How 37signals handles communication, meetings, and setting work boundaries with Rosa Gutiérrez

What did it feel like when you first joined 37signals? How do you call this? Withdrawal symptoms? I go into my phone, clicking Slack, like, no, no, for at least two weeks, because I was like this sense of being always online. And yeah, it takes a while. From Tuple, this is Distributed, where we show how world-class engineers and their teams tackle

the challenges of remote work. I'm Jack Hanna, your host. Hey, everyone. In this conversation, we chat with Rosa Gutierrez. Rosa is a principal programmer at 37 Signals, where she's worked for the past eight years and an 11-year veteran of remote work itself.

She has a really interesting background and it's somewhat untraditional for somebody as talented as her. She didn't really get into software until university. She actually won a software competition to join industry in the first place. And so digging into what life is actually like at 37 Signals and her tips and tricks.

from being effective was incredibly fun. And so this conversation was a blast. I hope you enjoy it as well. So Rosa, I understand growing up, you weren't really that big into programming. Fast forward to today, you're a principal programmer at 37signals.

Most folks know the company. It's the maker of Basecamp, of Hay. Of course, it's the birthplace of Ruby on Rails. Tell us a little bit about your current role and what your team is responsible for before we transition to talk a little bit more about what life at 37signals is really like. So I work as a programmer in the SIP team. SIP stands for Security Infrastructure and Performance.

And in practice, I've been in this team the whole time. I've been here for eight years and a half and I've been always in this team. I've always only moved a few times for very short periods to the product team. But yeah, I've been mostly in this team. We basically have two teams with web programmers. We also have a team for iOS and a team for Android, very small teams, but for web.

and we have those two teams and basically the difference is the product team they do new features and new products and we do everything else my team does everything else which is a lot of things we besides security we we manage our book bounty program we do all kind of work that's to do with security or with privacy besides that we also do any kind of infrastructure work for example when we move from the cloud to on-prem

That was a joint effort of my team and our SRE team. We call it OPS, but it's our SRE team. So we work very closely with them in all those infrastructure projects. Yeah, and then we do also any sort of performance. We also take care of maintaining our legacy apps. Usually our product team works in new apps, in the apps that we currently develop.

So that's Basecamp, the last version, and Hey, the email service. And a new app that we're going to be launching later this year. So they do that. But we had a collection of apps. that we no longer develop, but we still maintain until the end of the internet. We maintain our products until the end of the internet, which means we have some apps from 2005 still running.

even from before, and people are still using them. So they need work. Of course. No, that's really helpful context. DHH has talked a lot about the move from the cloud to on-prem. put into context that it would be sensible that you or your team would have worked on that.

Pretty high profile thing, saving the company, I think, millions a year as a consequence of the change and something a lot of folks doubted would be a reasonable move. Let's talk more about 37 Signals. It's an interesting company for myriad reasons, including the fact that... basically wrote the book on remote work well before it became such a popular mainstay. And so could you talk to me a little bit about

the writing culture at 37signals and how it differs from cultures you've seen at other companies. Yeah, it's incredible. Before joining 37signals, I worked remotely for another company. It was also fully remote.

but we did everything in Slack and we spent a lot of time just chatting in real time. Joining 37signals was a total shock in that sense because we almost never... I mean, we do, but the work, the majority of the work happens truly asynchronously. We do a lot of long-form writing.

and for example today i didn't i only chat with my colleagues once and it was all social chatting like telling them about an event i had been to so nothing was related but it was all i all i did via chat today everything has happened asynchronously i i put comments base cam is really really built for this i basically somehow it forces you to to to do this and and so i've been basically posting comments in in cards we have a sort of kanban tool and there are cards with things we need to do

So I've been posting comments there. I've been writing. We also don't do any stand-up meetings, any sync meetings with the team or anything. Everyone needs to answer an automated question. What have you worked on? We answer that. The question is asked every day, but you don't need to answer every day. Most people do maybe two days, three days. So today, for example, I answer the question for Monday and Tuesday.

And that would be about 600 words or so. Like I reviewed this pull request by whoever. And I work with someone on this thing. And then the nice thing is that... sometimes those check we call it automated questions or check-ins they prompt other conversations like if you are blocking something and someone reached it and they offer help or or they post another you can post comments in in check-ins answers so so also discussions happen there and all of that happens

When the person is ready and free, you are not interrupting anyone. For example, I posted this in the morning here, early. But then maybe my teammates, Jeremy, who is in the West Coast in the US, he will read it at 6 p.m. in my time. And then he will... post something and the comments I post in other things they are in other cards they are also for whenever especially it's very it's very useful for people who are in different time zones but even even in the same time zone sometimes I

I post something for my colleagues in Europe, but I don't expect them to read it in that very moment because they may be focused on something else. So it's always like the expectation. of not getting an instant response is very, it's really in the company culture, like it's really nobody expects. a direct answer from you unless it's an emergency of course in emergencies we have other we have payer duty we have other tools to bring people

Like right now. And that works. But that's the exception to the way we work. Yeah, I think...

it can't be understated how different that is than almost every company that I've ever worked at or that I think most would have worked at. And so what did it feel like when you first joined 37signals and you... It's your first day, your first week, if you can remember eight years back.

