Stewart Butterfield: Why thinking is what kills your product

1. 0:00 – 4:58

   Introduction to Stewart Butterfield

   1. SBStewart Butterfield0:00

      (instrumental music) 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 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 designing the product.

   2. LRLenny Rachitsky0:24

      Slack was famous for being one of the early consumerized B2B SaaS products.

   3. SBStewart Butterfield0:29

      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 our customers. And you can put effort into demonstrating that you have created this value. It's not like that, but there's no substitute for actually having created it.

   4. LRLenny Rachitsky0:45

      Something else I heard that you often espouse is friction in a product experience is actually often a good thing.

   5. SBStewart Butterfield0:51

      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 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 the number one goal, or reducing the number of clicks or taps to do something, and instead focus on how can I make this simple? How do I prevent people from having to think in order to use my software?

   6. LRLenny Rachitsky1:15

      You started two companies, both famously pivoted. I imagine many people come to you for advice on pivoting.

   7. SBStewart Butterfield1:19

      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.

   8. LRLenny Rachitsky1:34

      (instrumental music) Today my guest is Stewart Butterfield, a founder and product legend who rarely does podcasts. Stewart 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, 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 and questions for this conversation. This is a really special one and I really hope to have Stewart 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. And if you become an annual subscriber of my newsletter you get 17 incredible products for free for an entire year, including Devin, Lovable, Replit, Bolt, Innit, Linear, Superhuman, Descript, Whisperflow, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, Cheppi RD, and Mobbin. Head on over to lennysnewsletter.com and click Product Pass. With that, I bring you Stewart Butterfield after a short word from our sponsors. Here's a puzzle for you. What do OpenAI, Cursor, Perplexity, Vercel, Plat, and hundreds of other winning companies have in common? The answer is they're all powered by today's sponsor, WorkOS. If you're building software for enterprises you've probably felt the pain of integrating single sign-on, SKIM, RBAC, audit logs and other features required by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer platform built specifically for B2B SaaS. Whether you're a seed stage startup trying to land your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise ready and unlocking growth. They're essentially Stripe for enterprise features. Visit workos.com to get started. Or just hit up their Slack support where they have real engineers in there who answer your questions super fast. WorkOS allows you to build like the best with delightful APIs, comprehensive docs and a smooth developer experience. Go to workos.com to make your app enterprise ready today. This episode is brought to you by Metronome. You just launched your new shiny AI product. The new pricing page looks awesome but behind it, last minute glue code, messy spreadsheets and running ad hoc queries to figure out what to bill. Customers get invoices they can't understand, engineers are chasing billing bugs, finance can't close the books. With Metronome you hand it all off to the real time billing infrastructure that just works. Reliable, flexible and built to grow with you. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand and keeps every team in sync in real time. Whether you're launching usage-based pricing, managing enterprise contracts or rolling out new AI services, Metronome does the heavy lifting so that you can focus on your product, not your billing. That's why some of the fastest growing companies in the world like OpenAI and Anthropic run their billing on Metronome. Visit metronome.com to learn more. That's metronome.com.

2. 4:58 – 6:44

   Stewart’s current life and reflections

   1. LRLenny Rachitsky4:59

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

   2. SBStewart Butterfield5:02

      Thank you for having me. I'm excited.

   3. LRLenny Rachitsky5:05

      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 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 Stewart. I'm curious what you're up to. Hopefully you're just chilling.

   4. SBStewart Butterfield5:28

      I'm mostly just chilling. I left Salesforce, um, two and a half years ago and I have 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, while they're young. Um, 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 this cycle because Cal Henderson who was the CTO of Slack and who also we worked 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 if you can find some way to make software that helped people use their phones less often, then that would be uh, a big winner. But I 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,

3. 6:44 – 10:13

   Understanding utility curves

   1. SBStewart Butterfield6:44

      and stuff like that.

   2. LRLenny Rachitsky6:45

      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.

