Remote Work Interviews

Conversations with leaders and innovators about how industries and organizations think about the future of remote work.
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Gonçalo Silva: CTO of Doist
April 24, 2019
Interview by Sophia Bernazzani
Photography by Gonçalo Silva
Gonçalo Silva is the CTO of Doist, which powers workplaces of the future with productivity tools that promote a more balanced way to work and live.
Gonçalo Silva is the CTO of Doist, which builds productivity tools for workplaces of the future to help people lead more balanced lives. In this interview with Owl Labs, he talks about building and scaling remote teams and how remote works helps people do their best work.

Owl Labs (OL): What's your elevator pitch answer for how you got to where you are in your career today?

Gonçalo Silva (GS): I'm not a fan of elevator pitches because they lack a lot of context. For example, I've always been privileged and I've always had the support structures in place to let me be free of worries and focus on my work, and this is important context through which to view my story. Most people aren't in that same situation of privilege, and it's important to say this because the story of my career is biased by my background.

When it comes to my story, I've always been a very curious person, and that's had a massive impact on my work and my career. It makes me focus continuously on learning and growing as a person. There is only so much we can do at one time, and I've found that many people who are very talented sometimes get lost in all of the different things they could be doing. It's so important to focus on impactful work, so for me, being curious, continuously learning, and focusing on work that really matters have shaped the progression of my life and my career.

OL: Your company, Doist, is a fully-remote company, and I read a line that I liked on your careers page that said: "Nobody has to move to take a job here." The team is clearly very committed to the remote work ethos, because not only does nobody have to work on a specific schedule, but nobody has to work more than 40 hours per week, either. Can you share why those disclaimers are so important to your mission and your culture as a company?

GS: Our company's mission is to build the workplace of the future, but this wouldn't make a lot of sense if the workplace of the future wasn't based on trust. We're all adults, and we need to build a company and a culture that's built around the concept of trust if we're going to be able to successfully advocate for remote work ourselves. We have five core company values, and two of those are independence and communication. These values go hand-in-hand with making workplace flexibility work. If you communicate often and effectively, and if others can rely on you to work independently and get everything done, there should be no problem with you working whenever you want, wherever you want.

I've always been a very curious person, and that's had a massive impact on my work and my career. It makes me focus continuously on learning and growing as a person. There is only so much we can do at one time, and I've found that many people who are very talented sometimes get lost in all of the different things they could be doing.

OL: Where do you work and live?

GS: I'm based in Porto, Portugal. I mostly work from home, but we also have a small office near me where the employees based in Porto gather and work together sometimes. Nobody works there every day, but since there are a few of us based here, instead of subscribing to a coworking space, we rent a small office and hang around there whenever we want to.

OL: How many of those hubs like that do you have in other cities around the world?

GS: These hubs are very informal and we don't have a fixed structure of these co-located spaces but I think three. There's one here, there's one in Barcelona, and there's one in Taipei as well.

OL: These hubs are for those who aren't located in those port cities and are working from home. Other than that, there are no other office spaces?

GS: Correct. At Doist, we have a budget for perks which includes a coworking space. There are varying prices and conditions to working spaces and we try not to look at this as an expense so everybody is free to make an investment to help them focus better and work better. We don't want our employees to feel so isolated because, of course, working from home five days a week can be isolating.

OL: I like when companies offer it as a perk so they're walking the walk and not just talking the talk. I talked to somebody from Buffer who said they have a coffee shop stipend which you could use for coworking too. It's nice that it allows you to get out of the house if you need to.

GS: We spend a lot of time working on these perks. Our coworking perk has never been part of a fixed budget, it's more of a number to validate with our COO. I don't think he has said 'no' to anyone, ever. We also have a slew of other perks around health and learning, so you could spend up to a fixed amount on books and a fixed amount on music and a fixed amount on healthy fruit and snacks.

