Lessons from scaling Stripe | Claire Hughes Johnson (ex-COO of Stripe)

0:00

what I say to people at stripe in our onboarding I used to run a session I was like if you're not sure who the decision maker is one it's probably you and I'd rather you act that way than not because you're gonna like slow the whole company down follow a process and get it done and don't forget to actually make a decision

0:18

and if you don't know who decision maker is and you're worried it's not you just ask like don't get stuck too many people get stuck and it makes your like work terrible right I mean what do we all care about progress impact momentum I mean if if anything I would say about like advice to people generally is be a force

0:42

for positive momentum and it will it will be actually a real career maker foreign podcast where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products today my guest is Claire Hughes Johnson Claire was most

1:03

recently Chief Operating Officer at stripe for the past seven years where she helped scale them from a small startup to the legendary company that it is today before that she spent about 10 years at Google where she was a VP of self-driving cars mipi of global online sales director of sales and Ops for Gmail YouTube Google Apps and AdWords

1:22

before that she was in politics she's also on the board of HubSpot and the Atlantic and this week she's releasing an incredible book called scaling people which in my opinion should be and likely will be on every Founder's bookshelf in our conversation we dig into many of the meaty topics that her book covers

1:39

including building your operational Cadence defining your company and personal operating principles your company's operating system also tons of tactical advice around saying things that you can say building self-awareness distinguishing management from leadership so much more I say this a couple times in our conversation if you

1:59

enjoyed my newsletter and podcast and the fact that it's very tactical and full of templates and Frameworks you will love Claire's book and you will love learning from Claire I had such a good time chatting with Claire and I know you'll learn a lot from this conversation with that I bring you Claire Hughes Johnson after a short word

2:16

from our wonderful sponsors this episode is brought to you by linear let's be honest the issue tracker that you're using today isn't very helpful why is it that it always seems to be working against you instead of working for you why does it feel like such a chore to use well linear is different it's incredibly fast beautifully

2:36

designed and it comes with powerful workflows that streamline your entire product development process from issue tracking all the way to managing product roadmaps linear is designed for the way modern software teams work what users love about linear are the powerful keyboard shortcuts efficient GitHub Integrations cycles that actually create

2:55

progress and built-in project updates to keep everyone in sync in short it just works linear is the default tool of choice among startups and it Powers a wide range of large established companies such as versel retool and cash out see for yourself why product teams described using linear as magical visit

3:16

linear dot app slash Lenny to try a linear for free with your team and get 25 off when you upgrade that's linear dot app slash Lenny this episode is brought to you by vanta helping you streamline your security compliance to accelerate growth if your business stores any data in the cloud then you've likely been asked or you're

3:38

going to be asked about your sock 2 compliance sock 2 is a way to prove your company is taking proper security measures to protect customer data and builds trust with customers and partners especially those with serious security requirements also if you want to sell to the Enterprise proving security is

3:55

essential sock 2 can either open the door for bigger and better deals or it can put your business on hold if you don't have a sock 2 there's a good chance you won't even get a seat at the table beginning a society report can be a huge burden especially for startups it's time consuming tedious and expensive enter vanta over 3 000 fast

4:17

growing companies use vanta to automate up to 90 of the work involved with stock 2. vanta can get you ready for security audits in weeks instead of months less than a third of the time that it usually takes for a limited time Lenny's podcast listeners get one thousand dollars off vanta just go to avanta.com Lenny that's

4:38

v-a-n-t-a.com Lenny to learn more and to claim your discount get started today Claire welcome to the podcast thank you Lenny so you wrote this book it's called scaling people it's coming out this week I actually read a preview copy and it's incredible everyone listening to this should buy it especially if you're a fan of this

5:03

podcast it's full of Frameworks and templates and guides and all these things that I try to do with my newsletter and podcast and so if you like what I do you're going to love this book and I can't imagine how much work it must have taken to write a book like this so my first question just how relieved are you that you're done with

5:19

this book and you can move on with your life I'm so relieved Lenny it was the writing this book was not my idea uh Patrick and John Carlson Stripes co-founders really sort of pushed me into it and I'm glad they did I will admit that but as I am with most things they push me into but it it was a lot more work than than I thought it would

5:39

be and it's very reward I mean very rewarding to have it have it done of course though I've been re-looking at it and realizing there are things I want to add information or tweak what I originally said but maybe we'll have to do a second edition we'll see that's the benefit of a newsletter I can just edit

5:57

things and they're immediately live yes I want to talk about John and Patrick a little bit but before that yeah something I wanted to ask is I I find that when I write stuff I am able to better understand and crystallize my own thinking and I'm curious having written this book what is it that you are able to better understand and

6:17

crystallize in your own thinking through that process it's true and it's funny because if you asked me I would have said I crystallize more by talking and speaking but whenever I do write something down I'm glad I did so I probably do more crystallizing my writing than I would admit but maybe I'm just lazy and I just like to talk

6:35

there's a part of the book I think it's toward the end of the third chapter which is about hiring and that's a really long chapter turns out I had a lot to say about hiring and hiring leaders and processes and what you want to set up and and as I got to the end of the chapter I found myself saying to the reader

6:54

you maybe have read this and thought is this is is she like for real like you need to do all this work you need to put all of this in and I had to say well look I started the chapter saying if you believe that Talent you know is everything then your hiring process is everything and so yes you do need to put that work in but I think Lenny to your

7:15

point when you see all the templates and the Frameworks and the examples and the advice from my career and you know I was at Google for almost 11 years I joined Google when it was about 1800 people pre-ipo and left when it was about 60 000 I had like eight different jobs while I was there and then joining

7:32

stripe when it was about 160 people and now we're over 7 000 people like yeah I have a lot of examples but really what's crystallized is how much work it is to build to build a company you know this and there's not really I mean I hope this book is a bit of a shortcut but there are no shortcuts it I hope it will accelerate people's

7:54

knowledge so that they can get down to work with their product and with their customers there's a story you share at the end of the book I think it's an acknowledgments about how people went and took like John Collison out for dinner and were just like picking his brain on how did you scale stripe how

8:09

did you build this amazing machine of a company and he often came back from these dinners and he's just like Claire they just want to talk to you you did all these things not me and it sounds like that kind of encouraged you to write things down and then led to this book one is that true and then two I'm curious what else did you learn from

8:27

John and Patrick Olsen they that have stuck with you imagine there's a lot but kind of what stands out no that's absolutely I I think it is true that it's right we're fortunate where we have so many users customers who are themselves Founders or interesting companies growing up around the world whether at scale like Amazon or scaling

8:45

you know I've I've spent time with Discord and toast and you know all kinds of interesting companies that are growing up around us and a lot of their questions are not necessarily about Stripes products always they're really about well how do you guys do this thing or we're having this challenge are you having this

9:03

Challenge and John yeah would often come back from trips he would travel more and he is often probably meets with more customers than anyone in the stripe leadership team maybe other than our sales leaders and they would ask about scaling and he he would joke he's like we need Claire in a box so I think the book is you know Claire

9:21

in a box I guess but Patrick also would have that same experience and when I contributed a chapter to elad gills high growth handbook even though if you look at high growth handbook which I also I really do recommend not just because I'm in it I'm probably the least I don't know celebrity participant in

9:43

his chapters and my chapter got a lot of traction because I think it was very specific it was very tactical and um a lot actually helped me to realize like look examples and details and Frameworks my working with Claire document is in there is like he said it's catnip and I think that is also what inspired Patrick to push me to to

