The Challenges of Remote Work
Remote work has become increasingly popular in recent years, offering several benefits, such as increased flexibility and the ability to work anywhere globally.
However, there are some challenges that come with remote work and it’s certainly not for all companies.
In this episode of the Rework podcast, 37signals co-founders Jason Fried and David Heinemeier Hansson discuss these issues and how they’ve overcome them from their book, Rework.
They share insights on how to work together across different time zones, ways to stay connected while working remotely, and the benefits of remote work for both employees and employers.
Listen in to find out what remote work has to offer, along with its challenges and benefits, from two seasoned advocates.
[00:36] - 37signals is as remote as they’ve ever been.
[01:02] - The challenges of time zones in a remote work environment, especially when training or mentoring new employees.
[02:22] - Jason discusses the importance of scheduling and pairing employees with compatible time zones, depending on their experience level.
[03:57] - David shares why from his perspective, four hours is the ideal amount of time zone overlap for remote collaboration.
[05:32] - Why it’s essential to be strategic about where you hire from, given the challenges of time zone differences.
[06:13] - While asynchronous communication is useful, synchronous communication is needed to crack through some tasks.
[07:52] - How 37signals twice-yearly meetups are more of an investment than an expense, unlike the cost of an office.
[08:35] - Humans are not built for fully remote work—why meeting in person is necessary to reduce loneliness, recharge batteries, and create better team relationships.
[10:57] - Why simply installing communication tools like Slack and Zoom without changing work practices offers the worst of both worlds and results in a subpar remote work experience.
[12:20] - The potential pitfalls and tradeoffs of the new hybrid work model.
[14:10] - The benefits of being able to hire the best talent from anywhere in the world and allowing employees the freedom to live and work in multiple locations.
[16:22] - Jason discusses why some companies are requiring employees to return to the office after the pandemic and both advantages and disadvantages.
[17:46] - David shares why either way is OK—some companies thrive with having an in-person culture catering to the needs of employees who prefer working in an office, while there should be more remote work options for those who prefer working from home.
[20:38] - Busting the myth that remote work is impossible, creating more options for people, but the future of work remains to be seen.
[22:39] - Leave a voicemail at 708-628-7850 or email us with questions for David and Jason about remote work or running a business for a chance to have it answered on an upcoming episode.
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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, co-founders of 37signals. Jason Fried and David Heinermeier Hansson have been talking about the benefits of working remotely for decades. They even wrote a book about it in 2013 called “Remote: Office not Required.” With more than 20 years heading up a remote company, they certainly are experts, but there are still some challenges that they continue to work through, and David and Jason are here on the podcast to talk about them. Before we do that, guys, I know, let me just clarify, even though there’s some challenges, you two are still a hundred percent on Team Remote, correct?
Jason (00:36): Yeah, yeah. We’re remote. We’re very remote. We’re as remote as we’ve ever been actually. We almost, we’ve almost historically always had an office, kind of, either a sublet or a space or something, but now we have nothing, so we are all in.
Kimberly (00:50): Okay, perfect. Well, we always talk about why remote is so great, as we all know and love, but what are some of those challenges? I would imagine time zones just amongst employees is probably one of the biggest ones, but that’s just my assumption.
Jason (01:02): Time zones are tricky. Like David and I only have, uh, like two hours overlap on a given day typically, and for me it’s really early in the morning and for David it’s like at the end of the day before dinner. So it’s, it’s not just the overlap, it’s like when is the overlap? It’s tough. Right. Um, and then, you know, it’s, I think it’s especially hard actually for new employees for, for kind of getting into the swing of things, for training, for understanding how things are done, for mentoring, especially when you’re working on projects. So our project’s typically, a feature project would be two people, a designer and a programmer. And if they’re seven time zones away and they’re new each or it’s , it can be challenging. So there’s definitely some pitfalls and some challenges. I think we have to be mindful of the fact that those exist and that different people in different positions might be in a tougher spot given the fact that they’re not together. Um, but all that being said, everything’s a trade off and it just still feels like a, a much bigger win in general to, to be remote and to hire the best people we can find all over the world to be able to work wherever you want versus, you know, shoving everyone in a room and thinking that that solves the problems.
Kimberly (02:10): So on this pairing up Jason that you mentioned with a designer and a programmer, are you guys thinking about time zones in that regard or is it like, no, we’re gonna figure it out cuz we just figure it out?