Again, this is correlated with something we discussed a little earlier – we are all adults, right? And we need to base this on trust. So, we've actually made changes within the last month to have more of a fixed big budget for everyone. As long as you keep your own interests and the company's interests in mind, you can spend this on whatever you would like. A coworking office is still separate from this because this can be wildly expensive, depending on your location. But for everything else – your Spotify subscription, the books you read or listen to every month, your apples and oranges, whatever you need to stay healthy and productive – these things can just go within a single budget for everything.

It's crucial that companies and people working remotely master the ability to communicate and to actually do things asynchronously so that no one is ever blocked by a teammate being asleep or on vacation.

OL: You have employees all over the world. What have you learned and what would you suggest to other remote teams about communicating and collaborating effectively when you're doing it across so many different time zones and with so many different people in different areas?

GS: I would say the number one is asynchronicity. It's crucial that companies and people working remotely master the ability to communicate and to actually do things asynchronously so that no one is ever blocked by a teammate being asleep or on vacation or something like that. This can be a direct contrast to the usual way people work. If you're a developer in an office and you need an icon from your designer, you can just go to their place and ask them for it. Perhaps even grab a coffee while they work on it. If you're a designer and you're missing some insight into a product spec, you can just go to your product manager and ask the question. Now, what happens when you are in Portugal like me and your designer is in the U.S., 7-8 hours behind? And your product person is in Taipei, 7-8 hours ahead? You cannot rely on everyone being online at the same time. I think there is a big shift from synchronous to asynchronous work.

If we look at a lot of the workflows that currently exist, it's very, very optimized for synchronous work. For example, Slack is very popular and it really focuses on synchronous chat. If you miss a conversation and you come in 12 hours later, you'll likely not participate because you don't want to bring it back. Everything is said and done. There is a mentality shift involved in making things asynchronous.

One of the biggest advantages to working asynchronously is that you have a lot more time to think and ponder over things before participating or sharing your opinion. It's kind of like the difference between chat and email. If you get an email, you have the time to read it, let it sink in, and think about a response. While, if you're chatting, you'll usually just reply immediately. Asynchronous communication leads to much higher quality and more thoughtful discussions.

The biggest difficulty is in the work itself. In the day-to-day work, people must find ways of not being blocked by other people. This can mean very different things depending on what you're working on. My background is in engineering, so, for me, this has usually been about keeping a backlog of things that I can work on. If I get to a point where I'm blocked by someone else, it's not a problem. I have a number two priority that I can switch to immediately and get to work on that. And the next day, or in a few hours, I can switch back to the thing I was working on before. It's sitting down and thinking about the most efficient way you can work asynchronously while still being as productive or more productive as if you were in an office co-located with everyone else.

If you're running a centralized company and then you try to attach remote work as an appendage, that usually doesn't work. But if you design a company to function under the assumption that people won't be in the same office, then remote work perfectly doable.

OL: How can leaders build and maintain company culture when there are so many different locations and so many different offices where people aren't seeing each other every day, in-person? What do you focus on to keep that culture alive at Doist?

GS: It's very important to communicate often and effectively. It can be easy to neglect the effect of being in the same office with everyone else because the CEO of a regular company might not make public announcements very often. But just the fact that people share an office and they bump into each other at the water cooler and in the kitchen, it's a very organic way of spreading culture. We don't have any of that when we work remotely. Being a lot more strict about the way and the frequency in which we communicate is very important.

It's also important to be transparent, and I think this is a trend that's coming together with the rise of remote work. Humans are very good at reading each other through body language but most remote companies communicate most often via text. We lose out on a lot of context. Being very transparent or as transparent as possible about everything – the work you do, why you do it, internal metrics – helps provide context that we probably miss via these more distant interactions.

Then there's everything else. It's important to maintain face-to-face, so team leads should have one-on-ones with everybody on their team and talk about non-work things. If you are going through a rough time, you might need a different support system in place. Another trend that's been very successful for remote companies is having yearly retreats. Getting everybody together for a week to put a face behind the voice on the other end – these things are very important to provide the necessary context so that the next time someone reads a message from someone else, they are more aware of the context and their intentions. Those are the most important things in maintaining culture in a remote setting.