Coming from a place where there's this constant communication synchronously happening in Slack or whatever your chat tool was, what did it feel like to not see that, not experience that, and not have that really short and tight feedback loop? Yeah, it's interesting. You need to adapt. I remember having, how do you call this? Withdrawal? Symptoms? Yeah. I remember having withdrawal. I go into my phone.

clicking the slack like no no like for for at least two weeks because i was like this sense of being always online and and yeah it takes takes a while but it's also great for newcomers because i remember getting there getting added in my first day to the base can account and seeing all that available like so much context about everything i didn't have to bother people all the time to find answers because i could just search and yeah everything was there it was also a bit

a high pressure theme for me in the beginning because I saw everyone writing this well and so much good content like quality in the beginning I spent too long maybe like going over also i don't speak english as as my first language so i will go through everything multiple times you know to finding finding different words making sure things look good It was a bit high pressure and stressful in the beginning but I got very quickly used to that and I've seen people when they start.

I haven't seen anyone struggle with this. For example, some people just write a bucket list of things and that's totally fine. Some people answer daily. Some people answer once per week. You can see everyone finds their style, but everyone needs to adopt this way of communicating because otherwise it will be very hard to work here. Yeah, well...

This approach is obviously very different than I think what most people are used to. And I'm sure there's pros and cons to the approach. So when you think about how it affords the way that y'all work at 37 Signals, what is having this strong writing style and these habits?

afford you as an individual developer, as a team? I'd love to better understand what you think this gets you. I think it's for me, I mean, personally, it's the... the flexibility of not having to be working at a fixed time every day like I can totally do whatever I need during the day I have total flexibility.

Also the time, it gives you so much time to focus on things. You actually own your own time. You don't need to be paying attention on having to sync with anyone. You can just organize your day and your work. as you want. And also having everything in writing for context is just fantastic. You can find everything there. I always search for answers, especially.

Even things I've done in the past, I don't remember after all those years, I find them there. Or even if I had, you know, I remember, yeah, I remember running into something like this, whatever. So I search for that.

find it and it's all there written sometimes with with links sometimes with links to pull requires links to stuff is so useful it's basically as i remember one thing i did before working at base camp um i i used to write some this was something i i saw sound somewhere i don't remember even where but i used to maintain our very i know other people do this like you write what you've been doing notes things that you

that you find your problems i remember writing this i remember using google docs then evernote whatever but it was just for me and only my my notes this in base can will be having the whole company doing that in public for everyone. So it's super, super useful. Does it ever feel lonely?

a bit yeah yeah it can it can feel lonely for sure because we don't have meetings almost my team though we have one meeting per week like we we have this one is 40 minutes and Usually we talk about work but also some social things and I think that For me, at least, it's enough. I can see how for other people it may not be enough because it's very little. I know other people go without any meetings at all, like the son of the programming team. It also depends on the...

I will always say that we tend to be introverts, introverted people. I don't think I'm that introverted as some of my colleagues.

Sometimes I can imagine feeling or I can feel a little bit lonely, but I try to find... a more human contact and socialization outside work and we still have the the yearly so we do two meetups we have the yearly meetups we do two meetups a year uh where we see each other in person um but definitely with the pandemic we went for about three years without seeing each other and that was very very tough like you could feel how you

you felt disconnected from your colleagues. And I understand this is not for everyone. Because in the end, you tend to feel... It's not the same to work with someone who you are seeing and you listen, you watch their face as someone that is just an avatar, you know, in a document.

Yeah, it's definitely a different experience. And one of the things I enjoy most about doing this podcast is getting to talk to so many different high-performing people and teams who... work in totally different ways it really helps you understand that there is not a one-size-fits-all approach that is universally best but instead a bunch of different ways to be productive feel fulfilled and do amazing work and and so it's been a joy

talking to different folks to unpack some of the stuff to hopefully surface some things that folks can use. Certainly plenty that we've been experimenting here with. Another thing 37Signals is famous for, of course, is ShapeUp.

style product development work. How does ShapeUp work for you as someone who's not on one of the core product teams? Yeah, that's a question I get a lot from people that when I want to talk about the team, because the truth is that we don't apply shape up as the product team does. It's just because the nature of the projects we do sometimes doesn't, it doesn't.

allow it. For example, right now one of my teammates, Jeremy, who is incredible he's in race quarantine and he's one of the probably the smartest person i know he so he's working on bringing the last piece of the cloud of the clouding he's bringing of uh he's bringing in all the storage. The last thing we have in AWS is there's three buckets and all the files that we have in all our apps, they are still there. And so they are moving them on-prem.

