Slack founder: Mental models for building products people love ft. Stewart Butterfield

0:00 This is two thousand and fourteen. 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 right now is just a giant piece of shit. It's just terrible and we should be humiliated that we offer this to the public. To me, that was like you should be embarrassed. If you can't see almost limitless opportunities to improve, then you shouldn't be dividing. Slack was famous for being one of the early consumerized B2B SaaS products. At more than one company all hands. I made everyone in the company 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 demonstrating that you have created 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. You should always be trying to remove friction when the challenge is really 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 goal or reducing the number of flexor taps or something, and instead focus on how can I make this simple? How do I prevent people from having to think.

1:13 in order to use my software. You started two companies both famously pivoted. I imagine many people come to you for advice on pivoting. The decision is about like have you exhausted 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 it's fucking humiliating. Today my guest is Stuart Butterfield, a founder and product legend who rarely 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 work like activities.

2:03 What he's learned about product and craft and taste and Parkinson's Law, why you need to obsess with not making your users think. The backstory on his legendary We don't sell saddles here memo. And so much more, a huge thank you to Noah Weiss, Chris Cordle, Ali Rail, and Johnny Rogers for suggesting topics for this conversation. This is a really special one and I really hope to have Stuart back to delve even deeper. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously.

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4:56 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

5:09 Towards the very top of my wish list of guests I have on this podcast ever since I started this podcast a few years ago. So I'm very excited they're finally making this happen. I have so many questions for 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 chillin'.

5:28 I'm mostly just chilling. I left Salesforce. Um Two and a half years ago and a half a two and a half year old. So she was actually born three 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 Well, um

5:46 No new company to announce or anything like that. Um I do get a lot of emails and texts like basically like every three to six weeks there's the cycle because Cal Henderson, who's the CTO of Slack and who also we work together on Flickr, so have worked together now for twenty

6:04 Three years. I've 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

6:14 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 of a

6:28 a big winner, but uh 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. Two prep for this chat. I talk to so many people that have worked with you over the years.

6:49 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, it starts arcing up and then there's a really steep part and then it levels off again. And

7:17 on the horizontal axis. Uh you can think of Cost or effort. And on the vertical axis it's value or convenience. It kinda depends exactly what you're talking about.

7:31 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

7:47 example I can think of is let's say you're making a hammer. And on that. On access it's now. Quality. And if the hammer

7:54 uh has a handle that breaks with any impact then 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 doesn't matter anymore. If you're making an app, okay. This app's gonna have users and so let's make a users table and a database and so far you have generated no value. The reason I I felt like this was so important is because

8:18 We would Talk about like Uh feature. Um and usually features are thought of as as binary, like you either have this feature or you don't. And so

8:29 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 diminished d point of demission returns and it just doesn't matter. And I I think in many cases people will

8:48 out of future. 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 try something in in testing and they don't get the results they want. And so they decide that this is a thing isn't worth doing. And so we would try to really

9:06 investigate and and decide whether we were on the First chala part of the curve, the second chala part of the curve, or we don't Yeah, 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

9:22 Featur. But um I think it was ultimately helpful in getting people to Like. Understand whether something was

9:29 Was it worth that 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 it's a different way of thinking about getting to uh the aha moments for someone where they see, Okay, saved items. I get it, I need to use this constantly.

9:51 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 lens you use. to figure out where to spend product resources because if you don't get up that curve to

10:09 I get it and I can't live without it. Nothing else matters. Is that the way is that the framework? Yeah, yeah. And I think then you layer on another concept like the um Bases used the term. Divine discontent. Um

10:24 The line actually moves because once people are familiar with A 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.

10:38 And again, this access can be the utility is the best general term for it, but it can be Quality, convenience, um speed it could be any of any number of things. But as you improve your search capability or if if 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

11:05 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 ones. And then If they're lucky, they get improved upon. Periodically.

11:17 most things get improved upon. Very infrequently and some things get improved upon never. And You know, just I'm gonna give an example at the absolute extreme because I d don' actually don't know How long this has been.

11:31 I try not to criticize other people's software so much because I very familiar with the trade offs and prioritization and how hard it can be and blah blah blah blah. But okay. So It uh most people have the Gmail calendar app on their phone. I travel A fair bit.

11:46 I'm mostly in The eastern time zone. Sometimes in mountain time, sometimes in Pacific, sometimes in English time and sometimes a Uh

11:56 Japan, Central Europe. Just like a P Maybe ten time zones, twelve time zones. Um That I would ever Choose.

12:06 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 in alphabetical order. And that's Like

12:18 I mean there's probably worse. Orderings, but that there'sn't 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 trying to set an appointment for next week when I'm back in New York.

12:36 And I type in E A S T. And I get a bunch of garbage. Okay. East Earn E R N. And then the first one is East 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 fuck what I

12:56 I can't remember which one is Dale's Havens and which one is Standard Time and 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

13:08 Bananas how bad it is. There's so many Okay. There's all these clever things you could do. Like You know me. I'm on the West Coast.

13:18 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 Yeah. Time. Because

13:28 I don't even know. Like a 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 eight billion people. And there's Newfoundland. You know like the same width. China time, which is like twenty five percent of the world population in this Anyway.

13:52 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 gonna switch True.

14:03 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

14:22 In some cases that can be really positive, like they would recommend it and when they switch companies or decide to start their own company, they choose to use this product or advocate for it because of that emotional connection and vice versa, they'll also be like hate this thing. This drives me bananas. I really think we should stop using it or Yeah, advocate for the alternative.

14:42 Uh and I I think people just don't appreciate or come back to those things often enough. And then there's this category of like really essential parts of the app. Again, like Account creation sign up. For that password.

14:56 Yeah, things like that. But 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.

15:09 across the board and and continually goes up. Let's go down that rabbit hole a little bit more around delight and craft. Slack was famous for being one of the early Let's say a consumerized B2B SAS products Slack leaned into delight and experience and craft and A great experience. And you just as a product leader, I'd say is are are known as as very taste

15:31 forward, very craft oriented leader, which is pretty rare. And I think continues to be rare. So there's a few things I wanna talk about here. One is A taste? I heard at a talk you got of a really unique You gave a talk on taste and you have a really unique perspective on just what taste is. What

15:46 Product taste looks like. Can you share that? There is a lot of You're 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.

