Lists and Growing Organically with Doist’s Gonçalo Silva

Today’s guest is Gonçalo Silva, CTO of Doist. Having started as a freelancer hired by the company’s founder, Gonçalo is a great example of how you can grow your career even working remotely, and be part of something big.

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Goncalo Silva

Luis Magalhaes: Greetings, ladies and gentlemen. This is Luis. Luis from DistantJob your host here at the DistantJob Podcast, a podcast about building and leading remote teams that win. Today my very special guest is Goncalo Silva from Doist, he is the CTO there. But before I introduce Goncalo, let’s talk a bit about DistantJob.

Luis Magalhaes: So what is DistantJob all about? Well if the podcast is about how to lead and manage the teams, DistantJob is all about building the team. That’s because we can find you the best people all around the world, vetted by our expert recruiters who are experts in their fields, and select the best people based on your specific requirements and your company culture. Our network and experience combined with the possibilities of remote work allows us to tap into the worldwide workforce to find you better people, faster.

Luis Magalhaes: So Goncalo Silva has a career path that is becoming the norm in the remote workplace, in the workplace of the future. He started as a freelancer, actually, doing programming work for Doist and then he joined the company because they enjoyed his work and he is now CTO. So his career path is something that is going to become more and more common as remote work … well, along with remote work becoming more and more common. And we talk about that, but we talk about a lot of other things as well. In this interview, we’ll learn about how it happened that Doist became a remote company from its inception, but we also figure out what they find valuable when interviewing for remote employees and how they track their productivity. And here is a question for you, can you imagine what a book that is over 80 years old can teach us about empathy in remote work? Well, if you want to figure that out, be sure to listen to the following hour or so of remote work-related conversation. Ladies and gentlemen, I give you Doist’s Goncalo Silva.

Luis Magalhaes: Welcome, ladies and gentlemen, to the DistantJob Podcast, a podcast about how to build and lead remote teams that win. This is your host Luis. And with me today I have my very special guest is Goncalo Silva, CTO at Doist.

Goncalo Silva: Hello. Hi everyone. I’m very happy and honored to be here with Luis today. As he said, I’m CTO at Doist. We are a fully distributed company that builds Todoist and Twist. You’ve probably heard of at least one of them. We are about … we are over 60 people now and we work from 25 different countries, pretty much all continents.

Luis Magalhaes: That’s a lot. That’s a lot. That’s a lot. We actually, at DistantJob, we also work from several different continents, but not as many countries. We may have to work on that. So tell me what’s the story behind that. What’s the story? I mean I know you were fully remote since the company’s inception, but what’s the story behind that decision? Was it a conscious decision or did it just happen?

Goncalo Silva: The truth is it’s very organic. Briefly, the story of the company is, Amir, back in 2007, he was working two jobs, he was studying for university.

Luis Magalhaes: That’s your founder, right?

Goncalo Silva: Yes. And he needed some kind of to-do list to keep him in check. So he tried some solutions in the market and he was not happy with any of them. So he built Todoist for himself. And after some friends got a sneak peak, they also wanted it for them, so over time he kind of realized that other people also want this, so I’m gonna turn this into a product. And for a few years, Todoist was a side project. But the core here is Amir, at the time, did not plan to create a company. So when he needed someone to handle support and other things that he didn’t want or that he didn’t have time to, he ended up hiring freelancers. He did not restrict himself to his location. In fact, he was traveling around at the time. So the truth is when all of this started feeling like it should be a company, there was already kind of a distributed system in place, working with freelancers from all over the world to build Todoist at the time. So yeah, I guess that’s the core motivation behind this. It was very organic but obviously it was also organic because it made sense to him. So Amir and also to the initial people that worked with him.

Luis Magalhaes: Okay. Again, it’s so nice that it worked so organically. It was just a matter of there was … did you ever consider the possibility of just renting an office and building the company there? Or was it like several of our key people are already remote so let’s just go with this?

Goncalo Silva: No, of course we considered. This is something we occasionally talk about. Actually not anymore, but a few years ago we did. For a little time, I mean we were always fully distributed, so this was not an exception, but for a little time we actually had a majority of people here in Porto, Portugal. Because as I’m sure you know, a lot of companies in the beginning, they grow out of referrals. So I had a friend who was working with Amir in Chile, he referred me and then I referred another friend, and the two of us together, we kind of referred three or four people who kind of like became the backbone of Doist at the time around iOS, Android design. During that time, until we expanded further, there was kind of like a core part of the company was in the same location and also we, together, all of us decided to rent an office where we could come and co-work. So it was not really a company office, just like instead of going to a co-working space, since there was like five or six of us here, we rented a small office and we would just come in whenever we wanted and be with each other.

Goncalo Silva: So I would say that was the least distributed time for Doist, specifically because Amir, who was in Chile at the time, he also decided to spend a couple of years in Porto. So then it was us and him and we were all here. And actually, this was a time where we learned a lot because we made some mistakes like having discussions and sometimes making decisions without using the usual means of communication that we should be using. And I am actually glad for this time because I think we have strengthened our processes and our workflows to make sure that everybody … even if I am with a coworker within the same office, within his co-working space, because all of us travel a lot and sometimes you meet with each other, but we always go the extra mile to make the whole conversation open and transparent and let others weigh in. And I think this is something we learned during this initial time where we were still distributed but there was in fact a lot of people from the same location.

