for people who haven't worked there in that environment and that continuous Improvement mindset that's
like so important and you know one of the forums that was a great learning with sort of the wbr our weekly Business review or later called consumer Business Review so this was a forum where Jeff would lead the meeting it would be a series of metrics for different parts of
the business everywhere from fulfillment to customer support to traffic to category teams to programs and I would present on Amazon smile there and the way he would run that meeting and kind of enable you to get through a metrics meeting for the entire North American retail business in one hour and it it
the way he ran that meeting would lead all those leaders to build these muscles because you wanted to be prepared to speak to the variances or Trends in your business in a key metric and know your business and know what you were doing based on that thing and so just this
hour a week of probing and asking questions and everyone there might be 100 people in that room prepared to answer questions about your business and it had this cascading effect that Not only was I or are there leaders there you know on the spot having to to answer
a question and being prepared but then I would do the same thing with my team Etc so I was trying to build those muscles in my team such that they could bring their insights and understanding and actions on things in this cascading effect so that was a mechanism which is
another really big thing at Amazon that led to all these like amazing behaviors and I think a lot of those mechanisms you know came from Jeff Wilkie or he he created an environment where they would be developed throughout the organization and then propagated and so that was one
thing just that that operational mindset and rigor that is you know being a product leader is not just about building new things it's about you know how well you run which you've already built and if you if you're really paying attention to the product that you operate it will give you ideas for
things you could do to double down on something that's happening well or to prevent something bad happening and I think that's been a very key reason for Amazon scale another thing I really respect about Jeff Wilkie and I think Doug Harrington has some of this as well
is that the notion of kind of a little bit of tough love you know and like I think that's important and that neither were you know but sometimes and especially you know Wilkie like you need to get that look kind of like your dad might you know look over his glasses at you and be like hey
um and so I think that was kind of the vibe that you would get it was professional it was respectful but sometimes everyone needs a little kick in the ass and I think that was something but it was you know it almost builds more respect from him and just incredible leaderly Behavior which I
really respect and I try to model and I try to try to do the same because I respected it so much and then the last I guess the last attribute of of Wilkie which I really saw was was like teaching and it wasn't just saying this is the right thing or this is the this is the
what what my decision is in a meeting but teaching the why and why the pattern the mental model that informs him to think this is the right thing and so I think he was just great at uh at kind of teaching taking a moment it might just take 10 seconds in a meeting to teach
and that's something that I've forgotten in different parts of my career especially as you get more experienced and you you know the right decision to do and you know what you want see whatever that may be the right thing but I think you'll have a lot more lasting effect if you could kind of abstract it
to a degree and teach the lesson because then that person will hopefully learn the lesson and can apply it to a bunch of future situations and also understand the why more and it helps them kind of sometimes disagree and commit more so than just being kind of given
prescriptive advice sounds like it must have been a an incredible experience learning from these two thanks for sharing all that I want to get to the working backwards stuff I feel like we've talked about this a lot we've talked about this on other podcasts with other guests I feel
like people understand the general idea yeah Amazon Works backwards they write a PR maybe there's a six-pager thing they do but I feel like there's not a lot of here's how you actually do this thing and so just to spend a little time on this when you see teams trying to work
backwards and be like let's work backwards we're going to be like Amazon what do you find they do wrong when they're actually trying to implement this idea of working backwards so it's the most common mistake do you find yeah well working backwards is all about the
problem and kind of starting there and obsessing about the problem and and being Guided by it to then go into the solution so when teams that do it wrong is they don't do that they don't work backwards they start they have something they want to build we've got these these things look
similar these two technologies or whatever we could combine them and then do this and and if you say we could and it's not grounded in a customer or customer's problem you're not working backwards and then you may use sort of quote unquote the working backwards process but you already have the
solution and so you're adding the problem after the solution you're kind of retrofitting the problem retrofitting the customer and so that I think is the number one thing is that it's they don't get the importance of truly starting with the problem that you're trying to
solve and being faithful to that and working backwards from the problem when I first started Amazon and Community we had sort of this this business of automated merchandising using Community content and that was kind of the core thing we were doing is to grow that but there was this Jeff idea that the team