16:01 But um I guess a couple of things about taste. So one is Can you learn to develop it? I think so, because like

16:09 The word literally comes from experiencing food and putting stuff in your mouth. And can people become better chefs with training? Yes, absolutely. Undoubtedly some people have a natural advantage and are are Yeah. born with this ability to

16:23 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

16:40 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 pretty obvious one. You meant by that. I would tell the story at Slack over and over again and actually made it part of the new higher welcome.

16:59 So uh I'm I'm going I'm in Vancouver. at our Vancouver office and I'm going for a walk with Brandon Velostok, who's our um at the time Creative Director for Product Development. I think that was his title. And uh we're in the Yale Town neighborhood in Vancouver, so there's like really narrow sidewalks'cause it used to be a warehouse district and now it's like you know fancy restaurants and nail salons and boutiques and stuff.

17:22 And as it does in Vancouver, it starts to rain. We don't have umbrellas. 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 would move their umbrella out of the way.

17:39 And of course, you know, the other person Their umbrella, the cokey bits are exactly at eye level for for people walking. Towards them, maybe we would get like you know, forced off the sidewalk or like having to duck down or

17:53 Whatever. It would it became a game, like we were guessing. Is this person gonna Tilt their umbrella out of the way so we can passed or not and Something like one third of the people would do it.

18:05 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 wanna get out there and dominate.

18:21 People. And cause you know. Suffering. So shouldn't ascribe to malice that which can be ascribed to ignorance. So that's probably, yeah, that probably is the explanation for a tiny Tiny tidy.

18:33 Percentage of people. But the other two explanations aren't that great either. One is That Uh, they see it's happening, they see they're pushing other people off the sidewalk.

18:42 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 something I could do about that. But I can't think of anything. And the last reason is

18:52 they just don't notice at all. Like they're just oblivious to their impact on on other people. Yeah, 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 it's like Tilting your umbrella.

19:07 is our opportunity. T that's not a great rephrase of a your margin is my opportunity, but your failure. to really be considerate and uh Exercises courtesy and really be empathic about

19:22 other people's experience is it an advantage you can create a critical advantage. There's many reasons why stock was successful at the moment. It was successful and oh I think we had a bunch of really wonderful tailwinds and and all that stuff.

19:37 But it wouldn't have grown the way it did without those little conveniences which caused people Two. form a a an emotional connection because a lot of our growth came from Yeah, startup A use the Slack and then

19:49 someone leaves startup A for startup B and startup B doesn't use Slock yet and they would be like, Oh my God, you guys are we really good this is This is so good, I'd be about to try it and uh And the the spread was driven by that. cross pollination and and people really Genuinely advocating for it.

20:06 That is an amazing metaphor. I I I love that one moment became like a value of Product craftsmanship. And to tilt your umbrella because is like was a very common you'd say in Van You know, company swag and and stuff like that. Is there an example I mean, I imagine there are many.

20:23 But from the time of building Slack, especially in the early days where you chose to go big on craftsmanship and experience and And the light. Versus speed. Where you thought looking back that was a really great idea and it worked really core to success.

20:37 Here's a bunch of little examples. Um, so Someone else came up with this idea. And um I'm trying to remember who it was.

20:47 Um but I Maybe Andrea Torres, maybe Ben Brown, something like that. Where it was like why why do we ask people for email address and password if um Thing.

20:59 They're ownership of the email address was the thing that allowed him to create the account in the first 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 of the mobile app came out. Right. Type in your password on your phone if you have any

21:15 Yeah, m minimal threshold of of password hygiene is a terrible experience. Capital H to lowercase Q six. Correct. Period. So let's just Have them enter the email address, we'll send them a link. The link will automatically open the app and and authenticate them.

21:31 So there's one one little example. Well so you guys invented the magic link, uh explaining. Someone else invent I want to be clear there. Uh 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 to my knowledge that that really kind of like scaled that and made it uh a 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 What's up?

22:03 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 a member of many channels and the messages may not be for you. And so that's why we have the Mm. attacking people and

22:20 We certainly didn't invent that. That was that was Twitter. Um But what we realized was People were signing up for Slack. Yeah, 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 what person would be like

22:38 I didn't get a notification. This is this is Bullshit. Uh. So we reluctantly decided that we had to send notifications for every single message. as the default for new accounts.

22:50 But once you had I don't remember what the thresholds were now. I think it's w once you had received ten 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 noisy for you. Would you like to switch to our recommended settings? And then they would just click a link and it would

23:06 you know, have what should be the default, which is you only get a notification if it's a DM or someone tags you. But we realized it was worth that investment. to get people over the hub. A much more Uh

23:20 Here's a I'll give one One more simple one and 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

23:32 you know, set the priority of a message for the recipients, always got to be used inside of every company. As as soon as someone does it, like everyone's like, okay, I'm gonna do that too for my message. And so all of your messages have the little flag and it's becomes useless. We have at everyone, which causes a notification to be sent to every member of the channel when the message is sent and people would start, yeah, look someone would Find this feature inside of a organization. They would bat everyone. Everyone would get a notification. And then the next person to send a message was like, Well, my thing's more important than

24:01 Um Bob's saying, I'm gonna also bat everyone. And it became really obnoxious if people would complain about it, but it was a I don't know. I guess tried to do the commons. It's not quite exactly the same thing, but it was a this real dynamic that happened over and over again. So um We came up with what was called the shoutie rooster. And internally we said

24:21 Don't be a cock. Um but we didn't. Obviously say that publicly. When you a everyone. A little rooster would.

24:28 pop up and it would have like the sound waving out of its mouth and being really obnoxious and say, Hey, this is gonna cause A notification for a hundred and forty seven people in eight different time zones. Are you sure you want to send us message with that hat everyone. Um and of course that work amazingly and it dropped off. Um and again, it was really trying to shape people's behavior so that they used

24:50 We want it that to be very flexible. Um but we knew that there was ways to use it that wouldn't annoying and and difficult for everyone and so try to shape the communication culture inside the organization to take best advantage of it.