And this project has been started last year. So it's not a cycle where you have a feature and you can cut the scope because you cannot cut the scope here. Like either you move the files or you don't move the files, but you cannot. say no let's just move some of the files you know this this is a project that you just cannot simplify I mean you can try to do it as

as simple and as efficiently as you can, but you cannot decide to reduce the scope because the scope is what it is. And so that's different. totally different project that doesn't follow any we still plan what we are going to do per cycle like we say okay this cycle we will do this part like we design whatever we start moving files for those apps we whatever

So we still organize it in that way, but we cannot apply the scope hammering, for example, or we also cannot not ship. Like with Shape Act, if you finish a feature. and you realize It wasn't exactly, or you run out of the time that they call in Shepard, they call it appetite. So they say this feature is good if we can spend, like we are happy to spend two weeks on it. But if it's going to take longer, we don't want to do it.

Sometimes after two weeks we've realized it was more complicated or whatever and we drop it. That's fine. That has happened. But in this project we cannot do that. So that's one thing. And the other thing is that we also deal with a lot of reactive work. because things come up and it's usually my team the one who responds to any emergencies, any things that come by surprise and that doesn't work with ShapeUp because in ShapeUp you're supposed to have focused time.

because otherwise it doesn't work like if you say you have two weeks for something but then you are three days doing something else then you are not you know you cannot calculate the appetite and everything but for my team that's more flexible. We have that flexibility that if something that is more important comes up, we just drop what we're doing and we re-evaluate priorities and it's okay.

What's your process for assessing the importance of something that comes up or reevaluating priorities so that you can work it into the queue to make sure that it gets done in the way that you expect?

So we have a system put in place also that we didn't have it when ShapeUp, the first version of the book, was published. We didn't have that exactly. We have now rotation with all programmers, including the product team.

where for one week we are we call it on call but it's not on call in the sense that you get waking up in like at 2 a.m but you are on call in the sense that you are the first responder for stuff usually this is customers reporting a bug or something that doesn't work or something to troubleshoot is normally normally comes from the support team and so we have a programmer or two depending on their experience assigned to do this for a week

And what we do with the product team is that they take this into account when they plan the cycle projects. So they know that this week they are going to be doing this on-call work, but the other weeks they are, you know... doing doing their own their own their own project for the cycle so in that so usually the person in on call is usually the the first person who identifies a problem and decides

whether it needs to be escalated and get more folks on it and usually is either a generalized customer problem that many people are reporting and it seems serious for example, or sometimes we get any kind of incident, outage that the SRE team detects and they need programmer help for that.

sometimes it's a security vulnerability that is discovered or a new yeah sometimes we get a this doesn't happen very often but a few times we've got a report from a security researcher about something that is serious and cannot wait and in that case we just We need to patch it or an important security release for some of our dependencies as well. We stop it and we do it.

It's usually things that break and are affecting customers, not just one customer, but... is something that is broken clearly broken for any reason an example we had was last week we found that the offline mode for the ios app was broken because there was some change in I don't know very well the details because it's not my area of expertise, but I think it was the way we were loading when we were loading the offline.

emails offline using a web archive library from from ios our javascript code wasn't running and so it led to the emails not showing up like we weren't running some javascript code that we needed to render the email in the in the window so in the web view, because in this case the emails are loaded in a web view. So anyway, the thing is that the result was that the offline mode wasn't working at all.

and so this was declared as an incident and this means in this case the ios team and so they were all in trying to to solve this and also a one of the on-call programmers I try to help as well and I try to help as well so I work for two days with them also trying alternatives and that so it's an example of something that just comes up and we just do it.

Yeah. So I think one of the features of ShapeUp is that for teams that adhere to it or practice it more strictly, you're only really working on one thing at once.

Yes. You know, your work in progress is confined to that thing and that has huge benefits and I think lends itself well to the setup that. 37 signals has where you have such an immense amount of flexibility over how you spend your time. There's no preset meetings, et cetera, et cetera. It's my understanding that in addition to you being on a team that works somewhat reactively, you're just a person who loves.

kind of changing up what they work on at any given time. Alberto, who introduced us, one of your former colleagues who now works at Tupole, I think he described your style of work to be very particular, different from anybody's style of work that he's seen before. And so I'd love to hear a little bit more about how you work specifically and how you work in managing the reactive work and doing so many different things at once.

