SEASON 2 - EPISODE 0103 - APRIL 3, 2024

The Wrong Time for Real Time

This episode of REWORK delves into an essay from the book “It Doesn’t Have To Be Crazy At Work,” co-authored by Jason Fried and David Heinemeier Hansson, advocating for the use of asynchronous communication for work projects. During the discussion, they explore the downside of chat and suggest it be reserved for informal discussions and social interactions.

Watch the full video episode on YouTube

Key Takeaways

00:36 - Different communication methods in the workplace – chat vs. asynchronous.
02:22 - The benefits of centralized communication for project management and how chat can hinder productivity.
09:20 - Managing multiple conversations for a single project.
11:28 - How project management tools reduce the need for frequent meetings, check-ins, and follow-ups.
20:05 - Data retention practices for both formal and informal communication.

Links & Resources

Transcript

Kimberly (00:00): Welcome to REWORK, a podcast by 37signals about the better way to work and run your business. I’m your host Kimberly Rhodes. In their book, It Doesn’t Have To Be Crazy at Work, co-authors Jason Fried and David Heinemeier Hansson talk about the wrong time for real time, and I thought this would be a good time to talk about that essay because it’s all about chat and I know when we released Campfire, a lot of people on Twitter were like, why does 37signals do chat? They don’t like chat. It’s actually not true. So, I thought we would talk about that today. Jason, do you want to get us started? I know we’re not anti-chat, but there’s just a right time for chat. Tell us a little bit about that.

Jason (00:37): We use chat a lot less than we used to. We primarily use it for, it’s usually one-on-one. There’s an awful lot of one-on-one kind of chat stuff and then more on the social side of things. But work is typically done asynchronously, long writeups, long reads, comments on your own schedule and I think that should be the default. So asynchronous, letting people read when they have a chance, letting people get back to 'em when you have a chance. Not having this expectation of an immediate response, but chat, of course is helpful and handy for all sorts of other things, social components, one or two people or well not one, I guess you could talk to yourself, two or maybe three people here and there riffing on something quickly or throwing some pictures in something just to look at something together really fast or look at a couple of links or whatever.

(01:24): But to sit in chat for hours on end trying to work all day is I think a terrible toxic soup. It’s bad, it’s bad way to work, flat out. Now you’d say why make a chat app then? Well, like I said, there’s other good reasons for chat and chat’s a nice thing to have as well. It’s a tool in the tool belt just like to-dos are a tool in the tool belt, but I wouldn’t want to be sitting around managing my to-dos all day, but you need 'em or Kanban, you want that, but chat shouldn’t be this thing that you sit and soak in I think all day long. I think it’s really quite bad for organizations. And by the way, it’s funny because for a while when we were building Campfire, we spent a lot more time in Campfire because we were sort of dog fooding Campfire and I found myself actually not liking working that way. It reminded me why I don’t like to work that way even though it was cool to see and cool to use and we’re still using it, but when we forced ourselves to use it a lot, it was a good reminder as to why it’s not a good way to work.

David (02:22): To me, the key difference with chat is trying to manage multiple balls at the same time. It doesn’t work. It’s the same reason why email is such a poor way to do project management as soon as you have more than one or two people, as soon as you have more than one or two open questions, it just doesn’t have its own single track. And if you try to jam that into chat like Slack has done with threads and so forth, it just becomes a mess where no one can find anything or keep up on anything. The beauty of the asynchronous communication that we default to that Basecamp really encourages and enforces is that everything has a perma link. I will go to this common thread to know everything about, I don’t know, our sidebar dms and it’ll be able to live for a long period of time without scrolling off.

(03:18): We can have a to-do that we added four weeks ago and it got an update three weeks ago, another update two weeks ago, and you can find all of the context in one place. Good luck trying to wrangle that context in chat. Chat is just interlaced with all the other discussions including the social, including the work that’s right now including the work of yesterday in one soup and it just scrolls away. Now you could try to do something about that, as I said, with threads or with search and something like Slack has fine threads and good search, but it’s the wrong tool. Again, this is such a proverbial example, but it’s like you take your screwdriver and you turn it the other way around and you try to use it as a hammer. You know what? A hammer will actually be better. It’s got the weight, it’s got the right material.

(04:09): You can knock in a nail with the other side of a screwdriver, but you really shouldn’t or you won’t be having a good time trying to do so. And what I find so interesting about chat is that we’ve been chatting, Jason and I and 37signals, for literally 20 years. We put out the original version of Campfire in 2005 when the rest of the world went like, what do you mean chat? That sounds silly. Why don’t you just pick up the phone? Can’t we just go into a meeting room? And then everyone got on chat in the 2010s and especially during Covid and now they’re like this person who finds the one shiny object. Woo! It’s so shiny, it’s so new, it’s so everything. No, it’s not everything. You’ll learn. It might take you a couple of years and this is one of the fascinating things about watching someone else, especially an entire industry, go through an adoption cycle that you went through literally two decades ago.