10:07

do basically a longer version of that chapter that I did with a lot but I've learned a lot from both of them you know I used to think that I was like my parents are teachers Lenny I used to think I was like very curious and I'm a learner and I'll seek out information and like I grew up in a very educatory

10:23

environment right well once I met the Collison like the two of them are huge sponges like seeking out knowledge constantly but also anytime we we're confronted with anything even things I felt I'd done before like that I had the experience and I was gonna we were gonna build it you know they were like well

10:42

who have you talked to or what have you read or you know and it was really good I mean I I learned I don't think I made enough phone calls in my earlier career and asked people's advice and asked for help and you know found the person who did that thing five years ago and found out what they learned and I think that's

11:00

probably my biggest lesson from working with both of them is how much it pays to seek out Knowledge from others because we're all just learning all the time is there a story an example of that comes to mind that was really beneficial where you actually ended up following that advice and reached out to someone

11:17

talked to someone and I changed the way you think change the way you operate there are two things that just jumped into my mind the first one is early on at stripe you know I joined we were about 160 people I started bringing in some leaders we were building out go to market we were starting to stabilize our support operations building out

11:35

recruiting and HR all the things we were really growing and it became very apparent that we needed to put in some kind of job structure like levels and ladders is what you would call it right which is there are different levels of pay and they have to do with your experience and your impact and their expectations of those different levels

11:56

right as an engine you know there's an engineering ladder and this stuff is probably making some people listening like their skin start to crawl because it's never fun or easy to Define all that and it's not perfect like you're immediately getting into something that feels pretty sub-optimal but it is worse

12:13

to have nothing because it starts to feel very unfair in the environment especially if you have to start to change up compensation and reward or reward systems right so I realized oh my gosh we're gonna have to put this in place we didn't know HR people so I I basically ran a project and the first thing I did though thanks

12:33

to Patrick and John is I went and talked I talked to square I talked to Airbnb and I talked to like two or three other companies but those two conversations I'm not gonna say who said this but one of them the person said oh you're that's a bloodbath they were not encouraging about what we were about to go through and another one

12:54

said you know what I'm so impressed that you're doing that so early we waited too long and actually that's what a lot of my book is about is like when should you start to think about this thing that you might need right and it's sooner than you think and so putting in levels of letters felt like ripping the Band-Aid off honestly but I

13:15

was glad I wasn't coming I talked to wait until they were like 800 people and it was apparently not fun because people don't like to be who likes to be categorized you know yeah and put at a level that maybe they're not happy with right they're like Oh I thought it was a lot more senior than that yep yeah exactly it's not easy it's

13:34

a form of change that's that's challenging and I would not say we did it perfectly but I'm glad we did it I think that that's that example uh was definitely one of them another was like we were really strong like we wanted to roll out you know 24 7 support in multiple channels email phone chat multiple languages and getting from like

13:55

where we were to where we wanted to be as quickly as possible not many companies have done at the scale right because stripe has millions of customers like we're B2B but we're B2B at a very high scale which actually Google uh was as well and so that was beneficial to me coming into the stripe environment

14:13

because I'd done parts of that for Google and again that's an example of something I thought I knew how to do sort of but we certainly didn't do it perfectly and and it's certainly different when you're talking about payments right that's people's money that is a business is like if they don't know how to contact you and they have a problem that

14:31

is a huge issue and so I did seek out a lot of advice and and I would say you know I did anything change dramatically what we did I think if anything the advice pushed me to go faster on some of my intuitions about for example using vendors and Outsourcing parts of the model and I realized like we're not going to

14:55

scale all this internally especially not at the speed that we're going but it's hard to start to use outside sort of contractors if you haven't figured out all your tools and processes right so that balance uh was you know sort of freaking me out but you just got to push through it there's a couple directions I want to go

15:16

but I'll go and an unexpected Direction at stripe you're kind of Infamous for your titles like when I I created this yeah it's like everyone's product manager they're like a VP or product potentially it's like product manager what's the rationale behind that and is that what I guess and what's the benefit of

15:34

that and but yeah you don't have to go too far down the road I'm just curious so this is something that Patrick and I actually really agreed on without a lot of discussion which you know is not always the case it has to do with a combination of optionality as you scale and grow and also culture right and so

15:52

they're sort of the minute you start titling a lot you're signaling hierarchy and Authority and the culture piece to stripe still today which is I think we could use more strong at least more overt trappings of structure because it can get confusing and I'll be the first to tell you that and I admit that this might have carried

16:13

on too far but but early on you know at stripe there's a real belief it's not a particularly hierarchical company and if you're the person who has the knowledge like you are the expert on the thing you better be in the room one in the room helping make the decision and two driving helping to drive the decision

16:31

and I don't care how senior you are right and that was that was the cultural signal that was important um which was about Mutual ownership and also expertise not sitting in hierarchy and then the optionality thing is probably a little more obvious which is like you can't don't make somebody the CMO or even the head of marketing if

16:53

your marketing team is two people right like yeah you might make the right choice but two years later your marketing team's probably gonna be more than two people say it's 20 like and and are you gonna have to layer somebody or have too many titles it just and then someone feels like they're losing something right it goes back to the

17:12

levels and Ladder segments worse because you've given something and then you're sort of taking it away and that's just not organizationally you want more flexibility honestly I also I'll say my final thing which is I have a little bit of a knit where you meet an a company I mean I get what's happened which is like

17:29

in order to hire this person they had to sort of say I'll make you the VP of sales or the VP of this but the company's like 25 people and there's seven VPS you know if you're like a customer or you're evaluating it you know you're kind of like really like it just doesn't it's not it's a little incongruous with the scale so we we kind

17:50

of like more flexible we had a lot of you know growth like ahead of this or growth lead I know you you're you're all about growth money well we we definitely took growth and find that very broadly but the other thing I've said to people internally sorry you can really get me going on this one I bet you didn't think

18:08

that is if you're a stripe and you're going out into the market actually speaks to the same thing which is you're going and trying to sell to a customer who's a lot bigger than you I'm not saying make up a title like don't say you're the VP of sales but you can be creative about how you represent your scope because you probably have really

18:29

big scope because you're one of the only people helping to sell the product and that will help you because a lot of more established mature companies are trying to do that hierarchy match we're like well bring your SVP because my SVP is coming to the meeting and we could be like we don't really have that

18:44

it just gives you a little more selling flexibility too I like that I like that combo where you can like just like say something that fits in this situation even that's not your technical term yes you can say oh yeah I actually am I'm in charge of optimization for our payments product I'm sure you are I'm sure that's what

19:01

you do coming back to something you talked about with the career ladder and I had a question around this you talked about how often times people do it too late and I'm curious why it's so important to think about the stuff that you wrote about in this book so early in your company's life cycle I think in the book you mentioned that it's oftentimes

19:21

as important to get your operational structure and cultural structures in place and correct as like finding product Market fit or finding your first few customers which I think would surprise a lot of people can you talk about why you found that to be so important not only can I talk about it already I wrote a whole book about it

19:39

um so let's try to restrain me but here's what I would say obviously product Market fit is the most important and what I do say in the book is focus on that and don't don't get too far like this my book is definitely not zero to one it's more like one and a half or maybe 0.5 to 1.5 or one to two because I do think when you're smaller

20:02

and focused on product Market fit and and finding your user and getting that traction that is that shapes a lot of how you work and your goals and who you hire and that all makes sense I think the thing that happens though is one some companies don't quite realize they're hitting it and they start to get