Jason (02:22): You do your best to schedule things as best you can. Uh, you just, you are mindful of that. Like, okay, this person’s in, you know, I don’t know in Spain, this person’s in, you know, California, that’s gonna be harder. So in that case, um, then you start to look at have they been around for a while? Is the one a veteran? Are you putting two rookies together? You know, that’s gonna be much harder. So you do your best. We don’t have that many people, so we don’t have like unlimited permutations, but you do think about it and go, you know what, this person’s new or they need some more help or this is a, a tricky part of the code base that they’re not really gonna be that familiar with or whatever. Uh, let’s pair them up with someone else. So you do the best you can, but you know, it’s not always a perfect fit.
David (03:04): I’d say that distinction between when in your career or engagement with a company are you making the split is quite important. I don’t think it would’ve worked when Jason and I first started working together. If we’d only had the two hours. That works because Jason and I have worked together for literally 20 plus years and we can be quite succinct in our collaboration style and we know how much of it we can do asynchronously and so forth that we at this point don’t need more. But in the earlier times, we’re quite, uh, explicit about the fact that we preferred four hours of overlap. Cuz that’s actually what we had when I was in Copenhagen and Jason was in Chicago. Um, Chicago has two time zone advantage on, on California in that regard in comparison to Europe, like four hours. I don’t feel, in fact, not only does four hours not feel like a a deficit, for me it felt like a bonus.
(03:57): Still does. It feels like a bonus that you have some time to yourself, so to speak, when you’re collaborating with someone else on the project. So you have your own time where you can get something ready and then you have a fair amount of overlap. And I think four hours really is the sweet spot for me. And that’s when we’ve had some challenges when we’ve paired up a programmer / designer working on some feature project when one of those are new and if they only get those two hours, even three, it’s really tough. If you can get it to four, there’s a lot more magic in it. And I think that’s also where sometimes you have to accept that if you’re gonna be a remote company and not just a remote company, but sort of like a global remote company or at least a two continent remote company, you have to give and take a little. I mean, Jason actually gets up quite early for some of these calls that we have to overlap with.
(04:49): And I sometimes go like, hey, do you know what I’m, I’m gonna be late for dinner tonight. You can’t be like that all the time. You can’t completely rearrange your life. Which is why for example, we don’t really hire to the product team from Australia, for example. It’s not that there are not wonderful people in Australia, it’s that we can’t make the overlap work without someone having to work the graveyard shift. We actually did try at one point and it was quite clear that asking someone to get up at three in the morning, do you know what? It doesn’t work even if someone goes into thing. No, no, no, no, it’s not gonna be a big problem for me. There’s endless amounts of studies of what happens to human health for people who work night shifts, graveyard shifts and it’s not pretty reading. So I think that’s one of the trade-offs you have to take.
(05:32): You think like, oh, remote it meets the whole world, eh, kind of doesn’t, it kind of means that you have to have overlap. Now on some of the other teams we have like operations, we have sort of around the sun thing where we have enough people that you can have some people in Asia, uh, some people in Europe, some people in the U.S. and there’s always sort of a handover, but it does still mean that like, uh, people in Asia and people in the U.S. they might not really see each other. We have some of that on, on operations as well, but the product team is not gonna work there. The team’s just too small. We typically have just two people working together. So you really have to think about what does remote work and not just go wild and think like, oh, it means anywhere in in the world.
(06:13): It no no, you still need the overlap. And in fact, that goes so far as to say that some of the animosity against remote, especially in the early days, came from the fact that the earliest exposures that a lot of people in technology had to remote was offshoring. And it was often people in the US working with someone, for example, in India and it was, everything had a one day turnaround. That is a awful way to work, to have a one day turnaround on everything that everything has to be an email, everything has to be asynchronous. Now we’re the biggest fans in the world of asynchronous communication, but only if you can also sprinkle in some synchronous when you really need to crack through something. So when you do the full separation, no it’s not a good time.
Jason (07:01): The other thing that happened with offshoring is that was seen as a cost savings. And so it just, it was like, you know, it, the whole thing was not… That’s not really remote work. That was like throwing work over the wall, letting someone else do it without a lot of guidance and then throwing it back primarily to save money. That’s not what what we’re in this for. In fact, everybody who works here at 37signals gets paid the same as if they lived in San Francisco essentially. So we have a compensation scheme that is not cheaper. It’s not cheaper to hire people remotely. It’s the same and that that, uh, that you know, keeps our quality bar high and also says like, we’re not at, we’re not doing this to save money.