Luis Magalhaes: So that’s something that I actually talked about a couple of months ago when I interviewed the lead mobile developer for Buffer, Marcus Wermuth. He actually talked a bit about transparency because they have a huge culture of transparency. So since you touched on the subject, and I want to go back to a couple of other things later, but since you touched on the subject, and since communication is so important when it comes to dealing with remote teams, I want to get your opinion on this. What are the expectations regarding the transparency of communication? Meaning I assume that by transparency you mean that instead of people, let’s say you use Slack, let’s say.

Goncalo Silva: We use Twist.

Luis Magalhaes: You use Twist, okay. I’m not familiar with how Twist works, but I take it that you mean that conversations usually happen in public and not in private messages. So how much do you expect people to be aware of the conversations versus when you’re talking to someone about a project, you take it upon yourself to bring them up to speed because you don’t think it’s reasonable for them to be aware of what’s happening? What’s the balance there?

Goncalo Silva: That’s a great question. I would say that Doist, by default, is a little, and a typical company in the ways we communicate. With the launch of Twist recently and our whole messaging around that time and afterwards, we truly believe in asynchronous communication. Being able to sit down and think about things and craft a response to something that is more meaningful than just a chat message, a real-time chat message. So Twist kind of promotes this behavior where the vast majority of conversations are public, the vast majority of confirmations are long form, and the vast majority of confirmation … of conversations are asynchronous. So we do still use private messages, but nothing or almost nothing that is mission-critical goes through private messages.

Goncalo Silva: You asked one specific thing which I didn’t address which is what is the balance between us expecting people to follow all of these conversations or just pinging them directly to bring them up to speed. And honestly, pinging people to bring them up to speed is not something we do at all. So the conversations are open, relevant people are notified. People who are not notified have a very easy way to access these conversations if they want to or when they want to. But I have to say that at times, we deal a little bit with information overload and this is something we have not truly nailed yet. We have made a lot of improvements and some of them are reflected in the platform that we’re building, Twist, but it’s still something we want to improve over time because if all conversation is public and everybody’s a part of the conversation, it’s like you have a big office and everybody’s shouting all the time. So when do you get to do the real work, the work that matters?

Luis Magalhaes: Yeah. I mean I’m definitely going to try Twist. I did try Todoist for a while and I did use it for a while, but I’m definitely going to try Twist because what I find is that when you talk about overwhelming, that’s why I quit Slack. Because Slack was just all the noise all the time in front of my head. And currently we’re using Basecamp, which I know is a different thing, it’s got more than the chat component to it, but in Basecamp, what I find is that it’s almost the opposite problem. It’s too easy to get things lost. Things get buried very easily. And it’s not that hard to keep track on them.

Luis Magalhaes: So from what I’m understanding now, correct me if I’m wrong, your approach is more like if you’re working on a project, let’s say if you’re building a Doist podcast, and you want Luis’s input on it, then instead of coming to me and having a conversation with me about here’s where our at for our project, we’re doing this and this and that, you’re telling me, “Hey Luis, the conversation has been happening for like two weeks, go there, search for these terms and get catched up on it.” Something like that?

Goncalo Silva: Yeah. Or I will just notify you. So Twist has this feature where you can notify specific people. So in the example that you gave, we would have a podcast channel with all podcast-related conversations there. And if I wanted your input on something, I would just ping you directly and you would get a small green circle … sorry, orange circle over the conversation and you would be … Basically, it would be very visible what you have to reply to, what haven’t you seen yet, etc. I mean, in a way, a better version of what you get with email.

Luis Magalhaes: Okay, that’s super interesting. Let’s go back a bit to the building of Doist, to how you built your original team. Apparently it was originally the founder and you and working with freelancers, then you started building the team, and you needed to build a team specifically with the idea of being remote because you had decided on that, correct?

Goncalo Silva: Yes. To clarify, I was one of these freelancers in the beginning. And I guess almost everybody was.

Luis Magalhaes: On some of your talks, you gave a couple of talks. You were talking at, it was Lisbon, was it, what was it? Web Summit? You talked at Web Summit Lisbon, correct?

Goncalo Silva: I think you’re referring to Pixels Camp, the remote workflows talk?

Luis Magalhaes: No, no, there was definitely some other at Lisbon, some other conference, maybe it wasn’t … It was definitely not Pixels Camp. I saw that as well. Anyway, you were talking about how important it was for people to be independent. That workers needed to be able to work independently. When you were giving advice on companies, you gave two kinds of advice. You gave advice on how individuals should face remote work and how companies should face remote work. And part of your advice to companies was to hire people that were independent. So this is very interesting to me because we are in recruitment business, this is what we do, and we run interviews and we prepare candidates and all of that. So what are the best interview questions that you use when you want to filter for independents? What do you ask, what are the kind of questions that you ask when you want to know … I know this person is a good, at his field, is an expert, but is he or she going to be good at remote?

Goncalo Silva: Let me just start by saying that I think interviewing is a dark art where –

Luis Magalhaes: It is. [crosstalk 00:15:28] that it’s my business.

Goncalo Silva: So it’s always a topic that’s hard to discuss because there are no … at the core, I’m an engineer, so I like specific things, measurable things, and interviewing –

Luis Magalhaes: [crosstalk 00:15:43] doesn’t like it, not hired.

