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

26:48And we told them that we were going to set a default for their organization, which I believe was either 7 p.m. to 7 a.m. in their local time zone or 8 a.m. to 8 p.m. And I can't remember which it was. But also that they could override that default. and also that the individual end users could override that system owner default. And finally, that the system owner could, if they change the default again, would override all of the end users' preferences, and then the end users could overwrite them again. And it wasn't to create this dynamic where people were at war, but so that you could change a policy and then people could still customize and stuff like that.

27:31But this was a much longer and more convoluted process, but it allowed the millions of people who were using Slack to get the feature without creating a bunch of conflict and without people turning it off automatically. And I think critically, with setting a bunch of defaults, because if we didn't set the default, most people wouldn't turn it on at all. If we didn't default you to do not disturb from 8 p.m. to 8 a.m., you probably, if you're the average person, wouldn't ever do it yourself. So that's another elaborate example where I think that investment made sense because it was a critical feature for a lot of people.

28:14And if we hadn't done it that way, I think it would have caused a lot of complaints and conflict and stuff like that. Those are amazing examples. I very much appreciate that do not disturb feature when you guys launched that. I still remember that coming out. I'm sure a lot of people are very thankful for that. Yeah. Something else I heard that you often espouse, which is counterintuitive to a lot of people, is about friction, friction in the product experience. That friction is actually often a good thing. It's a feature, not a bug a lot of times. If you use it well, talk about your experience there.

28:46Yeah. Well, so yes. And there's also another issue around friction, which is it became like a mantra or just like a kind of an assumption that you should always be trying to remove friction. And in some cases, that's true. You know, we would talk about it in Slack. It was hard to market. It's hard to explain what it was if you had never used it before. You could say a messaging app for businesses or whatever. But a critical disadvantage to Slack doing out-of-home advertising, putting up a billboard, versus beer or cars is no one needs to be explained why they would want a car or beer. But everyone would have to be explained why they want Slack.

29:30And so the problem there is comprehension. And this will come up 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 comprehension, it's perfect in this case, and 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.

30:08It doesn't really matter if the payments page airs out. You're going to persist and get through it. So obviously, they're better to reduce friction, but in some sense, there's not a huge amount of value in doing that. For most creators of products, there are a handful of cases where that really is true for you as well. And they include things like user registration, authentication, checkout flows for e-commerce. 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 I have to manually enter all of the fields of my address one at a time rather than having one of those address pickers.

30:54It's crazy, but the issue is my intent isn't always 100%, and the specificity of my intent isn't always 100%. Yeah. 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, this looks like a good t-shirt to me, but I'm rarely like 100 % intent. I might have like a very specific intent, but my intent's like 70%. So if the amount of friction is above that, I'm not going to 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 said 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.

31:58The specificity of their intent, like I need to get Taylor Swift concerts for this day to this venue, is also very low because they're like, it's a work thing. I'm not sure it's a spreadsheet or like a calendar or do you look exactly what it is? So they were coming in at 0.1 % over these these critical thresholds. 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?

32:39And what am I supposed to do next? And that creation of comprehension, in the sense of explaining stuff, that creation of comprehension in the sense of the design of the UI, of the screen, of the page or whatever, and the visual hierarchy and the affordances that are there and the indication of things to interact with 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 for them as quickly as possible. But if they don't know what they're signing up for, they don't know what it's going to do after, is it going to spam them?

33:22They don't know, am I going to have to pay on the next step or what? Then they're just going to back out. And this was like a lifelong battle because the remove friction kind of orientation is so deep in people. Again, it really makes a difference in those cases where people do have an intent and they do know what they're trying to do um it is 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 the options rarely have an idea and if you can't teach them or make it possible for them to discover what the capabilities are, then they're not going to take advantage of them and they're not going to get as much out of it.

34:20And I think that the trick is for most of the unique parts of any application, most of the specific things that your app, your product, your software does are areas where the challenge is going to be comprehension instead of friction. It really could be anything. Shopify, the purpose of the of the service for its end users is generally going to be kind of clear. But most people, most first-time store openers, don't know that they can get reports. Or if they know that they can get reports, they don't know what kinds of reports. And if they know what kinds of reports they can get, they don't know how they can tweak them and how they can, you know, what the timing should be and which things that are more important to display.

