Mental models for building products people love ft. Stewart Butterfield

This is 2014. That was the year that Slack actually launched. I was

interviewed by MIT Technology Review and asked if we were working to improve Slack. I said, I feel like what we have

Slack. I said, I feel like what we have right now is just a giant piece of [ __ ] It's just terrible and we should be humiliated that we offer this to the public. To me, that was like, you should

public. To me, that was like, you should be embarrassed. If you can't see almost

be embarrassed. If you can't see almost limitless opportunities to improve, then you shouldn't be designing the product.

Slack was famous for being one of the early consumerized B2B SAS products >> at more than one company all hands. I

made everyone in the company [music] repeat this as a chant. In the long run, the measure of our success will be the amount of value that we create for customers. And you can put effort into

customers. And you can put effort into demonstrating that you have created [music] this value and stuff like that, but there's no substitute for actually having created it.

>> Something else I heard that you often espouse is friction in the product experience is actually often a good thing. It it became an assumption that

thing. It it became an assumption that you should always be trying to remove friction when the challenge is really comprehension. If your software kind of

comprehension. If your software kind of stops me and asks me to make a decision and I don't really understand it, you make me feel stupid. If people could get over the idea of reducing friction as a number of goal or reducing the number of

clicks or taps to do something [music] and instead focus on how can I make this simple? How do I prevent people from

simple? How do I prevent people from having to think in order to use my software?

>> You started two companies both famously pivoted. I imagine many people come to

pivoted. I imagine many people come to you for advice on pivoting. The decision

is about like have you exhausted [music] the possibilities? Creating the distance

the possibilities? Creating the distance so that you can make an intellectual rational decision about it rather than an emotional decision is essential. And

the reason I say you have to be coldly rational about it is because [music] it's [ __ ] humiliating.

Today my guest is Stuart Butterfield, a founder and product legend who rarely does podcasts. Stuart founded Flickr and

does podcasts. Stuart founded Flickr and then Slack, which he sold to Salesforce in one of the biggest acquisitions in tech history at the time. There is so much product and leadership wisdom locked away in his head. I feel like our

conversation just scratched the surface.

We chat about utility curves, something he calls the owner's delusion, a hilarious pattern he sees at companies he calls hyper realistic worklike activities, what he's learned about product and craft and taste and

Parkinson's law, why you need to obsess with not making your users [music] think, the backstory on his legendary we don't sell saddles here memo, and so much more. A huge [music] thank you to

much more. A huge [music] thank you to Noah Weiss, Chris Cordal, Ally Rail, and Johnny Rogers for suggesting [music] topics and questions for this conversation. This is a really special

conversation. This is a really special one and I really hope to have Stuart back to delve even deeper. If you enjoy this podcast, [music] don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps

tremendously. And if you become an annual subscriber of my newsletter, you get 17 incredible products for free for an entire year, including Devon, lovable, replet, bolt, init, and linear,

superhuman descript gamma perplexity warp, granola, magic patterns, raycast, chappd, and mobin. Head on over to lenny's newswletter.com and click product pass. With that, I bring you

product pass. With that, I bring you Stuart Butterfield after a short word from our sponsors.

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>> Stuart, thank you so much for being here and welcome to the podcast.

>> Thank you for having me. I'm excited.

>> I'm even more excited. I'm so honored to have you here. Uh I never told you this, but you've been towards the very top of my wish list of guests to have on this podcast ever since I started this podcast a few years ago. So, I'm very

excited that we're finally making this happen. I have so many questions for

happen. I have so many questions for you. My first question is just what the

you. My first question is just what the heck are you up to these days? I feel

like ever since you left Slack, we haven't heard much from Stuart. I'm

curious what you're up to. Hopefully,

you're just chilling.

>> I'm mostly just chilling. I left

Salesforce um 2 and 1/2 years ago, and I have a 2 and a halfyear-old. So, she was actually born 3 days after my my last day, so a lot of time with family. And

it's like an enormous privilege to be able to spend time with young kids while they're while they're young. um no new company to announce or anything like

that. Um, I do get a lot of emails and

that. Um, I do get a lot of emails and texts like basically like every three to six weeks there's this cycle because Cal Henderson who's the CTO of Slack and who

also we work together on Flickr so have worked together now for 23 years have been talking about what we want to do next um if there is something but you

know honestly the the big challenge has been uh I think these things are kind of destroying the world um and What we're good at is making software. Um, so you

can find some way to make software that helped people use their phones less often, then that would be a big winner, but haven't come up with anything good.

A lot of philanthropic work. Uh, nothing

to announce there yet, but there's like some cool um projects that I'm working on and a lot of like just personal creative art projects and supporting other artists and and stuff like that.

To prep for this chat, I talked to so many people that have worked with you over the years to try to figure out what you taught them about building product, building teams, building companies that most stuck with them, that most helped

them build amazing products. The first

is a is a concept called utility curves.

This came up a bunch across so many people that have worked with you. Talk

about what is a utility curve, how you think use that to build better products.

This is pretty easy because it's a very familiar S-curve where you know you have uh it's flat and start it's arcing up and then there's a really steep part and

then it levels off again. And on the horizontal axis uh you can think of cost or effort and on the vertical axis it's

value or convenience. It kind of depends exactly what you're talking about. But

the idea is um the first bit of effort you put into something doesn't result in a huge amount of value and then there's some magic threshold where it produces an enormous amount of value and then

continued investment doesn't really pay off. The most basic example I can think

off. The most basic example I can think of is let's say you're making a hammer and on that bottom axis it's now quality and if the hammer uh has a handle that

breaks with any impact and is totally useless and if you make it a little bit stronger it's still pretty useless. And

it's kind of like junk, junk, junk, junk, junk. Okay, good. Great. Then it

junk, junk. Okay, good. Great. Then it

doesn't matter anymore. If you're making an app, okay, this app's going to have users and so let's make a users table in the database and so far you have generated no value. The reason I I felt

like this was so important is because we would talk about like a feature um and usually features are thought of as as binary like you either have this feature

or you don't. And so the argument I guess was have we just not invested enough in this or have we got all the value or

convenience or you know quality or whatever that we can get out of this um and and we've had dim pointed diminish returns and it just doesn't matter and I I think in many cases people will add a

feature it's not good enough um and so people don't use it or appreciate it but now you've added some complexity to the app and then people give up or take it back or you know they tried something in in testing and they don't get the

results they want and so they decide that this thing isn't worth doing. And

so we would try to really investigate and and decide whether we were on the first shallow part of the curve, the second shell part of the curve or we you know we're just coming up to it. So I

think it's a lot easier to understand the value of this when you're talking about a specific app and a and a specific uh feature. But um I think it was ultimately helpful in getting people

to like understand whether something was was worth it or not.

>> Okay. So just to mirror back what I'm hearing, there's kind of this if you visualize this curve at the bottom it's like I don't even know what this is. And

then up the curve is like okay I sort of get it and then at the top is okay I can't live without this now that I understand what this is for. It feels

like it's like a really it's a different way of thinking about getting to the aha moment for someone where they see okay saved items. I get it. I need to use this constantly. It feels like this

this constantly. It feels like this works both for a specific feature and also just for Slack, like getting people to even understand here's what Slack can do for you and then now I can't live

without Slack. And essentially this is a

without Slack. And essentially this is a lens you use to figure out where to spend product resources because if you don't get up that curve to I get it and I can't live without it, nothing else

matters. Is that the way is that the

matters. Is that the way is that the framework?

>> Yeah. Yeah. And I think then you layer on another concept like the um [snorts] Bezos used the term divine discontent.

Um the line actually moves because once people are familiar with a piece of software or the way a feature is

implemented or something like that, their standards go up and so the there's like this competition. And again this axis can be utility is the best general

term for it but it could be quality, convenience, um speed, it could be any any number of things. But as you improve your search capability or if if as as

you improve your login experience or your forget password experience or your checkout experience or whatever, everyone else is as well. And so there's this continued investment

and when you know forget about thinking about a new feature you're looking at how the product works overall and usually things get kind of implemented once and then if they're lucky they get

improved upon periodically. Most things

get improved upon very infrequently and some things get improved upon never. And

you know, I want to give an example at the absolute extreme because I don't actually don't know how long this has been, but I try not to criticize other people's software so much because I very familiar with the tradeoffs and

prioritization and how hard it can be and blah blah blah blah. But okay, so it most people have the Gmail calendar app on their phone. I travel a fair bit. I'm

mostly in the eastern time zone.

sometimes in mountain time, sometimes in Pacific, sometimes in English time, and sometimes in uh Japan, Central Europe.

There's like a, you know, maybe 10 time zones, 12 time zones um that I would ever choose.

When you uh hit the option to set the time zone on an event in Google Calendar on the iOS app, it presents all the time zones in the world in alphabetical

order. And that's like the I mean

order. And that's like the I mean there's probably worse orderings, but that there's there's no value in that.