Goncalo Silva: But regarding independents, there are exceptions to this, obviously, but I think it’s very important to hire people … if you hire people who care, and I’m gonna get into that a little bit more, but if you hire people who care, they will generally be independent. Now there are different levels of caring. Like you can hire, for example, an engineer who cares deeply about code. It’s something they truly enjoy, something they are passionate about, so they care about code. You can also hire a person who cares deeply about your mission. And when you have a strong mission, and I think Doist has, you can have a lot of people who care deeply about your mission. So that’s another angle on caring.

Goncalo Silva: In general, when people in some way are emotionally invested in the work that they do, it becomes easier for them to take initiative and be independent and take control. But, having said this, there are exceptions. Like you don’t need to use the passion page of the playbook to address this. Certainly there are people who might not seem to care who have a lot of initiative or independence. Or they are independent for a whole other reason. And this is something that sometimes it’s a bit harder to understand during interviewing. So something that we also have, and that we have found highly successful for a long time, is we have a trial period of three months after we hire someone where both parts, either the candidate or us, can walk away at any time if we feel like this is not gonna work. And the truth is we rarely use this, honestly it’s very, very rare for us to use this, but there has been a couple of instances where people have said after two or three months remote work, this is not gonna work for me.

Luis Magalhaes: That’s great because … I mean I love that because we do the exact same thing. The exact same time. We do have a, call it a trial period with DistantJob, where people work for us three months and if I have to say … Again, recruiting is in our blood, it’s what we do, so we like to believe that we don’t choose wrongly that often. So far, there were only like two people that we figured wouldn’t work since I’m in the company. But I think it’s important and we do advise that. So it’s very nice to see that we are on the same page. But do you find yourself asking some specific questions? Like I said, you talked about passion, it’s a bit of an iffy term. I don’t super enjoy passion, but I know what you mean. I know what you mean and it’s like … I like to say that passion is … sometimes work is just work and you need to be a professional, not passionate.

Goncalo Silva: No, for sure. I think passion is one of those cases where our industry destroyed this word by equivalent … Passion is right now equivalent to ADL or [inaudible 00:19:00] and etc. Which are also, by the way, things we despise and not ever support.

Luis Magalhaes: And it’s just look, as much as I enjoy my work, there’s never a case where the work is the same as the fun. My background is in … part of my background is in writing, before I was taking care of marketing I was taking writing. And as much as I enjoy writing, I also need a break to go have a Whopper, to go to the beach, or eat an ice cream, or etc. It’s not like enjoying something means that you can work on it 40 hours a week and have it constantly be pleasant.

Goncalo Silva: Yeah, yeah. For sure. For sure. That’s actually the biggest reason I used the word care, because I think caring is more … You can care about something and be professional about it, not necessarily passionate.

Luis Magalhaes: So you spoke about the onboarding. So tell me what’s the conversation like when you’re onboarding someone you … Specifically, how do you get them to understand how they are expected to communicate? And I ask this because I also know that you’ve talked at … we keep hitting this thing about communication with whoever I talk in the podcast. That it’s the main ingredient for successful remote work. And you, in particularly, spoke about this before saying that people need to know how much they are expected to tell you about what they are doing, communicate what they’re doing, because you can’t see them. You can’t guess.

Goncalo Silva: And also micromanagement really does not work in a distributed setting. I mean, I think if a company is trying to make micromanagement work in a remote setting, they’re gonna fail and it’s the wrong way to approach it.

Luis Magalhaes: That’s like your boss messaging, pinging you on Slack every hour, or every half an hour. It’s like I’m still working on that same thing that I was working 45 minutes ago!

Goncalo Silva: Yeah. The way we onboard people is basically, we have a very, very lightweight first week. This is very explicit. So when people join Doist, throughout the first week, they are not expected to make any meaningful, visible work. But we do provide them with a ton of materials to get them started. So for example, we have a Todoist project with a few steps, something like read this, read that. And these things could be the CEO’s message for the year, the examples of fine communication, examples of people getting out of their way to make something amazing happen, etc. Basically a bunch of links to relevant material, our values, the things we value the most, and how they are described, etc. So people get this from Todoist, and of course Todoist is just a hub to host links and materials. Throughout the first week, people are invited to go over that project, to go over that content, and just lurk. Lurk around Twist, see what’s happening, how it’s happening, etc. Get more familiar with how things are going down.

Goncalo Silva: Another thing we do is everybody we hire has a mentor. And the mentor is basically someone who has been in the team for longer from their team. And it’s someone with whom they hold a more constant conversation throughout the initial months and who can help them, who can clarify any doubts, who can answer any questions. On top of this, the new person can fly over to their mentor’s location and work with them for a week. It’s a little bit of … These are just some ways where the candidate can get more comfortable with getting to know how we work, getting their questions answered, being able to observe how things are happening. And yeah, we haven’t really hit any problems and I think it also helps that the vast majority of our communication is in the open. So literally anybody can see at any time.

Goncalo Silva: We have a leadership channel in Twist called [inaudible 00:23:37] and this channel is open. Pretty much everything is open. There are some exceptions, like salaries and a couple of other things, but otherwise literally everything else is open. And I think this helps onboarding people because they have a week and then even after that they can literally see anything happening.

Luis Magalhaes: Okay, but just to focus a bit to my question, it really is, when you’re having the conversation with the person, when the person is trying to understand how much they are supposed to communicate, how much are they supposed to touch base with you or with their manager about what they’re doing on any given day, what does that conversation look like?