was super excited about because I think in some meeting he's kind of sketched it out or whatever and so that there was already all this momentum to like build this thing that was actually a Jeff a Jeff project but I should have known at the time in hindsight I do because the
the name they had for this project was acin to acin linking and you know acin was kind of the identifier for a product on Amazon and so it was kind of this not working backwards idea ultimately of like if you could link to products by a subjective attributes and then you could
build a feature around it that allowed customers to to vote on these things and then it would be kind of a so it was not in spirit it really wasn't working backwards but the team was all excited and so we we kind of eventually wrote the press release and we kind of did it and you know what it turned out it
wasn't successful I ended up shutting it down later and so I learned a lot this was like the first year or two at Amazon about using the working backwards process but not really working backwards and so that's literally if I'm reviewing uh working backwards press release or
fact or even talking with someone about a new initiative my brain is kind of why wired now to not be able to process any information until I focus on the problem and the customer and then once we start talking about that then I can engage and and kind of literally work backwards to
say okay how do we solve that problem and what's the most elegant way to solve it or if there's three problems what's number one or two or three so it's probably a gap in in me that I can't like process information without working backwards from the problem but I find it
to be helpful when people do that so when people talk about working backwards the way you're describing it is is interesting where it's focused on start with the problem which I think generally product teams try to do like they're one pagers their prds often have like here's
the problem we're solving here's why it's a problem here's how we think about is that the core of working backwards I always imagine it was like the launch release and the pr thing and maybe the FAQ do you actually do working backwards at like uber and other and Airbnb like
do you actually do that for every project yourself at this point there's two parts of it one there's the concept of working backwards from what you're trying to accomplish and I still have absolutely do that with my teams as well like what are we trying to accomplish
for the business or accomplish for a customer and let's start there and if they have a problem that is interfering with their ability to be profitable for their ability you know if it's a business customer or it's a customer trying to accomplish a goal starting with that problem that's different from
the working backwards mechanism which is the press release and the fact which was the mechanism that Amazon used to enforce working backwards which I think is effective you know and I've tried to sort of teach that and write some some posts about with templates and things
like that because it's a great way to start of like the press release has a paragraph about the problem that's what you write and then you write the solution paragraph and then the customer quote and then the fact which is like is there a legitimate plan to succeed so if
you don't have that muscle to work backwards already in your team it's a great thing to try but that's not the only mechanism that can do it and eventually if you if you do it enough and you build that muscle to work backwards you can do it in any number of formats whether it's a something in a
PRD or or some other way but the key is that you don't just you don't think what we could build you think about the problem and then the solution that solves that problem got it okay so the press release is not core to it it's like a trick to get you to think about
the problem you're solving it's not like how you plan to announce it interesting I never thought about it that way so when you're doing this process at other places outside Amazon say you're a product leader that's trying to like I want to do this I want to improve the
way we think about product what is it that you suggest they do specifically is it write out here's the problem we're solving is there more to it what would you suggest there if it's a blank slate truly you could certainly use the working backwards process like Amazon does with
the internal press release and then the fact and so forth so that's that's fine but a lot of companies have a different way they go about it some companies are very much it's slide culture and presentations and so forth and so as a product leader you could think about what you do with your team and what you
do upwards or across and so you may have the latitude to use any process with your team you know and I've done that at some companies where using documents and if they're supportive the team and they've recognized the value of that like oh actually this is a good and this is a
great way to to write things down on paper and to have better information content and richer discussion that oftentimes I think people will find that versus a slide with a couple bullets is not great then you can kind of build that muscle and I found it's a great way
to kind of teach and and use those to dive deeper into the into product but depending on the organization you're at that may not wash to sort of train your your senior leadership to use the process you want to use and so then it might be a matter of finding the opportunities to try something and
saying you know are you open to are you open to doing something this way a review of a doc instead of a review of a whatever so that's it's a little separate than just working backwards but I think you just have to acknowledge the the environment you're in and also like
unless the organization has a specific format to do this if it does you probably just need to use it different leaders process information different ways you may find one formats effective with your leader but another one to sort of educate a broader organization but it's very kind of company specific so