Um and even when you start searching um it still presents them in alphabetical order by country with that turn. So if I'm in California and I'm

turn. So if I'm in California and I'm trying to set an appointment for next week when I'm back in New York and I type in EA S and I get a bunch of garbage. Okay, East

Narn. And then the first one is Eastern Australia, New South Wales. Um, and then Eastern Australia, Queensland. And then

Eastern Australia, Daylight Savings, and Eastern Australia, Standard Time. And

then you're like, well, [ __ ] what? I I

can't remember which one is Daily Savings and which one is Standard Time.

And you know what? I could keep going like this for a while. This is an app that's used by at least hundreds of millions of people, presumably every single Google employee. It's bananas how

bad it is. There's so many like there's all these clever things you could do like you know me I'm on the west coast first option should be the east coast and vice versa but it it definitely

shouldn't be that every time zone is presented with equal you know value there's I don't even know couple hundred time zones I grew up in Canada there's a Newfoundland has its own time zone which

is offset by half an hour the population of Newfoundland is about half a million people not that many people go to visit Newfoundland maybe a million people in all of history. So like a million and a half out of 8 billion people. And

there's Newf Finland, you know, like the same with China time, which is like 25% of the world's population in this study.

Anyway, I and that was a little bit longer than I intended to go on this example, but it is um uh it's crazy because no one's going to

switch to Gmail or to to G Suite, Google Calendar from Outlook Exchange because the time zone picker is good. So maybe

in some sense it doesn't matter, but at the same time there's a real value in in delighting customers and there's an emotional connection that they form or don't form. Um, and in some cases that

don't form. Um, and in some cases that can be really positive, like they would recommend it. And when they switch

recommend it. And when they switch companies or decide to start their own company, they're going to choose to use this product or advocate for it because of that emotional connection. And vice

versa, they'll also be like, I hate this thing. This drives me bananas. I really

thing. This drives me bananas. I really

think we should stop using it or, you know, advocate for the alternative. Uh,

and I I think people just don't appreciate or come back to those things often enough. And then there's this

often enough. And then there's this category of like really essential parts of the app again like account creation, sign up, forgot password, you know,

things like that that for most organizations very infrequently get a lot of love and and iteration and improvement despite the fact that the

kind of the quality bar has gone up across the board and and continually goes up. Let's go down that rabbit hole

goes up. Let's go down that rabbit hole a little bit more around delight and craft. Slack was famous for being one of

craft. Slack was famous for being one of the early, let's say, consumerized B2B SAS products. Slack leaned into delight

SAS products. Slack leaned into delight and experience and craft and a great experience. And you just as a product

experience. And you just as a product leader, I'd say is are known as as very taste forward, very craftoriented leader, which is pretty rare and I think continues to be rare. So there's a few

things I want to talk about here. One is

uh taste. I heard at a talk you gave of a really unique that you gave a talk on taste and you have a really unique perspective on just what taste is what product taste looks like. Can you share that? There is a lot of you going back

that? There is a lot of you going back to the utility curves again. People who

are obsessed with this one little thing and you know keep on adding more and more detail improvements beyond the point where it makes much of a difference. But um I guess a couple

difference. But um I guess a couple things about taste. So one is can you learn to develop it? I think so because like the word literally comes from

experiencing food and putting stuff in your mouth. And can people become better

your mouth. And can people become better chefs with training? Yes, absolutely.

Undoubtedly, some people have a natural advantage or are, you know, born with this ability to make discernments that are difficult for other people to make and stuff like that. But you can definitely practice and you can

definitely get better. The second thing I'd say is um you can create a real advantage for yourself, for your

product, for your company um by leaning into it because most people don't have good taste and don't invest. And so

you're probably familiar with the again Jeff Bezos line, your margin is my opportunity. Um and pretty obvious what

opportunity. Um and pretty obvious what he meant by that. I would tell the story at Slack over and over again and actually made it part of the new hire welcome. So, uh, I'm I'm going I'm in

welcome. So, uh, I'm I'm going I'm in Vancouver at our Vancouver office and I'm going for a walk with Brandon Velost who's our um at the time creative director for product development. I

think that was his title. And uh we're in the Yeltown neighborhood in Vancouver. So, there's like really

Vancouver. So, there's like really narrow sidewalks because it used to be a warehouse district and now it's like, you know, fancy restaurants and nail salons and boutiques and stuff. And as

it does in Vancouver, it starts to rain.

We don't have umbrellas and we're walking back to the office and most people have umbrellas and we're, you know, kind of on these narrow sidewalks with people coming towards us with

umbrellas. And we noticed how few people

umbrellas. And we noticed how few people would move their umbrella out of the way. And of course, you know, the other

way. And of course, you know, the other person like their umbrella, the pokey bits are exactly at eye level for for people walking towards them. I mean, we would get like, you know, forced off the

sidewalk or like having to duck down or whatever. And we it became a game like

whatever. And we it became a game like we were guessing, is this person going to tilt their umbrella out of the way so we can pass or not? And something like

onethird of the people would do it. And

we had this conversation about it where it's like, okay, I can think of three reasons why people wouldn't do it. One

is they have very few avenues in their life to exercise power and this is one of them and they're just like want to get out there and dominate people and

cause suffering. So shouldn't ascribe to

cause suffering. So shouldn't ascribe to malice that which can be ascribed to ignorance. So that's probably you know

ignorance. So that's probably you know that probably is the explanation for a tiny tiny tiny percentage of people. But

the other two explanations aren't that great either. One is that uh they see

great either. One is that uh they see it's happening. they see they're pushing

it's happening. they see they're pushing other people off the sidewalk um or poking them in the eye or whatever and they're just like, "Fuck, that's too bad. I you know, I wish there was

bad. I you know, I wish there was something I could do about that, but I can't think of anything." And the last reason is they just don't notice at all that they're just oblivious to their

impact on on other people and they're they're so in their head. And I can't really think of any other explanations for it besides that. And so we would say at like tilting your umbrella is our

opportunity. said that's not a great

opportunity. said that's not a great rephrase of a your margin is my opportunity, but your failure to really be considerate and uh exercise this

courtesy and really be empathic about other people's experience is a an advantage. you can create a critical

advantage. you can create a critical advantage and I think that there's many reasons why stock was successful at the moment it was successful and and I think we had a bunch of really wonderful

tailwinds and and all of that stuff but it wouldn't have grown the way it did without those little conveniences which caused people to form an emotional connection because a lot of our growth

came from you know startup A uses Slack and then someone leaves startup A for startup B and startup B doesn't use Slack yet and they would be like oh my god God, you guys, we really this is

this is so good. We got to try it. And

uh and the the spread was driven by that cross-pollination and people really genuinely advocating for it.

>> That is an amazing metaphor. I

[laughter] I love that one moment became like a value of product craftsmanship.

It >> tilt your umbrella was like was a very common saying on you know company swag and and stuff like that.

>> Is there an example? I I imagine there are many, but from the time of building Slack, especially in the early days, where you chose to go big on craftsmanship and experience and and

delight versus speed, where you thought looking back that was a really great idea and it worked really cord to success.

>> Here's a bunch of little examples. Um,

so someone else came up with this idea and I'm I'm trying to remember who it was. um by let's see maybe Andre Torres,

was. um by let's see maybe Andre Torres, maybe Ben Brown, something like that. We

was like, "Hey, why did we ask people for email address and password if um they their ownership of the email address was the thing that allowed them to create the account in the first

place? Why don't we just ask them for

place? Why don't we just ask them for their email address and then send them a link?" And so when Slack's first version

link?" And so when Slack's first version of the mobile app came out, we're like typing your password on your phone if you have any, you know, minimal

threshold of of password hygiene is a terrible experience. Say capital H

terrible experience. Say capital H lowerase Q sex correct period. But so

let's just have them enter the email address. We'll send them a link. The

address. We'll send them a link. The

link will automatically open the app and and authenticate them. And so there's one little example.

>> Wow. So you guys invented the magic link uh experience. someone else invented. I

uh experience. someone else invented. I

want to be clear that u I I had seen that idea somewhere else like someone else a blog post about it or something like that but we were the first ones that to my knowledge that that really kind of like scaled that and made it a

standard. There is another one which we

standard. There is another one which we you know we're really puzzled about in the very early days where people have a long history of using messaging apps

from like AOL instant messenger to SMS to um WhatsApp where their expectation is they get a notification for every message that's received and in the case

of Slack that doesn't make as much sense because you're a member of many channels and the messages may not be for you and so that's why we have the at tagging people And um you know we certainly

didn't invent that. That was that was Twitter. Um but what we realized was

Twitter. Um but what we realized was people were signing up for Slack you know and it's like one engineer on this team inside of this larger organization inside this larger company and they would pull in the person next to them

and they would say let's try it out and then they would send a message and then well personally be like I didn't get a notification. This is this is [ __ ]

notification. This is this is [ __ ] Um, so we reluctantly decided that we had to send notifications for every single message as the default for new accounts.