25:02 That feature still exists. I see that rooster all the time. Or no, I don't see it all actually I do at channel because I run a big Slack. Uh sorry, see that rooster the that survived. Yeah. Um yeah, that's what I've been and Good.

25:15 Uh because it's Sure. It was 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 or at channel Um

25:27 Right. Well. Didn't think about the cost. At least. Yeah.

25:32 Here's here's one more. Uh So we decided we were gonna do do not disturb. As a feature. Um

25:41 And We had this But conundrum. But we you're trying to take into account all the All the different uses of that'cause at the time we we implemented this.

25:51 Uh like two thousand seventeen there was You know. Tens of thousands of of pain. customers, the organizations, hundreds of 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

26:09 Ups. 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.

26:22 We realize that some of the decision makers, the owners of the organizations were gonna have really strong opinions about this. We also realize that some of the end users are gonna 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

26:39 elaborate system for the roll out, which was Wait. Told everyone um I'm sorry, every every Slack administrator that this was coming weeks before it came. And we told them

26:50 that we were gonna set a default for their organization. Which I believe was um Either seven PM to seven AM in their local time zone or or eight AM to eight PM and I can't remember which was. But also that they could override that default. And also that

27:06 the individual end users can override. That System owner default. And finally that the system owner Could.

27:15 If they change the default again would overwrite all of the the end users. Yeah. Then the end users could Uh.

27:23 overwrite them again. And it wasn't to create this dynamic where people were who were at war, but so that you could change a policy and then people could still customize and and stuff like that. But this was Yeah. a much longer and more convoluted process, but it allowed Then

27:38 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 on at all. Yeah, like there wasn't if we didn't default you to Do not disturb from eight PM to eight a.m. Um you probably

28:02 If you're the average person, wouldn't ever do it yourself. Uh 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

28:16 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.

28:31 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. The actually it's a feature, not a bug a lot of times. If you use it well. Talk about your your experience there.

28:47 Yes. Um And there's also a another um Issue around friction, which is It it became

28:57 Like a mantra or just like a kind of uh 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 it Slack like it was it was hard to market, it was hard to explain what it was if you had never used it before. Uh you could say a messaging app for businesses or or whatever.

29:15 But you know, like a critical disadvantage to Slack doing out of home advertising, putting up my 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 be explained one day by one fuck. Um And so the

29:31 Problem there is is comprehension. And this will come up. Uh An enormous amount. So now imagine

29:37 You want to get tickets to the Taylor Swift concert in San Francisco. And you go to the Ticketmaster 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.

29:53 And the degree of your intent is also kind of maxed out. So look, I really want to get these tickets. I know exactly what they are. They're Taylor Swift tickets for this date at this venue. And so in that Scenario. It doesn't really matter if Ticketmaster's website is slow. It doesn't really matter if the payments page airs out. Like you're gonna persist and and get through it. So obviously it's they're better to reduce friction. But

30:16 I in some sense it doesn't. There's not a huge amount of of value in doing that. Uh For most creators of of products.

30:26 There are a handful of cases where that really is true for you as 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.

30:42 Something like that. I'm significantly less likely to carry through. The purchase of something. Yes. The I have to manually enter all the fields of my address one at a time rather than having one of those address pickers

30:55 It's it's crazy, but like The issue is my intent isn't always a hundred percent. Right. And the specificity of my intent isn't always a hundred percent. So If you're

31:06 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 a hundred percent. Intent. I might have like a very specific intent, I might intent's like seventy percent. So if you're

31:23 Is Uh above that, I just I'm not gonna do it. But now okay. People coming to Slack.com. They had

31:31 Some Uh friend had mentioned Slack and kind of talk 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 And they finally said, Okay, I'm gonna go to this website. So they're In ten.

31:48 Is like at the absolute minimum threshold. Like it's Just there 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

32:01 I need to get Taylor Swift concerts for this date at this venue. Um is also very low because they're like Uh It's a work 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

32:16 Yeah. Point one percent over these These critical thresholds. Um What was the challenge?

32:23 It wasn't friction. Right. Because it's not like the 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 in in two senses. What is this thing?

32:39 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

32:52 The the UI of the screen of the page or or whatever and the um the visual hierarchy and the affordances that are there and the and the uh Indication of things to interact. up 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.

33:11 They're like I want to get people who come to my webpage to the sign up forum as quickly as possible. But if they don't know what they're signing up for, they don't know what it's gonna do after, is it gonna spam them? Um They don't know about I am I gonna have to pay on the next step or or what, then they're just gonna Back out.

33:29 And This was like a a lifelong battle because the remove friction Um Kind of Orientation is so

33:38 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

33:47 it is a a poor approach when the challenge is really comprehension. And I think the secret is most seventy percent, eighty percent or whatever of a product design is in that comprehension step because like People If they do ever open the preferences tab and look at all the options.

34:07 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 gonna take advantage of them and they're not gonna get as much out of it. And I think the the trick is For

34:22 most of the unique parts of any application, most of the like the specific things that your app, your product, your Software does. are areas where the challenge is gonna be comprehension and center friction. Mm. It really could be anything. Like

34:36 Shopify Um The purpose of the of the service for its end users is generally gonna be kinda clear. But most people

34:46 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 and which things that that are are more important to display and

35:04 I could go on and on and on and on. And people just don't recognize that. So like the I wanna see if this is still true. I'm just gonna open my i iphone. Um And a clock app. And they had the most

35:15 The the craziest description for alarms. Oh okay. It's still it's a little bit different. Um But people can look at their own phone.

35:26 So I have It says Alarms. And I says sleep. And a vertical bar, wake up.

35:33 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 out of your schedule they need to turn sleep on. So obviously but Sleep was a good

35:48 Name for this thing. If you already had a way of getting people to understand it. If you don't, it's like ungrammatical and incomprehensible and why would you ever do it? And I I Got a guess. It's it's been like this for years. ninety plus percent and and maybe like ninety eight percent of people just do what

36:07 I do, which is that you just create a like I want the alarm on and I'm gonna set the time for it. And I don't know what turning the sleep on. Does it be a good thing. 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

36:23 Turning sleep on, whatever that means. And people spend a lot of time on those features and it integrates with like biometrics and your watch or Who knows? I I again I still don't know. Because

36:34 turning sleep on is like I don't what does that do? And what is it gonna cost me and what impact it's gonna 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.

