Apple Podcasts 
Google Podcast 
Spotify Show Notes:
In this episode we talk to Gonçalo Silva, the CTO of Doist -- the company behind the popular communications app Twist and the productivity app Todoist. We get into hiring, focused work and building the future you want to work in! Gonçalo had some wonderful insights on remote work from an engineer’s perspective, as well as what he looks for in people he hires (it might be different from what you’ve heard before).
It was refreshing to hear an honest take on the struggles of working remotely, scaling a team and building a culture of innovation while not sharing an office; I think this was one of the best examples of the fact that even the most successful companies are still iterating on what it means to be a successful remote team. Doist is certainly one of the companies that is doing it right - their employee retention rate confirms that!
Please check out doist.com and their blog “Ambition and Balance”. Also, follow them on twitter at @doist and Gonçalo at @goncalossilva.
I hope you enjoy it as much as I did!
Transcript:
Matt H: Hello everyone. My name is Matt Hollingsworth and welcome to another episode of The Remote Show, where we discuss everything to do with remote work with the people who know it best. Thanks so much for listening. The Remote Show is brought to you by We Work Remotely, the largest community of remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire.
[00:00:25] My guest on today's show is Gonçalo Silva. Gonçalo is the CTO of Doist, the company behind the well-loved Todoist and Twist products. Doist is a bootstrapped, profitable and fully distributed company with over 50 employees. I encourage you all to check out what they're up to at doist.com. They have great blog full of remote work content that is super valuable. Gonçalo, thanks so much for coming on the podcast. We really appreciate it.
[00:00:48] Gonçalo Silva: Thank you for having me.
[00:00:49] Matt H: All right. So, why don't we start of with just going over how you got started because you are Doist's CTO. So, where did you get your start and how did things go when you first started?
[00:01:00] Gonçalo Silva: Yeah. The start is actually interesting because I was a freelancer, and actually, pretty much everyone except the founder from Doist was a freelancer in the beginning. So, in a very special way, we were already a remote company from the start. Of course, as the product wasbuilt up and it grew, we figured out this was not going to scale so I got hired, a lot of other people got hired as well in that beginning, and I was head of Android for a few years, and that evolved into the CTO role that I have today. So, short story.
[00:01:32] Matt H: That's great. How long have you been CTO for?
[00:01:35] Gonçalo Silva: About two years.
[00:01:36] Matt H: Two years. Nice.
[00:01:37] Gonçalo Silva: Right now. Yeah.
[00:01:38] Matt H: Cool. So, Doist runs two products. You've created two products. Do you have your hand in both of those products, as CTO, or is that something that you focused on one or the other?
[00:01:47] Gonçalo Silva: Well, the thing is I'm going through a transition actually right now, from less product development into a more technical side of things. I was more focused on Todoist throughout the past couple of years, that's my original product, and also the way we approached building a new product within the company was to ... I know this is a bit cliché, but we tried to create a small startup within the startup, and shield this team from outside noise and pressure. And that team has had full ownership upon roadmap development, etc.
[00:02:24] Now, we do keep things open so of course, me and everybody elsehas participated in a lot of the discussions, the brainstorms, etc. But this team has held the final say in most of the things so far.
[00:02:37] Matt H: Great. Just so people are aware, you started with a to-do list, and then you built out the Twist app.
[00:02:44] Gonçalo Silva: Yeah.
[00:02:44] Matt H: The communication and productivity app. Is that correct?
[00:02:48] Gonçalo Silva: Yes, yes. So, back in 2007, Amir, our founder, had a side project of his own. It was Todoist. He just basically wanted a to-do list for himself, and he was not a fan of any of the offers in the market at the time, so he built Todoist. That's how we started off, and for many years, that'sall we had. Although, as the company grew and we also adapted our mission statement to what we have now, which is we want to build the future we want to work in, we realized how important communication is, and we were also very angry and skeptical about the current offerings in the market, and the way they work. Things like Slike and Microsoft Teams, and all of the constant presence, always being online, FOMO, notifications everywhere, andwe always had a very different stance on this so we decided to build Twist for ourselves and obviously for other teams who think like ourselves. And the truth is, we truly believe this way of communication is the future. It's not what most teams are using right now.
[00:03:54] Matt H: I see. So, you obviously have had some success with that. You mentioned that there's quite a number of teams that are using Twistat the moment and share that vision. Was there any trouble getting started with that product or what was the pushback there, and how are things going within the Twist app?