But once you had I don't remember what the thresholds were happen once you had received 10 messages, we would pop up this little thing that says, "Hey, you have our default settings for notifications. We don't want Slack to be

notifications. We don't want Slack to be noisy for you. Would you like to switch to our recommended settings?" and then they would just click a link and it would, you know, have what should be the default, which is you only get a

notification if it's a DM or if someone tags you. But we realized it was worth

tags you. But we realized it was worth that investment to get people over the hub. A much more uh well, here's I'll

hub. A much more uh well, here's I'll give one one more simple one and then one kind of more complex one. people

would just like the I can't remember if it's called urgent or important but the flag in in Outlook that like you know set the priority of a message for the recipients always got abused inside of

every company as as soon as someone does it like everyone's like okay I'm going to do that too for my message and so all of your messages have the little flag and it becomes useless we have at everyone which causes a notification to

be sent to every member of the channel when a message is sent and people would start you know look someone would find this feature inside of an organization they would at everyone. Everyone would

get a notification and then the next person to send a message was like well my thing is more important than um Bob saying I'm going to also at everyone and it became really obnoxious and people

would complain about it but it was a I don't know I guess tragedy of the commons. It's not quite exactly the same

commons. It's not quite exactly the same thing but it was this real dynamic that happened over and over again. So, um, we came up with what was called the shouty rooster. And internally, we said, "Don't

rooster. And internally, we said, "Don't be a cock." Um, but we didn't obviously say that publicly. When you at everyone, a little rooster would pop up and it would have like the sound waves coming

out of its mouth and being really obnoxious and say, "Hey, this is going to cause a notification for 147 people in eight different time zones. Are you

sure you want to send this message with that at everyone?" Um, and of course that worked amazingly and it dropped off. Um, and again it was really trying

off. Um, and again it was really trying to shape people's behavior so that they used we wanted to be very flexible. Um,

but we knew that there was ways to use it that would be annoying and and difficult for everyone and so try to shape the communication culture inside the organization to take best advantage on it.

>> That feature still exists. I see that rooster all it or no I don't see it all.

Well actually I do at channel because I run a big Slack. Uh, so I see that rooster uh that survived.

>> Yeah. Um, yeah, that survived and and good because it was >> right >> it was a trivially easy thing to implement and made a really big difference, but it also taught people how the product worked because people

probably didn't know that at everyone rat channel. Um,

rat channel. Um, >> right, >> you know, didn't think about the cost at least.

>> Genius.

>> Yeah. Here's here's one more. Uh, so we decided we're going to do do not disturb as a feature. Um [clears throat] and we had this not conundrum but we

you're trying to take into account all the all the different uses of Zack because at the time we we implemented this like 2017 there was you know tens of

thousands of of paying customers the organizations hundreds of them probably millions of users maybe hundreds of thousands of organizations I don't remember how many um and everyone had set up stuff the way that they liked it

including things like ops alerts going into channels for on call engineers for for you know some of the biggest systems uh and and apps in the world and

so we couldn't just like deploy it right away. We realized that some of the

away. We realized that some of the decision makers, the owners of the organizations were going to have really strong opinions about this. We also

realized that some of the end users are going to have strong opinions and we wanted to figure out a way to kind of balance the concerns and give people appropriate means of control. So we came

up with this really elaborate system for the roll out which was we told everyone um I'm sorry every every Slack administrator that this was coming weeks

before it came and we told them that we were going to set a default for their organization which I believe was um either 700 p.m. to 7 a.m. in their local

time zone or or 8:00 a.m. to 8:00 p.m. I

can't remember which was, but also that they could override that default and also that the individual end users could

override that system owner default. And

finally, that the system owner could if they changed the default again would overwrite all of the the end users preferences and then the end users could

uh overwrite them again. And it wasn't to create this dynamic where people were at war, but so that you could change a policy and then people could still customize and stuff like that. But this

was, you know, a much longer and more convoluted process, but it allowed the millions of people who were using Slack to get the feature without creating a

bunch of conflict and without people turning it off automatically. And I

think critically with setting a bunch of defaults, um, because if we didn't set the default, most people wouldn't turn it on at all. You like, if there wasn't if we didn't default you to do not

disturb from 8:00 p.m. to 8 a.m., um,

you probably, if you're the average person, wouldn't ever do it yourself.

Um, so that's a another elaborate example uh where I think that investment made sense because it was a critical feature for a lot of people and um if we

hadn't done it that way, I think it would have caused a lot of complaints and conflict and and stuff like that.

>> Those are amazing examples. I very much appreciate that do not disturb feature when you guys launched that. I still

remember that coming out. I'm sure a lot of people are very thankful for that.

>> Yeah.

Something else I heard that you often espouse which is counterintuitive to a lot of people is is about friction.

Friction in the product experience that friction is actually often a good thing that you actually it's a feature not a bug a lot of times if you use it well.

Talk about your your experience there.

>> Yeah. Well, and so yes. Um, and there's also another um issue around friction, which is it became like a mantra or just like a

kind of an assumption that you should always be trying to remove friction. And

uh in in some cases that's true. You

know, we would talk about in Slack like it was hard to market. It was hard to explain what it was if you had never used it before. You could say a messaging app for businesses or or whatever, but you know, like a critical

disadvantage to Slack doing out of home advertising, putting up a billboard versus beer or cars is no one needs to be explained why they would want a car or beer. Um, but everyone would have to

or beer. Um, but everyone would have to be explained why they why they want slack. Um, and so the problem there is

slack. Um, and so the problem there is is comprehension. And this will come up

is comprehension. And this will come up uh an enormous amount. So now imagine you want to get tickets to the Taylor Swift concert in San Francisco and you go to the ticket master website. If you

think about both your your comprehension, it's perfect in this case and um that translates into the specificity of your intent and the degree of your intent is also kind of

maxed out. So look, I really want to get

maxed out. So look, I really want to get these tickets and I know exactly what they are. They're Taylor Swift tickets

they are. They're Taylor Swift tickets for this date at this venue. And so in that scenario, it doesn't really matter if Ticket Ptor's website is slow. It

doesn't really matter if the payments page errors out. Like you're going to persist and and get through it. So

obviously they're better to reduce friction, but in some sense it doesn't there's not a huge amount of of value in

doing that. Uh for most creators of of

doing that. Uh for most creators of of products, there are a handful of cases where that really is true for you as well. And they they include things like

well. And they they include things like user registration, um authentication, uh checkout flows for e-commerce, like I'm I am significantly more likely to

buy something if there's Apple Pay or Shop Pay, something like that. I'm

significantly less likely to carry through the purchase of something. If

the I have to manually enter all of the fields of my address one at a time, rather than having one of those address pickers, it's it's crazy. But like the issue is my intent isn't always 100%.

Right? And the specificity of my intent isn't always 100%. So if your thing is direct to consumer t-shirts and you acquire customers through Instagram ads,

all of them know what t-shirts are. It's

like I this looks like a good t-shirt to me, but I'm rarely like 100% intent. I

might have like, you know, very specific intent, but I might intent's like 70%.

So if you're the amount of friction is uh above that I just I'm not going to do it. But now okay people coming to

it. But now okay people coming to slack.com they had some uh friend had mentioned Slack and kind of talked their ear off at some point

months ago and then they saw a news article and then they saw someone's tweet and then they saw an ad on a website they were visiting and they finally said, "Okay, I'm going to go to

this website." So their intent is like

this website." So their intent is like at the absolute minimum threshold. Like

it's just it was before that last event happened they were below and now they're above but they're just above. The

specificity of their intent like I need to get Taylor Swift concerts for this date at this venue um is also very low because they're like at it's a work thing. I'm not sure it's a spreadsheet

thing. I'm not sure it's a spreadsheet or like a calendar or to look exactly what it is. Um so they were coming in at you know.1%

you know.1% over these these critical thresholds. Um

[clears throat] what was the challenge?

It wasn't friction right because it's not like they were aiming for something and they knew what they were aiming for and they were just trying to get themselves to that point.

What we had to worry about was creating comprehension and in two senses. What is

this thing? Um, and what am I supposed to do next? And that creation of comprehension in the in the sense of explaining stuff, that creation of

comprehension in the sense of the design of the of the UI of the screen of the page or whatever and the um the visual hierarchy and the affordances that are

there and the and the um indication of things to interact with and and which thing should be the next thing to do and all that stuff that becomes really critical and I think very very few

people recognize that. They're like, I want to get people who come to my web page to the sign up form as quickly as possible. But if they don't know what

possible. But if they don't know what they're signing up for and they don't know what it's going to do after, is it going to spam them? Um, they don't know what am I going to have to pay on the

next step or or what, then they're just going to back out. And this was like a a lifelong battle because the remove

friction um kind of orientation is so deep in people. Again, it really makes a difference in in those cases where people do have an intent and they do

know what they're trying to do. Um, it

is a a poor approach when the challenge is really comprehension. And I think the secret is most 70% 80% or whatever of of

product design is in that comprehension step because like people if they do ever open the preferences tab and look at all

the options rarely have an idea. And if

you can't teach them, you know, or or make it possible for them to discover what the capabilities are, then they're not going to take advantage of them and they're not going to get as much out of it. And I think

that the trick is for most of the unique parts of any application, most of like the specific things that your app, your product, your software does, areas where the challenge is going to be

comprehension, insider friction. It it

really could be anything like Shopify.