36:53 is because I didn't understand what they're gonna do and I don't give a shit. And if there is one mantra that I would use to replace that. It's Don't Make Me Think. I don't know if you remember that that book absolutely Yeah, and Honestly, it's been

37:07 many more than ten years since I read it. So I don't usually remember all the examples in the book, but as a mantra that was like up there with utility curves'cause for two reasons. One is it's just like it it It's expensive to make a decision like you literally burn glucose. Like there's a metabolic action. There's like A T P created in the mitochondria in your neurons and like a bunch of stuff is happening.

37:31 And people do get Decision fatigue and there is like Yeah, the 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, but I don't really understand it, you make me feel stupid. My climb back. I don't understand this.

37:48 Yeah. Some people are are Yeah, but maybe the orientation is okay. The software is stupid. But I think most people are like Oh, I'm done. And if you ever talk to you who aren't especially technologically savvy, you know like the canonical example is like people who

38:03 are under fifty talking to their parents about using some piece of software and what they're supposed to do, the parents almost always feel Stupid. They're the ones that are That are wrong. Um and so if you're causing people to think

38:15 In them. The best case it's like Unnecessary Use of their you have biological resources. And in the worst case, you've like now made them feel bad, like emotionally bad. And they're gonna associate that with the product forever.

38:30 And I mean these are things are just kind of rolling one into the other. So I'm at uh Keep going with one last thing. Which is along with reduced friction, it's like

38:43 reduce the number of clicks 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.

38:56 A single click or tap. by just exposing every single possibility on one screen that scroll for thousands and thousands and thousands and thousands of pages. Right. And obviously that's terrible. So why do people think that a a little bit of that?

39:11 Is good. And You know here's an example. You open a menu. There's fourteen things that people might want to do.

39:20 Uh Okay. Level one is group them into like items and put a vertical sorry, horizontal divider between them. So at least people can kinda chunk.

39:30 And and see what there is. Step two is present the two or three most common things or the five most common things or ever, and then have some form of other and you Yeah, then you go to a sub menu that has more items. And

39:44 Yeah. The decision of like how to tune that becomes incredibly important. Um I'm gonna pick on Google again, just because it is

39:53 I feel like I'm Donald Trump here, but I mean interrupt myself again with a story. It's I've got some some conference or event in Armorta was and this is Probably eight years ago and uh it's we're in the bar after the Session has ended of the thing and John Collison from Stripe is there. Come on.

40:11 And uh Sandar, CEO of Google is there. And John, uh sorry, Patrick goes up to the Sundar. Uh and they can talk about anything, right? Like

40:21 Yeah. So it wasn't at the hemith, it was now at at that point, but it's still like a you know, a significant company was up and coming. And what does uh Patrick want to talk to the cigar about? It's In the Gmail.

40:35 Um Uh The dragging of people like you When you reply all. um to a a message you often want to change

40:44 the two recipient to the C C and move someone from C C 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 is very high. It still hasn't been fixed. But it really struck me. But like

41:00 Patrick could have just for anything. It could have been any top. It could have been a partnership. It was like it was so Irritating to him. Um that it worked like this then. Can Couldn't quite get over it. So anyway.

41:12 Back to bashing on. And go up to In many respects, do an incredible job and there's all kinds of s amazing stuff they do in Bahwa. Right. The

41:21 The G mail 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 is an unlabeled icon.

41:35 is the only way to do it. And that's not 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 I think it's

41:49 Because some of them. have to do with that 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 Talk about me is read all of the options and say, Okay, that I've used the process of elimination and it's not here, so it must be It must be there.

42:11 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?

42:23 And other. And other was everything. Like change your payment method. Uh your location if you be a anything you could do an Uber. And that was perfect because

42:33 mm almost all the time people just wanted to choose where they wanted to go. Sometimes you wanted to change where your pickup was because you weren't there yet or or whatever. And that was just like What could be simpler then? I'm gonna tell you where I wanna go or I'm gonna achieve something else.

42:47 I really tried to push people to What is the thing that people Or what is the two things, what is the maybe three things that people could want to do here? And then put everything behind other. And then um

43:00 If it takes then eight clicks or taps to do something, but every single one is trivially easy. That's Great. If it

43:08 You know you reduce that. Two. Two clicks are 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

43:18 The more Comparing three things to each other is this difficult four things. It's kind of like geometrically more expensive to compare fifteen different options all to the other to see if this is the one that you might want. Um Yeah, yeah, just becomes impossibly

43:33 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 tops to do something and instead focus on

43:45 How can I make this simple? How how do I prevent people from having to think in order to use my software? How can I make the trivially easy? One one last example, uh, because this this was really influential for me. So I was going back and forth between Vancouver and 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 jet way. It took a long time. And I was watching her use Snapchat anyways. Insane. Like

44:10 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 do I wanna see this again? Do I wanna see the next story from this person? Do I ask shoot a different person? Do I wanna like instead? She um A notification came up, she answered someone's thing, she took a selfie of herself.

44:33 And everything was just like. So she was Yeah. Tapping four times a second. For

44:40 six minutes. I mean probably there were some some breaks in there. And that was like the highest and best use of Snapchat for a fifteen year old. girl in two thousand and s sixteen or whenever that was. Um And imagine if the goal was to try to make her

44:56 Capless. Yeah 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 product.

45:16 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 I'm happy with how things work. Yeah. I love just even the way you summarized this, just like a really good reframing of instead of obsessing with

45:32 reducing friction and reducing steps. Instead think how do I How do I uh reduce the amount of Thinking the

45:41 user has to do. Uh I l I've never heard of it described as like you have to think about the ATP and glucose being used 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

46:00 Stop we For a second. Close your eyes, take a couple of deep breaths, and then pretend that you're an actual human being. And

46:08 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 nother related cycle. But before I get into it,'cause I know that I'm

46:25 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

46:35 Two thousand and fourteen. So like that that was the year that Slack actually launched officially, um 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

46:51 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 shit. Like it's just terrible and we should be humiliated that we offer this to the public. Not everyone finds that motivational, though.