   3. SBStewart Butterfield7:07

      This is pretty easy 'cause it's a very familiar S curve where, you know, you have, uh, it's flat and it starts 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 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 then it's 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 user's 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 y- 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 could get out of this um, and, and we've hit the mi- the point of diminishing 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 shallow part of the curve, or we're on, 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.

   4. LRLenny Rachitsky9:30

      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 s- 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." So 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 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

4. 10:13 – 15:11

   The concept of divine discontent

   1. LRLenny Rachitsky10:13

      the framework?

   2. SBStewart Butterfield10:13

      Yeah. Yeah. And I think then you layer on another concept like the, um, Bezos used the term divine discontent. Um, 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. And again, this axis can be w- utility is the best general term for it, but it could be quality, convenience, um, speed. It could be any o- 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, you know, forget about thinking about a new feature, you're looking at how the product works overall and usually things get cut an- 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, just so... I want to give an example a- at the opposite extreme 'cause 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 m- very familiar with the trade-offs and prioritization and how hard it can be and blah, blah, blah, blah. But okay, so it, eh, 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 a- 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, 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 term. 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 E-A-S-T and I get a bunch of garbage. Okay, East Ern, E-R-N. 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, fuck, what... I- I can't remember which one is daylight savings and which one is standard time," and well, 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 timezone is presented with equal, you know, value. There's... I don't even know, like couple hundred timezones. I grew up in Canada. There's a... Newfoundland has its own timezone, 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 with China time, which is like 25% of the world's population in this time. Anyway, I... And that was a little bit longer than I intended to go on this example, but it is, um, uh, i- it's crazy 'cause no one's gonna switch to Gmail or to- to GSuite, Google Calendar from Outlook, Exchange because the timezone 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 could be really positive, like they would recommend it and when they switch companies or decide to start their own company, they're gonna choose to use this product or advocate for it because of that emotional connection and vice versa. They'll also be like, "I fucking hate this thing that 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 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 continually

5. 15:11 – 19:03

   The importance of taste in product design

   1. SBStewart Butterfield15:11

      goes up.

   2. LRLenny Rachitsky15:11

      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, consumerized B2B SaaS 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 forward, very craft-oriented 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 had 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?

   3. SBStewart Butterfield15:49

      There is a lot of, you know, 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 detailed improvements beyond the point where it makes much of a 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 chefs with training? Yes, absolutely. Undoubtedly, some people have a natural advantage and are- 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 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, um, I'm- I'm going... I'm in Vancouver at our Vancouver office and I'm going for a walk with Brandon Volostok, who's our, um, at the time, creative director for product development. I think that was his title. And, uh, we're in the Yaletown 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. 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 would move their umbrella out of the 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, and we would get like, you know, forced off the sidewalk or like having to duck down or 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 pass or not?" And something like one third 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 malice that which can be ascribed to 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 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 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, like, they're just oblivious to their impact on, on other people, and they're, they're so in their head. Um, and I can't really think of any other explanations for it besides that.

6. 19:03 – 28:32

   Tilting your umbrella

   1. SBStewart Butterfield19:03

      And so, we would say, at Slack, like, tilting your umbrella is our opportunity. Uh, that's not a great rephrase of a, "Your margin is my opportunity," but your failure to really be considerate and, um, exercise this courtesy and really be empathic about other people's experience is a- a- an advantage that you can credit, critical advantage. And I think that there's many reasons why Slack was successful at the moment it was successful, and, and we 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 a, a, 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, you guys, we really got... This is, this is so good. We've gotta try it." And, uh, and the, the spread was driven by that cross-pollination and, and people really, genuinely advocating for it.

   2. LRLenny Rachitsky20:07

      That is an amazing metaphor (laughs) . I, I love that one moment became like a value of product craftsmanship-

   3. SBStewart Butterfield20:13

      Yeah.

   4. LRLenny Rachitsky20:14

      ... at, at Slack.

   5. SBStewart Butterfield20:14

      And so, "tilt your umbrella" was this like, was a very common saying, and on, you know, company schwag and, and stuff like that.