despite what I might want to do I just got to recognize that I have more leverage down with my team versus up or across right is there a template that you use really consistently is that something you've published of just like how to frame the problem how to frame all these other elements I have shared
posts on I know for sure LinkedIn and I probably should put it on the newsletter on my newsletter that's sort of a working backwards template and some posts about how to do the process or you know tips on on how the Amazon does the process and so I'll make sure to put
those up on my newsletter as well and the template's free obviously anyone could just copy it and grab it awesome we'll link to that in the show notes definitely send that to me after we wrap this thing and I was going to ask does Amazon work backwards and every product
they work on slash do you suggest working backwards in every feature and product I think there's some scale below which it doesn't probably make sense to do this process because there's a little bit of overhead to it but I think if it's a significant if it's a new product
absolutely and I think there I'm sure there's some on Amazon that don't use the process but in general that was the way and and often enforce that you need to you know uh you need a working backwards review ideally that would happen kind of at the outset but sometimes it would be added later and
yeah I think it's a great thing whether you use the mechanism again it's a great template to start with and use if you have the flexibility to but I think it's also possible just to have the spirit and to try to be true to the spirit of working backwards from what you're
trying to do for customers and what problem that's the most important thing the template's just a mechanism to help ensure that happens got it you mentioned this a review what is that working backwards review well that would just be a meeting with leadership or other folks
to kind of review the concept review the press release review the fact and ask questions and in some cases that would be the gate to like approving it that was the case with with me and and Bezos before we went off and built the team and launched Amazon Smile as I would do
these reviews about different concepts and that was the one that we greenlit I mean that's often the case it's also just a great way to educate other people about what you're trying to accomplish ground them in the customer problem and solution and the fact is a whole other
concept it's about the legitimate plan to succeed one of their uh you know thing that I use I got a chance to have lunch with with Jeff Bezos who's probably back in 2008 or something like this and I sort of asked him like what's your criteria for sort of investing in something new
and he said well it's like three things one is it a big idea and then second is it something we should be doing so if maybe you have an idea if you have this new way to extract oil from Shale is it a big idea yeah it probably could be a big idea is it something Amazon should
be doing probably not and the third test is their legitimate plan to succeed and you gotta have all three of those things and I think the fact part of the working backwards process is that early stage legitimate test of whether this thing has a plan because you could have a this internal press release or big idea or
big idea for solution but the fact basically says okay I've thought through the the internal components or the finances or the the key technical hurdles or whatever and so that's one that's not written about as much how to do the fact but I think it's another way to kind of build trust that you've been
thoughtful enough given the stage of the product to deserve the resources or deserved to come kind of move forward with it that's awesome I feel like most PMS listening to this are going to be like I always start with the problem I'm always problem focused so I'm working
backwards so I'm good are there signs of just like no you're not you think you are but you're probably not doing this well is there like a symptom of like um you don't actually know you're not actually doing this correctly the most common thing that I see that kind of
tips me off is that when they talk about something there's different pieces in the pantry right and they're like we have these ingredients we could put them together we could add these two things together and make a meal out of it right and so it might be a technology it might
be a service it might be two different things or the building blocks are there and what's enabled if you add these two building blocks together is is something but that's not really working backwards it may be true that there's some leverage or some benefit from the
company having these Technologies or assets but that to me is often the first step that these two things look similar we combine them and it's all goodness and this new thing so if you start talking about those things or the technology I think that's the likely case that you're not really
working backwards as opposed to the opposite is if there's a customer problem that feels compelling even before you know the solution like yeah that does feel compelling and just like with every startup out there probably a lot of the pitches are like there's a big audience and a painful problem and
it's kind of the painkiller versus the vitamin thing and then we have a novel way to solve that that is worse that's kind of working backwards but the more often especially in a big company you'll have all these ideas because you have more ingredients in the pantry of ways
you could combine them and and try to feed it to someone but may not be working backwards awesome we've we're reaching about an hour chatting and so I want to let you go before we get to our very exciting lightning round is there anything else you want to share on
anything we've chatted about see no I mean I think we covered a bunch of Good Grounds it's been fun but nothing nothing particular okay great well then we've reached our very exciting lightning round we've got six questions here they'll be pretty quick and easy whatever comes to mind share and we'll