47:06 So I came into the office the next day and people had printed out on like forty pieces of eight and a half by eleven paper that quote and like and pasted it up on the wall. But To me that was like You should

47:19 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 individual pieces of work. But in the abrogate If you can't see Almost limitless opportunities to improve.

47:35 Then you shouldn't be designing the product where you shouldn't be in charge of the company. Or you should know. Um Almost nothing. You know, again you could reduce it down to a tiny feature. is anywhere close to to perfect.

47:50 And If A that's acknowledged freely inside the organization. And be people think about like continually improving as the goal. And that could be like Six Sigma Toyota Kaizen the bat kind of

48:04 side of thing. Or it could be that story that um I can't remember his name right now. The guy who started Bridgewater tells about um Michael J. Yeah, right on, yeah. Uh in his book talks about Um, Michael Jordan learning to ski.

48:18 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. That he could collect. And and she could you know, actually become a good skier and what he wanted to do was become a good skier.

48:31 That requires a lot of trust. Inside the organization. Um But if you can Get to the point where like, hey, we're our trying to

48:39 to find improvements trying to be critical because you're trying to make this as great as it can possibly be. Um N 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

48:57 Yeah, people are Uh grateful to have like the feedback, whether that's coming from their peers inside the company or from end users of the product, because you realize Oh yeah, that is That is

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49:51 So if you've been sitting on an idea, now is the time to bring it to life. Get started for free. At lovable dot dev That's lovable dot def. This makes me think about uh let's call it a rant that you have.

50:04 About how it takes a lot of work. To make anything work at all? Just the default state is not working. You just share share what you share there. Yeah. Um I mean so this is

50:15 A lot to do with. Um And maybe this is more recently shows up in politics a lot for me. Um But uh

50:24 By the way, if any of you anyone listening to this can help me find this tweet store from Somewhere between two thousand and sixteen and two thousand and twenty. I don't have a precise idea. And it was this guy's thread about how hard it was to get um a stop sign setup. And I think I believe it was in response to someone claiming that Bitcoin is gonna replace US dollars. Um There something something about crypto.

50:48 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 took and the number of agencies that were involved, like the engineering department, traffic planners, the HOA and I don't remember the all of the organizations. Um because I think 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.

51:16 the message that I hear from us politicians, and unfortunately this works really well, is Yeah. Things should be good. But they're not. Because someone is doing something bad which is preventing

51:28 The goodness. So Um Billionaires are making things unaffordable or immigrants are taking your jobs. Or um Lazy freeloaders are

51:41 sucking off the government teeth and causing us all have to pay more taxes or something like that. The reality is like Almost nothing works. It's Yeah. Actually another call I said in this case, John has a great encapsulation of this. I'm I'm sure you've 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.

52:02 Requires like Not just the resources and and effort. Yeah. Required to instantiate that thing in the in the real world, but all of the politicking and the sociology and the convincing and um

52:17 There's a book called Uh Why Nothing Works recently, which is like It's not an um I'm sorry to the author if they I doubt they're listening, but just yes. It's not like an amazingly written book. I I I found it like um A little bit repetitive.

52:33 Uh, but the the content was really incredible. Just explaining why it's so hard and How there's this progressive increase in the number of vetoes. that are available for any kind of course of action and how difficulties and this shows up in like, you know, in permitted and firm. new construction and stuff like that. But also shows up, obviously, inside of organizations. And the challenge is that people

52:58 A I think this is evolutionary biological Oh, it's hard for us to understand the world. Except. Bye.

53:07 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. Codes. Shopping last last year.

53:18 It's hard for people to actually like just that. Wow, weather is incredibly Complex and chaotic and ecosystems and climatologies. Same thing with the world, like if If I

53:29 Uh I'm struggling to Um Yeah, pay all of my bills and be able to afford like a little bit of luxury in the sense of like education or a present for my kids or whatever, it's gotta be somebody's fault. Like there has to be a decision that's made. Somewhere.

53:45 The reality is everything is so Complicated. Multivariate. Uh it's not satisfying. It's a terrible Political message.

53:55 Um it's much easier to say that there is like Yeah. 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

54:09 got rid of them or or you know, were 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 it is. organizations as well. Yeah. I'll pause there.

54:25 Uh I know kind of along those lines you're uh A big uh believer in something called Parkinson's Law. Yeah, so that The original of that is uh I think it's nineteen fifty six. It's an article in the Economist By Parkinson.

54:38 Um And Uh The maxim is work expands to fill the time available for its completion. And

54:49 The way that it shows up, this is a little bit subtle, so but Um One of the things I found. I don't have a job.

54:56 is there's much less time pressure and and that Max I'm like. Uh if you want something done, give it to a busy person. Then Inverse is also true that like

55:05 If you're not that busy Wow. Basic things take a really long time. And so Parkinson actually starts off with his example of like You know, writing and posting a letter. Um and it I don't remember who we use 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

55:21 The retired woman who has all the time in the world and it takes her a long time to write the 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 is um For me later when he talks about

55:35 the size of the organization. He uses a bunch of examples. This is again nineteen fifty, 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.

55:54 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 looking right along with it, and the number of administrators goes

56:12 Like this. And The reason this this ties into the work expands to fill the time available for its completion. Is um People

56:23 Higher. And they train and um Here's the kinda sad truth for anyone running a company. is there are exceptions. There's like certain types of engineers that are exception to this.

56:36 But the overwhelming majority of people you hire want to hire more people who report to that. And Because they're

56:44 evil and it's not because 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 the amount of money that you're paid, the uh amount of authority you have inside the organization, and on and on and on. So like we would hire twenty seven for all 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

57:10 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 it's to me very related to the everything is complex. Um

57:25 And uh if you I maybe this is my Butterfeld's Law, I haven't thought about this week 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.

57:40 Um So The the other side of that is like if something seems simple Probably you don't understand. And

57:50 Yeah, there's obvious exceptions to that. But f for anything that involves a large organization or a lot of human beings, if The problem seems simple. You don't. Get it.

58:01 So every Budget process. No Head of engineering, no head of sales, no CFO, no G C is ever gonna come back and say like oh I actually think like next year we can just hire a fewer people or we're gonna keep it five or we're gonna like shrink through attrition'cause we don't need any more people to do it.