Goncalo Silva: Oh, okay –

Luis Magalhaes: [crosstalk 00:24:29] that person is supposed … that person do, to write in the communications channel about what they’re doing, etc?

Goncalo Silva: I think there are more … This is also part of the Todoist project, by the way. So we don’t really have this in a conversation. We have a couple of processes that everybody uses in the company. We have something called weekly snippets, so on Mondays everybody goes in on Twist and shares what they have done last week, what they plan to do this week. We have this kind of self-rating system where you kind of evaluate yourself from the past week and also you make a small list of anything that’s blocking you. If you’re wanting on something, if it’s something [inaudible 00:25:18] particularly hard and you’ll have to look up the documentation, etc. So this is done by every single person in the company and it’s public. So this is the way we kind of like … If we want to sync up on an individual level, this is the way we do it.

Goncalo Silva: On top of this, most teams, this is up to the team, have a weekly meeting as well. The team lead and all team members have a team meeting where they also kind of like discuss the same topic but on a team level. So what are we gonna do as a team, who is gonna do what, etc.

Luis Magalhaes: That’s a very interesting approach. It tends to be the approach that we use. We used to do scrum like gel meetings, so every week, we did one week sprints, and every week we had the initial meeting and then the retrospective at the end of the week, but we actually scaled it down to one and it’s working nicely.

Luis Magalhaes: Let’s talk about lists. Because I’m a fan of lists. And I guess that you are, too. I wonder … I mean, I get the impression that you like lists. Let’s put it like this. Whenever I am, for example, running one of those retrospectives and we’re talking about the project, whenever we’re talking about something that went wrong and we’re trying to figure out how we could have avoided it going wrong, nine times out of ten I find myself saying, “You know, if we had the list with steps that we followed, checking every step, this issue wouldn’t have arisen.” I am constantly trying to sell my people on lists. Build lists and then we use lists for the project. I am a list fan.

Luis Magalhaes: That said, I’ve always used lists within certain platforms, certain project management platforms. Meaning I’ve used lists on Trello, I’ve used lists on Basecamp. You seem to manage your teams with lists. So how does that process work? How can you manage your team with lists?

Goncalo Silva: We don’t actually manage, like management is not very explicit at Doist and I think maybe that’s why it was a little bit hard to address the previous question. Management mostly revolves around unblocking people and letting them do their job. For example, the team meetings that I mentioned before, you said you did scrum, this is actually up to each team. Nobody at Doist uses scrum except the Windows team who uses scrum extensively. They have two week cycles, so it’s not a weekly cycle. This is pretty much up to any team. So the relationship of myself and the CEO to the team leads is very much like do what you think is best and that’s find. Just make sure to make it transparent and to share what you learn. Otherwise, do whatever you guys feel is best within your teams.

Goncalo Silva: And the team leads also have this approach with their own team members. We do use lists, but I would not say we use them to manage, for management. Basically, for example, we use lists for our roadmaps, of course, like the things we are working on, things we plan to do, when we plan to do them. We use them on a monthly basis. We have these work cycles. Okay, within the whole company, our work cycles last one month. This is when we have a little more formal planning of these are the things we want to accomplish by the end of January, for example. And of course we have a list of those things and who will because working on these things. But again, even the process of selecting who will work on what is pretty much totally organic. It is we need an Android developer, we need a designer, we need an iOS developer, and then people just volunteer and get added to those [inaudible 00:29:38]. There is literally very little management involved. But of course, there are a lot of lists, as you said.

Luis Magalhaes: Okay. Part of what you offer in Todoist are workflows and I’m wondering if there are any workflows that you use internally, for example on your own team. Do you have a favorite workflow for any specific kind of remote team? Or how does that work?

Goncalo Silva: A workflow?

Luis Magalhaes: Yeah.

Goncalo Silva: In the last few, I would say, in the last year or so, we have become more and more aware of the importance of documentation. This is probably related with us scaling as a company, and there are more people working on each project. Every new project has more people working on it. But I would say that right now we have gotten really, really good at documenting things. So for example, when we are gonna do something, a new feature, for example, we have something we call the product spec which lists what this feature intends to solve, use cases with direct quotes from our users, user stories, challenges that we foresee for this, and metrics, which basically is what do we want to improve, how can we measure if this actually improves what we want it to improve? This is just a first stage. Later on we have a very highly-detailed design spec which, as you guessed, has a lot of markups, some of them interactive, explaining behavior. We also have technical specs, which is how will this be implemented, the algorithms that are gonna be needed to make things happen, if there are any API changes, what’s the exact documentation of the APIs.

Goncalo Silva: So this is something we did not necessarily did before. Some [inaudible 00:31:45] before we would just say we’re gonna make a new scheduler with three tier buttons and then that was all. We would just get on and do some work. But as you scale, I think documentation and having a little bit of a more predictable process to how you implement new things or change existing things is very important. And I would say, right now, this is my favorite thing about the way we work. Our approach to documentation, from product to design to the technical specification of things is very thorough. And I think it’s very helpful in helping get everyone on the same page and it’s also an amazing resource in the future. If you look back, you have the documentation on what happened.