20:19

behind on actually building the company part because guess what it turns out product Market fit is just the product and that is not a company and that will not scale I mean to a point like the thing that's you know you see these companies that sort of fall over and like there's sort of a bad article about them and it's often it's

20:37

not the product it's the fact that they didn't actually build the company very well and that started to harm in fact harm the product and harm the Enterprise like the the mission you have this Vision you're going to solve this problem with this product and all of a sudden you can't solve it because you didn't scale the org properly you didn't

20:54

you didn't keep the cultural fabric strong as you grew right and so that's why I think it's so important and then so let's say you are hitting traction and hopefully you do notice it because I think a lot of Founders you know you're kind of paranoid like stripe I don't think Patrick and John's fully embraced

21:12

that they needed to start scaling maybe until I showed up and that was part of hiring me I was like yeah this is it it's happening like look at the you know it's not just look at the numbers it's like look at the inbound support demand look at the inbound sales leads like I just did the math and I was like this

21:28

company should be probably twice the number of people it is right now which of course freaked everybody out but it was very obvious to me because I was coming in outside with that perspective but more importantly not just scaling things like sales and support and you know as you probably know if you work in payments you've got

21:46

a lot of other functions that are very important around risk and compliance and you name it or you know the machine learning models and that that help you do those things but for the the sort of structures and operating processes that I talk about in the book I I really I do have this analogy which I think you picked up on to like

22:06

building a house right which is you have the supporting beam you know say it's a post and beam structure you you need the posts and the beams and then you're gonna have to do the Mechanicals right there's gonna have to be some amount of wiring in order for you I don't know if you have your solar panels but you got

22:23

to bring in the heat you got to bring in uh the cooling and and plumbing and then you have like foundational stuff that you have to build or the whole structure will fall over and I think of putting in the posts and beams and the Mechanicals and the foundation as actually essential to scale because if you do those things well

22:43

you build them in such a way this is almost like a Russian doll kind of thing but you build them so that they're replicable right so the way that you do goals as a company can start at the company level and this is how okrs were so beautiful for Google and they can replicate down to the individual and the same common structure allows that to

23:02

happen at really different levels of scale and that's what you're looking for is what are these common things we do not a lot of them by the way you can't you don't want to mandate a lot you don't want to put too much structure in place but enough that everyone can play with it up and down what I would think

23:16

of as the stack of the company and if you don't start putting those things in early people will just invent those things and then you'll have you know picture picture a house that got added on to 17 times and it's not even two years old it looks you know not super stable and then you're going to find yourself having to do a tear down

23:36

which I think we've all seen companies do that I definitely want to get into that uh that house structure and all the components of it but before we get there just if you're like a found early stage founder just like looking for product Market fit maybe the skipping ahead a little bit but like what which elements

23:53

do you think are the most important that they need to do now because they're you know they're going to read your book which gives them so much advice on all the things you can do yeah if you're like after if you have to pick a couple things that you have to like nail when you're just starting out before product Market fit what what do you think is

24:07

most important I think really that early keeping it very simple and and being focused on that goal of product Market which is like what is the problem you're trying to solve what's your vision I mean everything you have to do for an investor pitch deck matters not just for the investors by the way people forget

24:23

this a lot of the story you tell to investors the early ones especially is the story you should be telling internally to anybody you hire why do we exist what problem are we trying to solve what early customers have we attracted sort of and and what's their feedback like that that's what you mostly need but you need to remember to

24:43

share it and don't just use it for fundraising or don't just use it for a board meeting or an investor meeting use it internally and I think you can get pretty far actually with that core content as you start to I mean the first thing you're probably putting in place is a little bit of hiring process and I think that's going to matter

25:01

sooner than you think don't just be tempted to hire people you know and your friends think about what you need what capabilities you need to build even pre-pmf right and so there's as I said there's like a chapter about that but I think some of the simplest versions of it is how do we evaluate talent what

25:19

kind of talent are we looking for where do we go look for talent you know figure that out and sort of train people a bit internally on interviewing I think interviewing is not a skill that comes naturally people think it does it does not and there's really basic easy tips and tricks you can find even on the

25:37

interwebs about interviewing and I really recommend uh and my book has examples of like rubrics questions you can use how do you really get at because it's hard to really evaluate someone in 30 minutes or 45 minutes so I think interviewing some of your fundamental early investor kind of content you need but then when you

25:55

start to get some traction then you're starting to codify and actually document what I call more foundational content because if your pre-product Market fit you're probably small enough that you just can tell everybody all the things you don't have to send them the packet or have them sit in the onboarding but the

26:12

minute that you're starting to get any kind of hiring speed you're going to want to have documented more and you're going to want to start to put some very lightweight processes of how you get things done in place because again you're trying to replicate velocity it's easy when you're all in one room and everyone knows like oh this

26:31

is the most important thing to get done today hack hacking hacking away but then uh pretty quickly that is not going to be the case I definitely want to go one layer deeper on that but there's this area I wanted to get to before we dive into some of the into the weeds around that which is I found it really interesting that you started your book

26:47

with this idea of personal operating principles versus like here's how the company should work it starts with like here's how you should think about yourself so I want to go there's four of them but before I get into them can you just describe like what is the idea of a personal operating principle and why is

27:01

that important remember the book is about sort of two things company building and Company structures and all that replicating all that good stuff and management so the other thing that the book is really about is management tactical guides to I mean it would be easy to build companies if there weren't humans

27:18

involved right but there's humans and they're complicated and I'm complicated and you're complicated and there are things that motivate us there are things that demotivate us they're not the same things so Lenny and I I think you and I have some things in common but point is the book starts with you and I think a lot of people

27:36

think management starts with the team or even the company uh and actually I think Founders make this mistake Founders say Well it starts with my product and yeah I mean but it actually starts with you and so the book starts with sort of my belief system which is self-awareness which is the first operating principle

27:57

uh self-awareness to build Mutual awareness is actually the most fundamental thing you need to crack if you're going to succeed at company building or management in my opinion but I would say I'm not I'm one of those people who has strong opinions that are pretty loosely held this one is a strong opinion strongly held which is the more

28:18

that you can seek feedback seek to understand your motivators your strengths your blind spots your Tendencies and and take that on board and and expose it to others you're going to be a much more effective uh company Builder and manager so it starts with you and those operating principles that I articulate are sort of mine but

28:40

they're also foundational to the content of the whole book I do think authentic leaders tend to have their own right Lenny you probably have a few that you you maybe have not articulated them all out loud but I do have mine and they're in the book but I think you would also find that some of them you could adopt

28:56

if you were looking for if you were looking for some to start to use as a leader I would I would hope that I've put forward a couple that might be useful I want to talk about these four but um while you're on that topic what are ways to help crystallize your own operating principles like what advice would you give people to yes because to

29:14

your point people probably have them in their head but they haven't really been ridden them out that's right they haven't the book has an exercise that I recommend in it that's a little bit more about crystallizing your personal values but that's kind of the place you want to start and it's essentially there's a

29:29

whole menu and you can find these online of like say 70 or 80 different values and but by values I mean uh family ambition impact competition like people value education people value different things differently by the way and there's no judgment like you might value you know being a very competitive person

29:50

and I might value collaboration above competitiveness and that's fine we probably would both be very effective in a team for different reasons right so basically if you take a list of values and you say okay if I had to pick 10 of these that matter to me then if I had to pick five of them and then you really force yourself if I had to only pick