(05:07): You’re like, yeah, we used to think the chat was the greatest thing ever and then we didn’t even need anything else. And then you’ll see, you’ll see you’ll things get dropped, you’ll see things fall between the crack. You’ll see you can’t get context together. You’ll see you can’t add someone to a project late. What are they going to do? Scroll back through hundreds if not thousands of chat messages to somehow try to piece it all together in their head. That works very poorly. In the same way that email works very poorly for trying to keep seven different balls organized in one project. You actually need a project management tool. Now that sounds very self-serving because we sell one, but there are lots of them out there. It’s not like Basecamp is the only option and it’s not even like it has to be Basecamp, it just has to be asynchronous and it has to be topic aligned.

(06:00): You have to be able to come back to that one discussion about how the DMs and the sidebar should look four weeks from now and have complete context of everything that’s required to get up to speed on that. Someone who is added to the project. Hey Scott, can you look at this sidebar DM? That’s a very realistic example. We have it all the time. We’ll be working on some project and then we’ll bring someone new into the project as we’re getting further along and we ask them, can you tackle this problem? And they have to figure out where are we? What’s the context, what’s the current state of thing? Again, chat is just awful for that. The other thing chat is awful for is interruptions. If you think chat equals work and being at work means being in the chat room and constantly side eyeing every single line as it comes in in real time, your brain is just going to get scrambled, it’s going to get mush.

(06:58): We’re not built for that kind of task switching. You need to be able to say, Hey, all right, I’ve said my good mornings, now I’m going to go off and do my work and I’ll check in in a couple of hours. And if you can’t do that without it feeling like, oh, I really missed an opportunity to chime in, I don’t get to have my say. I don’t even get to understand what’s going on. You’re going to foster an environment where everyone is paying attention to chat all the time, which is actually, in my opinion, probably worse than having nothing at all. It’s probably worse than just having phone calls and in-person meetings. So chat can be good, but it’s one of those things where the dose makes the poison. You get too much chat. It’s not just toxic. I think it’s actually lethal to productivity, to mental cohesion, to your ability to collaborate with a broader set of people and actually make forward progress.

(07:58): This is the other trick about chat or side effect. It can feel productive. It can feel like you’re in touch with your coworkers. Everything is like, I have a question, I’m going to pop it into the chat and I’m going to expect a reply right away. That feels productive if you don’t account for the fact that you just bothered someone to get your answer right in that minute and did you really need the answer right that minute or could it have waited two and a half hours for someone to check in asynchronous when they were coming up from air out of their creative deep dive? So yeah, you can’t just do chat. It doesn’t really work alone as the main operating system for collaboration between larger teams. I’d say that’s a full on an anti-pattern and I would advise anyone not to buy even Campfire if that’s your intention. Say you have a team of eight, 10 people, don’t start chat. Start with the asynchronous stuff, then add chat as the way to get the social and the quick stuff.

Kimberly (09:01): I was going to say, one of the ways I think we use chat the best at 37signals is for social things. That’s when we feel connected, I would say. And you can step away from it and do your work and come back and be like, well, I didn’t really miss anything because we’re talking about french fries or whatever might be happening in a chat section.

Jason (09:20): This is why friends chat, group chat, perfect, friends, because there’s no depth there. I mean there’s depth with your friend, but there’s no topic depth that’s required. But in work there is and you need to be able to go deep and people would say, well, that’s why Slack has threads. But it’s not that. People who have not experienced true asynchronous work in a tool like Basecamp that is threads based and topic-based from the top down everywhere, they have no fucking idea what they’re missing. This is the thing, and this by the way, I’ve been meaning to do a video called you don’t fucking know what you’re missing and I’m going to do this at some point, but I’m like angry. I’m angry about this because Basecamp is so much better than working that way. And like David said, there are other tools too, but look, I’m going to talk about Basecamp because it’s built this way from the ground up for a fucking reason that it’s so much better to work this way for so many different reasons. You get so much more leverage when you work this way and people who have not been exposed to this don’t understand it. People who came up a different way working only in chat can’t imagine there’s a better way. There is such a better way. And the chat first methodology really hurts companies. It really fundamentally hurts companies. So anyway, I’ll get around to this impassioned product demo, which I really, really want to do soon. I’ve been thinking about it quite a bit.