Um, the purpose of the of the service for its end users is generally going to be kind of clear, but most people, most

first-time store openers don't know that they can get reports or if they know that they can get reports, they don't know what kinds of reports. And if they know what kinds of reports they can get, they don't know how they can tweak them and how they can um, you know, what the

timing should be and which things to that are are more important to display.

And I could go on and on and on and on and people just don't recognize that.

So, like the I want to see if this still true. I'm just going to open my iPhone.

true. I'm just going to open my iPhone.

Um, and the clock app and they had the most the craziest description for alarms. Um, okay. It's still it's a little bit

Um, okay. It's still it's a little bit different. Um, but people can look at

different. Um, but people can look at their own phone. So, I have it says alarms and then it says sleep and a

vertical bar wake up and says no alarm and a button that says change and then if you hit it, it says sleep is off. In

order to automatically turn on sleep features and edit your schedule, you need to turn sleep on. So, obviously

like sleep was a good name for this thing if you already had a way of getting people to understand it. If you

don't, it's like un-grammatical and incomprehensible and why would you ever do it? And I got to guess, it's been

do it? And I got to guess, it's been like this for years. 90 plus% and maybe like 98% of people just do what I do, which is you just create like I want the

alarm on and I'm going to set the time for it. And I don't know what turning

for it. And I don't know what turning sleep on does. Um, but it's just like the the lack of comprehension prevents people from getting the value. And I'm

sure that there's a bunch of value behind turning sleep on, whatever that means. And people spend a lot of time on

means. And people spend a lot of time on those features and it integrates with like biometrics in your watch or who knows. I again I still don't know

knows. I again I still don't know because turning sleep on is like I don't what does that do and what is it going to cost me and what impact it's going to

have. Um those examples are just to me

have. Um those examples are just to me all over the place. And the the reason I don't use most software where there was an actual choice point or the reason I don't use most features where there was

a choice point for me is because I didn't understand what they were going to do and I don't give a [ __ ] And if there is one mantra that I would use to replace that it's don't make me think. I

don't if you remember that that book.

>> Absolutely.

>> Yeah. And honestly it's been many more than 10 years since I read it. So I

don't know if you remember all the examples in the book, but as a mantra that was like up there with utility curves because for two reasons. One is

it's just like it it's expensive to make a decision like you literally burn glucose like there's a metabolic action.

there's like ATP created in the mitochondria in your neurons and like a bunch of stuff is happening and people do get decision fatigue and there is like you know cognitive cost of all these things but also there's an

emotional aspect which is if you if your software kind of stops me a second and asks me to make a decision and I don't really understand it you make me feel stupid right I'm like I don't understand

this I some people are are you maybe their orientation is okay that the software is stupid but I think Most people are like, "Oh, I'm dumb." And if you ever talk to

people who aren't especially technically savvy, you know, like the canonical example is like people who are under 50 talking to their parents about using some piece of software and what they're

supposed to do. The parents almost always feel stupid, like they're the ones that are that are wrong. Um, and so if you're causing people to think in the

the best case it's like unnecessary use of their, you know, biological resources, and in the worst case, you've like now made them feel bad, like emotionally bad, and they're going to

associate that with a product forever.

And I mean, these are things are just kind of rolling one into the other. So,

I'm going to uh keep going with one last thing because they just kind of come together, which is along with reduce friction, it's like reduce the number of clicks or taps it takes for someone to

accomplish something, which is almost always exactly the wrong thing. Like

it's um the easiest way like you could make any action in your app a single click or tap by just exposing every single possibility on one screen that

scrolls for thousands and thousands and thousands and thousands of pages, right?

And obviously that's terrible. So why do people think that a little bit of that is good? And you know, here's an

is good? And you know, here's an example. Like you open a menu, there's

example. Like you open a menu, there's 14 things that people might want to do.

Um, okay, level one is group them into like items and put a vertical, sorry, a horizontal divider between them. So, at

least people can kind of chunk and and see what there is. Step two is present the two or three most common things or the five most common things, whatever, and then have some form of other. and

you you know then you go to a submen that has more items and you the decision of like how to tune that becomes incredibly important. I'm going to pick

incredibly important. I'm going to pick on Google again just because it is I feel like I'm Donald Trump here but I'm going interrupt myself again with a story. It's I'm at some some conference

story. It's I'm at some some conference or event. And I don't remember wrote it

or event. And I don't remember wrote it was and this is probably eight years ago and uh it's we're in the bar after the sessions ended in this thing and John

Collison from Stripe is there um and uh Sundar CEO of Google is there and John sorry Patrick goes up to the Sundar uh and they can talk about anything right

like you know Stripe wasn't at the behemoth it was now at that point but it was still like a you know a significant company was up and I mean, and what does

uh Patrick want to talk to about? It's

in the Gmail um app, the dragging of people like you when you reply all um to a message, you often want to change the the two recipient to CC and move someone

from CC to two or something like that.

And just how physically like the the degree of dexterity that's required to do that inside of the Gmail app is very high. It still hasn't been fixed, but it

high. It still hasn't been fixed, but it really struck me that like, you know, Patrick could have asked for anything.

It could have been any talk. It could

have been a partnership. It was like it was so irritating to him um that it worked like this and couldn't couldn't quite get over it. So anyway, back to bashing on on Google who in many

respects do an incredible job and there's all kinds of amazing stuff they do and blah blah blah. But the the Gmail actions on an individual email are

broken into two very long menu items that are different. And

one of them doesn't exist on either menu. There's an unlabeled icon is the

menu. There's an unlabeled icon is the only way to do it. And that's to mark something as unread once it's read. Um I

have no idea why some of the actions are in one menu and some of the actions are in another menu. I think it's because some of them have to do with an individual email. Some of them have to

individual email. Some of them have to do with the whole thread, but it doesn't seem very consistent. Every possible

thing is listed there in one place. And

so it becomes incredibly difficult to use because sometimes you have to tap in both tap menus, read all the options and say, "Okay, that I've used the process of illumination and it's not here, so it

must be it must be there." The Uber doesn't work like this anymore, but when I first brought this up to people inside of Slack, there was a moment when the

Uber app when you opened it was just where would you like to go and other and other was everything like change your payment method, uh set your location if

you be any anything you could do in Uber. And that was perfect because

Uber. And that was perfect because almost all of the time people just wanted to choose where they wanted to go. Sometimes you wanted to change where

go. Sometimes you wanted to change where your pickup was cuz you weren't there yet or or whatever. And that was just like what could be simpler than I'm going to tell you where I want to go or I'm going to achieve something else. I

really tried to push people to what is the thing that people or what is the two things or what is a maybe three things that people could want to do here and then put everything behind other. And

then um if it takes them eight clicks or taps to do something but every single one is trivially easy that's great. if it, you

know, you reduce that to two clicks or taps, but every part of it is this fraught decision where I'm opening all of the menus and trying to figure out like which thing is the right thing and

and like the more comparing three things to each other is this difficult four things it's kind of like geometrically more expensive to compare 15 different options all to the other to see if this

is the one that you might want um you know just becomes impossibly expensive.

So to me those are all really um connected and if we if people could get over the idea of reducing friction as a number of goal or reducing the number of clicks or taps to do something and

instead focus on how can I make this simple? How how do I prevent people from

simple? How how do I prevent people from having to think in order to use my software? How can I make this trivially

software? How can I make this trivially easy? One one last example uh because

easy? One one last example uh because this this was really influential for me.

So I was going back and forth between Vancouver in San Francisco at the time when we were talking about all this inside of Slack and I was behind a teenager in line to board the plane and it was like, you know, we're on the jetway and it took a long time and I was

watching her use Snapchat and it was insane. Like she was tapping at least

insane. Like she was tapping at least four times a second, sometimes like six or seven times a second. It was like dismissing stories and doing stuff, but there was a fluidity to it because

everything was like a dead like do I want to see this again? Do I want to see the next story from this person? to ask

her to a different person. Do I like instead she she um a notification came up. She answered someone's thing. She

up. She answered someone's thing. She

took a selfie of herself and everything was just like so she was you know tapping four times a second for six minutes. I mean probably there was some some breaks in there and

that was like the highest and best use of Snapchat for a 15year-old girl in 2016 or whenever that was. Um, and

imagine if the goal was to try to make her cap less, you know, like how how much of an impediment it would have been to the experience that both her and

Snapchat wanted to create. It's so fun to listen to this and the examples you gave of it gives us a lot of insight into the way your mind works of just constantly unsatisfied with the way other products work with your products.

And I think that's core like Patrick is a good example of Stripe. I feel like that's a recurring theme with very successful product leaders, just constantly unsatisfied and unhappy with how things work.