30:08

three of them and it's actually good to have this in a dialogue with someone that you've worked with or you know well and you sort of had to explain well like why why when I'm really pushed do I have to have to hold on to say education or learning as a value or why do I have to hold on to Integrity as a value and I

30:25

tell a story in the book about a manager I worked with where transparency was a a very important value to him and the thing is you usually have a story behind that value right and in the book I I use the name Eli for him Eli ends up sharing this story at this off site that we had and the transparency value actually was

30:47

a little bit problematic to manage because Eli would tell everyone everything including his team even when we weren't finished with the plan right but Eli got up and told a story of being younger like seven or eight and realizing his mother was very sick and no one really told him what was going on and then unfortunately watching the

31:11

process of her her dying and then being taken out to lunch by by his stepfather and said and told your mother is gone and okay well this doesn't like your whole world view kind of explodes when you hear that and you're like oh okay this transparency thing is really real this was a formative experience for him and it has changed

31:34

how he operates and it will probably have changed it for his whole life and if you can get to that point on your own of telling yourself what was the story what was the thing that made this so important to me then you're starting to be in a mode of self-discovery and then you're starting to document

31:52

okay if these are my three top values and here's why uh and then I think what you want to look for are what are my what I would call my work style Tendencies and and so you get your values and then you sort of go on a I'm sorry I could go on about to say I warned you I wrote a book about this but basically all these work style

32:11

assessments Myers Briggs disk Enneagram you name it and I I by the way I would take all of them because I find that very good day I mean some of it you know it's just data you're just taking on data but a lot of them come down to are you introverted or extroverted are you more introverted or extroverted like

32:29

where are you on that Continuum and are you more tasked if you kind of picture a horizontal and a vertical are you more task or people oriented and so I would take your values and then I would plot yourself like am I a more extroverted task-oriented person which means you're kind of a director get you know what done kind of person or am I a more

32:49

extroverted people oriented person which might mean actually you're probably great at uh being very charismatic and buildings followership and maybe selling a vision very a lot of sales people are very extroverted people oriented people and then you start to see okay if this is my sort of tendency in my default and

33:08

this is my value system like what are what are the ways that I operate that really make up who I am right and and sort of becomes almost a belief system and my operating principles in the book you know one is the build self-awareness to build Mutual awareness another one is say the thing you think you cannot say

33:27

I think that I've come to believe that often your biggest strength one is also your weakness but two is something that you don't know is a big strength because it's almost like breathing right like for me saying something actually fairly openly and directly but in a non-threatening way is is a is a thing I do uh John Carlson actually once said to me

33:52

he's like it's so interesting when you give feedback that can be like actually pretty brutal I leave feeling really optimistic but but like you know I mean I I don't mean to be brutal but I think I can sort of unpack and say this thing like here's my observation here's what's going on and it's not judgmental it's

34:15

not threatening it's actually opening up an opportunity for people so say the thing you think you cannot say you would actually find that more of us can do that and then I come back to you know distinguish between being a leader and a manager which is something early in my career I did not do well Lenny which

34:30

before we get to that one actually just to briefly uh ask you a follow-up question because I I love that you're getting through all four here this is great but I was gonna ask is there something so clearly really good at saying the thing you cannot say and I love that many people are not good at this do you have any tactical advice for

34:47

someone that is not good at this for how to actually say something uncomfortable I think the the main thing is and Fred Kaufman has this in his book conscious business this concept of a left hand he calls it the left-hand column which is you're in a dialogue with me or you're watching a meeting happen and you've got a running

35:05

commentary in your head and honestly some of that stuff is pretty harsh right like you do not want to open your mouth and just say that thing but what Fred says is like learn how to detoxify the left hand column I would say think about a way to say that thing that you think you can't say like you you've filtered yourself out which I

35:27

don't like and I want you to think okay how can I and I think that the here are the tricks a couple of one is ask a question right a question is not threatening by the way the question could even be is there something we're not talking about it feels like to me and then you own so the next trick is you own it this is

35:49

your observation this is your perception this is not a judgment I am not saying Lenny I think you really botched that interview that's not useful if I said Lenny you know what I feel like I wonder if you missed an opportunity in that interview did you feel like you missed like an area that you know and then you're kind

36:07

of curious you're like what do you mean you know I'm like well I'm kind of looking at this with you and I'm standing next to you and I'm observing it right like that's less threatening so one ask a question two make an observation that you own so if I said I feel like there's something we're not talking about

36:22

and I wonder oh I own it I wonder if it's the fact that these two teams both seem to have the exact same project uh I talk in the book about a meeting I was in where it was like very clear that we had two teams in conflict and no one was saying the thing that was really pretty bad I was like this is pretty bad we have two teams that seem

36:44

like they both own a piece of work and are in conflict with one another but I would say if you do those two things ask a question own the observation yourself don't pass a judgment you will get way farther than you would have ever thought sharing and by the way that sharing one there's probably other people who just haven't

37:04

can't get out of their head and you have our opened up a door that a lot of others could probably walk through you're not alone you have this framework I think you call it being an Explorer not a lecturer is that is that what you just described is that how you describe it is and it to me what I just talked about was more of a meeting or a

37:22

conversation scenario but I think that this I'm glad you brought that up I think this is actually a very fundamental management framework of mine which is in a one-to-one interaction like your job as the manager first of all too many people think your job as a manager is to be the expert and tell people what to do no actually your job

37:40

is to enable people to be their very damn best on your team and you have to create an environment and a context and provide them information and then you need to provide them a form of coaching now again I think people sometimes think coaching is lecturing like let me coach you how to make this Excel model

38:00

you know and sometimes they do sometimes someone comes to you and says can you exactly show me how to do this thing fine but most of management is actually exploring with someone it is being curious it is saying I have seen this pattern of your work have you seen this pattern is there something like I I have

38:19

a whole other framework which is about hypothesis based coaching so instead of I think intuition as a word gets kind of a bad rap and I kind of get why look especially if you work with a lot of Engineers which I do it's not particularly always data driven but guess what guess what a scientific hypothesis is it's a well-informed piece of intuition

38:41

and I think too many managers wait until they have a million pieces of data to make an observation to someone about an area for improvement instead I would say take some data form a hypothesis and then explore it with the person because if you're well intended which I think any good manager is I'm bringing up this

39:02

thing because I'm trying to help you see it and tell me if it's true so that we can both help make it more effective better like I mean one very light example could be you know I I felt like in that meeting how did you feel that presentation went and the person sort of says I it's fine you know I think I got through the I got through

39:23

the material you say yeah I I felt like you were maybe a little bit nervous I'm just exploring were you and by the way the person could say oh no no no no no no no and and then then you're gonna you could back off or you could say oh well maybe it was just me but I noticed some physical like you your leg was shaking a

39:42

little bit your voice you know you were kind of repeating yourself and they're going like what and you're all you're doing is holding up a mirror you're saying Ma and you and you have to own it you have to say my experience of you in that meeting was that you seemed nervous to me maybe you were not but actually maybe

40:01

this is just a physical coaching thing right have you ever had that I have a few people on my teams who do this weird thing this is like pre-virtual world but like when they're sort of getting it uncomfortable in a meeting they put back their chair up the table right like sort of exit the circle and that is a very physically big statement

40:24

and they had no idea Lenny they had no idea I'm just watching the meeting and I'm like oh my gosh you're like four feet from the rest of the group because you do not like this topic and what I need to explore with you is how do you vocalize that instead of physically exiting the room or exiting the circle right these are just examples