   6. LRLenny Rachitsky20:20

      Is there an example... I imag- 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 s- core to success?

   7. SBStewart Butterfield20:37

      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, but I, it's maybe Andrea Torres, maybe Ben Brown, someone like that, who was like, "Hey, why, why do 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 their email address and then send them a link?" And so when Slack's first version of the mobile app came out, we were like, "Typing your password on your phone if you have any, you know, minimal threshold of, of password hygiene is a terrible experience," you know, capital H, lowercase Q, six, carat, period. "So let's just have them enter their email address. We'll send them a link. The link will automatically open the app and, and authenticate them." And so there's one, a little example.

   8. LRLenny Rachitsky21:33

      Wow, so you guys invented the magic link, uh, experience?

   9. SBStewart Butterfield21:36

      Well, I didn't... Someone else inv- I want to be clear there.

   10. LRLenny Rachitsky21:37

       Okay.

   11. SBStewart Butterfield21:37

       Uh, I, I had seen that idea somewhere else, like someone else-

   12. LRLenny Rachitsky21:40

       Wow.

   13. SBStewart Butterfield21:40

       ...uh, blog post about it or something like that.

   14. LRLenny Rachitsky21:42

       Yeah.

   15. SBStewart Butterfield21:42

       But we were the first ones that-

   16. LRLenny Rachitsky21:43

       Maybe.

   17. SBStewart Butterfield21:43

       ...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 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, 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, uh... We certainly didn't invent that. That was, that was Twitter. Uh, 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 one person would be like, "I didn't get a notification. This is, this is bullshit." 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 now. I think it's once, 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 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 that investment to get people over the hump. A much more, uh... Well, 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 would 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 gonna do that too for my message." And so all of your messages have the little flag, and it's become useless. We have @everyone, which causes a notification to be sent to every member of the channel when the message is sent, and people would start, you know, look, someone would find this feature inside of an organization. They would @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 gonna also @everyone." And it became really obnoxious and people would complain about it, but it was a, I don't know, a guess tragedy of the 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 be a cock." Um, but we didn't obviously say that publicly. When you @everyone, a little rooster would...... pop up, and it would have, like, these 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 to shape people's behavior so that they used... We wanted Slack 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 trying to shape the communication culture inside the organization to take best advantage of it.

   18. LRLenny Rachitsky25:02

       That feature still exists. I see that rooster all the ti- or no, I don't see it all-

   19. SBStewart Butterfield25:05

       Yeah. (laughs)

   20. LRLenny Rachitsky25:05

       Well, actually, I do @channel 'cause I run a big Slack.

   21. SBStewart Butterfield25:08

       Yeah, yeah.

   22. LRLenny Rachitsky25:08

       Uh, so I see that rooster. It's, uh, that survived.

   23. SBStewart Butterfield25:11

       Yeah. Um, yeah, that survived and, and good, uh, because it's-

   24. LRLenny Rachitsky25:16

       Yes, that's right.

   25. SBStewart Butterfield25:16

       ... it was trivially easy thing to-

   26. LRLenny Rachitsky25:19

       Yeah.

   27. SBStewart Butterfield25:19

       ... implement, and made a really big difference, but it also taught people how the product worked, 'cause I mean, uh, people probably didn't know that @everyone or @channel, um-

   28. LRLenny Rachitsky25:27

       Right.

   29. SBStewart Butterfield25:27

       ... well, didn't think about the cost at least. Um-

   30. LRLenny Rachitsky25:30

       Genius.
7. 28:32 – 45:07

   Balancing friction and comprehension

   1. LRLenny Rachitsky28:32

      I heard that you often espouse, which is counterintuitive to a lot of people, is, is about friction, friction in-

   2. SBStewart Butterfield28:38

      Mm-hmm.

   3. LRLenny Rachitsky28:38

      ... a product experience, that friction is actually often a good thing, that you actually... it's a feature, not a bug a lot of times-

   4. SBStewart Butterfield28:43

      Yep.