35:03And I could go on and on and on and on. And people just don't recognize that. So, like, I want to see if this is still true. I'm just going to open my iPhone and a clock app. And they had the craziest description for alarms. Okay, it's still a little bit different. People can look at their own phone. So I have, it says alarms, and then it says sleep, and a vertical bar, wake up, and says no alarm, and a button that says change. And then if you hit it, it says, sleep is off. In order to automatically turn on sleep features and edit your schedule, you need to turn sleep on. So obviously, sleep was a good name for this thing.

35:49If you already had a way of getting people to understand it, if you don't, it's ungrammatical and incomprehensible. And why would you ever do it? And I got to guess, it's been like this for years, 90 plus percent, and maybe 98 % of people just do what I do, which is that you just create, like, I want the alarm on and I'm going to set the time for it. And I don't know what turning sleep on does. But it's just like, the lack of comprehension prevents people from getting the value. And I'm sure that there's a bunch of value behind turning sleep on, whatever that means. And people spend a lot of time on those features, and it integrates with like, biometrics and your watch or who knows.

36:31Again, I still don't know, because turning sleep on is like, what does that do? And what is it going to cost me? And what impact is it going to have? Those examples are just, to me, all over the place. And 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're going to 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 book. Absolutely. Yeah. And honestly, it's been many more than 10 years since I read it.

37:08So I don't even remember all the examples in the book. But as a mantra, that was like up there with utility curves, because for two reasons. One is it's just like, it'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 and your neurons and like a bunch of stuff is happening and people do get decision fatigue and there is like, you know, cognitive cost of all these things. But also there's an emotional aspect, which is if you, if your software kind of stops me a second and asks me to make a decision and I don't really understand it, you make me feel stupid, right?

37:45I'm like, I don't understand this. I, some people are, are, you know, maybe their orientation is, okay, that the software is stupid, but I think most people are like, oh, I'm dumb. And if you ever talk to people who aren't especially technologically 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. They're the ones that are wrong. And so if you're causing people to think, in the best case, it's like unnecessary use of their biological resources.

38:23And in the worst case, you've like now made them feel bad, like emotionally bad. And they're going to associate that with the product forever. And these are things that are just kind of rolling one into the other. So I'm going to keep going with one last thing. Because they just kind of come together, which is along with reduced 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 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.

39:05Right. And obviously that's terrible. So why do people think that a little bit of that is good? And, 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 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 wherever and then have some form of other and you you know then you go to a sub menu that has more items and the decision of like how to tune that becomes incredibly important.

39:49I'm going to pick on Google again, just because it is, I feel like I'm Donald Trump here, but I'm going to interrupt myself again with a story. It's some conference or event, and I don't remember what it was, and this is probably eight years ago. And we're in the bar after the sessions ended at this thing. And John Collison from Stripe is there. And Sundar, CEO of Google, is there. And Patrick goes up to Sundar. And they can talk about anything, right? Like, you know, Stripe wasn't the behemoth it was now at that point, but it was still like, you know, a significant company was up and coming. And what does Patrick want to talk to Sundar about?

40:32It's in the Gmail app, the dragging of people. Like, When you reply all to a message, you often want to change the two recipient to the CC and move someone from CC to two or something like that. And just how physically, 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 Patrick could have asked for anything. It could have been any topic. It could have been a partnership. It was so irritating to him that it worked like this and couldn't quite get over it. So anyway, back to bashing on Google, who in many respects do an incredible job and there's all kinds of amazing stuff they do and blah, blah, blah.

41:19But 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 mark something as unread once it's read. I have no idea why some of the actions are in one menu and some of the actions are in another menu. I think it's because some of them have to do with the 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 menus, read all of the options and say, okay, I've used the process of elimination and it's not here, so it must be there.

42:11Uber 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, set your location, anything you could do in Uber. And that was perfect because 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 whatever. And that was just like, what could be simpler than, I'm going to tell you where I want to go or I'm going to choose something else.

42:47I really tried to push people to what is the thing that people, or what is the two things, what is maybe three things that people could want to do here, and then put everything behind other. And then if it takes then eight clicks or taps to do something, but every single one is trivially easy, that's great. If 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 which thing is the right thing. And comparing three things to each other is this difficult. Four things, it's kind of like geometrically more expensive.