Kimberly (07:42): Well, on that money front, are we saving any money by people working remote, not having that office space versus these meetups that we do twice a year. Is it kind of a wash between the two?
Jason (07:52): Mmm… The meetups are getting more expensive now because we fly people, like the last one we flew, you know, 60-ish people to Amsterdam and maybe the next time we’ll fly everyone somewhere else and every six months we’re basically taking everyone somewhere. So that’s, that’s expensive. And you have food and lodging and airfare and all that stuff, you know, so depending on how much you pay for rent, it could be a wash, it could be a plus, it could be a minus. I, I think for us it’s, it’s a little bit more expensive, but it’s a lot more worth it. I think ultimately, like these meetups are really worth it and I actually don’t even see that as an expense. It’s more of an investment. This is kind of how I’d look at it and uh, you know, unlike an office actually felt more like an expense to be honest, while these meetups feel like an investment. And that’s, I think a good way to look at this.
David (08:35): I think the other factor with that is we saw what happened when you don’t have that at all, when you just go like, we’re all remote all the time and everyone is just an avatar or assume 2D image, um, not a happy place to be for humans. I think what really surprised me was the fact that meeting someone twice a year is enough of a recharge on the human batteries to power a full year. That you can have great human relations where someone is not just an avatar if you meet them, um, a couple times a year that it doesn’t actually need to be every day or every week or even every month. But the difference between a couple times a a year and nothing is enormous. It is different worlds actually. I’d say it’s a different kind of working. And I think actually perhaps that’s also one of the reasons some folks soured on remote during the pandemic because it was that, right? It was fully remote. You’re not seeing anyone. There are people who manage to start a job, work at that job for quite some time and then leave that job without ever seeing a coworker in person. We’re not built for that as humans.
Kimberly (09:46): Well, and I also think some of those companies that are doing remote are just on Zoom calls all day, long every day and are doing remote but not asynchronous, which I think is extra challenging.
Jason (09:57): Yeah, it’s a great point. I mean there, there’s a place for real time, but it’s just some of the time. Most of the time it should be asynchronous and then yeah, I mean Zoom, Zoom gloom or whatever you wanna call it, sitting on, you know, sitting on camera like we’re doing now, right? But doing this six hours a day with six different groups of people, it’s just, yeah, it’s bad. Yeah, it’s really bad and worse, far worse than physical in-person meetings. So it’s, it’s kind of amplified. It’s like two x is bad or something, so let’s call it six is equal to 12 in-person meetings a day or something like that. Terrible. So yeah, that, that’s, you know, we wrote about this early on is that remote working is not working the same way far apart. It’s working differently. It’s thinking about time differently. It’s thinking about communication styles differently. It’s thinking about approach differently. It’s a different platform, just like porting one piece of software over to another platform and you can tell the software was ported, it’s not quite right. It’s not native to the platform. Same thing is true with remote work. You can’t port local work over to remote and expect it just to work the same way. You really need to think about it differently.
David (10:57): And I think this is where a lot of companies just went astray, particularly at the start of the pandemic and some had never got out of it, was to think, oh, all we need to do is install Slack and Zoom and then carry on with the same meeting schedules, the same calendar tetris, all our same practices as before. And then we go through that for a couple months and we go, why is everyone so miserable all the time? Yeah. Why do you think? Because that port is the worst of both worlds, right? Like it it has all the sort of distance of remote with none of the upsides in terms of ways of working together better with more flexibility. If you still have the schema put over your day, um, it doesn’t give you all the true benefits of remote. So I think you’re actually better off doing either native remote, real remote, asynchronously, mostly remote or just accepting we’re not doing that, we’re doing the office rather than trying to do the office on the remote platform.
Kimberly (12:00): And I think the other hybrid model that we’re seeing is some people in the office and then some people working remotely, which also has its own challenges of like not everyone being in the same place, but some people are, some people are working in the same room in a impromptu meeting that other people are excluded from. I think that could be hard.