   5. LRLenny Rachitsky28:43

      ... if you use it well. Talk about your, your experience there.

   6. SBStewart Butterfield28:46

      Yeah, well, and so yes, um, and there's also another, um, issue around friction, which is it, it became, I don't know, like a mantra or just like a kind of a- 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, 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, 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 a beer, um, but everyone would have to be explained why they, why they want Slack. Um, and so the problem there is, 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 Ticketmaster website. If you think about both your, y- 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 like, 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 errors out. Like you're gonna persist and, and get through it. So obviously it's- they're better to reduce friction, but 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, 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 or 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 my intent's like 70%, so if you're... th- the amount of friction is, uh, above that, I just- I'm not gonna do 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 decided, "Okay, I'm gonna go to 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 'cause 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, you know, .1% over these- these critical thresholds. Um, 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- or whatever, and the, um, the visual hierarchy and the affordances that are there and the- and the, um, indication of things to interact, uh, 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 webpage to the sign-up form as quickly as possible." But if they don't know what they're signing up for and they don't know what it's gonna do after, is it gonna spam them, um, they don't know w- uh, "Am I gonna have to pay on the next step?" Or- or what, then they're just gonna 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 a product design is in that comprehension step because like, people, if they do ever open the preferences tab and look at all of 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 gonna take advantage of them and they're not gonna get as much out of it. And then I think the- 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, are areas where the challenge is gonna be comprehension instead of friction. It- it really could be anything, like, Shopify, um, the purpose of the- of the service for its end users is generally gonna be kinda 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- 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 wanna see if this is still true, I'm just gonna open my- my phone, um, and the clock app. And they had the most, the- the craziest description for alarms. Uh, okay, uh, it- it's still, it's a little bit different. Um, people can look at their own phone.

   7. LRLenny Rachitsky35:26

      Mm-hmm.

   8. SBStewart Butterfield35:26

      Uh, 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, ungrammatical and incomprehensible and why would you ever do it? And, uh, I gotta guess, it- it's been like this for years, 90+% and- and maybe like 98% of people just do what 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 sleep on does, um, but it's, uh, just like, the- the lack of comprehension prevents people from getting the value and I'm sure that there is a bunch of value behind turning sleep on, whatever that means, and people spend a lot of time on those features and it integrates with like, biometrics in your watch or who knows? I- I, again, I still don't know because turning sleep on is like, I don't, what does that do? And what is it gonna cost me and what impact is it 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, is because I didn't understand what they were 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.

   9. LRLenny Rachitsky37:02

      Absolutely.

   10. SBStewart Butterfield37:04

       Um, yeah. And honestly, it's been...... many more than ten years since I read it, so I don't even remember all of 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, i- i- 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- 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 know, maybe their orientation is, okay, th- 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 technologically s- 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 b- 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 gonna associate that with the product forever. And, I mean, these are things that are just kind of rolling one into the other so I'm gonna, uh, keep going with one last thing, 'cause 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- a little bit of that is good? And, y- you know, here's an 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, uh, sorry, 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 submenu that has more items. And you-

   11. NANarrator39:44

       Mm-hmm.

   12. SBStewart Butterfield39:44

       The decision of, like, h- how to tune that becomes incredibly important. Um, I'm gonna pick on Google again, just because it is... I'm feeling like I'm Donald Trump here, but I'm gonna interrupt myself again with a story. It's-

   13. NANarrator39:57

       Yeah, that's too right.