43:25To compare 15 different options all to the other to see if this is the one that you might want just becomes impossibly expensive. So to me, those are all really connected. And if people could get over the idea of reducing friction as a number of goal or reducing the number of flex or taps, 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? How can I make this really easy? One last example, because this was really influential for me. So I was going back and forth in Vancouver and San Francisco at the time when we were talking about all this inside Slack.

44:00And I was behind a teenager in line to board the plane. And it was like, we're on the jetway. 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 dead the draw to see this again do i want to see the next story from this person do i ask her to a different person do i 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 so she was you know tapping four times a second for six minutes i mean probably there were 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 cap less you know like how much of an impediment it would have been to the experience that both her and Snapchat wanted to create.

45:06It's so fun to listen to this and the examples you gave of, it gives us a lot of insight into the way your mind works of just constantly unsatisfied with the way other products work, with your products. And I think that's core, like Patrick is a good example of Stripe. I feel like that's a recurring theme with very successful product leaders, just constantly unsatisfied and unhappy with how things work. Yeah. I love just even the way you summarize this, just like a really good reframing of instead of obsessing with reducing friction and reducing steps, instead think, how do I reduce the amount of thinking the user has to do?

45:42I've never heard of it described as like, you have to think about the ATP and glucose being used to actually think and your goal is to reduce that versus let's just reduce friction, reduce clicks. Yeah, I think in my more cynical examples, I would say to people, 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 action you're supposed to take, or what the impact will be if you take that action?

46:19there's a whole another related cycle but before i get into it because i know that i'm verbose um i want to wrap up your your last example of people being unsatisfied so here's the quote that i was trying to find this is um 2014 so like 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 MIT Technology Review and asked if we were working to improve Slack. 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. It's just terrible, and we should be humiliated that we offer this to the public.

47:03Not everyone finds that motivational, though. So I came into the office the next day, and people had printed out on 40 pieces of 8.5x11 paper, that quote, and pasted it up on the wall. But to me, that was like, you should be embarrassed by it. Like, it should be a perpetual desire to improve. You should never be like, oh, this is great. And you could be proud of individual pieces of work. But in the aggregate, if you can't see almost limitless opportunities to improve, then you shouldn't be designing the product, or you shouldn't be in charge of the company, or you shouldn't, you know. um almost nothing you know again you could reduce it down to a tiny feature is anywhere close to to perfect and if a that's acknowledged freely inside the organization and b people think about like continually improving as the goal and that could be like six sigma toyota kaizen like that kind of side of thing or it could be that story that um i can't remember his name right now the I started Bridgewater tells about Michael Jordan.

48:12Ray Dalio. Yeah, Ray Dalio in his book talks about Michael Jordan learning to ski. Every time he messed up, he wanted the skier 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 he could 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. But if you can get to the point where like, hey, we are trying to find improvements. We're trying to be critical because we're trying to make this as great as it can possibly be. 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.

48:56It is like, you know, people are 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 bad and we should fix it. 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.

49:32It's perfect for marketers spinning up tools, product managers prototyping new ideas, and founders launching their next business. Unlike NoCoTools, 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, let's call it a rant that you have. about how it takes a lot of work to make anything work at all, that just the default state is not working.

50:10Can you just share what you share there? Yeah. I mean, so this is a lot to do with, and maybe this is more recently, it shows up in politics a lot for me. But by the way, if anyone listening to this can help me find this tweet storm from somewhere between 2016 and 2020. I don't have a precise idea. And it was this guy's thread about how hard it was to get a stop sign set up. And I believe it was in response to someone claiming that Bitcoin is going to replace US dollars. It was 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.

50:54And the literal years it took and the number of agencies that were involved, like the engineering Department, Traffic Managers, the HOA, I don't remember all of the organizations, because if I did, then 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 most places. The message that I hear from most politicians, and unfortunately this works really well, is things should be good, but they're not because someone is doing something bad, which is preventing the goodness. So billionaires are making things unaffordable, or immigrants are taking your jobs, or lazy freeloaders are sucking off a government and causing us all have to pay more taxes or something like that.

51:45The reality is almost nothing works. Actually, another call I said in this case, John has a great encapsulation of this. I'm sure you're familiar with it, that it ends with the world is a museum of passion projects because for anything to get done at all requires not just the resources and effort required to instantiate that thing in the real world, but all of the politicking and the sociology and the convincing. And there's a book called Why Nothing Works recently, which is like, it's not an, I'm sorry to the author if they're out there listening, but it's not like an amazingly written book. I found it like a little bit repetitive, but the content was really incredible.