Jason (12:20): Yeah, we used to do that, um, to some degree when we had an office, but the majority of people at 37signals have always been remote essentially for the past 20 years. And so we’ve always had the remote first approach because we had to accommodate for the fact that most people were that way. So even though we did have in-person things occasionally, again, usually for us it’s two people and it might have been those two people were in the same office and that was fine. We didn’t have to include the third. If we did, we did, but um, we still, even though we still were in the same city often, um, we still worked as if we were not, I think that’s, that’s important. I think when you have, you know, 75% in-house and then 25% remote, that’s really hard because the, the bias is gonna be for, for, you know, everyone who’s local. And you’ll see this too with, with um, career progression. People talk about this like it might be harder to get a promotion if everyone else is closer. People are gonna pick who’s closer to them. There are a lot of pitfalls there. So I think you’ve gotta, you’ve gotta be at least 50- 50 and if not, you wanna be more remote than local if you really wanna make remote work. Otherwise, I think it’s gonna get squeezed out.
David (13:27): I think the only way that hybrid model works where there is quite a few people in the office, more people in the office that are remote is if everyone essentially has the opportunity to come into the office. This is what I’ve seen here in Copenhagen for example, that there’s quite a few tech startups who do have an office but also allow remote. And those remote workers might be working remotely three or four days a week and then they come in, uh, to the office like one or one or two days a week. That I’ve seen more success from rather than this like, hey, we have 75% who have access to the office and come to the office all the time. And then you have 25% who might live in another country or in another city and don’t have access to that community that develops in person.
(14:10): That really is the worst possible way of making hybrid work. But I wouldn’t poo poo the other part too hard, which was actually a little bit how we had it in Chicago. I mean, I lived in Chicago and Jason did for many years and we had an office and I would come into the office once a week because we would just use that office time when Jason or I or others were like, do you know what, here’s, we need to, we need to hash this through. Here’s something we can’t do asynchronously. And then the rest of the time I just sit at home even though I only had a 10 minute commute to the office that I just preferred working at home. And again, that model could work too. But yeah, it’s, it, it really is. It is a trade off, right? For us, a huge advantage of remote has been the power to hire the best wherever they are.
(14:58): Like right now we have more than half of the programming staff are now in Europe. Um, this was something that wasn’t true earlier in the company’s lifecycle. And it feels like it’s barely noticeable. I mean there’s a little bit with the time zone overlap, but it’s so outweighed by the fact that we’ve gotten access to just this incredible talent wherever it is. And that some of that talent also really takes advantage of it. Like Michelle, one of our designers, I think she’s lived and worked in something like 20 cities in the last year or something. And would the people who work with her even notice or know if it wasn’t because she posted these amazing updates to what have you done this weekend? Probably not. And I’ve taken advantage of the same thing. I’ve lived in a bunch of different places, um, over the years, different countries and I just think like, it, it’s so foreign to me to think like, if I moved, I had to change jobs. What? Why? Why do I have to change If I like my job? Why do I have to change it just because I moved to a different city?
Kimberly (16:00): So I’m curious what your thoughts are on this relatively new, this return to work that we’ve seen in the post pandemic world. I feel like for at some period of time in 2020, it was like, we’re working remote 'cause we have to. And then some companies embraced it as like, this is a better way to work. Now we’re seeing some companies who were remote demanding everyone come back. Do y’all have thoughts about that?
Jason (16:22): I’m not surprised to see this. There’s a number of reasons. First of all, um, if you’ve been working locally for 20 years and then you get forced into working remotely for two and you’re not ready and you don’t really know how and you’re doing it the the bad way, naturally you’re gonna fall back to what’s comfortable and what, you know. So I, I understand that there are some advantages of being together here and there. So I get that too. And there’s a romanticization of of like, you know, oh so much better when we’re all together and you forget of all the things that weren’t better. But, so there’s some of that. There’s also real estate that companies are paying for that, you know, they built a huge tower, well probably want to use that or they feel like they want to use that. So I think there’s a, there’s a obvious weight and momentum attached to being in person, especially if you’ve been doing it forever.
(17:06): And I think there’s also, it’s a bit of scapegoating like, well things aren’t going so well, like let’s just go back to the way things were when that may or may not have been the reason things were going better or worse at the time. So I, I guess I’m not surprised you’re gonna have some whiplashing and I think you’re gonna have some things settle out, you know, pendulum swings, swings, swings. I think also the other reality is that everyone was forced into remote work and being forced into something. It, it, it’s hard to like fall in love with that I think. Um, so people may have to fall back into the way it was before and then realize, you know what, this isn’t actually as good as we thought. Now we’ve learned something. So that, that’s how I think it’ll probably end up settling out. But I’m not really surprised is to hear and see what’s going on right now.