   14. SBStewart Butterfield39:57

       ... I'm at some, some conference or event, I don't remember where it was. And this is probably eight years ago, and, uh, it's... We're in the bar after the session's ended in this thing, and John Collison from Stripe is there, um, and, uh, Sundar, CEO of Google is there, and John... Uh, I'm sorry. Patrick goes up to, to Sundar, uh, and they can talk about anything, right? Like, you know, Stripe wasn't, uh, the behemoth it was now a- at that point, but it was still, like, a, you know, a significant company. It was up and coming. And what does, uh, Patrick want to talk to Sundar 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 s- the, the To recipient to the CC and move someone from CC to To or something like that. And just how f- 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 really struck me that, like, you know, Patrick could've asked for anything. Like, it could've been any topic. It could've 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 s- 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 is an unlabeled icon, is the only way to do it, and that's to, 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 because some of them have to do with an individual email and 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, uh... Tap in both menus, 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." 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 a... Any- anything you could do in Uber. And that was perfect, because m- almost all of the time people just wanted to choose where they wanted to go. Sometimes you wanted to change where your pickup was 'cause you weren't there yet or, or whatever. And that was just, like, what could be simpler than, "I'm gonna tell you where I wanna go or I'm gonna choose something else"? I really tried to push people to, what is the thing that people, or what is the two things, or what is the 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, th- you know, it 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 the number one 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 having to think in order to use my software? How can I make this trivially easy?" One, one last example, uh, because this, this was re- 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 jetway and it took a long time. And I was watching her use Snapchat, and it was 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 den- like, "Do I wanna see this again? Do I wanna see the next story from this person? Do I wanna switch to a different person? Do I..." Uh, like instead, she, she, um, a notification came up, she answered someone's thing, she took a selfie of herself, and everything was just like... (makes rapid firing noises with mouth) So she was, you know, tapping four times a second for 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 15-year-old girl in 2016 or whenever that was. Um, and imagine if the goal was to try to make her tap 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?

   15. LRLenny Rachitsky45:06

       It's so fun to listen

8. 45:07 – 47:06

   The value of constant dissatisfaction

   1. LRLenny Rachitsky45:07

      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, 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.

   2. SBStewart Butterfield45:27

      Yeah.

   3. LRLenny Rachitsky45:28

      I love just even the way you summarized this, just like a really good reframing of instead of obsessing with reducing friction and reducing steps, instead think, "How do I, h- how do I, uh, reduce the amount of thinking the 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 to actually think, and your goal is to reduce that, versus, "Let's just reduce friction, reduce clicks."

   4. SBStewart Butterfield45:52

      Yeah. Uh, I think, um, in my more cynical examples, I would, I would say to people like, "Stop what, 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 nother related cycle, but before I get into it, 'cause I know that I am verbose, um, I wanna f- wrap up your, your last example of people being unsatisfied. So here's the quote that I was trying to find. This is, um, 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 shit. Like, it's just terrible, and we should be humiliated that we offered this to the public." Not everyone finds that motivational, though.

9. 47:06 – 50:03

   Embracing continuous improvement

   1. SBStewart Butterfield47:06

      So, I came into the office the next day, and people had printed out on like 40 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 be embarrassed by it. Like, it should be a perpetual desire to improv- You should never be like, "Oh, this is great." I mean, you can 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, a- 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 Bridgewater tells about, uh, Michael Jordan l-

   2. LRLenny Rachitsky48:11

      Ray Dalio.

   3. SBStewart Butterfield48:12

      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 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 the point where like, "Hey, we are trying to, to find improvements. We're trying to be critical because we're trying to make this as great as it can 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, 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 of the product 'cause you realize, "Oh, yeah. That is, that is bad and we should fix it."

   4. LRLenny Rachitsky49:10

      This episode is brought to you by Lovable. Not only are they the fastest growing company in history, I use it regularly and I could not recommend it more highly. If you've ever had an idea for an app, but didn't know where to start, Lovable is for you. Lovable lets you build working apps and websites by simply chatting with AI. Then you can customize it, add automations, and deploy it to a live domain. It's perfect for marketers spinning up tools, product managers prototyping new ideas, and founders launching their next business. Unlike no-code tools, Lovable isn't about static pages, it builds full apps with real functionality, and it's fast. What used to take weeks, months or years, you can now do over a weekend. So if you've been sitting on an idea, now is the time to bring it to life. Get started for free at lovable.dev. That's lovable.dev. This makes me think about, uh, a... Let's call it

10. 50:03 – 54:27

    The complexity of making things work

    1. LRLenny Rachitsky50:03

       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. Can you just share- share what you share there?