40:44

sorry I could keep going but I really think that that attitude of exploration and mutual sort of collaborative let's discover some things about you and by the way it can be mutual they can go right back at you and say well I observe this great great I mean one of my favorite I've interviewed a lot of people for the

41:04

book different leaders and managers from lots of different fields but one of them was Reid Hoffman who's a more typical but read we were talking about the other operating principle which is management versus leadership and Reed was like pretty honest he's like look I'm more of a leader I'm not a manager it's like I'm not a great manager and then he told me

41:22

the story he's like he had in his first company that he was building uh he had a guy that he hired who was more operational and read uh read was like sort of making an observation to him about something they should do and the guy goes to him read I wouldn't hire you to manage McDonald's and Reed was like okay good so tell me

41:45

what we need to do so we can fix this thing but what actually reads operating principle interestingly when I unearth that whole thing was that he Pride some like it's very important to him to create an environment of open feedback uh he said what I love about that story yeah is it's funny and embarrassing but

42:04

actually that that guy was comfortable saying to me I wouldn't trust you to manage a McDonald's and and I think that actually I found inspiring because I don't think everybody who founded a company or who's managing someone has created an environment with that much trust in it right and that's how Reed thinks he gets a lot of stuff done is

42:22

people just come right back at him with the feedback this episode is brought to you by dovetail the customer insights platform for teams that gets you from data to insights fast no matter the method there's so much customer data to get through from user interviews to NPS sales calls usability tests support

42:41

Tickets App reviews it's a lot and you know that if you're building something hidden in that data are the insights that will lead you to building better products and that's where dovetail can help dovetail allows you to quickly analyze customer data from any source and transform it into evidence-based

42:57

insights that your whole team can access if you're a product manager who needs insights to motivate your team a designer validating your next big feature or a researcher who needs to analyze fast dovetail is the collaborative insights platform your whole team can use go to dovetailapp.com learning to get started today for free

43:15

that's dovetailapp.com Lenny so we've done three of the operating principles that you personally use which I love I love that you're gonna go through distinguish between management and Leadership is the third one yep and then the just to summarize real quick the second one was to say the thing that you cannot say the first one was say the

43:34

thing you think you cannot say yeah and then first build self-awareness to build Mutual awareness yep and and what's cool is you're sharing all these Amazing Stories and tactics in the book you actually have like templates to do each of these things for yourself which so like a lot of this is pointers to like

43:49

if you actually want to do this go check out the book and you can actually do this it's not just you know a bunch of high-level stuff and then the fourth is come back to the operating system um let's talk about it so this one is sort of like I was talking about Touchstone documents that you might create for your company like this is our

44:08

operating principles or our values this is my Touchstone which is I think that especially high growth environments but every environment you operate in can get really chaotic and there's a lot of ambiguity there's a lot of stuff you don't know and it's kind of easy to get paralyzed or to sort of give

44:25

in to the chaos and you're like oh my gosh I don't know what this day is going to bring I'm just going to randomly assign some stuff and I'm just gonna get through it and all you're doing in a lot of those moments is creating more chaos and I think a really important role of definitely managers but some leaders too is to create a

44:47

a stability when there doesn't feel like there's a lot that's stable and where stability comes from is in ritual and in common practices that you share so we set quarterly goals or monthly goals I don't you know and that's a ritual and that's a thing we do and it's actually a source of stability and yeah it feels like a process it

45:09

might feel like a way of managing but it also has like a Cadence to it and I think one of the things that happened is like you picture yourself sort of spinning out of control you think how do I come back to this is the order I do things this is how I get decisions made this is how we make plans this is how we

45:27

make decisions those touchstones are not processes to run the thing they're actually stable if they're done well they're stabilizing because they're a common way of approaching that everybody has so they can at least hold on to that even when all the other stuff is going haywire like you've got a customer churning and you've got a big launch

45:49

happening the next day like oh my God oh my God like come back what's our launch how do we launch products we have a way of doing that we do not need to spin out of control and reinvent the wheel here right and that's that's a stabilizing thing and and the other thing on come back to the operating system for me was

46:05

as my career scaled as I went from a Mana like an individual contributor to managing a small team to managing a bigger team to managing multiple teams to managing managers you get it I realized actually and I started to have multiple functions right so I was context switching between like at Google there was a point where I had like some

46:24

product people industrial design operations like really BD really different functions actually how I fundamentally ran them at the Bare Bones at the house architecture level was the same and that gave me a stability as a leader where I would like dive into a meeting I'd be like all right let's look at the

46:43

metrics that matter we all had we had them for every team let's look at the the goals we said you know and that also helps you stabilize when you're context switching between you know seven different projects or seven different teams uh and so I wouldn't say it's the operating principle that I talk about the most but I think if you were like

47:04

what's your sort of how do you scale yourself I would say well I actually have a common operating system like a computer you know and that and that is how I maintain a sense of stability perfect segue to the next kind of broad area I want to spend time on which is this house metaphor and the three components of it that you talked about

47:24

and this is kind of like the core of the book can you talk about again the three kind of pillars of this house structure and then let's just go through each of these things yeah I mean it's definitely the beginning of the book is about company building and the company structure chapter is all about the sort of

47:39

supporting beams the Mechanicals and then the foundational stuff and interestingly it's sort of well I guess when you build a house you build the foundation first so one is the founding documents that you might create which I'm happy to talk about and then another of these supporting structures which are

47:55

some of the ways you do things right we talked to like quarterly business reviews or okrs or how you use planning to create a structure that everyone and then the Mechanicals are what I might call the operating Cadence which is essentially the rhythm of how you work right we all like just the calendar the year that we all experience tends to

48:17

dictate a little bit how we work Mondays feel different than Sundays right well companies have that same kind of a Cadence which is often also calendar driven but also can be event driven I mean I I've we we've talked often at stripe about how our customer event which we have called stripe sessions is as important internally as it is for the

48:37

customers because it's a forcing function right for our Cadence how we plan our products what we want to have achieved by that point what we want to demonstrate and that's true for a lot of companies but we actually use it in our thinking about our Cadence of the year and actually we've built this other

48:53

event that I usually help run which is an internal event that happens generally about six months before that which is great because you can demo the stuff you think you want to demo internally you know like you sort of create a Cadence of we're going to push ourselves to do some crazy like wild stuff internally

49:10

demonstrate it and then see if we can externalize it you know by the time we hit the customer event but that is a Cadence you know quarterly business reviews are part of your Cadence Etc so that that's the fundamental but but really what I'm trying to do is say one I don't think this stuff is super hard you know this it's kind of hard work

49:29

it's just like putting it in place and then actually using it I think where a lot of leadership teams go wrong especially of young companies is they experiment with different vehicles to try this stuff and then they either don't actually follow them or they throw them out the window after like they haven't tried it for very long

49:49

and it creates a lot of chaos so I would say do very few things consistently and try to do them well and then see if they're working for you and then you know once a year maybe think about a revision but don't keep throwing out new things you heard that other companies do and it turns into like a weird grab bag

50:10

of operating operating stuff I don't uh you're nodding because you've seen this too yeah I think a problem I've seen is people think there's going to be this perfect system and process that's gonna not have any flaws and they're always like oh it's not perfect we get optimize it further and what I find is it's

50:26

always just like this is the best one you can come up with at the time that's the best idea you have now there's gonna be flaws just work around those flaws but just know there's never going to be the one thing that works there is no one there's no perfect org structure there's no perfect operating approach there's no