58:19 Not because they're evil, not because they're stupid. Uh but it's uh Almost overpowering. impulse inside the organization that often leads to disasters results. And so there's a I'll give one example from

58:31 Flax 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

58:42 important to the example of that it's not disguised as how I'll just reiterate that the people involved aren't stupid or Where evil. Um and one example that's um This from the outside. So the example inside of Slack was um

58:57 We introduced threads, which is the ability to reply to a message inside of a channel. And Let's say you any Post a message. I, Stuart, reply to it. you will automatically get a notification.

59:10 And now Sarah later on replies to The same message, both you and I. Um, as people who have post an thread will receive a notification that there's been more activity. And so what. So like yeah. Every single time anyone replies to it. So in the future.

59:25 First was um Released or like when we did the final product review before it was released. The Input box was pre populated with

59:34 Yeah. the person before you in the thread. And Uh yeah. I was using the feature and I would like

59:41 Put the insertion point there, select all, delete, and then start writing my message. And it's Even if I wanted to at sub one. specifically I almost never wanted to start my sentence with at I'cause it just made it hard to Yeah, reference what they were saying before.

59:57 So I said get rid of this because A I think most people Won't use it. uh if you did want to add someone they're not gonna want to do at the beginning of the sentence. And by the way

1:00:08 you're teaching them to use the product crop. Because it's important that everyone understand. that every previous poster in this thre will automatically receive a notification unless they've Yeah. So okay we release it.

1:00:21 Six months goes by. And suddenly the thing comes back. And so I messaged someone on the team and I said, Hey, there's been a regression this super weird. I don't know what happened, but like the the at thing came back. And we said, Oh no, this is on purpose. We did a bunch of research. And so I was like, what?

1:00:38 And I went through this. And it was If I recall correctly, it wasn't even like T ninety five. certainty on this analysis, but it was something like

1:00:50 When we do this Threads are two point one seven messages long versus two point one four messages long on average for when we don't do it. And so first of all Why is a longer thread?

1:01:04 Maybe a shorter thread is better. Like if 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

1:01:15 The actual statistical analysis. So I'm not gonna claim that it was um Incorrect, but I appreciate this was outside the the bounds of of Certainly that they can have had. But the real thing was

1:01:25 Oh my god. So You guys Foot flags into the product, you A B tested it, you did the instrumentation, you created

1:01:34 tables in the in the database or whatever we're using. To record all 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 unpacking all of the things that would have had to happen for this to come back. And it's like, you know.

1:01:52 thousands of person hours kind of at a minimum'cause any Feature. change at at that scale of organization. It's involving like a dozen people. Engineering QA uh analytics teams project managers User research and stuff like that.

1:02:09 The problem with that Well. I think it was a bad idea. Right. But the problem with that was

1:02:15 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 at least.

1:02:29 Like there's just there's no world in which anyone could imagine. Put in the attention. 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 for people and and all that.

1:02:46 But you know. Ben. To like put the future flags in and to Ship new versions of the product.

1:02:53 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 the 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 things. Like Yeah, guaranteed loser. And I know.

1:03:16 But you that f free. Told you to ask me about this. Yeah. hyper realistic work like activities. And so here's my my My grand theory.

1:03:26 Um hyper realistic work like activities is goes along with this other concept called known valuable work to do. And when I say known, I mean Both.

1:03:37 You know what it is, and you know that it's valuable. And it 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 gonna be valuable. So like starting a business.

1:03:51 Open a bank account because like There's almost infinite generator 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 okay, I'm

1:04:04 Mike. creating a user's table and 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

1:04:15 Everyone's going to work in the morning, they're like Right on and like I have ten things to do and every single one I've done is like something I know how to do and it's like definitely gonna 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 got hired. Every product manager wants to hire a junior product manager.

1:04:36 Every new person, you know, 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 people on my team to do more risk and compliance work, which probably, you know, to some degree is right, but we're gonna have more and more of those people and they're gonna call meetings with 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 FedRamp High and make a Gov Slack?

1:05:04 version, which is gonna 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 it

1:05:21 Complexity is going to be when we wanted to update so the software'cause we updating two totally separate independent systems and It just gets out of whack. And so people end up Like if you hire seventeen product marketers, you're gonna have seventeen 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 gonna do other stuff. Again. Very important. Stupid, not because they're evil, but because they're like, I'm a product marketer and I wanna like

1:05:50 be recognized for my work and my spouse is like Has um uh criticize me because they think like I should have already got promoted in the last cycle and I really gotta demonstrate some wins here and whatever 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

1:06:11 That hyper realistic work like activity is superficially identical to work. Like We are Sitting in a conference room.

1:06:20 And you are pr there's something being protected up there and we're all talking about it. And that's exactly what work Yeah, but yeah. No, hopefully not all of work in for everyone inside your company. But you know, that's Uh

1:06:33 exactly what we do when we're working, but this is actually a fake bit of work and it's So subtle. Good. Hold it. You know, our board members will do it. Every exact

1:06:43 Do it. the further you are from like having all of the context and all the information and Um Then decision making authority and stuff like that.

1:06:52 the easier it is to get trapped in the stuff and people will just perform enormous amounts of hyperrealistic work like activities and have no idea that that's what they're doing. And Yeah. Yeah, the result of that, I guess, is that if you are a leader, if you're manager, director, an executive, the CEO, it's on you to ensure that there is sufficient supply of nonvaluable Do you

1:07:14 Um And There almost always is. Yeah, it's creating the clarity around that, creating the alignment, making sure everyone understands it that's what they're supposed to be doing and and then obviously

1:07:25 Do it. Amazing. I could listen to uh Stuart Rands all day. Hyperrealistic work like activities. We need a coin this. Uh and unfortunately it doesn't make a good acronym. It's pretty ugly. And just to close the loop on that, the The solution is

1:07:41 uh the leader recognizing this is happening and stopping it, telling people why are we spending time on this thing that is not gonna get us anywhere. Yeah. What you just said probably isn't the best way because that sounds like they're yeah. You're chiding them and they're done when it's actually your responsibility to make sure that there's Yeah, sufficient clarity.

1:08:00 Around what The priorities are And Yeah, explicitly say no to things up front and stuff like that. Rather than pen merging and say like, Hey, you guys are much idiots wasting your time on this thing that doesn't matter.