OL: Where do you usually go for company retreats?

GS: Our employees are spread across more than 26 countries and we've only had four retreats. We'll actually have our fifth one soon. We have been in Menorca, Spain, we have been in Iceland, we have been in Athens, Greece, and we have been in Chile. Soon, we're going to Azores in Portugal. We usually try to use these retreats as an opportunity for team bonding and different activities but also to just look inwards and spend time with one another.

It's important to be transparent, and I think this is a trend that's coming together with the rise of remote work. Humans are very good at reading each other through body language but most remote companies communicate most often via text. We lose out on a lot of context. Being very transparent about everything – the work you do, why you do it, internal metrics – helps provide context that we probably miss via these more distant interactions.

OL: I'd love if you could share some of the leadership or company management trends you see today – both those you like and dislike.  

GS: One of the things I like is that more and more people are waking up to remote work and it's no longer a niche or weird thing that people do. Most people that I see nowadays, even on social media, are either very interested in it or cautiously curious about it. Some folks who were very skeptical at first are now becoming more interested, rather than being outright skeptical and saying it doesn't work at all. This is great because it's an acknowledgment that, at the very least, remote work is a very, very interesting proposition. It's a very good mentality shift, and it'll help all remote companies and employees.

On the other hand, there is this small trend that I do find a bit concerning and that's the idea that remote work is easy and laid-back in a pressure-free, stress-free environment. You know, it's a "mojitos on the beach" job. And this is just not true. I'm concerned that people think this might be the case. Of course, remote work does give you the flexibility to organize your work and your schedule in a way that's most productive for you. And this is very important because you save time, you can spend a lot more time traveling, and you can spend more time with your family. But there are still times when you're 'at work' and it requires mastery, focus, and ambition.

Remote work is no exception to this. In fact, since there are no rulebooks for remote work, in some ways it can actually be more stressful than regular work. A lot of times you have to experiment and do what you think is best. It's definitely not a totally relaxing environment as some people have this idea that it can be.

OL: How can other entrepreneurs balance that sense of ambition of wanting to grow your business and wanting to grow revenue with the idea of work-life balance? How do you prevent burning out?

GS: That's a great question. This is actually one of the things that I've personally struggled with the most since starting to work remotely. I've always had a little bit of a hard time disconnecting from work. Even when I worked in an office, I would often bring work home with me. When I started working remotely, it was just a recipe for disaster.

Over time, I've found two things to be very important. This is a bit cliche and everybody says this but it's really true: Rest is very important. And time off is very important. Most people that I know do their best work after proper rest. After you come back from a vacation, you are full of energy and there's a direct correlation between resting properly and being away from work and then the quality of work that you do. If you just spend all your time working, it might feel like you're doing a lot but you're actually not doing your best work. You're not performing to the best of your ability. I could argue all day about this. You are also burning yourself out. There's this aspect of rest that needs to be respected. It's one of the most – if not the most – important thing for quality work.

At the same time, we need to separate deep work from all the supporting activities that we do. It's crucial that we answer our emails and get back to other people in time but this is not deep work. Deep work is when you sit down in silence, or with your headphones on, and you focus on a hard task for one or two hours, or maybe even longer on end. It's physiologically very difficult to do deep work for 12 hours a day because you just don't have enough energy. Deep work is very rewarding and very productive but it's also very draining. In productivity terms, it's not uncommon for you to be ten times more productive as when you are in that deep work state than when you are out of it.

You need to rest properly and then, when you are working, you need to organize your schedule in a way that prioritizes deep work as much as possible. I don't book any meetings for my mornings. Period. No exceptions. The morning is the time when I don't open my email, I don't open Twist, I don't talk to other people. I just look at my to-do list and then after lunch, I relax and have my meetings. It's very important that people define a schedule for themselves, and people will realize that working long hours, or working yourself to death, is a lot less productive than having an optimized schedule.