    2. SBStewart Butterfield50:13

       Yeah. Um, I mean, so this has a lot to do with, um... And maybe this is more recent than the other. It shows up in politics a lot for me. Um, but, uh, by the way, if any of your- everyone listening to this can help me find this tweet storm from somewhere between 2016 and 2020, 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 set up. And I think it- I believe it was in response to someone claiming that Bitcoin is going to replace US dollars. Um, there's 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 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 had I did, then I could search better-

    3. LRLenny Rachitsky51:07

       (laughs)

    4. SBStewart Butterfield51:07

       ... 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, un- 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, um, lazy freeloaders are sucking off the government teet and causing us all have to pay more taxes, or something like that. The reality is, like, almost nothing works. It's, uh, actually another cause in this case, Jon has a great encapsulation of this, I'm- 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 re- 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 re- recently, which is like, it's not an am- I'm sorry to the author if they're... I doubt they're listening, but just it's not like an amazingly written book. I- I found it like, um, a little bit repetitive, 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- of vetoes that are available for any kind of course of action and how difficult it is. And this shows up in like, you know, in permitting for new construction and stuff like that. But it also shows up obviously inside of organizations. And the challenge is that people, A, I think this is evolutionary, biological, oh, 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.

    5. LRLenny Rachitsky53:18

       (laughs)

    6. SBStewart Butterfield53:19

       It's hard for people to understand like just that, well, weather is incredibly complex and chaotic and ecosystems and climatology, blah, blah. Same thing with the world. Like if- if I, uh, am struggling to, um, 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 is so complicated. Everything is so multivariate. Um, it's not satisfying. It's a terrible political message. Um, it's much easier to say that there is like, um... 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- 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 of organizations as well. I'll- I'll pause there.

    7. LRLenny Rachitsky54:25

       Uh, I know, kind of along those lines, you're

11. 54:27 – 1:03:17

    Parkinson’s law and organizational growth

    1. LRLenny Rachitsky54:27

       a- a big, uh, believer in something called Parkinson's law.

    2. SBStewart Butterfield54:31

       Yeah. So that, the original of that is, uh, I think it's 1956. It's an article in The Economist 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. So 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 maxim 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, uh-Um, and it- I don't remember who he used for his 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 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 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. A 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, te- 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 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 of engineers that are exception 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, because everyone knows that the number of people who report to you correlates with, like, your career trajectory, your, the, the amount of money that you're paid, the, um, amount of authority you have inside the organization and on and on and on. So like we would hire 27 year 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."

    3. NANarrator57:11

       Classic.

    4. SBStewart Butterfield57:12

       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 that everything is complex. Um, and, uh, i- if you... Maybe this is my Butterfield's law, I haven't thought about this one 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 overpowering impulse inside the organization that often leads to disastrous results. 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 Slack was, um, we introduced threads, which was the ability to reply to a message inside of a channel. And let's say you, Lenny post a message. I, Stewart, 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 in 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 pre-populated with "at" the person before you in the thread. And I'd, 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 because A ) I think most people won't use it or if they, uh, if they did want to @ 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 muted it. So okay, we release it, 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 is super weird. I don't know what happened, but like the, the @ thing came back." And they said, "Oh no, this is on 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, maybe a shorter thread is better, like it'd 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, uh, certainty that they could've had. But the real thing was, oh my God, so you guys put flags into the product. You A/B tested it, you did the instrumentation, you created tables in the, in the database or whatever we were using t- 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 unpacking all of the things that would have had to happen for this to come back and it's like, you know, thousands of person hours kind of at a minimum. 'Cause any feature change at, at that scale of an organization is involving like a dozen people, engineering, QA, uh, analytics teams, project managers, user research, and stuff like that. The problem with that we- 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. Like there's just, there's no world in which anyone could imagine putting the @ 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. 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 'cause someone couldn't make it, to have everyone sit down and look at the thing, like, you know, guaranteed loser. And I know that y-

12. 1:03:17 – 1:13:23

    Hyper-realistic work-like activities

    1. SBStewart Butterfield1:03:17

       that Farid told you to ask me about this-

    2. LRLenny Rachitsky1:03:19

       Mm-hmm. Yeah.