Luis Magalhaes: So can I get you to describe to me a bit more in detail, if you can of course, how that documentation process works? Because I totally get why it’s necessary. In fact, my team, my marketing team, tends to work a bit [inaudible 00:32:47] like, “Hey, let’s do this thing. Okay.” And everyone goes and they start working on it and everyone’s excited. But then when we have leadership calls, we basically have a call where we get the leaders of all departments in the company together to talk about what we’re doing in our respective departments. Every now and then I joke a bit because I’m like, “Well, we’re doing this.” And it’s like I want to go into more specifics, “Well I suppose that person is working on that and this person is working on this,” but sometimes I feel that I don’t bring enough documentation to the table. So I definitely need that in my life. What’s your process like, if you can share?

Goncalo Silva: Yeah, yeah, I can share. This is all tied to a while back I said we worked on a monthly cadence internally, and everybody does this. So every month we have new projects we wanna complete. Of course, this means breaking down some projects into different parts. But for all of these initiatives for each month, pretty much all of them have this thing I call the product spec describing on a high level product’s vision, what exactly will be done, use cases, user stories, etc. So everybody does that it’s pretty much we have not … This is not written in stone, but everybody pretty much does that and it has become a part of the workflow. It’s expected, I would say.

Goncalo Silva: The thoroughly detailed design specs was mostly an initiative by the design team. So this was an explicit transformation where before we had mock-ups going around in private messages, mock-ups lost in our Google Drive, our Dropbox, and now, at some point we decided to make a change to make things have a single source of truth. So one document, all of the mock-ups, describing behaviors, etc. Sometimes there are two documents, one for mobile, another for desktop, but you get the idea. The technical specs have been the latest addition. This is, again, I think like a lot of things that happen at Doist, this has been very organic.

Goncalo Silva: So we’ve had problems. Because we’ve had problems, we’ve openly discussed them. Like this did not go well so let’s talk about why it didn’t go well and what we can do to prevent these things in the future. This has happened with overall plans for new features, which I guess is why we have product specs right now. This has happened with designs. In the past there has been one or two situations where people were implementing older versions of the design because that’s what they had at hand and we didn’t have everything under a single document. I guess that’s why we made the change there, as well.

Goncalo Silva: And the last one is, the technical one, is literally because we, in the past couple of years, we started realizing that we had a harder time than we would like dealing with more complex technical changes. I guess this affects every single technology company in the world, but still, it’s something we wanted to improve. And one of the things that we noticed is that we had a big lack of documentation which, when you’re working on something bigger or more complex, having no documentation sometimes makes it harder for certain people to participate. If the information lives in your head and mostly in your head then for me that’d be a little harder to get into it.

Luis Magalhaes: So in a way, and that’s part of what I try to transmit to my team as well, it really is just an extension of the concept of transparency. Just as communication can’t live only in private messages, documentation shouldn’t live only in your head. It’s a different kind of communication but it’s communication nonetheless. Communication of how it was done, why it was done, and when, even.

Goncalo Silva: It’s a little more formal because you follow formats and you have some rules but it is, as you said, I think that’s a very good point, it is just a different form of communication and one that you really need in the long run.

Luis Magalhaes: All right, so shifting topics a bit. You can’t see it, because … Well, maybe you’ll be able to see my cat if she jumps here, but I’m in my living room and again, people at home are only listening to this, I don’t provide the video feed, it’s an audio only podcast, but I do have always with me in my living room a shelf of foundational books. And on that shelf of foundational books, I think we’ll find something in common, because the most worn out book, it is literally, it is marked, it is written all over. It’s like the pages look like it weathered a couple of storms in a dozen backpacks. The book is literally falling apart. Is a book by Dale Carnegie called How to Win Friends and Influence People, which I know that you’ve recommended in the past. I mean feel free to give your own interpretation, but for me, the book’s essential point is empathy, is how to put yourself in other people’s shoes in order to figure out what will motivate them, and what makes them tick. That’s the main message that I take from the book. It’s a terrible, very scammy-sounding title but the wisdom inside is great.

Luis Magalhaes: I want to ask you about how do you find any challenge, and if so how do you surpass them, in applying what you learned in this book to dealing with remote people. Because it’s hard. I keep bringing this up during the podcast. The reason the podcast is audio but I do it with video is to establish connection with the person I’m talking to. So how do you think you can apply those lessons to [crosstalk 00:39:04]?

Goncalo Silva: I think Dale’s lessons are … First of all, this is a very old book. You didn’t mention this, but this book is almost a century old by now.

Luis Magalhaes: Yeah, but if it works, so far it has proven valuable to me, constantly.

Goncalo Silva: But I totally agree with what you said. The core message of the book is around empathy. In fact, if I had to summarize the book in two words, it could be be reasonable, because that’s basically what the book describes. But in general, I think remote, working remotely, working in a distributed team, there is a big lack of body language. And body language can play a huge role when you talk with someone. Like for example, if we are working together and I have a … and I want to criticize something you have done, I think it’s a very … When we are face-to-face, I think it’s much easier to do this, to have this possibly tough conversation than when you are doing in writing. Because when you are writing, it’s not as clear as to how … You have the content but you don’t know exactly how the content was delivered. This is actually a big challenge sometimes and one of the reasons I really enjoy our yearly retreats, which are in-person, face-to-face, is that you get to put a face behind the words that you read on your computer.

Luis Magalhaes: Where was the last one?

Goncalo Silva: The last one? When was the last one?

Luis Magalhaes: Where. Where. I’m interested in the location. For our first one, we were thinking the Spanish Coast, Mediterranean coast.

Goncalo Silva: We were in Chile last year.