52:35Just 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 difficult it is. And this shows up in permitting for new construction and stuff like that, but also shows up, obviously, inside of organizations. And the challenge is that people, A, I think this is evolutionary, biological, it's hard for us to understand the world except by anthropomorphizing it. And so 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 year. It's hard for people to understand just that, wow, weather is incredibly complex and chaotic and ecosystems and climatology.

53:26Same thing with the world. If I am struggling to pay all of my bills and be able to afford a little bit of luxury in the sense of education or present for my kids or whatever, it's got to be somebody's fault. There has to be a decision that's made somewhere. And the reality is everything is so complicated. Everything is so multivariate. It's not satisfying. It's a terrible political message. It's much easier to say that there is like, oh, we understand why things are bad in the way that you're concerned about, and it turns out that it's someone's decision, and because of them, it's bad. And so if we got rid of them or were able to overcome their decision, overturn it, and institute our own thing, then things would be good for you.

54:19And this really, to me, shows up inside organizations as well. I'll pause there. I know kind of along those lines, you're a big believer in something called Parkinson's law. Yeah. So the original of that is, I think it's 1956. It's an article in The Economist by Parkinson. And 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 one of the things I found, since I don't have a job, is there's much less time pressure. And that makes sense, if you want something done, give it to a busy person. The inverse is also true, that if you're not that busy, wow, basic things take a really long time.

55:09And so Parkinson actually starts off with his example of writing and posting a letter. And I don't remember who he used for the first example, but someone who's 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 room, 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 for me later when he talks about the size of the organization. He uses a bunch of examples This is, again, 1950s, and he's British.

55:43So he's looking at 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, and the number of administrators. and very familiar graph 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, 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 ties into the work expands to fill the time available for its completion is people hire and they train.

56:24And 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 accepting to this, but the overwhelming majority of people you hire want to hire more people who report to them. And it's not because they're evil and it's not because they're stupid. In fact, they're smart because everyone knows that the number of people who report to you correlates with your career trajectory, the amount of money that you're paid, the amount of authority you have inside the organization, and on and on and on. So we would hire 27-year-old product managers in Slack who immediately want to hire someone.

57:01It's like, what the hell? What would that person do? And they articulate it this way, but essentially it's like, well, that person would do the product management and then I would do strategy. Classic. It's really, I think, the essential thing to understand about this is it's not because people are evil and it's not because they're stupid. And it's, to me, very related to the everything is complex. And if you, maybe this is my... Butterfield's law, I haven't thought about this before, but I tweeted this a very, very long time ago. So everything is simple if you have no idea what you're talking about.

57:42So the other side of that is if something seems simple, probably you don't understand it. And 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.

58:22But it's an almost overpowering impulse inside the organization that often leads to disastrous results. And so I'll give one example from Slack's history. And I have tried in the past to disguise this example so that no one feels bad about it. But 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 evil. And one example that's from the outside. So the example inside of Slack was 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, Stuart, reply to it, you will automatically get a notification.

59:09And now Sarah, later on, replies to the same message, both you and I, as people who have posted that thread, will receive a notification that there's been more activity, and so on. So every single time anyone replies to it. So when the feature first was released, or 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 was using the feature, and I would put the insertion point there, select all, delete, and then start writing my message. and it's even if i wanted to add 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 add someone they're not going to want to do it at the beginning of the sentence and by the way you're teaching them to use the product wrong because it's important that everyone understand that every previous poster in this thread will automatically receive a notification unless they've e-chered it.

1:00:19So, okay, we release it. Six months goes by, and suddenly the at thing comes back. And so I messaged someone on the team. I said, hey, there's been a regression. It's super weird. I don't know what happened, but the at 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?

1:01:04Like maybe a shorter thread is better and it can 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 incorrect. I'm pretty sure this was outside the bounds of certainty that they can have. 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 database or whatever we were using to record all of that, you wrote queries to pull that, you created charts based on that data, you had meetings to discuss it, and just kind of unpacking all of the things that would have had to happen for this to come back.

1:01:50And it's like thousands of person hours at a minimum, because any feature change at that scale of organization, it's involving a dozen people, engineering, QA, analytics teams, product managers, user research, and stuff like that. The problem with that, so I think it was a bad idea, right? But the problem with that was the difference that you could possibly achieve between having this feature and not having this feature is this much, whatever units you want. The cost of doing the analysis was this much. So it's guaranteed to be a loser. There's no world in which anyone could imagine putting the at previous respondent in the thread at the beginning of the message could possibly make that much of a difference to the quality of Slack and how much utility it provides for people and all that.