>> Yeah. I love just even the way you summarize this just like a really good reframing of instead of obsessing with reducing friction and reducing steps,

instead think how do I how do I uh reduce the amount of thinking the user has to do? I I I've never heard of it described as like you have to think about the ATP and glucose being used to

actually think and your goal is to reduce that versus let's just reduce friction, reduce clicks.

>> Yeah. I I think um in my more cynical examples, I would I would say to people like stop what you're doing for a second, close your eyes, take a couple deep

breaths, and then pretend that you're an actual human being and open their eyes again and then look at this thing and see can you figure out what it's supposed to do or say or what you're what action you're in supposed to take

or what the impact will be if you take that action. There's a whole another

that action. There's a whole another related cycle. But before I get into it,

related cycle. But before I get into it, because I know that I'm verbose, um I want to wrap up your your last example of people being unsatisfied. So here's

the quote that I was trying to find.

This is um [snorts] 2014. So like that that was the year

2014. So like that that was the year that Slack actually launched officially uh in February and this is now like near the end of the year. I was interviewed

by uh MIT Technology Review and asked if we were working to improve Slack. Uh I

said, "Oh god, yeah, I try to instill this into the rest of the team, but certainly I feel like what we have right now is just a giant piece of [ __ ] Like it's just terrible and we should be humiliated that we offer this to the

public." Not everyone finds that

public." Not everyone finds that motivational though. So I came into the

motivational though. So I came into the office the next day and people had printed out on like 40 pieces of 8 and 1 half by 11 paper that quote and like and pasted it up on the wall. But to me that

was like you should be embarrassed by it like it should be a perpetual desire to improve.

You should never be like oh this is great. I mean you could be proud of

great. I mean you could be proud of individual pieces of work but in the aggregate if you can't see almost limitless opportunities to improve then

you shouldn't be designing the product or you shouldn't be in charge of the company or you shouldn't you know um almost nothing you know again you could

reduce it down to a tiny feature is anywhere close to to perfect and if a that's acknowledged freely inside the organization and b people think about

like continually improving as the goal and that could be like six sigma Toyota Kaizen like that kind of side of thing or it could be that story that um I

can't remember his name right now the guy who started Bridgewwater tells about um >> yeah Ray Dalio uh in his book talks about um Michael Jordan learning to ski

every time he messed up he wanted the ski instructor to tell him exactly what he was doing wrong because to him every one of those was like a gem um that he could collect and and he could you know actually become a good skier and what he

wanted to do was become a good skier that requires a lot of trust inside the organization. Um but if you can get to

organization. Um but if you can get to the point where like hey we're are trying to to find improvements we're trying to be critical because you're trying to make this as great as it can

possibly be. Um,

possibly be. Um, not always, not with every person, but most of the time with most people, you can get them to the point where that like really direct criticism is actually

motivational. It is like, you know,

motivational. It is like, you know, people are uh grateful to have like the feedback whether that's coming from their peers inside the company or from end users or the product because you realize, oh

yeah, that is that is bad and we should fix it.

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This makes me think about a let's call it a rant that you have about how it takes a lot of work to make anything work at all. that just the default state is not working. You just share share

what you share there.

>> Yeah. Um I mean so this is a lot to do with um and maybe this is more recent than other shows up in politics a lot for me. Um

but uh by the way if any of your anyone listening to this can help me find this tweet storm from somewhere between 2016 and 2020. I don't have a precise idea.

and 2020. I don't have a precise idea.

And it was this guy's thread about how hard it was to get u a stop sign set up.

And I think I believe it was in response to someone claiming that Bitcoin is going to replace US dollars. U was

something something about crypto. And

his point was like, here's what happened when we tried to get a stop sign put up on a residential street in my neighborhood. And the literal years it

neighborhood. And the literal years it took and the number of agencies that were involved like the engineering department, traffic planners, the HOA, the I don't remember the all of the

organizations. Um because if I did that,

organizations. Um because if I did that, I could search better and find this again because it was truly a masterpiece of how difficult it is to get a stop

sign put up in in most places.

The message that I hear from most politicians, and unfortunately this works really well, is, you know, things should be good, but they're not because someone is doing something bad, which is

preventing the goodness. So, um,

billionaires are making things unaffordable or immigrants are taking your jobs or, uh, lazy freeloaders are sucking off the government and causing

us all have to pay more taxes or something like that. The reality is like almost nothing works. It's actually

another colise in this case John has a great encapsulation of this. I'm sure

you you're familiar with it like that it ends with the world is a museum of passion projects because for anything to get done at all requires like not just

the resources and and effort you know required to instantiate that thing in the in the real world but all of the politicking and the sociology and the

convincing and um there's a book called uh why nothing works recently which is like it's not an I'm Sorry to the author if they out there listening, but just it's

not like an amazingly written book. I

found it like um a little bit repetitive. Uh but the the content was

repetitive. Uh but the the content was really incredible. Just explaining why

really incredible. Just explaining why it's so hard and how there's this progressive increase in the number of of vetos that are available for any kind of

course of action and how difficult it is. And this shows up in like you know

is. And this shows up in like you know in permitting for new construction and stuff like that but also shows up obviously inside of organizations. And

the challenge is that people a I think this is evolutionary biological um it's hard for us to understand the

world except by anthropomorphizing it.

And so it like if it didn't rain this year, it's because a god is mad and probably because we didn't sacrifice enough goats or something last last year. It's hard for people to understand

year. It's hard for people to understand just that wild weather is incredibly complex and chaotic and ecosystems and climatology blah blah. Same thing with

the world. if if I uh am struggling to

the world. if if I uh am struggling to uh you know pay all of my bills and be able to afford like a little bit of luxury in the sense of like a vacation

or a present for my kids or whatever.

It's got to be somebody's fault. Like

there has to be a decision that's made somewhere. And the reality is everything

somewhere. And the reality is everything is so complicated. Everything is so multivariate. Um it's not satisfying.

multivariate. Um it's not satisfying.

It's a terrible political message. um

it's much easier to say that there is like uh oh we understand why things are bad in the way that you're concerned about and it's turns out that it's someone's decision um and because of

them it's bad and so if we got rid of them or you know we're able to overcome their decision overturn it um and institute our own thing then things

would be good for you uh and this really to me shows up inside of organizations as well I'll I'll pause there I know kind of along those lines you're a a big uh believer in something called

Parkinson's law.

>> Yeah. So that the original of that is I think it's 1956. It's an article in the economist by Parkinson. Um and uh the maxim is

by Parkinson. Um and uh the maxim is work expands to fill the time available for its completion.

And the way that it shows up this is a little bit subtle. of like um one of the things I found since I don't have a job is there's much less time pressure and

and that maximum like uh if you want something done give it to a busy person the inverse is also true that like if you're not that busy wow basic things take a really long time and so Parkinson

actually starts off with this example of like you know writing and posting a letter and I don't remember who he used the first example but someone who's like you know incredibly busy and has all these things they have to respond to and then another case like a a retire robot

who has all the time in the world. It

takes her a long time to write the letter. It takes her a long time to put

letter. It takes her a long time to put it in the envelope and then go to the post office and post it. But the real meat of it is um

for me later when he talks about the size of the organization and he uses a bunch of examples. This is again 1950s so uh and he's British. Um so he's

looking at the the Royal Navy and specifically he's looking at a chart that shows the relationship between the number of capital ships in the Navy, the number of sailors uh and the number of

administrators. and very familiar graph

administrators. and very familiar graph for for people looking at like any part of government, any part like the relationship between the number of administrators at a university and the

number of students and faculty, the teaching faculty where it's like okay the number of ships goes like this and the number of sailors is like right along with it and the number of administrators goes like this. And the

reason this this ties into the work expands to fill the time available for its completion is um

people hire and they train. And um

here's the kind of sad truth for anyone running a company is there are exceptions. There's like certain types

exceptions. There's like certain types of engineers that are accepting to this, but the overwhelming majority of people you hire want to hire more people who report to them. And it's not because

they're evil and it's not because they're stupid. In fact, they're smart

they're stupid. In fact, they're smart because everyone knows that the number of people report to you correlates with like your career trajectory, your the amount of money that you're paid, the amount of authority you have inside the

organization and on and on and on. So

like we would hire 27y old product managers in Slack who immediately want to hire someone. It's like what the hell what would that person do? And like they articulate it this way, but essentially it's like well that person would do the

product management and then I would do strategy.

>> Classic. It's it's really I think the essential thing to understand about this is it's not because people are evil and it's not because they're stupid and it's

to me very related to the everything is complex. Um and uh if you maybe this is

complex. Um and uh if you maybe this is my Butterfills law I haven't thought about this before but I I tweeted this a very

very long time ago like if you um everything is simple if you have no idea what you're talking about. Um

so the the other side of that is like if something seems simple probably you don't understand it and you know there's obvious exceptions to

that but for anything that involves a large organization or a lot of human beings if the problem seems simple you don't get it. So every budget process,

no head of engineering, no head of sales, no CFO, no GC is ever going to come back and say like, oh, I actually think like next year we can just hire fewer people or we're going to keep it flat or we're going to like shrink

through attrition because we don't need any more people to do what we're doing.