Luis Magalhaes: Wow, nice. Look, I faced that problem myself. Just today, the president of DistantJob was changing messages with me and I have had it on a couple of … I have had him on a couple of podcasts, so people know that we’re like best friends when we’re talking. But when we’re messaging, I just read his messages and he reads mine and we’re like it sounds like we’re angry at each other. Kind of have to step back and say, “Whoa, wait a minute. If I was talking to him, through Zoom, would I be having this reaction? I most certainly would not.”

Goncalo Silva: Exactly. And this is very relevant for remote. If we think about Dale’s very old book, when remote work was not even really in imagination, probably, I do feel like his advice on trying to … always trying to see stuff from the perspective of others becomes critically important in a remote setting. Because again, if you communicate regularly via text, you don’t have that accessory information like body language and the way things are said. It’s only what the things were said. I think sometimes it’s very easy to read in between the lines things that don’t exist and get worked up for no reason, basically. And sometimes it’s very, very, very critical to make that exercise of I’m gonna pretend I’m the other person, try to understand their context, try to understand their reasons that led to this point and then with this context I am going to reread the text. This is a very relevant lesson, I think, from the book.

Luis Magalhaes: Basically, the lesson is don’t use Twitter, like ever. I guess that’s the lesson.

Goncalo Silva: Yes. I was not expecting that.

Luis Magalhaes: Okay, well.

Goncalo Silva: I have another, since you mentioned books, I would like to –

Luis Magalhaes: I was going to ask you about more books, so go ahead.

Goncalo Silva: Oh, you were? Okay, then let’s go.

Luis Magalhaes: Seriously, books or tools or resources or [inaudible 00:43:27] that you think are useful for this new enterprise of building and leading your remote team. What would you say?

Goncalo Silva: One of the, probably the best, book I have read in the last few years was The Score Takes Care of Itself. I think this is, for everybody that’s working on their own product or service or anything in that vein, this book has opened my mind to … By the way, I didn’t mention who this was from, this was from Bill Walsh, the famous coach. And basically the message of the book is, I think this is very, very relevant nowadays, because we are living in a time where we see companies like Facebook, Amazon, Google, and then all of the startups following their footsteps where we are trying to maximize our optimization towards certain goals without … we are focusing on the goals, not on the process. And this book, I don’t want to spoil it, but also anything I say is not nearly good enough as the book itself. So this book focuses a lot on the message that you can see in the title. If you focus on doing this right, you have a good process, you do your own product, service, you execute really, really well, the score, which in this case would be the users or the revenue or whatever, will take care of itself.

Luis Magalhaes: I agree completely. Again, that’s the point of the podcast. The reason I started this is because I wanted to learn more from the people I interview, but also expand through the world the knowledge of what it takes to build processes that make remote teams successful. Because as you pointed out in one of your talks, it’s not all roses, there’s definitely challenges to remote work. So do you have any favorite, any processes that you think should be baseline? Any ways that you think … You’ve mentioned before that all the teams at Doist can independently decide what’s best for them. But do you feel there are some recommendations? Some things that remote teams should prioritize?

Goncalo Silva: Well, that’s a good question. The thing is, there are so many angles to this question that I am trying to decide which one I’m gonna pursue. I think that approach that I mentioned before is very, very tied to our DNA. Everybody has a lot of freedom to do things the best way they think they can. And this reflects throughout the whole company. Leaderships, teams, every individual, etc. That’s one of the reasons we have almost no common processes. Of course we have some, we have the weekly snippets that I mentioned, everybody does them, we also have to-do system, the monthly planning of workloads that I mentioned, everybody also does that. But otherwise, there’s very little common ground. But of course, we’re all adults, we’re all smart people, there is a tendency to share stuff that you learn and different teams learn from different teams and some of the processes are common. Like the weekly team meeting, this is not actually written anywhere that it must happen and every team has a weekly meeting. That’s one of those things.

Goncalo Silva: The absolute baseline process for remote work, I think there are a few. The first one is the standard way of running or managing or working within a company, which involves quite a bit of micromanagement, if we’re honest, it just does not work in remote. And I think it’s better to find better processes or just see work from a different angle than to try and force micromanagement into remote work because it’s just gonna be very frustrating for everybody involved. So I would personally argue that micromanagement does not even make sense in any setting, not just remote work. In remote work, it’s kind of like impossible. Good luck with that.

Luis Magalhaes: It’s not impossible, but just counterproductive. First, if you’re constantly checking up on every remote employee, number one you need to do it at very small intervals because otherwise you’re just trusting them, which is what you should be doing in the first place, and number two you won’t be getting anything done yourself. That will be your full-time job, poking people every 30 minutes or so.

Goncalo Silva: And as you said, it’s nonproductive. That would definitely be the first thing. The second thing is … So I’m just gonna go over a few that came to my head.

Luis Magalhaes: Please do.

Goncalo Silva: The second thing is I think, especially in the beginning when you are not … Doist is right now almost 12 years old, so there’s a lot of experience going around distributed work and remote work, but especially when you’re new or when you’re getting adjusted to this, I do feel like you need to pay a lot of attention to the way you communicate. As I said, we had this experience where we had a significant amount of people in the same location and we made some mistakes around this. It’s just too easy to talk to the person next to you and make a decision and go ahead. If you’re going for creating a remote company, if you’re going for a healthy remote culture, one that is aimed at the long term, I would definitely recommend making sure that your communication flows, your communication processes always invite … You will probably have a common tool, email, Twist, maybe even Slack [crosstalk 00:49:55], you should make sure that the majority of the communication goes through those platforms so that everybody has access to them. This is very important. [crosstalk 00:50:05].