1:02:45But you know that to 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 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 thing. Like, you know, guaranteed loser. And I know that Fareed told you to ask me about this, hyper-realistic work-like activities. And so here's my grand theory.

1:03:26Hyper-realistic work-like activities 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 going to be valuable. So like starting a business, open a bank account because like there's almost infinite generated value of opening a bank account. You have to do it. It's very simple to do. And so at the very beginning of any startup, they're like, okay, I'm creating a user's table and I'm doing salting passwords and doing all the things that are absolutely necessary.

1:04:12And everyone knows exactly what they are. And so everyone's going to work in the morning. They're like, right on. And I have 10 things to do. And every single one of them is something I know how to do. And it's definitely going to be valuable. Time goes on and the relationship between the supply of work to do and the demand for doing work just starts to change. More and more people get hired. Every product manager wants to hire a junior product manager. Every new person, the first person you bring in on the risk and compliance team is like, oh my God, there's so many risks and things we have to be compliant with.

1:04:45We better hire more people on my team to do more risk and compliance work, which probably to some degree is right. But we're going to have more and more of those people and they're going to call meetings with each other. 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 version, which is going to require us to have wholly separate physical infrastructure for the hardware that runs the software, and also a whole different operations team, which has only US citizens on it?

1:05:16what is the possible number of dollars that we could make from doing this and how much complexity is going to be when we want to do updates to the softworks and be upping to totally separate independent systems. It just gets out of whack. And so people end up like, if you hire 17 product marketers, you're going to have 17 product marketers worth of demand for work to do. And if you don't have sufficient supply of product marketing work to do, they're just going to do other stuff. Again, very important, not because they're stupid, not because they're evil, but because they're like, I'm a product marketer and I want to be recognized for my work.

1:05:52And my spouse has criticized me because they think I should have already got promoted in the last cycle and I really got to demonstrate some wins here and whatever it is. And so people are 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 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 there's something being projected up there and we're all talking about it. And that's exactly what work is. Hopefully not all of work for everyone inside of your company, but that's exactly what we do when we're working.

1:06:34But this is actually a fake bit of work. And it's so subtle that I'll do it. You know, our board members will do it. Every exec will do it. And the further you are from, like, having all of the contacts and all of the information and 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 result of that, I guess, is that if you are a leader, if you're a manager, a director, an executive, the CEO, it's on you to ensure that there is sufficient supply of non-valuable work to do.

1:07:15And there almost always is, but 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 then obviously doing it. Amazing. I could listen to Stuart Ranz all day. hyper-realistic work-like activities. We need to coin this. Unfortunately, it doesn't make a good acronym. It's pretty ugly. Okay, I'm going to try. And just to close the loop on that, the solution is the leader recognizing this is happening and stopping it, telling people, why are we spending time on this thing that is not going to get us anywhere?

1:07:48Yeah, and that, what you just said, probably isn't the best way because that sounds like you're chiding them and they're dumb when it's actually your responsibility to make sure that there's sufficient clarity around what the priorities are and explicitly say no to things up front and stuff like that, rather than where James had like, hey, you guys are a bunch of idiots wasting your time on this thing that doesn't matter. Whose fault is it? It's the manager's fault. It's the VP of whatever's fault. It's the CX whatever. Ultimately, it's the leader of the organization that has the responsibility to make sure that there is sufficient, no valuable work to do.

1:08:29And that's actually harder than it might appear. Okay. Before we run out of time, I want to touch on two other topics. One is when people think of Stuart Butterfield, I think a lot of people think of, we don't sell saddles here. Your legendary Medium post that is just, I don't know, it's become a historic piece of literature in the annals of product building and in startups. I haven't heard people ask you much about this recently. Let me just ask a couple of questions. One is just, what was the reason you put that out? What was the backstory on writing that memo? Why was it necessary? Well, it really was an internal memo.

1:09:04And there's a bit of a digression. One of the crappy things about Slack is if all your 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. if it's Slack, once you're turned off, 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 absolutely verbatim. I did not change a word of what I said inside the company. When I think we were still eight people, maybe, I had most 10, but I think it was eight people.