Not because they're evil, not because they're stupid. Uh but it's an almost

they're stupid. Uh but it's an almost overpowering impulse inside the organization that often leads to disasters. And so there's a I'll give

disasters. And so there's a I'll give one example from Slack's history and I you know I have tried in the past to disguise this example so that no one

feels bad about it but I fortunately the specifics are so important to the example that it's not disguised and so I'll just reiterate that the people involved aren't stupid or or evil. Um

and one example that's um that's from the outside. So the example inside of

the outside. So the example inside of Slack was um we introduced threads which is the ability to reply to a message inside of

a channel and let's say you Lenny post a message I Stuart reply to it you will automatically get a notification and now Sarah later on replies to the same

message both you and I um as people who have posted that thread will receive a notification that there's been more activity and so on. So like you know every single time anyone replies to it.

So when the feature first was um released or like when we did the final product review before it was released the input box was prepopulated with at

the person before you in the thread and I you know I was using the feature and I would like put the insertion point there select all delete and then start writing

my message and it's even if I wanted to at someone specifically I almost never wanted to start my sentence with at because it just made it hard to, you know, reference what they were saying

before. So, I said, "Get rid of this

before. So, I said, "Get rid of this because a I think most people won't use it or if they uh if they did want to add someone, they're not going to want to do it at the beginning of the sentence. And

by the way, you're teaching them to use the product wrong because it's important that everyone understand that every previous poster in this thread will automatically receive a notification

unless they've needed it. So, okay, we release it. Six months goes by and

release it. Six months goes by and suddenly the at thing comes back. And so

I messaged someone on the team and I said, "Hey, there's been a regression."

I this super weird. I don't know what happened, but like the the at thing came back and they said, "Oh no, this is on purpose." We did a bunch of research.

purpose." We did a bunch of research.

And so I was like, "What?" And I went through this and it was if I recall correctly, it wasn't even like P95

certainty on this analysis, but it was something like when we do this threads are 2.17 messages long versus 2.14

messages long on average for when we don't do it. And so first of all, why is a longer thread better? Like

maybe a maybe a shorter thread is better. like it be fewer messages that

better. like it be fewer messages that people have to go back and forth. Also,

that's such a tiny difference. Also,

again, I don't remember the actual statistical analysis, so I'm not going to claim that it was um incorrect. I'm

pretty sure this was outside the the bounds of of certainty that they could have had, but the real thing was, oh my god. So you guys put flags into the

god. So you guys put flags into the product. You AB tested it. You did the

product. You AB tested it. You did the instrumentation. You created tables in

instrumentation. You created tables in the in the database or whatever we're using to record all of that. You wrote

queries to pull that. You created charts based on that data. You had meetings to discuss it. And just like kind of

discuss it. And just like kind of unpacking all of the things that would have had to happen for this to come back. And it's like you know thousands

back. And it's like you know thousands of person hours kind of at a minimum because any feature change at at that scale of organization it's involving

like a dozen people engineering QA uh analytics teams product managers user research and stuff like that.

The problem with that, so I think it was a bad idea, right? But the problem with that was the difference that you could possibly achieve between having this

feature and not having this feature is like this much, whatever units you want.

The cost of doing the analysis was this much. So it's guaranteed to be a loser.

much. So it's guaranteed to be a loser.

Like there's just there's no world in which anyone could imagine putting the at previous respondent in the thread at the beginning of the message could possibly make that much of a difference

to the quality of Slack and the how how much utility it provides to people and and all of that. But you know that to to like put the feature flags in, to ship

new versions of the product, to put the instrumentation in, to have it all the API calls, to record every action that people take, to to do all the analytics, to create the dashboard, to put that,

you know, paste a screenshot of that into a Google Slides presentation, to send the invitations to the meeting, to reschedule the meeting because someone couldn't make it, to have everyone sit down and look at the thing, like, you

know, guaranteed loser. And I know that you that Fared told you to ask me about this um hyper realistic work-like activities. And so here's my my my grand

activities. And so here's my my my grand theory. Um hyperrealistic work-like

theory. Um hyperrealistic work-like activities is goes along with this other concept called known valuable work to do. And when I say known, I mean both

do. And when I say known, I mean both you know what it is and you know that it's valuable. And the problem with

it's valuable. And the problem with almost every organization at the very beginning you have an enormous amount of work that you know what to do and you know that it's going to be valuable. So

like starting a business, open a bank account because like there's almost infinite generative value of opening a bank account you you have to do it. You

it's very simple to do. And so at the very beginning of of any startup they're like I'm like creating a users table and I'm like doing salting passwords and like you're doing all the things that

are kind of absolutely necessary and everyone knows exactly what they are.

And so that's like everyone's going to work in the morning. like right on and like I have 10 things to do and every single one of them is like something I know how to do and it's like definitely going to be valuable. Time goes on and

the relationship between the supply of work to do and the demand for doing work just starts to change. More and more people get hired. Every product manager wants to hire a junior product manager.

Every new person, the first person you bring in on the risk and compliance team is like, "Oh my god, we have there's so many risks and things we have to be compliant with. we better hire more

compliant with. we better hire more people on my team to do more risk and compliance work which probably you know to some degree is right but we're going to have more and more of those people and they're going to call meetings with each other. Um and now suddenly you have

each other. Um and now suddenly you have all these people with work to do and you've done all the easy obvious stuff and now your questions are like god should we do fed ramp high and make a

gov slack version which is going to require us to have wholly separate physical infrastructure for the hardware that runs the the software and also a

whole different operations team which has only US citizens on it. what is the possible number of of uh dollars that we could make from doing this and how much complexity is going to be when we want to do updates to the software because we

be updating two totally separate independent systems and it just gets out of whack. And so people end up like if

of whack. And so people end up like if you hire 17 product marketers, you're going to have 17 product marketers worth of demand for work to do. And if you don't have sufficient supply of product

marketing work to do, they're just going to do other stuff. Again, very

important. Not because they're stupid, not because they're evil, but because they're like, "I'm a product marketer and I want to like be recognized for my work and my spouse is like has um uh

criticized me because they think like I should have already got promoted in the last cycle and I really got to demonstrate some wins here and whatever it is." And so people are like calling

it is." And so people are like calling meetings with their colleagues to preview the deck that they're going to show in the big meeting to get feedback on whether they should like improve some of the slides. And that hyperrealistic

worklike activity is superficially identical to work. Like we are sitting in a conference room and you are there's something being projected up there and we're all talking about it and that's

exactly what work is. And you know hopefully not all of work in for everyone inside of your company but you know that's uh exactly what we do when we're working but this is actually a

fake bit of work and it's so subtle that I I'll do it you know our board members will do it every exact will do it and the further you are from like having all

of the contacts and all the information and um the decision-m authority and stuff like that the easier it is to get trapped in that stuff and people will just perform enormous amounts of hyperrealistic worklike activities and

have no idea that that's what they're doing and the you know the result of that I guess is that if you are a leader if you're a manager director an

executive the CEO it's on you to ensure that there is sufficient supply of known valuable work to do um and there almost always is but you know it's creating the

clarity around that creating the alignment making sure everyone understands that that's what they're supposed to be doing and and then obviously doing Amazing. I could listen to Stuart Rans all day. Hyperrealistic

worklike activities. We need to coin this.

>> Uh, and >> unfortunately it doesn't make a good acronym. It's pretty ugly.

acronym. It's pretty ugly.

>> Try.

>> And just to close the loop on that, the the solution is uh the leader recognizing this is happening and stopping it, telling people why are we spending time on this thing that is not going to get us anywhere.

>> Yeah. and and and that what you just said probably isn't the best way because that sounds like they're you know you're chiding them and they're dumb when it's actually your responsibility to make sure that there's you know sufficient

clarity around what the priorities are and you know explicitly saying no to things upfront and stuff like that rather than words and say like hey you guys are much idiots wasting your time

on this thing that doesn't matter whose fault is it you know it's it's the manager's fault it's the VP of whatever's fault it's the CX whatever it's the C ultimately it's like it's the

the leader of the organization that has the responsibility to make sure that there is sufficient known valuable work to do.

>> Um and it's that's actually harder than it might appear.

>> Okay. Uh before we run out of time I want to touch on two other topics. One

is when people think of Stuart Butterfield I think a lot of people think of we don't sell saddles here.

your legendary Medium post that uh is just I don't know it's become a historic piece of literature in the in the annals of product building and in startups. I

haven't heard people ask you much about this recently. So let me just ask a

this recently. So let me just ask a couple questions. One is just what was

couple questions. One is just what was the what was the reason you put that out? Why what was the backstory on

out? Why what was the backstory on writing that memo? Why was it necessary?

>> Well, it really was an internal memo and there's a bit of a digression.