Goncalo Silva: The problem is that otherwise you get into this situation where some employees will feel like second-class employees. You never wanna be in this situation.

Luis Magalhaes: I was actually talking a few weeks ago with Nassim Kammah, which is, he is an engineering manager at MailChimp, and he has this rule which he calls the remote, all remote rule. Which means that if one person in the team is remote, then everyone, then the meetings are done by Zoom with each person on their screen and that’s it. You don’t have two or more people in the same room because those people … the power dynamic will be tilted toward those people. And then you’re having decisions made based on proximity and not on ideas.

Goncalo Silva: We actually do the exact same thing. And it’s also a mistake we did, remember the Porto story’s getting old by now, but we did have meetings with everybody together on the same computer. And exactly, we had issues long-term with … It’s very easy for that group to take over the whole conversation, even if by accident. Right now we definitely have separate meetings in separate … Like if we have a meeting with multiple people from Porto, they will be in different computers in different rooms even if we are in the same office on that day, we will be separate. So we kind of follow the same rule there.

Luis Magalhaes: It’s been almost an hour, and I want to be respectful of your time. A couple of questions that I wanted to do before we say our goodbyes. Number one, is there any specific tool that you find particularly useful for working remote? Or putting it in another way, if you were going to buy for your whole team a tool that was €100 per person, let’s say, what would you buy? What would you give everyone in the team?

Goncalo Silva: Well, Doist builds tools for remote companies. So we would buy our own tools. And we would have some spare money.

Luis Magalhaes: Great. I can go with that. I was thinking more along the lines of laptop stand, green screen, etc. [crosstalk 00:52:27] coffee mug. But that works, too. That works, too. I can’t speak about, again, I haven’t tried Twist, I look forward to, but I definitely enjoyed Todoist.

Goncalo Silva: No, I mean on a team level, Twist is what drives the vast majority of our communication. On a team/company level, I would definitely, I think Twist is what’s driving Doist right now as a communication platform, so that is definitely what is most important. But if you mean like a hardware thing, I would totally … that would totally be up for each and every employee, like what do you want? Do you want a mug or a laptop stand? But one thing that’s very critical is having a really good internet connection. So if that counts, that very helpful.

Luis Magalhaes: It is. It is definitely. And I would add a microphone. One of the things that I like to do is just buy people microphones. Just buy a good microphone to people. Because if not people will just be using their own laptop microphone and that’s got problems. Not always, but … The Apple ones are actually quite good, but most laptops have problems.

Goncalo Silva: You run a podcast, of course you would give people microphones.

Luis Magalhaes: That’s fair enough. No, but it’s just so annoying when you’re trying to have a meeting and there’s these people that talk … this one person in the meeting that talks like Darth Vader, is like …

Goncalo Silva: Yeah, definitely.

Luis Magalhaes: Anyway. My other question is just a question that I ask every guest. Imagine that you’re organizing a dinner at a Chinese restaurant and all the big shots in Silicon Valley are there. All the CTO’s, all the people, all the CO’s from the companies of Silicon Valley. And the topic that’s going to be discussed in the round table of the dinner is really the future of work as far as remote work is concerned. What is the message that you as a host would put inside of fortune cookies that those people would open at dinner, knowing that the topic is remote work?

Goncalo Silva: I think I would write you are doomed.

Luis Magalhaes: Okay. That sounds like something that will come in a fortune cookie but I will have to ask you to explain because I’m curious now.

Goncalo Silva: Yeah, yeah, yeah. I would definitely write you are doomed and the reason is if we look at Silicon Valley I do feel like Silicon Valley is the direct opposite of remote work. It’s a place that invites everybody to move from wherever they live, sometimes a different country, to go over there, pay insane rents, to work co-located with everybody else. That is in many ways the very opposite of remote work. The thing is, for the people, and I am one of those people, who believe that remote work is the future, so it is a strength, it’s something that will make companies stronger, it’s something that will make companies more productive, more competitive. The reason I would write you are doomed is because these people are working towards something that goes against what I believe to be the future.

Goncalo Silva: Maybe it’s working out right now, but I am unsure, once remote companies are able to nail the fundamentals, because … Okay, we can take a little bit longer because I think this question is very, very interesting, if you don’t mind. The truth is, remote work is great. But there seems to be kind of like this invisible barrier of size that has not been surpassed yet. One of the original remote companies, GitHub, they grew, they grew, grew, grew, and then suddenly they had problems and one of their solutions was kind of like retrace their steps and go back in the whole remote thing. So they stopped being a truly remote company, they became kind of remote-friendly, depending on who is using your site, but they retraced. There are a lot of examples like this of remote companies that, as they grow, they give up a little bit on the whole remote work thing.

Luis Magalhaes: And even companies that went remote and then backtracked like IBM and Yahoo, the commonality that I find, and maybe I’m just being a bit arrogant, I don’t know, but the commonality that I find is that, again, it tends to be very big companies and the thing that big companies aren’t is agile. They tend to fossilize and they tend to get into a control mentality. I like to say that when you start having … when you start building your company, making your business decisions, to benefit shareholders instead of to benefit the company’s bottom line, that starts being an issue. Because it’s not like you need … so a small company, relatively small company like ours, we have to build enough business in order to pay everyone a nice salary and to get some extra to build our war chest and to invest in R&D, and we’re happy when we get that.