go through them relatively quickly so sound good all right let's do it let's do it what are two or three books that you've most recommended to other people I said getting real by 37 signals and it's specifically the chapter on epicenter design I've shared that many
many times you can link to it that's definitely the most thing I shared for fun the wool Trilogy by Hugh Howie he's probably my favorite author and a great series and then for learning just a recent one that I thought be super fascinating was energy and Civilization by vac love
smell so it might not be on the best seller list but I thought it was interesting what's another favorite podcast of yours other than this one possibly I think how I built this is really interesting just to kind of decompose how interesting businesses and products came about and then just
because of my work EV News Daily is kind of a daily digest of what's going on in the electric vehicle space so that's that's a very good use of my time five minutes a day to to get up to speed very Niche I love it what's a favorite movie or TV show you've recently seen
Yellowstone that's definitely my favorite can't wait for the next season Montana is my happy place although I'm probably the kind of person that they rail about in the show so it's kind of ironic I think the movie The I was everything everywhere all at once I love
movies that are not predictable and I thought that was just very creative I'm shocked by how many people on Yellowstone died that show is just murder left and right it was not expecting that on a ranch ranch oriented show it's a harsh environment quite harsh turns out especially if you mess
with the duttons next question favorite interview question that you like to ask when I'm coming out of left field I ask people like at this stage in your career what have you learned about yourself how are you different from other people no one's prepared for that what do you look
for in their answers I don't know I mean there's not one specific thing and there's no right answer which maybe makes it unfair but just maybe a little self-reflection and maybe they will have understanding their strengths and that might be a good bit of self-awareness
about what makes them uh different where they can harness that that makes them a better PM or engineer or something and so that's kind of what I'm I'm looking for but there's no set answer it's more just to throw them off balance interesting favorite app right now it's
probably not too interesting but to be honest YouTube it's like the you know Eighth Wonder of the world and just Every Day I'm Amazed if I want to learn about something new like a couple summers ago I had some time off and so I basically taught myself how to do Woodworking and built a kitchen and
other stuff and so it's just like it continues to be this resource and this Jewel that helps me kind of grow and learn about anything I imagine some people are watching this on YouTube right now all right I just read a story about a javelin Olympic Javelin thrower who learned how to do this watching
YouTube he was somewhere in I think maybe Africa he had no coaches around and you just watched this one other Javelin guy that just shared lessons on how to do this and became incredibly good it's insane and I didn't I mean I'm I'm old so I didn't have this when I was
growing up like I remember going to the library and like sending away for a brochure in the back of a magazine and things like you like learning was not so easy back then the internet obviously was was a huge resource and is but then YouTube as well to see somebody do it
it's also interesting to see somebody live so anyway I'm uh I'm a fan final question who else in the industry do you most respect as a thought leader someone you look up to you I said Gibson Biddle I think that he is one just tremendous amount of product experience that I think is valuable he he I respect the
fact that he takes the time to share it he doesn't have to but he does and he's also a great communicator and he invests in being you can tell like you know he measures Seaside of his talks and things like this like he's invested over his career to be a great communicator so I
think he's a good a good kind of role model for me and I think for others out there that guy's a force I'm happy that we've had him on this podcast I'm hoping that everyone eventually that people mention in this question we end up having on this podcast so that's great
to check I also love Gibson he's got a great newsletter ass cubes.substack.com I think Ian thank you so much for being here this was amazing I really appreciate you sharing all this wisdom with us two final questions where can folks find you online if they want to reach out learn more and how can
listeners be useful to you yeah I guess Twitter is a great place so Ian McCall i-a-n-m-c-a-l-l as my handle and then you know I've started the newsletter I'm not that frequent to be honest I have a lot of good intentions and a bunch of ideas Ian mcallister.substack.com and so that's
something to kind of connect and feel free to subscribe and if hit me up on Twitter if you have ideas for posts or questions and if I can answer in a tweet I will if not I might put it on the Queue of things to write about and yeah thanks for having me on Lenny it's like
I was we were talking earlier about like writing or doing other things and like the value of that is just like making connections with people and so that was what I was one just to reconnect with you is awesome and to whatever extent I get a chance to make new Connections in
the world that's a that's a good thing amazing yeah and we originally connected over that piece that you wrote so it all circles back 10 years later maybe thanks Ian all right thanks Lenny thank you so much for listening if you found this valuable you can subscribe to
the show on Apple podcast Spotify or your favorite podcast app also please consider giving us a rating or leaving a review as that really helps other listeners find the podcast you can find all past episodes or learn more about the show at lennyspodcast.com see you in the next episode [Music]