Yeah, that's true. And I will say this is common to other of my teammates. And I think in my particular case, what happens to me is that I cannot focus on the same thing for very long. easily unless unless i'm really really hooked into something but that doesn't always happen and sometimes i get stuck when i cannot when I'm not making progress and I'm not able to push and make progress I need to change and I find I'm way more productive if I have the possibility of switching things and also

taking a break from work. I take many breaks. This is probably what Alberto finds a bit strange. I usually work throughout the day rather than in a fixed time. Yeah, so I may work in the morning. For example, today I started working at 7.30 or so, but then I left to go to the gym, and then I came back, and after showering and everything, I worked for... two hours and a half and then I left for an event that I had today and then I came back in the afternoon and then I worked for

two hours and then i went to work my dog and then now i'm doing this podcast and then i will probably continue working for maybe a couple of hours more later in the evening i usually work in the many, many evenings because I've been out in the middle of the day doing other stuff. But I just find that if I'm sitting for... or even stand, like I have a standing desk, even if I'm in the same place, for four hours or five hours, I find that I'm not doing anything anymore. It only happens...

It's not always the case. Sometimes I'm super, super into something totally in the flow and working and I can be six, seven hours doing the same thing. But for me, it's rare. I tend to get tired. I tend to get distracted. And I don't know, I need to, I need a change of, you know, doing something else. And sometimes I crave the... This is also probably happens to other people, but sometimes I just crave the achievement that when you get to complete something that is...

Like, you know, when you're working on something long and it may be a few days and you don't have anything yet and nothing finished. And I start to get in. I need to finish something like finish, do something and finish and ship it. And that's it. It's done. And you get. to check, to mark the card as no, to check the to do. And I find like I'm very, maybe it's probably not.

The best. Probably some people will say it's not correct, like I should change this attitude, but I can't help it. I really like to feel the accomplishment and the achievement of completing things. So sometimes I... I just go for that. And I'm also very, I love helping people as well. Like I love it. It may be a part of missing like this.

interaction but I love helping people so and I love also the strange bugs and cases like when someone is posting something that looks strange or that looks mysterious or very you know a weird bug like that or something I just I have to look at that. I cannot help it. I have to look at it. I am looking at the clock, though, and we are running out of the time that we had allotted, and I want to be respectful of your time, Rosa. So before we wrap up, I would love to ask just what's one question?

about remote work that you don't yet have the answer to. Yeah, that will be for sure how to manage to stop working and to work sensible hours. I know this happens. I always find it funny when... People think that remote workers are like slacking and not working, like sleeping and having, I don't know, you know, like watching TV and with a hand in the keyboard like that, answering or whatever. Because I think...

Most people that I know that work remotely, and it's quite a lot. I have many friends who work remotely. They work more, like way more. I remember I work way more than at 20 I work in the office. We work a lot, but I still work less there because you will just leave the office and that's it. But here at home, I have my... It's very hard to stop and it's very easy to overdo it. It's very easy to work too much.

Quarmades do it as well. Some of them, maybe because of family situation, perhaps, some of them who have children, small children, they obviously have something more important that they need to tend to. brings them out of work. But for me, for example, for some of them who have older children that they don't need them so much, I find it's very hard to...

to just stop working and not being looking at work all the time. No, I totally relate to that. Do you have any tips or habits that you've developed that have helped you find that?

Yeah, get out of the house. For me, that's what works. I need to go out and leave the laptop here and try not to look at the phone, though sometimes I do. getting out. It's also good just for another thing, this doesn't happen to me but I know some people struggle with being always at their home inside and that can be also bad for your health in general.

I'm lucky I live in the center in a city, so I just can't go out of my flat and have things to do. But I think it's very important to make sure to leave the house. I fully agree. There have certainly been times where I'm halfway through a day, particularly in the winter where I am, where there's less of an enticement to go outside. And I'll think to myself.

I have not been outside in 36 hours. That is not good. That is, that is like. Exactly. Yeah, it's bad. It's bad. Yeah, it's definitely bad. You need to move. You need to. get fresh air, even if it's cold or even if it's raining. It's very important.

Totally. Yeah, that's good advice. So thank you so much, Rosa, for being generous with your time and perspective. I've really enjoyed this conversation. If folks want to learn more about you or your work or anything else that you're up to, where should they go?

I think they can just go to my website, it's rosa.coach, C-O-D-E-S, because my pronunciation is not always the best. And there are links to... to my blue sky profile and i plan to there is not much there but i plan to add some confidence talk in the future and if i ever get to write stuff it will be there Good deal. Well, we'll link that in the show notes for folks as well. And so thank you again and hope to catch up again soon. Yeah, same. Thank you so much.

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