Um, one of the the crappy things about Slack, um, is if all your or corporate communication is on email, depending on exactly how it works and what system you use, you probably walk away with an

archive of everything you said at company X. Um, if it's Slack, once

company X. Um, if it's Slack, once you're turned off, you like you lose access to all their history. And so,

it's kind of like, oh man, if I had only exported all of my messages before I left, I would have all this stuff. But

that was it was absolutely verbatim. And

I did not change a word of what I said inside the company. What I think we were still eight people maybe, you know, at most 10, but I think it was eight people.

>> It was before Slack launched even.

>> Yeah, it was before Slack launch. was

like when we're doing a private beta and the point of it was to like to start to instill those ideas as early as possible and really

create this alignment inside of that small team so that it could persist and survive as we grew and and scaled. Um,

and yeah, that that was the that was the idea. And the gist, just for people that

idea. And the gist, just for people that aren't super familiar with it, but we'll link to it, is just it's not enough just to build a great product. You just as much have to put effort into communicating what this does for them,

the problem this is solving for them, the outcome this is going to achieve for them. Is that a good way to think about

them. Is that a good way to think about it?

>> Yeah. And again, you know, like comparing it to beer or cars, um, beer is goes back to pre-ivilization.

cars were obviously I didn't but you know so at some point you had to convince people why they would win a car instead of a horse um

for your new um AI based recruiting tool or your calendar app or whatever there's some reason why people you think that people should use yours instead of the thing

that they're using now which might be like a wholesale one for one replacement or more often is like a change in the way that you're working that has a bunch of other agencies and you want to expand into these other categories and model

you're not just responsible for creating the product but also to certain degree creating the market and and creating you know there's this book uh positioning um which is an absolute classic it's very

short I would recommend everyone read it where the the point of it is from my perspective it's almost impossible to create a net new idea in someone's head

it's much easier to take a couple of existing ideas and and put them together so it's much easier to say it's like jaw meet Star Wars Star Wars or it's Uber for pets or something like that than to

come up with like an a actual new idea.

But you you have to do that cuz you look if your thing is different in any significant way from the alternatives and you're not just creating the product, you're creating the market.

They're really kind of one and the same.

The reason I wanted to touch on it is I think still people continue to not listen to this advice and can continue to overinvest in more features, more more products, things like that. Just

the the specific example of we don't sell saddles here just to quickly communicate this to folks and correct me if I'm missing anything is just instead of hey look at this amazing saddle we've bought. Would you want to communicate us

bought. Would you want to communicate us here go horseback riding look at this incredible experience you can have and and then they decide oh [ __ ] I need to go buy a saddle to do that.

>> Yeah. and and

100% um that aspect of it is is not original because I think that's something that marketers have done for a long time. Certainly in the in Marcom

long time. Certainly in the in Marcom and advertising like if you want to sell Harley-Davidsons, there are people who are going to geek out on the engines and stuff like that and like the quality of the leather and stuff like that. But

what you're selling is not the motorcycle, you're selling like the open road and freedom and the wind in your hair. And if you're Lululemon, you are

hair. And if you're Lululemon, you are obviously selling yoga pants, but you're also selling like health and aspiration and being the best version of yourself and you know a bunch of other stuff. So

selling that.

>> Oh my god, I forgot the classic version of it. You know, like

of it. You know, like >> there's the selling this screwdriver.

>> Oh. Oh yeah, the nail.

>> Yeah, the nail. Anyway,

>> yeah. What is that one? [laughter]

There's the Well, there's the one I think about is instead of trying to convince men to build a ship, instill a yearning for the sea.

>> Yes, exactly. That's a goes back in uh in history.

>> Okay. Let me ask you about pivoting. Uh

you are potentially the king of pivots.

You started two companies, both famously pivoted, both from video games, which is why I asked you about that at the beginning, into very successful companies. I imagine many people come to

companies. I imagine many people come to you for advice on pivoting. I I let me just ask when folks come to you asking should I stick with my idea, should I pivot, what sort of advice do you find

most helps them?

>> Yeah, I mean I think it's um partly uh an intuition because like obviously the decision is about like have you

exhausted the possibilities? Um, and in the case where, you know, we were working on Glitch, this game where we used IRC for internal communication, and we added a bunch of IRC, which became

the proto Slack. And I think Slack had an enormous advantage in the fact that we were working on this for several years without actually explicitly working on it and only doing the minimum

number of um features that were, you know absolutely guaranteed to be successful in the sense that it was so irritating that we couldn't stand it anymore or such an obvious improvement that we couldn't

help but take advantage of it. We still

had like $9 million left and everyone still liked the game and we were all happy working on it. But I think by that point I had exhausted every non

ridiculous longshot idea to make it commercially successful. Um and so

commercially successful. Um and so decided to um to abandon it. But you

know the default advice for anyone in anything is persevere is like you know a kitten hanging off the branch and a poster says hang in there. And you know, I think there's a idea that you just

like and then there's so many stories of like so and so started out going door todo and was rejected by everyone and then suddenly there was Nike or or something like that and like just if you

stick out stick with it long enough you'll eventually be successful. I think

you have to really be coldly rational and um now some of this shows up in the book um thinking about some of it's in Annie Duke's second book the title of which

I'm forgetting right now but someone will will know it >> bets and then yeah what was the last second I forget >> uh she actually uses glitch and and

slack as an example of like a smart fold basically like my expected value here has diminished to the point where this

alternative looks more attractive. And

the reason I say you have to be coldly rational about it is because it's [ __ ] humiliating, you know, like like we I convinced so many and you have to convince so many people to get a company

out there. You have to go to investors,

out there. You have to go to investors, you have to go to early employees and say like you should leave your other job and come work for this because you know here's the the an incredible future we're imagining. you have to go to the

we're imagining. you have to go to the press and you have to make all these promises and you have users and you've like committed things to the users and you've convinced them to give up their time for this thing. And so it's I I

think for a lot of people uh it feels better to just keep doing it until it dies um of suffocation

due to lack of capital or something like that. Uh then to to admit like okay I

that. Uh then to to admit like okay I was wrong. This didn't this didn't work.

was wrong. This didn't this didn't work.

And it's it's humiliating. It's painful.

It's like it's wrenching. It has a bad impact. You know, like there's when we

impact. You know, like there's when we shut down Glitch, there's a lot of people who loved it and would spend all of their free time and couldn't wait to get home from work to go play it more.

And that was their community. And the

community just like disappeared. All

these people and all these identities have been created. And obviously people lost their jobs and and people who had like moved their families to a different city in order to take this job now weren't going to have a job anymore. So

pivots aren't something I take lightly.

And you shouldn't be um I think it's very different to be like there's three of us and we started making this app and then we pivoted to a different app. That doesn't even really

different app. That doesn't even really count. You know, like if you're 6 months

count. You know, like if you're 6 months into something, you're just you're still messing around. You're trying to figure

messing around. You're trying to figure out what it is that you're you're building. It's not really a pivot.

building. It's not really a pivot.

Obviously, in this case, it worked out great and there's survivorship bias and that doesn't mean that everyone should pivot all the time. Um but I I think it

is creating the distance so that you can make an intellectual rational decision about it rather than an emotional decision is is essential.

>> I love also your piece of advice of just exhaust once you've exhausted all the ideas that's a really good time to see what else is out there.

>> Yeah. Exhaust all the all the good ideas.

>> All the good ideas.

>> All the realistic. Yeah.

>> Yeah. The uh the point you made about just kind of persevering. Uh I just had Melanie Perkins. of Canva in the

Melanie Perkins. of Canva in the podcast. Uh they went through a hundred

podcast. Uh they went through a hundred investors rejected her before somebody finally decided to invest and she just kept pushing.

>> Yeah. But I think that's a slightly different example, right? Because like

the she believed in the Yeah. Then she

believed in the in the concept of the in the product and like in the in the vision and was just trying to figure out the right articulation to get investors who ended up being obviously very very happy.

>> Extremely happy. Oh jeez. Okay. Maybe a

final topic depending on how time goes.

I want to talk about generosity.

I talked to a bunch of people as I said that have worked with you and the number one theme that came up again and again and again when I asked them about you and what they what has stuck most with them is is just generosity. So I'm going

to read a few examples that I heard from folks uh that are examples of your generosity over the years. So, one

person shared that uh he needed a little money before Christmas and you he said, "Steuart literally walked me out of the building, went to the cash machine, handed me $500, told me to go home to my

family." Other folks shared that when

family." Other folks shared that when you you talked about Glitch just recently when you had to lay people off that you cried real tears when you were laying people off and then you spent an incredible amount of time helping them

find new jobs and extending their severance pay and just taking it extremely extremely seriously much more than I think most people feel like CEOs do. Someone else shared that you paid

do. Someone else shared that you paid 100% of employees health insurance to give them just fewer things to think about. uh when you went public you did a

about. uh when you went public you did a you basically created the best possible situation for employees no lock up direct listing >> also with the structure of the Slack deal people said the acquisition was

very employee friendly there's also just a bunch of that's employees there's also just the way you thought about customers a few examples you gave free credits to businesses who were struggling to pay the bills during co you released this

fair billing which I think was very innovative at the time where you didn't charge you stopped charging people for seats they weren't using even though signed a deal to charge for those seats.