1:08:12 Whose fault is it? Yeah. It's It's an manager's fault. It's the VP of whatever is fault. It's the C X whatever. It's a C Up. It's the the leader of the organization that has the responsibility to make sure that there is sufficient

1:08:26 No valuable work to do. Um And it's that's actually harder than it might appear. Okay.

1:08:33 Uh before we run out of time, I wanna 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

1:08:43 legendary medium post that uh is just I don't know it's become a historic piece of literature in the in annals of product building and s in startups. I haven't heard people ask you much about this recently. So I'm let me just ask a couple of questions. One is just what was the what was the reason you put that out? Why what what was the backstory on writing that memo? Why was it necessary? Well, it it really was an internal Memo and

1:09:06 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.

1:09:22 Uh. Company X. Um if it's slack. Once you're turned off, you like you lose access to all that 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

1:09:36 verbatim I did not change a word of what I said inside the company. Well, I think we were still eight people, maybe Yeah, I had most ten, but I I think it was eight people. It was before Slack launched even. Yeah, it before thought much. It was like when we were doing uh Prior Beta and

1:09:50 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

1:10:05 grew and and scaled. Um And yeah, the That was the that was the 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.

1:10:18 you just as much have to put effort into communicating what the does for them, the problem this is solving for them, the outcome this is gonna achieve for them. Is that a s a good way to think about it? Yeah, and again, you know, like comparing it to Beer or cars. Um

1:10:34 Years. goes back to pre-civilization. Cars were obviously medd in but yes, at some point you had to convince people why they would win a car instead of a horse. Um For Your New um

1:10:48 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 adjacencies and you want to expand into these other categories and ball. Your not just responsible for creating the product, but also to a certain degree creating the market and and creating, you know, this is book uh positioning.

1:11:16 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

1:11:25 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 Jaws meet Star Wars, Star Wars, or it's Uber for Pets or something like that. than to come up with like a uh actual new idea, but you you have to do that'cause you look

1:11:47 If your thing is different. in any significant way from the alternatives. Um you're not just creating the product, you're creating the market. They're really kind of one in the same. The reason I wanted to touch on it is I think still people continue to not listen to this advice and continue 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 this to folks and correct me if I'm missing anything, is just instead of, hey, look at this amazing saddle we've bought.

1:12:15 Would you wanna communicate us here? Go horseback riding. Look at this incredible experience you can have and And then they decide oh shit I need to go buy a saddle to do that. Yeah. And A hundred percent. Um

1:12:27 That aspect of it is is not original because I think that's something that marketers have done for a long time, certainly in in the the Marcom and and advertising, like if you want to sell Harley Davidson's there are people who are gonna 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's not the motorcycle, you're selling like the open road and freedom and the wind in your hair. And if you're Lou Lemon. you are obviously selling yoga pants, but you're also selling like health and aspiration and being the best version of yourself and

1:12:53 Yeah, a bunch of other stuff. So selling that Oh my God. I forgot the classic version of it, you know, like There's the ship. Oh yeah, the nail correct anyway. Yeah, what is that one?

1:13:09 There's the well, there's the one I think about is instead of trying to convince men to build a ship uh and still a yearning for the sea. Yes. Exactly. in history.

1:13:20 Mm. 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 you for advice on pivoting. I uh I d let me just ask when folks come to you asking, should I stick with my idea? Should I pivot?

1:13:41 What sort of advice do you find most helps them? Yeah, I mean I think it's Um Partly Uh.

1:13:51 Yeah. 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

1:14:07 Fact. had an enormous advantage in the fact that we are 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.

1:14:29 We still had like nine million dollars left and everyone still liked the game and we were all happy working on it. But it w I think by that point I had exhausted every None. Ridiculous. Long shot.

1:14:42 idea to make it commercially Successful. Um And so Decided to

1:14:49 Um To abandon it. But Yeah, the default advice for anyone in anything is persevere. It's like you know, kitten hanging off the branch and then

1:15:01 Poster says hang in there. And you know, and 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 to door and was rejected by everyone and then suddenly there was Nike or Or something like that.

1:15:17 Sticking with it long enough, you'll eventually be successful. I think you have to really be coldly rational. And um 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 I'm

1:15:33 Someone will know it. Yeah, yeah, it was the last second I forget. Uh She actually uses glitch and and Slack as an example of like A smart fold, basically. Like a

1:15:46 my expected value here has diminished. This alternative. looks more attractive. And the reason I say you have to be coldly rational about it is because It's fucking humiliating.

1:15:58 Yeah, like like We I convinced So many and you have to convince so many people to get A company have to go 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

1:16:11 Yeah. Here's the the an incredible future 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 and I think for a lot of people Uh

1:16:24 It feels better to just Keep doing it until it dies. Um Of suffocation. due to lack of capital or something like that.

1:16:35 Uh, than to to admit like, okay. Yeah. I was wrong. This didn't This didn't work. And it's it's humiliating, it's painful. It's like

1:16:44 it's wrenching has a bad impact. 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 gonna have a job anymore. So pivots aren't something I take lightly in You shouldn't be um

1:17:13 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 count. Yeah, like if you're Six months into something.

1:17:25 You're just you're still messing around. You're trying to figure out what it is that you're you're building. It's not really a 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

1:17:40 Creating the distance. So that you can make an intellectual rational decision about it rather than an emotional decision is This is essential.

1:17:50 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. Good ideas. Yeah. Yeah. The uh The point you made about just kind of persevering, uh I just had Melanie Perkins, you have Canva in the podcast.

1:18:08 Uh they went through a a hundred investors rejected her before w somebody finally decided to invest and she just kept pushing. Yeah. Slightly different example, right?'Cause like the She believed in the Yeah, then she then she believed in the in the concept in the in the product and like in the in the vision. It was just trying to figure out the right articulation to get

1:18:27 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.

1:18:41 As I said, that have worked with you and The number one theme that came up again and again and again when I asked him about you and what Bas what has stuck most with them is It's just generosity. So I'm gonna read a few examples that I heard from folks uh that are examples of your generosity over the years.