50:39

perfect yeah performance and management and level system but having one and committing to it is good and don't let the perfect be the enemy of the good there's another point you mentioned that I thought would be fun to talk about that it's often chaotic at a company I imagine people think about straight from

50:57

the Out Center like oh they've got it all figured out so smooth just runs like a machine and I think people look at other successful companies and they're like man things are so crazy at our company this this isn't normal but I think you tell me if I'm wrong most places are crazy and chaotic internally for long for a long time and often right

51:15

yeah I mean they're different kinds of chaos but um it's so true I mean what is that there's like a saying you know don't don't ever believe your best press or your worst press it's never as bad as whatever someone's saying is Never As Good it's just normal is you know not pretty like it's a lot and that is true it's happening everywhere I

51:39

used to have a friend who was building a company um we would see each other we both were from the Boston area and it's a long story but we'd end up on the same flight often a red eye like coming back to Boston occasionally for stuff for family and we'd be in the we'd be getting yelled at by the passengers could we be

51:56

in like the uh in the aisle of the airplane comparing notes about stuff that was broken and we had this expression it's like oh and then I picked up the Rock and oh under that rock were some really ugly creepy crawlies you know but that's just like the way it is is it's never perfect but I guess I would go back to what I just

52:16

said about having some stabilizing ways of doing things because that can create I don't know I'm not trying for a perception that the thing runs like a machine but more of a like that is a well-run thing right and how do you create that perception because you adhere to some ways of running things and that are

52:38

consistent and it feels better even to the outside even if there's a lot of chaotic stuff going on coming back to the founding documents could you just talk about like what are in this group of founding documents and I think even more interestingly what's a sign that you should invest more time in this area as

52:54

a startup very classic stuff is in here nothing that you haven't seen or examples of so one is I think it's good to have a mission uh when I joined stripe we did not it came to be apparent that to increase the GDP of the internet was probably the mission but because people kept repeating that back to us uh and Patrick had written it on some

53:18

website copy early on but it was interesting that candidates and customers kind of grabbed it it was very striped because it's a little bit intellectual and pointy-headed and aspirational but also it is the GDP does involve economic progress which we're all about right we're building infrastructure for Commerce and payments

53:36

for not just the internet actually but anyway point is have a mission or at least the beginning of you know what's your one line of what you're you're seeking to accomplish and then I really think I'm a big fan of writing sort of what what we at stripe called our long-term goals which were just not our

53:57

short distance but our longer distance like why did we exist and so the mission is one line so you need a little more meat behind that right and and actually I think if you looked at our long-term goals which by the way I thought would be like a three to five year goal I would say they're still relevant today

54:12

but one of stripes on term goals is to advance the state of the art in developer tools which would not be something that everybody especially every customer of stripe would initially call out but when you think about it Lenny you just did it you think about it for a minute you're like yeah like the API and the docs and a lot of stuff that

54:34

we've open sourced like stripe cares like our forever user is fundamentally a developer it's the person who's integrating Stripe Right at any by the way simple integration complex integration anywhere in between we really care about their experience and we care that the tools are excellent because how are you going to increase

54:54

the GDP of the internet if you don't Advance the state of the art of developer tools right anyway point is that that articulating that because until I said that to you and I could talk about it with you and say you came to work at stripe you might not understand why we invested in certain things or why it meant so much to us in

55:15

terms of our user experience and the mission so articulate those things and some of them might be a little bit aspirational but they should feel at least real enough that you can have that conversation about like I mean I look at anyone who works in a company what they choose to do all day with their time

55:31

should be guided by things like what are we trying to accomplish what are our long-term goals so if they don't know them how are they going to make the right choices so that's one and then another is is a lot of companies write company values or stripe we wrote operating principles I think you had AKA demiliano on and she talked about these

55:52

and we even sort of took a version of ours and put them out for candidates so that they could evaluate do I want to join this company because I kind of want to know what it's like to work there and I think that's really valuable to do because not every company is right for every candidate and the more you can

56:08

mutually match the better but having some operating principles matters I think you can go farther than that but that's where I would sort of start is those three things awesome I like the Simplicity oh and how do you know you don't have enough how you know is people are asking you especially new new hires are asking you a lot of questions

56:26

about like what's important or why do we do it this way or you know like I mean you said it yourself at the beginning doesn't writing something down crystallize it time to write it down and crystallize it for everybody who works there and just to summarize it was a mission your operating principle slash values

56:44

what was the third one yeah uh long-term goals long-term goals sort of more details on why you exist what are you really trying to accomplish interesting and are those like numbers in your experience or is that like a story of like what those are a little bit more I think headlines and and I think your shorter term goals have numbers against

57:03

them right so if you looked at your long-term goal which might be another one of Stripes is is about accelerating globalization and if you thought about what would that require that would require us to be in a lot of markets that would require us to have uh users and customers in a lot of Market you know like and also to eliminate

57:26

friction across borders so those things which is a very high friction thing unfortunately in payments and and moving money which it shouldn't be if you want to advance globalization accelerate it right and so that can then become numerical goals and short-term goals like basically objectives and then yeah

57:42

it's sort of like the longer term objective and then the key results part is early is shorter term but actually if you're having trouble writing your company goals actually zooming way out and being like well what are we really gonna if we're gonna meet this Mission what do we have to accomplish in the long term you can then walk back from

57:58

that and be like oh yeah every goal we ever have probably fits in these three to five buckets bam like and then you write your short-term goals actually more easily because you know there's always going to be one about say International expansion there's always going to be one about additional products because we're trying

58:17

to do X you know you can't do it with one product or whatever you can imagine the example awesome and I know your book has actual examples a lot of this stuff so yeah again pointer to that okay so that's the founding documents the next piece is operating system maybe we go there just like what fits into an

58:34

operating system for a company like what are the components of that I mean I think a lot of the components we've sort of touched on which is do you have some sort of goals this is now goes back what we're just talking about like for stripe we have an annual set of numeric targets that we put together we have a system of

58:52

goals or okrs objectives and key results but sort of like what is your structure for setting Milestones that you want to achieve whether they're numeric or or more like a binary we got this thing launched we didn't and then qbr so quarterly business reviews how do we review parts of the business what is the Cadence you know well first what is

59:14

the form by which we do that which would be this I I share examples in the book of like this might be the template you fill out if you're a team and you're reporting on how it's going versus your strategy and your goal and then there's also sort of getting into metrics and dashboards what are things that you look

59:28

at internally to measure progress the input metrics and the output metrics and I give some examples of that and and then mostly I mean I think there are other as I said there could be less frequent forms you use like a user event or a launch or way of launching products Etc but it's really simple it's mostly like

59:49

goals and how do you review the business planning I talk a lot about planning which is I mean you you said this earlier and you and I think both agree which is there's no perfect process to plan for the next year or the next two years but you still need to fight your way through having something especially after a certain stage and every CEO I

1:00:09

meet with we like sort of ring our hands together we're like oh planning and everyone hates us like two burdensome but like you still gotta keep trying you gotta do it um and so we talk about planning processes and what they might look like and how you set them up and then that's how you'd use goals and Oak and qbrs to

1:00:26

measure against the plan right so those are some of the operating systems and then the Cadence is just how often do you do these things actually one of our big lessons I think companies that are moving quickly and that are younger tend to resist some of the calendar-based cadences of more mature companies