(10:44): But anyway, it is different. It is radically different and I guess when you’re just not exposed to it, it’s actually similar to another podcast we just did talking about Windows and the Mac. When you’re like the Mac is just the best. It’s just the best always. It’s always been the best. It’s all I’ve ever known. It’s all I’ve ever used. And the only thing that matters is the precision of the aluminum housing and you actually realize maybe it’s not that. Maybe it’s the best on some variables, but maybe it’s not the ones that really matter and maybe there’s other things that matter too, and maybe you can actually make a lot of progress using something else and giving up other things. And same thing with the phone. When you’re cooked in a certain way and you’re baked in a certain way, you just don’t really realize that there’s something else that you can try. So anyway, that’s my little mini rant there.

David (11:27): I think the proof is also just in the freaking pudding, the productivity that we are able to, I was about to say extract, which sounds like you think of people as resources, but the productivity we’re able to post and impress on customers and the rest of the industry, how much software we produce this way could only be produced this way. There’s no way we would be making products the way we do, be as productive as we are, be as on top of things as we are, if we had to do all of it just in chat. If that was literally the only tool we were allowed, our productivity would plummet, absolutely plummet. We would not be able to have this overview. We would not be able to keep track of things. We would not even be able to maintain the same level of trust. That’s one of the things that has really dawned upon me how Basecamp is so different.

(12:26): It allows you to run an organization that is far more, I wanted to say lenient, but that sounds incorrect, but it is far more loose in its cadence of requirements of check-ins in person, follow ups, hey, where are we on this? Because this concept of radiating information, because you have tools like Move the Needle. Because you have a way of getting an oversight on a lot of projects that are in progress at any one time. I mean Jason or I, when we look upon everything that’s going on inside this company, there’s a lot going on. There’s a lot going on. And most other companies, that level of inquiry into where are we, what’s shipping, where’s it going, requires meetings. It requires, hey, where are we? It requires pings, it requires all this kind of follow up. And with Basecamp it just doesn’t. I’m remarkably surprised on almost a weekly basis of like, you know what?

(13:30): I didn’t actually have any status meetings. I didn’t have any check-ins with people this week and I know what’s going on. I know where we are. I’m not stressed about any of the projects because I know these two over here. Yep, they’re dealing with that issue. These three, they’re on track and then we have the other four. They’re coming up in two weeks time. Cool. I can lean back and let people just get the job done. We ran a campaign on this slogan actually that was extracted from this observation, just let me do my job. And it spoke to this feeling I think a lot of people have when they don’t work this way is that there’s constantly someone tapping them on the shoulder. Where are we? What’s next? Are you going to be done? When are you going to be done? Have you started on the other thing?

(14:19): What about the last thing? Is that done? That’s just aggravating to have to work like that, to have to work with that level of persistent nagging. With Basecamp, you don’t need nagging. The system sort of nags. You could say it’ll post like, hey, can you answer the question of what did you work on today? But that feels so much less invasive than having your freaking boss breathing down your freaking neck to get an update on stuff. So it allows you to run a much higher trust organization. And that’s one of those secret, you don’t fucking know, as Jason would say, you don’t know. You don’t know what it could be like working like this. You don’t know. And I’ve asked a lot of people this, you don’t know what five hours without interruption even feels like. You haven’t had that experience maybe for years, literally been unable to conceptualize what a creative deep dive can feel like.

(15:23): I’m going to tell you it feels amazing, amazing being able to just go like bop, put a sock in it, all of it, no notifications, no nothing. Just like the thing, I’m going to solve the thing. I’m going to do it for five hours and you know what? Tomorrow I’m going to do it for five hours too. That’s not how most people work. It just isn’t. And the productivity shows. A lot of companies have a lot of people and they’re not always getting a lot done. And the irony here is that no one likes that. No one likes not getting stuff done. Productivity is a sauce for good spirit, a sauce for motivation. When you are moving quickly and you look back upon the past week and you go like, wow, we got a lot of stuff done. I know where things are and I feel prepped for the next week, it feels great and it feels like you can take the weekend off and be completely at peace. We did great work. Do you know what doesn’t feel great? Getting to Friday and going like, oh shit, I had so much stuff as a book title would be, it was crazy at work. Oh, what did you do? Oh, we did.

(16:38): Yeah. And then the thing, oh man, I had so many meetings. And you’re like, but what? That’s not nourishing in an existential sense. You can’t sustain yourself in good spirit and high motivation on that. It’s like it’s junk productivity, it’s fake productivity. You need some fucking protein and you’re only going to get it if you get these long stretches of uninterrupted time and you’re only going to get that if you work asynchronous and you are only going to work asynchronous if you use a tool that can work that way. So it kind of all feeds down. And the final equation is Basecamp equals productivity proteins.

Kimberly (17:19): I love that. One of the things I also think is interesting, going back to Basecamp and the product, chat history doesn’t stay forever, which I think just speaks to the point of chat shouldn’t be permanent. Chat is quick and to the point. It’s not a permanent record. I’m assuming that was an intentional design.