1:18:57 So one person shared that uh He needed a little money before Christmas and you He said, Stuart literally walked me out of the building, went to the cash machine Handed me five hundred dollars. Told me to go home to my family.

1:19:10 Other folks share that when you you talked about glitch just recently when you had to lay people off that you cried real tears. When you're laying people off and then you spend 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 COs too.

1:19:29 Someone else share that you paid a hundred percent of employees' health insurance. To give them just fewer things to think about. Uh when you went public you did a You basically created the best possible situation for employees. No lock up, direct listing.

1:19:42 Mm-hmm. Also with the structure of the Slack deal, people said the acquisition was very employee friendly. There's also just a bunch of ex 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 COVID. You release this fair billing.

1:19:59 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 they Sign the 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.

1:20:14 Stewart 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 me I just want to celebrate you. I think it's really rare and inspiring to

1:20:30 meet a leader like that. Clearly it 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 gonna be

1:20:42 very generous and help people because I know this will help long term. How much of this just in any of 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 raise me right. But I think there's also um

1:20:58 There is a little bit of a lesson there and I'm just gonna assume people's familiarity with the the prisoners' dilemma. Um But You know, acts of generosity to me are oh I am demonstrating that I am going to cooperate.

1:21:11 As we iterate in this game. Um and If you do that, then people will also cooperate and you brought benefit. Oh. Whereas if you never really know if the other person is gonna de fact.

1:21:22 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 at the prisoners dilemma. Um I think another thing.

1:21:37 Yeah, 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

1:21:51 It was In the long run, the measure of s of our success will be the amount of value that we create for 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

1:22:15 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 it I think it's Uh literally true, but it's also like an a an ethical way to run a business and And

1:22:33 Um it's not just that the ethics are 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 gonna be a better place for everyone to work and you're gonna be happier and you're gonna have fewer internal problems and and all that stuff. Um But I think it

1:22:49 really is true that There's no like Especially in the long run. Mm. You can't like

1:22:55 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 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. Um is incredibly important and that implies a real

1:23:17 Generosity. negotiating terms with an an enterprise deal or that's like Policy decisions. I think one one time that it blew up in our face was

1:23:32 Our SLA was like for any downtime you get a hundred times your money back. Um Which was like 'Cause it's from my perspective, it's like you know, if if we're down for two minutes, it doesn't it it's like pennies, it doesn't really make any difference. If we're down for like ten hours or something like that, then we have bigger problems than paying back. People

1:23:49 Great. 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 was, but it was like m 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.

1:24:11 was like Eight million dollars or some something like that. Which had to be um it didn't cost us any money because we just gave it to people with the former credits, but it meant that a bunch of revenue that we had already anticipated for the next quarter wasn't gonna show up because people's credits were gonna offset what they would have otherwise.

1:24:31 Pay us, um And so uh we we definitely change 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, they were all really important decisions that were helpful in Um and us becoming successful.

1:24:47 Was that policy it was automatic, like you didn't even have to claim it. It was just automatically get this credit. And and then the default is you don't have to pay. If you let us know. This was we will automatically, like proactively, preemptively, without any input from you to 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.

1:25:07 for downtime, even if the issue didn't affect you as a customer. You found the the edge where you might want to be. Yeah. 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.

1:25:28 Incredible. I'm just trying to picture the entire team at Slack. It felt very like Chin Jelong or like Stalin or something like that. Well on that note, most people don't know this about you, but you're Uh your actual name when you were born is not Stuart. It was Dharma.

1:25:46 Yeah. And this all makes sense as you learn that. Yeah. My name is Dharma Jamie Batterfelt, that's what my parents named me. And when I was twelve, I changed it because I just luckily wanted to be normal. And for some reason I thought Stuart was a normal name. And by the way, You'll notice this now that I said it.

1:26:01 Any character. Except for Stuart Little, the mouse. Uh anytime you see a character in in a movie, a novel, T V show, whatever There's only the loser steward. And the assholes do it.

1:26:14 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 realize that Dharma and Greg had already come out, it would have seemed like I was

1:26:25 Like Yeah, bandwagon jump in and People thought it was a girl's name, even now in India, it's obviously. Only a boy's name. I'm gonna add just one last little tidbit because I forgot about this earlier on and I think it helps tie things together.

1:26:38 And it's called the owner's delusion. And this is based on something I post on 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 was a long time ago. When restaurant websites have gotten better and

1:26:55 It doesn't really matter because Google Local has taken over everything. But this is like let's say ten years ago. There's five things you could possibly want when you go to a restaurant's website. And is

1:27:05 Street address. Their phone number. The menu. The hours of operation. My God, we're getting the fifty.

1:27:13 Oh, and and making your reservation. How to make a reservation. Um And again, this problem has like to some extent taken care of. It's all at least a brood. But what you would get was like the super slow loading photo with the Ken Burns effect as it goes. And like yeah and then like

1:27:31 fading in and then some music starts playing. And then if they show you the phone number It's not clickable and it turns out 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 effort. And it's just like what

1:27:47 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 it the owner's delusion. And I was like, Oh God, that's perfect. And I think that

1:28:09 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 can possibly mean. And that's why like people anticipate

1:28:26 Um despite the fact that When they get to their web your website for the first time, they're Their intent is Absolutely. the minimum number of micro points above the threshold required for actually take that action.

1:28:41 You're like Alright. Like welcome to my website and there's 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.

1:28:56 And I don't recognize that you Or 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 that you're concerned that your kids will fuck up and they're getting in trouble at school and stuff like that. You know?

1:29:14 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 gonna bounce in a a fraction of a second. And so everyone should always be conscious of the other solution. I love that. What's the solution? Is it have other people look at it and give you feedback? Yeah, and and like recognize it. And unfortunately it's one of those things like Murphy's Law, like even Yeah. You go wrong when you like even when you take into account Ruffy's Law. But if you if you don't name it and recognize it and discuss it and like

1:29:45 Train yourself to think in that way. That Yep, take a breath. pretend you're a regular person and then look at this again and see if it makes sense. I love that. You're screwed.

1:29:55 I love that you threw this in here. I have a billion other questions I w I'm gonna ask you in part two when we do this someday. Uh Stewart, 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.

1:30:10 Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show. at Lenny's podcast dot com. See you in the next episode.

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