1:00:47

because they seem slow you're like really you're going to just achieve that goal in like three months or like are you artificially restricting yourself right to some lowest common denominator of time and so I get that fear and I would say your Cadence doesn't have to be one quarter or one sixth month or even 12 months it could be like stripe

1:01:08

we did sort of six-month processes for a while so instead of a year we did it in six months or you know we CH I mean still there were things that took by the way a year or longer but I think that play around with the time frame and don't feel restricted by what other companies do but one of our lessons on

1:01:25

the qbrs was sometimes those quarterly because that stands for quarterly right those quarterly business reviews were were too infrequent especially for new product areas that were still in development that we're still getting a lot of feedback launching a lot and so we just said okay they're not they're not quarterly anymore they're like every

1:01:45

six week business reviews fine change your Cadence the point is to have one because then it's predictable for teams they know what they're marching toward they know when they're going to be reporting out and they can set their goals in a way that makes sense to make progress in that time one quick question there what's a sign

1:02:03

that your Cadence is off like what's a yeah what's this flag that like oh we should go shorter or longer well everyone usually complains about these things but I think if the one nothing like you said it's probably too fast if not enough progress is being made in between whatever your review or your reporting function is and it's probably

1:02:23

too slow if the content you're reviewing seems stale and you're like well we knew this or like we already did that thing or like yeah we already had the meeting where we talked about that that's another thing that's interesting is like some companies will have a pretty frequent metrics review Cadence and then an

1:02:39

infrequent strategy review Cadence and what happens is the metrics review becomes the strategy review because you don't you're not talking about the strategy often enough and so you're talking about it through the data and so then by the time you get to the strategy review you're like we already had this meeting right

1:02:55

and that's just a sign that some things are just off and it's just to me it's about like timeliness and freshness of the content but also that there's actually new content if there's not new content you're you're creating work for people by the way give them time to work and so I think that don't fool yourself that

1:03:14

thinking having more frequent checks on things is going to actually make things run faster I would say that the opposite can be true and so be very wary of actually slowing velocity down by creating overhead I mean one thing we try to do at stripe is if we're looking at metrics let's just look at your dashboard live let's not create a

1:03:35

special presentation like I actually just share your screen please on your dash right which is a good discipline because one that means you have to have a really good dashboard that's real Time That's web accessible you know like no one had to pull or massage the data right that's a good sign but it's also

1:03:54

you're not wasting people's time prepping all that information which happened even by the way at stripe even when we put that in place we still ended up with versions of that problem yeah AKA I think mentioned that I think there's a term for it like data something where you randomly get chosen every week and someone has to like

1:04:10

present your data from your meeting yes yeah it's like the next day you're gonna have to share your meetings and yeah we call it the spin the wheel the spin the wheel on who gets to present but you know that that has a logic in it which is don't over prepare because then you're not working to just prepare it right that's awesome

1:04:28

I love that policy there's so much more I want to chat about there's like chapters on hiring self-development personal development all these things theme development yeah what was that there's a yeah intentional there's a team building team building and Performance Management yeah it's like okay so we could go through all

1:04:44

that stuff instead I want to talk about the CEO role broadly yes I asked on Twitter preparing for this chat uh what people wanted me to ask you about and most of the questions ended up being about the CEO role and things like that so I just have a few questions lined up here for you sure okay so Amir soliff

1:05:02

handic with a little accent at the end there he has just at what point do companies need a CEO and how would you judge if someone is a fantastic CEO oh yeah well I would first say I most companies if you looked at the universe of all companies do not have a CLL I think it's like fewer than 20 uh it's definitely fewer than 30. and I think that's

1:05:27

something to know that I don't think it's an automatic role to have or hire and I think you see it in more prevalently in earlier stage or high growth companies you also by the way see it in certain business models I actually think Apple was an interesting version of this right where where Steve Jobs was oriented in

1:05:51

terms of product and design but also that Apple has like it's like very intense to manufacture software and Hardware that then works together I learned that when I worked on self-driving cars at Google and you need a very intensely operational detailed manufacturing hit the marks hit the timelines person and that's like so I

1:06:11

think some businesses that have a very deeply operational say a manufacturing component that role might be more prevalent but point is it's not an automatic I think it's useful in a high growth in an environment where you're having think about the founder CEO of a company that is achieving product Market

1:06:31

fit and also having to build a company and hire all the leaders that is a lot because you are building the product and the business you are building the company and you are building all the people like bringing them all in and that is where I think a COO type of role can give you leverage right which is essentially it's a layer that takes some

1:06:53

of those functions and helps build them with you and on your behalf and also in some cases bring some experience in in you know maybe there's a particular function like go to market that needs to be built and I think that's where you see it come up what I've said to some people recently is I'm a little worried

1:07:12

just like there's a mythical founder that there's some mythical Silver Bullet CEO higher that everyone's like I'll just find that person and first of all we're all human beings I'm not perfect like I'm I certainly did some things well when I joined stripe and other things not as well and and I think and

1:07:29

I'm working on my self-awareness of what those things are but I would say one lower risk strategy could be to bring in say a a head of business operations or a role that sort of coo like and try a couple of functions with someone and see if they scale with a company and with the role and then maybe you decide they're a CEO or I mean I

1:07:55

mentioned Stripes business operations team you could hire a business Ops leader and sort of say hey build this team to help be the Swiss army knife to help scale the company and then maybe that turns into more or there's some CFOs that are quite operational they could they could take on more scope sometimes but I think there are other

1:08:12

paths to getting that leverage and there are also ways to de-risk the higher because you could end up searching forever right and I I worry that it's become too much of a Panacea on the in people's minds right like somehow they're gonna find and people will call me and they're like I just need to find you and I'm

1:08:32

like you know one I may not be right for your company but two that was like a lot of work and I think we actually in the end maybe got pretty lucky on how would you know someone is fantastic someone said something very smart to me which was I was in a meeting it was me and Patrick so Patrick is the co-founder

1:08:51

and CEO of stripe and they said that having just the right amount of tension in our relationship was how you knew it was working for the company and it it like gave us both a little bit of pause but we end up having quite a good conversation after that meeting which is there has to be like Mutual understanding and trust and

1:09:16

an ability for Patrick to say hey can you go do this thing and then believing I will do it at the level of quality and and intensity and intentionality that he would like but there also has to be some friction where I would maybe say no I'm not going to prioritize that I don't think that's important for the company

1:09:34

or I'm going to give you feedback that I don't think we're doing this well or he's giving me feedback the customer experience is suffering you're all your scale stuff is is degrading this thing right like that so so fantastic is not all hunky-dory fantastic CEO is just the right amount of friction and tension with forward momentum and mutual

1:09:57

trust because then the whole is greater than the sum of its parts right that's what you're looking for I was actually going to say I've worked with some Founders and they have this concept that they hire a CEO and it would just solve all these cultural issues they're having these like relationship issues and

1:10:14

sounds like that's exactly what you're saying is that that is not often the solution to somebody's deepest right well that would be the other problem is actually believing I mean I was getting recruited Lenny and people would essentially I felt like the founders were saying to me I'm gonna give you all of the things I don't like doing as your job

1:10:33

and I was like um even if I'm by the way not qualified to do all those things number one and two is you know sometimes that list would be quite long and that would make me nervous I was like do you really not like running a company actually is that what's going on here and really I think they weren't confronting

1:10:53

elements of their work that needed to evolve and change and what I loved about joining stripe was I think people also think like I'm just gonna hand all the stuff to this person and like I'd love to say I took all this off of the Collison's plate and and Billy and John and the other people who were there at the time and no we actually were more