Jason (17:38): Yeah, I mean look, it’s there if you want to scroll back and spot it, but basically it is within the window that you’re looking and that’s on a conveyor belt. It’s always moving unless the chat’s just dead, then it sits there and then it’s not really chat either, which can be useful by the way. You can just throw some stuff in there and there it sort of sits, but if something’s moving, it inherently is not going to be steady and stable. And what David’s been trying to explain and what I’ve been trying to get to too is the stability of knowing that this is the one URL that you have to go to, to only read about this particular topic and have everyone chime in one place is hugely valuable – stability, the expectation that it’s going to be there, the completeness of the entire idea being there versus here in this chunk and then scroll back in this chunk which was interleave with this other chunk.

(18:36): And then there’s another chunk up here and there’s another thing up there. People know who use threads in Slack that the thread is never trusted. There is maybe a thread, but the way chat works, it’s more convenient just to spew into the conveyor belt. So the medium is not a native medium for actually organized conversation. It’s just not. It’s great for throwing something in there really quick. Obviously it’s great for that, but when we default to that then we don’t know where things are. And so you never know when use chat that if you found a block that it’s the only block that matters. There may be yet another block three scrolls up that you won’t know about until you find it. And so what do you have to do? Look at everything back through history to find and then piece it back together. What? That sucks versus going to a URL where one thing has been discussed for months, for days, whatever it is, but you know it’s in one place.

(19:30): That alone is so valuable. The leverage there is enormous. And again, it’s essentially our fault. I think that we haven’t really figured out a way to really explain, I mean obviously millions of people who’ve used Basecamp get this, but that’s a small fraction of people who use work tools. We need to figure out a better way to get this word out to people so they understand it because it sounds so stupidly simple. How can that be so valuable? But it really, really, really is. And anyway, just knowing that you can go to one place and knowing in your head that’s everything. That’s the whole story. Huge.

David (20:05): The other point with that is data retention. So we actually build a feature into Basecamp, we’ve turned it on where chat will literally get deleted after two years. And that’s partly because we want to encourage this idea that if you want something to be permanent, chat is not the place to put it. If you want something to stick around and others to be able to find it, don’t put it in chat, put it somewhere that’s permanent. Secondly, the US, for better or worse is a very litigious society. If you keep every piece of banter information until the end of time, all of it is going to show up in what’s called discovery. That is when you get sued by someone, they say, give me all your records and you have to hand over all of it. And this is an enterprise technique, actually an enterprise feature.

(20:55): There’s a lot of companies that run data retention on their email that no emails will be persisted beyond even a year. I talked to one company that has it down to six months. I think the data retention windows get shorter and shorter the more you get sued. So the people who are most involved with lawsuits are usually the most who are on top of this. But I think it actually has these positive side effects that you know when you’re putting things into a Basecamp to-do item, it’s a little more formal. It just is and you treat it a little more business versus the stuff you put into chat. The recent chat is so helpful with the gelling is that it is looser and it is a little funny and it is all these things. And as someone said, you should never put something in writing that you don’t want read out in court in monotone by opposing counsel.

(21:49): A lot of chat does not read out well by opposing counsel in a monotone voice. So I think that’s just a general realization a lot of companies have come to in the US in particular because it is so litigious and other platforms have this, I think the enterprise version of Slack has it as well. But you can also look at that constraint and go, we should embrace it for other reasons. Chat should literally feel like the river, it’ll flow away. It won’t ever be the same. You can’t step in the same one twice. And then anything else that we don’t want to flow away, we put it on safe ground, we put it in Basecamp, we put it in To-dos, we put it in a document, we put it in a message, put it in any of these locations that we know how to get back to it.

(22:32): We know how to refer to it. And it’s actually remarkable. I mean we’ve been using Basecamp for 20 years, literally. Basically it’s been around for 20 years. We’ve been using Basecamp from 20 years. We’ve gone back to threads like they were seven years old and found highly illuminating nuggets of experimentations, A/B tests, whatever the history of the company at times. And you go, could you even imagine trying to find that in chat? It’s inconceivable, inconceivable that you’d go back seven years and get a coherent picture of how a decision was made over the course of two months. What? Chat literally cannot deliver that to you. Basecamp can. Asynchronous tools can writing things down in places that stick can.

Kimberly (23:20): Okay, well this essay, The Wrong Time for Real Time is from It Doesn’t Have to be Crazy at Work. I know we talk about REWORK all the time and it’s the name of this podcast, but also It Doesn’t have to Be Crazy at Work, the follow-up book we’ll link to that in our show notes. REWORK is a production of 37signals. You can find show notes and transcripts on our website at 37signals.com/podcast. Full video episodes are on YouTube and Twitter. And if you have a question for Jason or David about a better way to work and run your business, leave us a voicemail at 708-628-7850. You can also text that number and we just might answer your question on an upcoming show.