More and more people are waking up to remote work and it's no longer a niche or weird thing that people do. Most people that I see nowadays, even on social media, are either very interested in it or cautiously curious about it. Some folks who were very skeptical at first are now becoming more interested, rather than being outright skeptical and saying it doesn't work at all.

OL: What do you make of the idea of hybrid teams where some people are remote and some people are in an office? Do you think that they can be successful, or do they need to be all or nothing?

GS: It's definitely possible and I don't see why it wouldn't be. However, I do think it's very hard. The biggest reason most of these hybrid companies fail is when you have first and second class employees, and the key to avoiding this is effective communication and keeping people in the loop. At Doist, we use our own product, Twist, to communicate. Twist serves as the tool we use to communicate, as well as our knowledge base. Sometimes I work from the Porto office with other people who also live in Porto. The interesting thing is we will talk to each other face-to-face about problems, but everything always ends up in Twist.

We dump all of the information there out of habit to keep everybody on the same level. When I look at other companies and speak to friends who work for these hybrid companies, I often hear they don't really have systems in place. If you're a U.S. company with a small team in Portugal, occasionally you will discuss things within your own office, you will make decisions, and sometimes you will just communicate these decisions and other people will lack the context and why it reached the conclusion it reached. If you have second-class employees, you've failed to build a true hybrid company.

If you are a hybrid company and you want to continue to be a hybrid company, my suggestion would be to think long and hard about how you can make sure that everyone, regardless of their location or their role, will feel like a first-class employee. This will revolve around the way you communicate, how transparent you are, and where your knowledge base is. Is it in your head? Or somewhere else?

OL: What do you think is keeping more companies from either being started as remote companies or keeping them from becoming gradually more remote? Do we need different leaders? Do we need better tech? Do we need better trust in the workplace?

GS: It's due to a combination of all of those reasons. Remote work is inherently riskier, and most people won't go for it for this reason alone, but that's a mistake. In some ways, it improves your odds. You can hire everywhere across the globe and you don't need to compete with Facebook or Google or whatever big local company you have. But sometimes this benefit is offset by the risk involved

When I say "risk," I mean that remote work involves a lot more trust than most companies have to deal with nowadays. I'm not saying traditional companies don't or shouldn't involve trust – I'm pretty sure all workplaces should be based on trust. In remote work, this becomes almost mandatory because there is no other way. How can you micromanage people across the globe and across time zones? You can't. So, it just becomes impossible. There's no rule book, and there isn't a big, successful remote company we can look to for guidance. There's no Facebook or Apple or Google of remote work yet.

Can it work for small companies? Absolutely. There are a ton of them out there, but I think the remote community needs a big winner -- a massively successful company that's fully distributed. This will prove that it works at scale and will help create those guidelines that we were talking about before that don't exist right now. A lot of remote companies nowadays are just experimenting with things. We do it all the time, and then we talk with other companies like Buffer and Zapier. Many times when you think you have the answer, it turns out that you grew a little bit more and it stops working again, and you need to reiterate. The changes in how much trust you actually need to have and not having a rulebook of how things should be done does kind of increase risk. If you're a new founder, it's acceptable to have questions about how you should approach this because it's not black and white. It's not like remote is the clear winner. There are things that you need to consider before moving ahead with this.

OL: That's such a good point. Right now, business schools are still teaching cases from the early 2000s, when remote work wasn't happening to the degree that it is now.

GS: We're still writing those pages of the future business school books.

We need to separate deep work from all the supporting activities that we do. It's crucial that we answer our emails and get back to other people in time but this is not deep work. Deep work is when you sit down in silence, or with your headphones on, and you focus on a hard task for one or two hours, or maybe even longer on end. It's physiologically very difficult to do deep work for 12 hours a day because you just don't have enough energy. Deep work is very rewarding and very productive but it's also very draining.

OL: Exactly. Speaking of the future, what do you think the future of the landscape of remote work will look like 10 years from now?