A lot of times just you slipped release schedules because you just wanted to make features better and better for people. And I'll end with this quote.

people. And I'll end with this quote.

Stuart is a leader who takes the responsibility he feels for his employees personally and to which he extends the most generous circumstances he could muster. That feels worth celebrating.

So first of all, I just want to celebrate you. I think it's really rare

celebrate you. I think it's really rare and inspiring to meet a leader like that. Clearly, you've had a lot of

that. Clearly, you've had a lot of impact on a lot of people. I don't know exactly the question I want to ask, but I guess was this is this like an in what part is this intentional just like this is how we win. I'm going to be very

generous and help people because I know this will help long term. How much is this just in this just the way you are as a person?

>> I I think a lot of it is just the way I am as a person and uh I had wonderful parents who raised me, right? But I

think there's also um there is a little bit of a lesson there and I'm just going to assume people's familiarity with the the prisoners dilemma. Um the you know

acts of generosity to me are a way of demonstrating that I am going to cooperate as we iterate in this game.

>> Um and if you do that then people will also cooperate and you both benefit. Um

whereas if you never really know if the other person is going to defect at the first opportunity um then your best bet is to defect. And so you know there is a game theoretic aspect usually in games

that are much much much more complicated than the prisoners dilemma. Um, I think another thing, you know, one thing we uh I I didn't touch on before, but to me

was important enough that at more than one company all hands, I made everyone in the company like repeat this as a chant. Um, it was in the long run the

chant. Um, it was in the long run the measure of of our success will be the amount of value that we create for customers. Um, and I wanted to be super

customers. Um, and I wanted to be super clear and explicit about that because it should be if anything you're doing feels like a little bit shady, a little bit

cheating, a little bit like um maximizing um in the in the at the wrong moment or taking advantage of a customer or anything like that, we definitely

shouldn't do it because to me it was just like I mean I think it's uh literally true, but it's also like and

uh an ethical way to run a business and and um it's not just that the ethics are good. It's like there's advantages for

good. It's like there's advantages for you like you're able to attract a better class of employee. Like if all your employees are are ethical, then it's going to be a better place for everyone to work and you're going to be happier and you're going to have fewer internal

problems and and all that stuff. Um, but

I think it really is true that there's no like especially in the long run.

You can't like destroy value for your customers and expect to be successful.

You have to actually make their lives better. Um, and you can put effort into

better. Um, and you can put effort into like pointing it out to them and and demonstrating that you have created this value and stuff like that, but there's no substitute for actually having

created it. I think that um is

created it. I think that um is incredibly important and that implies a real generosity whether that's in

negotiating terms with an any enterprise deal or that's like policy decisions.

You sometimes say one one time that it blew up in our face was our SLA was like for any downtime you get a 100 times your money

back. um which was like because from my

back. um which was like because from my perspective it's like you know if we're down for two minutes it doesn't it's like pennies. It doesn't really make any

like pennies. It doesn't really make any difference. If we're down for like 10

difference. If we're down for like 10 hours or something like that then we have bigger problems than paying back people that okay fast forward we you know we now have hundreds of millions of

dollars in revenue and we've gone public and like shortly after we go public we have like one of the biggest outages we ever had. I don't remember how long it

ever had. I don't remember how long it was, but it was like many hours. But by

the time we got to that scale, a hundred times the money back for like the third of a day that we were down was like

$8 million or some something like that, which had to be um you know, it didn't cost us any money because we just gave it to people with former credits, but it meant that a bunch of revenue that we

had already anticipated for the next quarter wasn't going to show up because people's credits were going to offset what they would have otherwise paid us.

Um and so uh we we definitely changed the terms of service after that because being a public company is a little bit different but you know in every other respect I think you know there were all

really important decisions that were helpful in um in us becoming successful.

>> Was that policy it was automatic like you didn't even have to claim it. It was

just automatically get this credit >> and like and then the default is you don't have to pay if you let us know and this was we will automatically like proactively preemptively without any input from you apply this credit to your

account and just like send you a message and it happened and by the way >> we will do it on the aggregate for downtime even if the issue didn't affect you as a as a customer.

>> Too generous. You found the the edge where you might want to be. [laughter]

>> Yeah. What was that mantra again that you uh had the company chant? I think

this is a really nice way to end it.

>> In the long run, the measure of our success will be the amount of value we create for customers.

>> Incredible. I'm just trying to picture the entire team at Slack.

>> Like hundreds of people. It felt very like Chin or like Stalin or something like that. [laughter]

like that. [laughter] >> Well, on that note, most people don't know this about you, but your uh your actual name when you were born is not Stuart. It was Dharma.

Stuart. It was Dharma.

>> Yeah. And this all makes sense as you learn that.

>> Yeah. It's like I had my name is Dharma Jeremy Butterfeld. So my parents named

Jeremy Butterfeld. So my parents named me and when I was 12 I changed it because I just like really wanted to be normal. And for some reason I thought

normal. And for some reason I thought Steuart was a normal name. And by the way, you'll notice this now that I said it. Any character except for Steuart

it. Any character except for Steuart Little. Um anytime you see a character

Little. Um anytime you see a character in in a movie, a novel, TV show, whatever, there's only the loser Stewart and the [ __ ] Stewart. It's it's like

it's obviously in the collective consciousness a terrible name and I shouldn't have chosen it and I regret it. But by the time I realized that

it. But by the time I realized that Dharma and Greg had already come out and would have seemed like I was like, you know, bandwagon jumping and people thought it was a girl's name even though in India it's obviously only a boy's

name. I'm going to add just one last

name. I'm going to add just one last little tidbit because I forgot about this earlier on and I think it helps tie things together.

>> Let's do it.

>> And it's called the owner's illusion and this is based on something I posted on Twitter. the person who came up with the

Twitter. the person who came up with the name later deleted their account and so I have no idea who it was of who to credit for this but what I had posted was and this is a long time ago be when

restaurant websites have gotten better and it doesn't really matter because Google local has taken over everything but this is like let's say 10 years ago there's five things you could possibly want when you go to a restaurant's

website and is their street address their phone number the menu the hours of operation oh my god I forgetting the fifth

Oh, and and making a reservation. How to

make a reservation. Um, and again, this problem has like to some extent taken care of itself or at least to brute. But

what you would get was like this super slow loading photo like Ken Burns effect as it go and like and then like fading in and then some music starts playing

and then if they show you the phone number, it's not a clickable editor.

It's not even text that you can copy because it's yes, it's an image.

um and they don't have the hours, they don't put the address or whatever and it's just like what for sure whoever made this website for the restaurant owner and the restaurant owner themselves have definitely been in the position where they went to somebody

else's restaurant website because they wanted to get the address or the opening hours or the phone number or whatever.

So, how why does it end up like this and what should we call this? And the

whoever replied to the tweet um she said we should call the owner's delusion. And

I was like, oh my god, that's perfect.

And I think that um is incredibly powerful and it what ends up with the result like Apple naming whatever that feature is called sleep which is like

it's too hard to understand what could that could possibly mean and that's why like people anticipate um despite the fact that when they get to their web

your website for the first time their their intent is absolutely the minimum number of micro points above the threshold required for them to actually

take that action. You're like, "All right, like welcome to my website." And

there [laughter] there's a bunch of like BS and there's a bunch of like stuff that doesn't make any sense and the buttons are inscrutable and it's unclear what to do

next because I think that my thing is so important and I don't recognize that you are at work and you were late this morning and you have to go to the bathroom and you're just like you're

just like a regular human being who has like stuff going on. You're concerned

that your kids will [ __ ] up and they getting in trouble at school and stuff like that. They don't they're not like

like that. They don't they're not like subjects who paid money to go to your play and are sitting in the audience and waiting for the curtain to go up.

They're like people who are going to bounce in a fraction of a second and so everyone should always be conscious of the honor solution.

>> I love that. What's the solution? Is it

have other people look at it and give you feedback? Is it

you feedback? Is it >> Yeah. And and like recognize it. And

>> Yeah. And and like recognize it. And

unfortunately, it's one of those things like Murphy's law, like even >> you go wrong when you like even when you take into account Murphy's law.

>> But if you if you don't name it and recognize it and discuss it and like train yourself to think in that way that you know, take a breath, pretend you're a regular person, and then look at this

again and see if it makes sense. Then

>> I love that you're screwed.

>> I love that you threw this in here. I

have a billion other questions I I'm going to ask you in part two when we do this someday. Uh Stuart, thank you so

this someday. Uh Stuart, thank you so much for doing this. Thank you so much for being here.

>> Yeah, thank you for having me, Lane. I

really enjoyed it.

>> Same. Same here. Bye, everyone.

Thank you so much for listening. If you

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