1:11:13

collaboratively worked together and I think it helped well one you don't feel is isolated because you're in a team but also there's more joint work than people realize I think in at least in the companies I'd like to work for for our final uh tennis minutes we have together and they have to run I was thinking I could go through just like a

1:11:36

rapid fire set of tactical questions and see like maybe one piece of advice you would share with someone that's maybe struggling with this thing okay and the first is from uh also Twitter person uh manual Bruce Bruce brewski and he just had a question around as you're scaling keeping alignments strong is challenging

1:11:55

what would be something you'd recommend to someone that's scaling quickly and trying to keep people aligned well a lot of what we talked about right having common codified documents of what we believe in how we work and then using communication practices very intelligently never think that one communication meaning an email

1:12:16

or in all hands reaches the audience you have to be smart about how you communicate awesome amazing and a different podcast we talked about how the leaders often the repeater in Chief just having to repeat the same thing again and again yes and use different just like a marketer use different channels some

1:12:33

people read emails some people watch videos some people attend the meeting repeat love it that'll be your own clip to take away from this um I was watching an interview with you and you talked about the value of off-sites for creating cohesion within the team can just talk about like why off-sites are so important to a company

1:12:52

and team I think offsite is really a vehicle the concept is the following which is When You Yank people out of their day-to-day routine you create space and and also you imprint memory and so if you say we're going to do a very different thing with your time today or the next two days we're not going to do our emails we're

1:13:14

going to do our regular meetings we are going to sit and work together we're gonna brainstorm like you're basically activating new parts of their brain and then you're also having a group experience that cements a belief system usually or a set of plans and it also helps bring people along like we formed this thing together like it's very it's

1:13:35

not effective if I say I locked myself in a room for three hours and then I came out and here's the plan you want to lock yourselves as a group as a team in a room for three hours like how do you do that and so that's why I think it's valuable it's just out of time in a way like you're taking it out of your

1:13:50

day-to-day time and I I can't I've not found a good substitute for that on a different topic one of the most common questions I get from product managers and just Founders that I haven't tackled yet and I'm curious what your take is is around just keeping the company updated on what's Happening broadly what have

1:14:08

you found works for just keeping people informed on what's Happening across the company and having really smart communication practices is something that I think a lot of companies don't invest in early and it's partly because it feels like extraneous but it's a lot of time like if you're going to communicate well you have to

1:14:24

invest in you know your intranet site and what's on it like ideally everyone logs in and sees information on the home page of your of your company internally do you have a newsletter do you have Founders do like a message or a quick video whether that's on slack or email like there's a lot of Smart Tools you

1:14:43

can learn a lot from social media right in some ways but you actually need a strategy for it and you need a set of people who help make sure it happens so that again it creates stability and Cadence and if I want to find information about X this is where I go and I think there's also that if you do it well it can replicate down to teams

1:15:03

right which is well we have our weekly snippet stock that everybody can see the important news or whatever it is but you need to create those things because they won't just they'll start to spring up but then you'll have a million of them and you won't you won't be able to point people to the core messages but it is

1:15:20

not a thing to be taken lightly and I think having someone who really not focuses on internal marketing I'm talking about just good here's what's important here's what you need to know sales teams actually do this really well because they have to because they have to keep this the sellers up to date on the product and up to date on how to how

1:15:40

to pitch it and so it actually is worth talking to Smart sort of sales leaders who scaled and saying what do you do that keeps everyone on the same page as you're talking I realized AKA who we mentioned a couple times she is working she left ritual and she's working on a startup that is trying to solve this

1:15:54

problem I think it's cool it is it is a lot about what they're working on and it's because it is again an unsung thing that is critical and that I don't think people naturally come to next question what are like one to two or maybe three things that people can do to run more effective meetings I saw you give this

1:16:10

like master class on running more effective meetings and just to boil down what are like a couple things people could probably change I do have a video on YouTube about running an effective meeting but I think the number one thing is the work of a meeting is not calling the meeting calling a meeting is easy in fact that is a problem the barrier is

1:16:29

very low and it should be higher what you really want to know people need to know why are we meeting and what is the point of like what's the objective of this meeting is it to make a decision is it to share information who needs to be here like just be one of my favorite things to say is make the thing that's

1:16:46

implicit explicit too many meetings are implicitly about something and not explicit enough and I'm like no no I want to know why I'm here are we making a decision who's making the decision and how and and even better you say like does anyone not need to be here because we'll just send you a note afterwards about

1:17:07

what happened right make it more efficient but be really explicit about the point of the meeting and really inquire like do some inquiry on whether it's important whether it's needed maybe a final question is around decision making so product managers who are a lot of the audience of this podcast have to one make a lot of

1:17:26

decisions get people to alignment but they also don't classically have authority over anyone what advice do you have for aligning and decision making I love product management so much accountability so little authority like such a hard job what a fun what a fun everyone's like I want to be a product manager I'm like

1:17:42

man that is like one of the hardest jobs in Tech yeah but anyway how do you get people to a decision yeah actually it's exactly you know and I mentioned in my book gokul's Spade framework but which you can look up he has like a coda on it but actually it's the same thing that I said about meetings which is making it very

1:18:03

explicit that there is a decision to be made who is making the decision the criteria by which the decision is going to be made who will be informed you know there's all these models there's racy and radar and like there's a million different decision models just pick one make it explicit explain that's what's happening and get people through it like

1:18:22

follow the model and do it and I think and and by the way you can always have like an asterisk which is if we want to revisit this decision this is what we do but I think too many teams get paralyzed because they're afraid like well maybe they're I'm not the decision maker or maybe what I say to people at stripe on

1:18:39

our onboarding I used to run a session I was like if you're not sure who the decision maker is one it's probably you and I'd rather you act that way then not because you're gonna like slow the whole company down but really I I think the other thing is in the framework in the book I talk about this framework that Bezos uses

1:18:57

type 1 type 2 decisions like is it high impact is it irreversible is it not like really evaluate what kind of decision is this how hard is it and then follow a process and get it done and don't forget to actually make a decision and if you don't know who the decision maker is and you're worried it's not you just ask

1:19:15

like don't get stuck too many people get stuck and it makes your like work terrible right I mean what do we all care about progress impact momentum I mean if if anything I would say about like advice to people generally is be a force for positive momentum and it will it will be actually a real career maker

1:19:40

I love that I might maybe we'll make that the title of this interview with that Claire I know you have to run anyone listening you gotta buy this book like I've said at the beginning if you like my newsletter it's exactly my newsletter but as a book about operations oh thank you scaling people scaling people is there a website they

1:19:57

can go to to go check it out Amazon or is there they can they can go to press.stripe.com forward slash scaling Dash people or Amazon just search scaling people on Amazon but thank you Lenny I appreciate it absolutely uh just do final questions where can folks find you if they want to maybe ask you questions follow up reach out and then

1:20:17

to any other way people can be helpful to you other than maybe pre-ordering the book well definitely pre-ordering the book and giving me feedback on that I I guess Twitter is probably the best place to find me I'm at see Hughes Johnson on Twitter but honestly I I do hope hope you'll consume the book in some form and

1:20:34

and interact with it because the goal is to make it use we talked about this Lenny your podcast my book is just trying to be abuse and and I hope it is a positive a positive force for positive momentum and I really appreciate the opportunity absolutely thanks for making time for this thank you thank you so much for listening if you

1:20:55

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