1:09:45It was before Slack launched even. Yeah, it was before Slack launched. It was when we were doing private beta. And the point of it wise to like to start to instill those ideas as early as possible and really create this alignment inside of that small team so that it could persist and survive as we grew and and scaled um and yeah that that was the that was the idea and the gist just for people that 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 going to achieve for them.

1:10:26Is that a good way to think about it? Yeah. And again, comparing it to beer or cars,

1:10:35beer goes back to pre-civilization. Cars were obviously made. At some point, you had to convince people why they would win a car instead of a horse. for your new AI-based recruiting tool or your calendar app or whatever, there's some reason why 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. You're not just responsible for creating the product, but also to a certain degree creating the work and creating, you know, there's this book, Positioning, which is an absolute classic.

1:11:18It's very short. I would recommend everyone read it, where 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 put them together. So it's much easier to say it's like Jaws meets Star Wars, or it's Uber for pets or something like that than to come up with like an actual new idea. But you have to do that because you like, if your thing is different in any significant way from the alternatives, you're not just creating the product, you're creating the market. They're really kind of one in the same.

1:11:56The reason I wanted to touch on it is I think still people continue to not listen to this advice and continue to overinvest in more features, more products, things like that. But just the specific example of we don't sell saddles here, just to quickly communicate this to folks and correct me if I'm missing anything, is just instead of, hey, look at this amazing saddle we've bought. Would you want to communicate us here? Go horseback riding. Look at this incredible experience you can have. And then they decide, oh, shit, I need to go buy a saddle to do that. Yeah. And 100%, that aspect of it is not original because I think that's something that marketers have done for a long time, certainly in the Marcom and advertising.

1:12:33Like if you want to sell Harley Davidson's, there are people who are going to geek out on the engines and stuff like that and like the quality of the leather and stuff like that. But what you're selling is not the motorcycle. You're selling like the open road and freedom and the wind in your hair. And if you're Lululemon, you are 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. There's the ship. Yeah, instead of.

1:13:02The screwdriver. Oh, yeah, the nail. Yeah, the nail. Anyway. Yeah, what is that one? Well, there's the one I think about is instead of trying to convince men to build a ship, I'm still yearning for the sea. Yes, exactly. It's something that goes back in history. Okay, let me ask you about pivoting. 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. Let me just ask, when folks come to you asking, should I stick with my idea?

1:13:40Should I pivot? What sort of advice do you find most helps them? Yeah, I mean, I think it's partly

1:13:51an intuition, because obviously the decision is about, have you exhausted the possibilities? and in the case where you know we're 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 are working on this for several years without actually explicitly working on it and only doing the minimum number of features that were you know absolutely guaranteed to be successful in the sense that it was so irritating that we couldn't standard anymore or such an obvious improvement that we couldn't help but take advantage of it.

1:14:28We still had like$9 million left and everyone still liked the game and we were all happy working on it. But I think by that point, I had exhausted every non-ridiculous long shot idea to make it commercially successful. And so decided to abandon it. But, you know, the default advice for anyone in anything is persevere is like you know kitten hanging off the bridge and then poster says hang in there and you know i think there's a idea that you just like and then there's so many stories of like so and so started out going door to door and was rejected by everyone and then suddenly there was nike or something like that and they just if you stick out stick with it long enough you'll eventually be successful i think you have to really be coldly rational and um now some of this shows up in the book um thinking about some of it's in annie duke's second book the title of which i'm forgetting right now but someone will will know it yeah thinking bets and then 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 my expected value here has diminished to the point where this alternative looks more attractive.

1:15:54And the reason I say you have to be coldly rational about it is because it's fucking humiliating. I convinced so many, and you have to convince so many people to get a company out there. You have to go to investors, you have to go to early employees and say, you should leave your other job and come work for this because here's 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 feel like committed things to the users and you've convinced them to give up their time for this thing. And so I think for a lot of people, it feels better to just keep doing it until it dies of suffocation due to lack of capital or something like that than to admit like, okay, I was wrong.

1:16:39This didn't work. And 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's a lot of people who loved it and who spent 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 we're going to have a job anymore so pivots aren't something i take lightly and you shouldn't be um i think it's very different to be like there's three of us and we started making this app and then we pivoted to a different app that doesn't even really 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 building it's not really a pivot obviously in this case it worked out great and there's survivorship bias and that doesn't mean that everyone should pivot all the time um but i i I think it is creating the distance so that you can make an intellectual, rational decision about it rather than an emotional decision is essential.