GS: That's a good question. I think there will be a lot more answers to specific struggles, issues, and approaches with remote work. Doist is a 12-year-old company but we really only started growing about eight years ago. Many things have become clearer over the years. For example, communicating and working asynchronously and finding systems to support this. There were some hints that this might be the case but it was not as clear at the time. So, working asynchronously is huge, as well as trust. Doist has always been built around trust. Trust and transparency.

I hope that, in 10 years, we'll have a lot more answers to things like, what is the proper way to communicate? I know a lot of teams are still using email. Others are using Slack or other chat tools. Some are using Twist, our own product, or Discourse, or other tools that focus on thoughtful, longer form discussions. With more answers to these pressing questions, we'll be able to spend time on other important things in the future.

I am unsure though, not to be pessimistic, if the current way of remote companies is going to be the breakthrough wave. We are not the first ones. Yahoo has put a lot of emphasis on remote work in the past. We've also had GitHub, which grew a little bit, moved all across the U.S. and even into Europe, and became almost a fully distributed company. They worked this way for many years until they called back most people to the office again and reverted on this decision.

Those companies could be called the first remote work generation. They used to embrace remote work, but most of them have failed at it. It's not as if they failed and went bankrupt, but they went back on this decision and they changed the way they approach this.

Now, we're starting to see the second wave, with companies like Doist, Buffer, Zapier, and others where they're starting out as distributed companies. The context of the present is different, and today, we're a lot more remote friendly and actually fully distributed than those original companies were. And the result will probably be different because the context and the approach is different. Maybe in 10 years, Doist, Buffer, and Zapier will no longer be fully distributed. Perhaps some kind of third wave of companies will try things out in a different way. I'm hoping that we have less questions and more answers in 10 years.

OL: It's encouraging to see companies like yours and others being born distributed. They aren't being born out of Silicon Valley and then becoming distributed, because nobody can afford it anymore.

GS: One of the big mistakes some of these first wave companies made is while they were remote they kept the leadership in the Valley, which goes against the idea of transparency. If all of your leaders are co-located and everybody else is remote, you miss out on a lot of transparency and communication that's happening. If you don't work in that de-facto hub, you start feeling like a second class employee, which is problematic.

OL: What do you love most about what you do?

GS: How much experimentation remote work involves. I'm an engineer, and my work is generally creative in nature. I love that the company I'm building with all of my colleagues also requires a great deal of experimentation. There's no rulebook, because we're writing the rulebook as we go. I know this can be stressful and frustrating for other people, and at times it is even for me, but it's very, very exciting for me to be working without a rulebook. Experimenting with things, seeing how it goes, and being able to iterate. These are definitely my favorite things about the work that I do.

One of the big mistakes some of these first wave remote companies made is while they were remote they kept the leadership in the Valley, which goes against the idea of transparency. If all of your leaders are co-located and everybody else is remote, you miss out on a lot of transparency and communication that's happening. If you don't work in that de-facto hub, you start feeling like a second class employee, which is problematic.

Key Takeaways


1. You can't build a remote company without first laying a strong foundation of trust.


Gonçalo reminds us that remote work involves a lot more trust than most traditional companies have to deal with. This trust ultimately bleeds into the company's culture and how productive the overall workforce is. Without it, the company can quickly crumble.


2. The key to working asynchronously in a remote setting is being able to prioritize your schedule and your work goals.

If you're working in a team where your colleagues are spread across time zones, you need to have a plan in place so that you're not prevented from completing work if another person is asleep or on vacation. This is where communication plays a significant role as well.


3. The key to work-life balance, especially for entrepreneurs, is to respect the notion of resting and taking time off.

You can put in all the hours you want, but if you don't take proper time to rest and recharge, you'll actually be doing a disservice to your company and employees. As a leader, it's your responsibility to set the tone and allow others to feel good about taking time off when they need it. Working yourself to death, Goncalo says, is a lot less productive than having an optimized schedule.

To learn more, read our interview with Jonathan Gheller, founder of One Fix, next.

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