[00:04:10] Gonçalo Silva: Yeah. I mean, to be honest, there is always, I think, a lot of pushback when you build something new.
[00:04:16] Matt H: Sure.
[00:04:16] Gonçalo Silva: And bring it to the market. So, we obviously had alot of pressure to make Twist more like Slike and the like. We have had many numbers of requests to do things like adding online presence indicators and synchronous communication workflows, and it's always very tough to balanceour vision for what a product should be, and what people expect from it. The truth is, we have been scaling down on many of the things that people are actually requesting us to add.
[00:04:32] Matt H: Oh, interesting.
[00:04:32] Gonçalo Silva: So, it's been quite a challenge because I think ourbiggest struggle, and this will be the case for many or at least I expect so, is that Twist is not only a new tool, it needs a mentality change so people need to approach communications, people teams, companies, etc, and this, obviously, always takes a long time. We need to prove, slowly, that this is better than what is already out there.
[00:05:15] Matt H: Right. You mentioned your mission and changing the way people communicate, and people work. What is the end goal and what would you consider to be success for Twist and also Todoist, just in terms of your mission and your roadmap?
[00:05:29] Gonçalo Silva: So, although the missions for both products are different, they collide in the whole mantra of we want to build the future we want to work in.
[00:05:36] Matt H: Right.
[00:05:36] Gonçalo Silva: For Todoist, in general, our feeling is that most people in the world don't use any productivity system, and the thing is, of course, we humans, we are incredibly smart and capable, but we just can't keep track of everything at all times. And one thing we have found is that most people who start using a productivity system and of course, we promoteand develop Todoist, over time become just a lot more capable of managing their life and their work. In the end, they just become more productive and have more time for what really matters.
[00:06:11] For Twist, there is a little bit of a difference because it's more focused on teams. It's focused on communication and in general, we are huge fans of a synchronous communication. The reason being that we do our best work when we are truly focused, what's so-called deep work, and the way to achieve this is to block uninterrupted time to work on something. And if you have something like Slike or Microsoft Teams, or whatever else you're using, pinning you and distracting you all the time, this is something that's very difficult to do. And even if you control notifications and for example, reserve time slots to catch up later on, when you have a single stream of information, it becomes very hard to catch up and some discussions will probably be over by the time you get there, and that generates FOMO, etc.
[00:07:01] So, what we're really trying to do with Twist is provide a platform where a synchronous communication is key, where you are totally in control of your notifications and where we also don't let the discussion topics just slide up into some kind of a history log where you'll spend a lot of time catching, and in general, might not even be able to bring it back on. So, I guess we could see this as just making communication much more efficiently and people more productive.
[00:07:30] Matt H: I think that's definitely something that I've heard before with remote team specifically is, both from the management side of things aswell from the employee side of things, is that people often trying to figure outa way or a process to make sure they have time devoted to specific things, sothey can really dive into it, really dig in whatever they're doing and focus specifically on that.
[00:07:50] Gonçalo Silva: Yeah.
[00:07:50] Matt H: But there's also part of it too that you do want to have some accessibility, and you do want to be able to ping somebody on a projectbecause otherwise you do feel a bit isolated. So, how do you balance those two things? How do you balance allowing for deep work but also allowing for some level of openness and approachability in your daily work?
[00:08:09] Gonçalo Silva: Well, if I'm fair, we don't. So, what happens is we truly focus on a sync and then, we have different processes for when people can do face-to-face, and they can synchronize. For example, all of our teams have weekly meetings where they all get together and discuss deadlines for that week. All of the leads have one-on-ones with everybody on their team. We have a yearly retreat where everybody gets together face-to-face for a week. But the truth is, on a day-to-day basis, we don't really count on having people online and synchronous at the same time. The reason being, we don't really believe this is feasible at scale. We are over 60 people in over 25 continents. We pretty much span all timezones you can imagine, and actually, in some teams, we have all of the world covered. So, what this means is even the team meetings that I just mentioned become increasingly complex, so anything else on top of that can just be very frustrating. So, it's something we try to avoid and just have a better overall process to achieve that.
[00:09:19] Now, you mentioned something that I find very interesting, and I think would pay a lot of attention to this, which is isolation. Something we do is 99% of our conversations are public. I mean, even our head channel which has all of the team leads, that's a public channel so all of there are discussions there are public. Now, people are not notified about them because that would spam, but they can go there anytime they like, and see what's being discussed. So, we keep, basically everything open. From product development to leads discussions, to the groundwork on each specific feature, etc.