1:17:50I love also your piece of advice of just exhaust. Once you've exhausted all the ideas, that's a really good time to see what else is out there. Yeah, exhaust all the good ideas. All the good ideas. All the realistic. Yeah. Yeah. The point you made about just kind of persevering, I just had Melanie Perkins, CEO of Canva, in the podcast. They went through 100 investors rejected her before somebody finally decided to invest, and she just kept pushing. Yeah, I think that's a slightly different example, right? Because she believed in the concept, in the product, in the vision. It was just trying to figure out the right articulation to get investors.

1:18:27And Labine, obviously, very, very happy. Extremely happy. Oh, geez. Okay, maybe a final topic, depending on how time goes. I want to talk about generosity. I talked to a bunch of people, as I said, that have worked with you. And the number one thing that came up again and again and again, when I asked them about you and what has stuck most with them is just generosity. So I'm going to read a few examples that I heard from folks that are examples of your generosity over the years. So one person shared that 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$500, told me to go home to my family.

1:19:10Other folks share that when you talked about glitch just recently when you had to lay people off, that you cried real tears when you were laying people off. And then you spent an incredible amount of time helping them find new jobs and extending their severance pay and just taking it extremely, extremely seriously, much more than I think most people feel like CEOs do. Someone else shared that you paid 100 % of employees health insurance to give them just fewer things to think about. When you went public, you basically created the best possible situation for employees. No lockup, direct listing.

1:19:42Also with the structure of the Slack deal, people said the acquisition is very employee-friendly. 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 released this fair billing, which I think was very innovative at the time where you didn't charge, you stopped charging people for seats they weren't using, even though they signed a deal to charge for those seats. A lot of times, just you slipped release schedules because you just wanted to make features better and better for people.

1:20:12And I'll end with this quote. Stuart is a leader who takes the responsibility he feels for his employees personally, and to which he extends the most generous circumstances he could muster. That feels worth celebrating. So first of all, I just want to celebrate you. I think it's really rare and inspiring to meet a leader like that. Clearly, you've had a lot of impact on a lot of people. I don't know exactly the question I want to ask, but I guess was this, is this like, in what part is this intentional? Just like, this is how we win. I'm going to be very generous and help people because I know this will help long-term.

1:20:46How much of this is just innate, and that's just the way you are as a person? I think a lot of it is just the way I am as a person and uh i had wonderful parents who raised me right but i think there's also um there is a little bit of a lesson there and i'm just going to assume people's familiarity with the prisoner's dilemma um the you know acts of generosity to me are oh i am demonstrating that i am going to cooperate as we iterate in this game um and if you do that then people will also cooperate and you both benefit. Whereas if you never really know if the other person is going to defect at the first opportunity, then your best bet is to defect.

1:21:26And so there is a game theoretic aspect, usually in games that are much, much, much more complicated than The Prisoner's Dilemma. I think another thing, one thing 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 repeat this as a chant. It was, in the long run, the measure of our success will be the amount of value that we create for customers. 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 maximizing at the wrong moment or taking advantage of a customer or anything like that, we definitely shouldn't do it.

1:22:21Because to me, it was just like, I mean, I think it's literally true, but it's also like an ethical way to run a business. And 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. If all your employees are ethical, then it's going to be a better place for everyone to work and you're going to be happier and you're going to have fewer internal problems and all that stuff. But I think it really is true that there's no, like, especially in the long run, you can't, like, destroy value for your customers and expect to be successful.

1:22:59of all, you have to actually make their lives better. And you can put effort into like pointing it out to them and demonstrating that you have created this value and stuff like that. But there's no substitute for actually having created it. And I think that is incredibly important. And that implies a real generosity, whether that's in negotiating terms with an enterprise deal, or that's like policy decisions. Sometimes, say one time that it blew up in our face was our SLA was like, for any downtime, you get a hundred times your money back. Which was like, because from my perspective, it's like, you know, if we're down for two minutes, it doesn't, it's like pennies.