Luis Magalhaes: Now a bigger company, they start having shareholders and then it starts happening that they just have to grow every year. It doesn’t matter if there’s enough money to go around or not, it needs to be grow, grow, grow. And I think that a bit of agility is lost in that.

Goncalo Silva: For sure, but the truth is, there is no remote Facebook or remote Google or remote Amazon or remote Apple. And I do believe that for remote work to really take off, we’re gonna need one of these huge companies being run remotely successfully. I think for everybody’s sake, this is what will help prove or disprove remote work, is having a truly big company being run remotely. I mean GitHub backtracked, Reddit as well, as you’ve said, you’ve also talked about Yahoo. And we have some new contenders, we have GeekLab with over 350 people working fully remotely. We have Buffer, we have Doist, there is a new wave. But I do feel like it’s important to mention this challenge because I really believe that for remote work to be the future somebody or some company will need to figure this out so that we know it’s possible. Because right now, we haven’t seen this yet. We don’t know if this is possible. But I do believe this is possible. And if it is then you are doomed is what I would write in their fortune cookies.

Luis Magalhaes: Well, I hope to see you on the other side, is what I can say. So anyway, all right. So speaking of seeing you on the other side, it’s time we wrapped this up. Please tell our listeners how they can find you in the internet, how they can find your talks, and let them know if there are any upcoming talks that you are going to give relatively soon. I guess I’m going to do that now, but I highly recommend that people look up the Doist blog, I’m going to include a link in the show notes. I know you haven’t a lot of articles written there by yourself, but it’s just such a great resource that I really recommend everybody [crosstalk 01:00:32].

Goncalo Silva: Yeah, I’m very proud of our blog. So as for me, generally I’m a very private person. I actually, Twitter is probably the only public place where you will see things written by me, although it’s not long form. So there is my Twitter.

Luis Magalhaes: So if people want to get angry at Goncalo, you know where to go.

Goncalo Silva: Twitter, yeah. Twitter. Twitter is the best place to get angry with me. I also do a few talks, as Luis said. The next one, I’m not entirely sure because there are a few things unconfirmed yet, but I will definitely be trying to go again to Pixels Camp this year with a much more technical talk than last time. I like to change up, keep things interesting. And I do have a few conferences liked up for the year. But I’m unsure if the talks will be accepted or not. For example, I would love to speak at the Lead Dev and a few others. But anyway, if you check my Twitter, whenever I’m accepted to do a talk, I will definitely share the details there and keep people up to date. And of course, the Doist blog, it’s an amazing blog run by amazing people with amazing content. And hopefully there will be more stuff by me there soon as well. It’s totally my fault that there isn’t.

Luis Magalhaes: Well you know, you only have 24 hours in a day, right? You have a lot on your hands.

Goncalo Silva: Well the blog should be one of them.

Luis Magalhaes: There you go. Okay so thank you very much man, this was a pleasure.

Goncalo Silva: Yeah, for me, too. Thank you for having me, Luis, and have a great week.

Luis Magalhaes: Yeah, you too. Bye-bye.

Goncalo Silva: Bye.

Luis Magalhaes: And that’s it, ladies and gentlemen. Thank you for being here for one more episode of the DistantJob Podcast. If you want to continue the conversation with Goncalo or get angry with him on Twitter, he is @goncalossilva and you can also find him by the same handle on GitHub. I will include the links in the show notes. In the mean time, if you enjoyed the show, please keep on doing what you’ve been doing and sharing the episodes on social media, it’s very appreciated. And also leave a review in iTunes or your podcast listening service of choice. Reviews are the main thing that help us grow and reach more people. And as we reach more people I can get more awesome guests to interview on this show. So it’s a win-win for everyone.

Luis Magalhaes: Now what happens if you’ve heard a really awesome tip from Goncalo or something that you wan to apply in your own business? But it’s a bit of a hassle to scan through the podcast, trying to figure out that tidbit of information, you don’t always have a notepaper and pencil around. Well, if you go to the DistantJob website, if you go to the podcast section on our blog, you can actually subscribe and you get access to show transcripts. So you can get all that information goodness in written form. How’s that for a deal?

Luis Magalhaes: Finally, you can also, in case you want to build a wonderful remote team, get in touch with DistantJob. We can find you the best people worldwide. The best talent, and quite fast as well. Actually 40% faster than the industry standard. So if you need great people, if you need them better and faster, think worldwide, think remote, think DistantJob. See you next week.

More ways to listen:

What does it look like when a company is naturally born remote? Gonçalo Silva, the CTO at Doist – makers of Todoist and Twist – tells us about this, how it influenced his career path, hiring approach, and much more in this week’s episode of the DistantJob Podcast

Obviously, we dig into the importance of checklists and process in managing remote teams, but we also talk about a lot of other things, including, but not limited to: how to test potential employees for remote skills; what are some good ways to document decisions in a way to have a single source of truth; and what an 80-year-old book can still teach us about management, even when it comes to the Future of Work.

As always, if you enjoy the podcast, we humbly ask that you leave a review on iTunes or your podcast syndication service of choice – and if you could share it, that would be even better!

Need that one incredible employee to bolster your team?  Get in touch and we’ll find you who you need.