    3. SBStewart Butterfield1:03:20

       ... um, hyper-realistic work-like activities. And so here's my, my, my grand theory. 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 you know what it is and you know that 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 gonna 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, "Okay, I'm like creating a user's 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 it's like everyone's going to work in the morning, they're like, "Right on, and like I, 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 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 get hired. Every product manager wants to hire a junior product manager. Every new person, uh, you know, the first person you bring on 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 GovSlack 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 is, complexity is gonna be when we wanna do updates to the software 'cause we gotta update two totally separate independent systems and..." Right? It just gets out of whack. And so people end up, like if you hire 17 product marketers, you're gonna 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 gonna 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 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 gonna show in the big meeting to get feedback on whether they should, like, improve some of the slides. And that hyper-realistic work-like activity is superficially identical to work. Like, we are sitting in a conference room and you are pre- there's something being projected up there and we're all talking about it. And that's exactly what work is. (laughs)

    4. LRLenny Rachitsky1:06:27

       Yeah.

    5. SBStewart Butterfield1:06:27

       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 exec will do it. A- and the further you are from like having all of the context and all of the information and, um, the decision-making authority and stuff like that, the easier it is to get trapped in this stuff. And people will just perform enormous amounts of hyper-realistic work-like 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 it, that, that's what they're supposed to be doing and, and then obviously doing it.

    6. LRLenny Rachitsky1:07:26

       Amazing. I could listen to, uh, Stewart Rans all day. (laughs) Hyper-realistic work-like activities. We need to coin this.

    7. SBStewart Butterfield1:07:33

       Yeah.

    8. LRLenny Rachitsky1:07:33

       Uh, and the-

    9. SBStewart Butterfield1:07:34

       It's- unfortunately, it doesn't make a good acronym. It's pretty ugly. speaker<|agent|><|en|>

    10. LRLenny Rachitsky1:07:36

        Okay, okay. (laughs)

    11. SBStewart Butterfield1:07:37

        It's a consequence of violence.

    12. LRLenny Rachitsky1:07:37

        I'm gonna give it a try.

    13. SBStewart Butterfield1:07:38

        (laughs)

    14. LRLenny Rachitsky1:07:38

        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 gonna get us anywhere?"

    15. SBStewart Butterfield1:07:48

        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, exclusively saying no to things upfront and stuff like that. Rather than speaker 2 marge in and say like, "Hey, you guys are bunch of 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.

    16. LRLenny Rachitsky1:08:27

        Mm-hmm.

    17. SBStewart Butterfield1:08:28

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

    18. LRLenny Rachitsky1:08:32

        Okay. Uh, before we run out of time, I wanna touch on two other topics. One is, when people think of Stewart 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 annals of product building and s- and startups. I haven't heard people ask you much about this recently, so let me just ask a couple questions. One is just, what was the, what was the reason you put that out? Why, wha- what was the backstory on writing that memo? Why was it necessary?

    19. SBStewart Butterfield1:09:01

        Well, it really was an internal memo. And as a bit of a digression, um, one of the, the crappy things about Slack, um, is if all your cor- 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 you're turned off, you like, you lose access to all that history.

    20. LRLenny Rachitsky1:09:27

        Mm-hmm.

    21. SBStewart Butterfield1:09:27

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

    22. LRLenny Rachitsky1:09:45

        It was before Slack launched even.

    23. SBStewart Butterfield1:09:47

        Yeah, it was before Slack launched. It was like when we were doing, uh, 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 process to survive as we grew and, and scaled. Um, and yeah, that, that was the, that was the idea.