1:23:43It doesn't really make any difference. If we're down for like 10 hours or something like that, then we have bigger problems than paying back people. Okay. Fast forward, we now have hundreds of millions of dollars in revenue and we've gone public. And shortly after we go public, we have one of the biggest adages we ever had. I don't remember how long it was, but it was many hours. But by the time we got to that scale, 100 times the money back for the third of a day that we were down was$8 million or something like that, which had to be, you know, it didn't cost us any money because we just gave it to people in the form of credits, but it meant that a bunch of revenue that we had already anticipated for the next quarter wasn't going to show up because people's credits were going to offset what they would have otherwise paid us.

1:24:32And so we definitely changed the terms of service after that because being a public company is a little bit different. But, you know, in every other respect, I think, you know, they were all really important decisions that were helpful in, um, in us becoming successful. It was that policy. It was automatic. Like you didn't even have to claim it. It was just automatically get this credit. And then the default is you don't have to pay. If you let us know, and this was, we will automatically like proactively preemptively without any input from you to apply this credit to your account and just like send you a message that it happened.

1:25:04And by the way, we will do it on the aggregate for downtime, even if the issue didn't affect you as a customer. Too generous. You found the edge of where you might want to be. Yeah. What was that mantra again that you had the company chant? I think this is a really nice way to end it. In the long run, the measure of our success would be the amount of value we create for customers. Incredible. I'm just trying to picture the entire team at Slack. Hundreds of people. It felt very like Chin-Jolong or like Stalin or something like that. Well, on that note, Most people don't know this about you, but your actual name when you were born is not Stuart.

1:25:44It was Dharma. Yeah. And this all makes sense as you learn that. Yeah. My name is Dharma Jeremy Butterfield, so my parents named me. And when I was 12, 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've said it. Any character, except for Stuart Little, the mouse, anytime you see a character in a movie, a novel, TV show, whatever, there's only the loser Stuart and the asshole Stuart. it's it's like it's obviously in the collective consciousness a terrible name and i shouldn't have chosen it and i regret it but by the time i realized that dharma and greg had already come out it would have seemed like i was like you know bandwagon jumping 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 let's do it and it's called the owner's illusion and this is basically something i posted on twitter the person who came up with the name later deleted their account.

1:26:46And so I have no idea who it was and who to credit for this. But what I had posted was, and this is a long time ago when restaurant websites have gotten better and it doesn't really matter because Google Local was taking over everything. But this is like, let's say 10 years ago. There's five things you could possibly want when you go to a restaurant's website and is their street address, their phone number, the menu, that hours of operation, oh my God, I'm forgetting the fifth thing. Oh, and making a reservation. How to make a reservation. And again, this problem has like, to some extent taken care of.

1:27:22It's all for release to Brute. But what you would get was like this super slow loading photo, the Ken Burns effect as it got. And like, yeah, and then like 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 it's not even text that you can copy because it's, yes, it's an image. And they don't have the hours. They don't put the address or whatever. And it's just like, what? For sure, whoever made this website for the restaurant owner and the restaurant owner themselves have definitely been in a 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.

1:27:58So why does it end up like this? And what should we call this? And whoever replied to the tweet, she said, you should call the owner's delusion. And I was like, oh my God, that's perfect. And I think that is incredibly powerful. And 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 that can possibly mean. And that's why people anticipate, despite the fact that when they get to your website for the first time, their intent is absolutely the minimum number of micropoints above the threshold required for them to actually take that action.

1:28:40You're like, all right, welcome to my website. And there's a bunch of BS and there's a bunch of stuff that doesn't make any sense. and the buttons are inscrutable and it's unclear what to do next because I think that my thing is so important and I don't recognize that you are at work and you were late this morning and you have to go to the bathroom and you're just like a regular human being who has stuff going on. You're concerned that your kids will fuck up and they're getting in trouble at school, stuff like that. They're not like subjects who paid money to go to your play and are sitting in the audience and waiting for that curtain to go up.

1:29:20They're like people who are going to bounce in 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 like recognize it. And unfortunately, it's one of those things like Murphy's Law, like even you go wrong when you take into account Murphy's Law. But if you don't name it and recognize it and discuss it and like train yourself to think in that way, that, you know, take a breath, pretend you're a regular person, and then look at this again and see if it makes sense, then you're screwed.

1:29:54I love that you threw this in here. I have a billion other questions I'm going to ask you in part two when we do this someday. Stuart, thank you so much for doing this. Thank you so much for being here. Yeah, thank you for having me, Lane. I really enjoyed it. Same here. Bye, everyone. 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'sPodcast.com.

1:30:30See you in the next episode.