David (17:46): I’ll do something that’s um, uncommon for me. I’ll take an even more charitable view, which is that I think it’s also okay that there are some companies who choose to say we are an in-person company. Cuz I think what we found is that we’ve had people at 37signals over the years who clearly did not prefer to work remotely, who would’ve preferred to work in an office if that was an option. And in some cases when that option then came along, they took it because we are just all different people. If you were to sample 37signals along, uh, an ax axis of introverts and extroverts, we would not be representative of the human population. I mean, in the human population, something like 75% of everyone is an extrovert, meaning they get energy from being together with others all the time. And 25% are introverts, which means they cost them energy to be together with others.
(18:36): I think we, we are perhaps the other way around 75% introverts and 25% extroverts, right? But that means that there’s a bunch of people in this world who actually would prefer to be around a bunch of other humans for eight hours a day when they’re at work. And there should be companies that go like, that’s what we do. Because I think just like I felt like in this start of my career that it was really oppressive to me that I was being forced into an office. I felt like I was doing really bad work. My career didn’t, uh, take a great turn until I started working from home and, and gotten into the groove and gotten into the flow. I can appreciate that someone could feel exactly the opposite that, oh, I have to work from home. I’m so isolated, I’m all alone. I’m not getting these things I want, um, from work.
(19:24): Why, why can’t we have something that flatterers the people who, who enjoy working from home or remotely? Boom! Ton of companies available for them. That was the fight we had to do for so long, right? To say, do you know what? There needs to be more than like five companies doing this. And now obviously there are many. We should also accept that like on the other side, that there’s availability for that. Now the hard part and the most publicized cases like Twitter or Apple and so on, was if you take a huge company, thousands of people, you are gonna have that split. There’s gonna be hundreds if not thousands of people who think, oh, I had a taste of remote for the last two years, this was awesome. I’m never giving this up again. Which is also something you’d find that 37signals, I think a fair number of people you’d ask here, would you ever go back to the office? And it’s like, no way, I’m no way. I’m never, I will quit before you force me back into the office, right? Which was what happened to these big companies. Well, at the same time there’d be a bunch of people go like, thank heavens, finally going back to the office. This nightmare is over. Right? And that’s a difficult transition, but it doesn’t mean that the ultimate destination that some companies just decide, hey, we have an in-person culture and some companies decide we’re remote.
Jason (20:38): And I, by the way, I totally agree with that too. I 'm not here to, and I don’t think we’ve ever been here to say every company should be, must be remote, that it’s always better. So I think that that’s true. Um, it it’s gonna be hard though. It’s gonna be hard for, as David said, people have a taste and some of those people don’t wanna go back and you can see the struggles playing out publicly. Apple had a policy, I think they shifted it a little bit and they’re trying to figure out where this is all gonna settle in. So yeah, I don’t know what’s gonna happen, but, um, I think it is important to know that this is at least an option for, for companies when three years ago there was a myth, which is like you could not work remotely. And now people realize they can, even if it wasn’t ideal for them at the time, like it’s possible. Companies didn’t go under, you know, in the way they thought they would’ve gone under if they weren’t all together in the office. So I think anytime a myth is busted, it’s a good thing and it’s a good thing to have in the tool belt and uh, we’ll see how it all shakes out over time.
David (21:32): I think it’s also just releasing a bunch of energy because this myth was so pervasive and so strong that it almost had its own gravitational pull. Like for example, startups that were trying to raise venture capital for the longest time, the venture capitals were basically all saying, well you know what, you need to be in San Francisco, you need to be close. This is where the magic happens. This is where the connections are, da da da da da, blah blah, right? Like it was bullshit. That myth has been busted and it’s been busted in a way that even for, again, not what we would advocate for, but for startups that go that venture capital round, they can now be funded and founded in other places, which is absolutely a net gain that we don’t have to gather all of them up into, to one city with, uh, limited real estate and, and see all the mess that comes out of that. So busting the myth, super helpful, making options, so many options available that everyone can choose. Hey, do you know what I found I like remote. Tons of remote companies I can go work for. Hey, I found I don’t like remote. Or I’m at a stage in my career where I don’t like remote. Wonderful. I can go work at Apple. Great.
Kimberly (22:39): Well with that, if you have any questions for David and Jason about remote work or anything else about how to run your business, leave us a voicemail. That’s 708-628-7850 and we just might answer it on an upcoming show. Rework is a production of 37signals. You can find show notes in transcripts on our website at 37signals.com/podcast.