    24. LRLenny Rachitsky1:10:11

        And the gist, just for people that aren't super familiar with it but will 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 gonna achieve for them. Is that a s- a good way to think about it?

    25. SBStewart Butterfield1:10:28

        Yeah. And again, you know, comparing it to beer or cars, um, beer is, goes back to pre-civilization. Cars were obviously made then. But at some point, you had to convince people why they would want 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 adjacencies and you want to expand into these other categories and blah, blah. You're not just responsible for creating the product, but also to a certain degree creating the market an- 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 Jaws 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 'cause you... Look, 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 and the same.

    26. LRLenny Rachitsky1:11:56

        The reason I wanted to touch on it is I think still people continue to not listen to this advice and con- con- 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 which we want to communicate is here, go horseback riding. Look at this incredible experience you can have." And, and then they decide, "Oh, should I, you know, go buy a saddle to do that?"

    27. SBStewart Butterfield1:12:23

        Yeah. And it, and, uh, 100% um, that aspect of it is, is not original 'cause I think that's something that marketers have done for a long time, certainly in the, in MarCom and, and advertising. Like, if you want to sell Harley-Davidsons, 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 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 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, you know, the selling the-

    28. LRLenny Rachitsky1:13:00

        There's the ship?

    29. SBStewart Butterfield1:13:01

        The, those, those like-

    30. LRLenny Rachitsky1:13:01

        Yeah, instead of-
13. 1:13:23 – 1:18:36

    Advice on when to pivot

    1. LRLenny Rachitsky1:13:23

       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, (laughs) into very successful 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?

    2. SBStewart Butterfield1:13:43

       Yeah. I mean, I think, it's, um, partly, uh, a, 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 it w- I think by that point, I had exhausted every non-ridiculous long shot idea to make it 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 the 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. 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, know how to ... You know, some of this shows up in the book, um, thinking about, some of it's in Annie Duke's second book, uh, w- the title of which I'm forgetting right now, but I'm, someone will, will know it.

    3. LRLenny Rachitsky1:15:35

       Yeah, 15 Bets and then-

    4. SBStewart Butterfield1:15:36

       And she actually uses-

    5. LRLenny Rachitsky1:15:36

       ... yeah, what was the last, second one, I forget.

    6. SBStewart Butterfield1:15:38

       Yeah. Uh, she actually uses Glitch and, and Slack as an example of like-

    7. LRLenny Rachitsky1:15:43

       Mm-hmm.

    8. SBStewart Butterfield1:15:43

       ... a smart fold basically, like-

    9. LRLenny Rachitsky1:15:45

       Mm-hmm.

    10. SBStewart Butterfield1:15:46

        ... I, I, 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 fucking humiliating, you know? Like, like, w- we, I convinced so many ... And you have to convince so many people to get a company off the ground. 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 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 to convince them to give up their time for this thing. And so it's, I mean, I think for a lot of people, uh, it feels better (laughs) to just keep doing it until it dies, um, of suffocation due to lack of capital or something like that, uh, than to, to admit like, "Okay, th- I 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 shut down Glitch, there was 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 had 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 those job now weren't gonna 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 count, you know? Like if you're six months into something, you're just, you're still messing around. You're trying to figure out what it is that you're, you're building. That'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, 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.

    11. LRLenny Rachitsky1:17:50

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

    12. SBStewart Butterfield1:17:56

        Yeah. Exhaust all the, all the good ideas.

    13. LRLenny Rachitsky1:17:59

        All the good ideas.

    14. SBStewart Butterfield1:18:00

        All the realistic. Yeah.

    15. LRLenny Rachitsky1:18:01

        Yeah. The, uh, the point you made about just kind of persevering. Uh, I just had Melanie Perkins, CEO of Canva on the podcast. Uh, they went through a, 100 investors rejected her before somebody finally decided to invest, and she just kept pushing.

Episode duration: 1:30:35