[00:09:56] Matt H: That's interesting. I think Doist is probably the largest organization that I've been able to learn about through this podcast, but that's really interesting. One of the questions I was going to ask, with being so large and growing, and scaling as you have, how have you come up with an effective way of disseminating information amongst the teams, and how do you make sure that the people who need to know the information get the information and that sort of thing? So, I think it's interesting how that stays open all the time. Did you start that way or is that something that evolved as you grew, or how did that go?
[00:10:27] Gonçalo Silva: This has been constantly changing. In the early beginnings, I think up until the point where we were about 20 people, we didn't have any kind of formal process. Things just happened and we were comfortable with it, which was nice but of course, as you grow, this is not always the case and we had to adapt. I think we do a lot of things to make this happen. So, I will just focus on two which I think are the most important. We use a work system called The Do system.
[00:10:54] Matt H: All right.
[00:10:55] Gonçalo Silva: And within this system, I think we could say we have one month sprints, but the really interesting thing about this is that we assemble squads of people from different teams to work on a specific topic. We borrowed this idea from Spotify, but the really great thing about this is that people who never would work together end up working together, and we switch things up every month to keep things fresh. And because we have this system, we have, of course, in the beginning of each month, we distribute thework, we detail the work and so, everybody who will be working on something has the information necessary to be working on it.
[00:11:35] Yeah, so, I guess that's the number one thing we do. Something else we have started doing more recently is these monthly updates, company-wide updates. We do these per team but we also do it per topic. So,for example, we have a monthly Todoist update, the stuff we've been workingon, the stuff we plan to work on, what's the longer term roadmap, how are things changing. We do the same for Twist, but we also have monthly updateson people ops, so who are we hiring? Why are we hiring them? Who joined the team? Etc. And these, I think, have also been very effective in aligning everybody behind the common pillars of how we operate.
[00:12:18] Matt H: Yeah. It's interesting you bring that up. I think the peopleops side of things, and we can go back to the engineering side, which is obviously your area. I was interested in how people within, especially larger distributed teams, manage to build a company culture and how you keep thatculture maintained as you grow, and what do you look for in people that will fit well within the team. And I did a little bit of research before the show, and Isaw that your retention rate for your employees is crazy high, and I think they said that there is only one person that left voluntarily or something like that, that might've changed, but how have you managed to do that and maintain those crazy high retention rates for your employees?
[00:12:58] Gonçalo Silva: I think we pay a lot of attention, and we really focus on having a workplace that is inspiring for all of us. So, I know for example, Amir, our founder, he spends a lot of time thinking, and you can hear actually a lot of comments in this direction like if I was an employee here, how would I feel about this? And this is an exercise we do very often. When we are looking for people, when we're hiring people, we have these fivecore values we uphold throughout the company. We talk about these all the time, we try to look at everything through the lenses of these five core valueswhich are independence, mastery, communication, balance, and impact. And for example, when we are hiring, we look a lot at the candidates and see how they match around these values.
[00:13:46] Let me give you an example, there's a very high correlation between the success of the hire, and this particular aspect, are side projects. People who have side projects, they maybe have a podcast or they wrote a book, or they stream online, gaming or even coding, or they just maintain a library, an opensource library. The truth is that if you are doing any of these things, you are showing independence, you are showing mastery, in some cases, you are showing that you are good at communication, especially to deal with other people in the case of opensource. So, we look for these thingsand try to have the best match possible.
[00:14:25] Now, the truth is, it hasn't worked all the time. We have honestly had people who struggled in the beginning, and despite our best efforts, in the end we parted ways. I personally maintained contact with a few of them, and the truth is they found a local job afterwards, and they are really happy right now. So, in a way, remote work is not for everybody or at least that's what we've been finding, but we can definitely make it work most of the time.
[00:14:50] Matt H: Right. Do you look for people that have worked remotelyprior to coming on-board or is that something that you require, or how does that work?
[00:14:59] Gonçalo Silva: Not at all, actually.
[00:15:00] Matt H: No. Okay.
[00:15:00] Gonçalo Silva: I would say we are very excited to have newcomers to remote work and be able to help them make the shifts. We have a process in place that helps with this, so for example, every newcomer has a mentor for three months, with whom they are expected to maintain a constant conversation to help them sort out not only how the company operates, but also how to approach remote work and change any habits around this. We also have a trial period. We have a very tight feedback loop system. So, we are eager, honestly, to introduce people to remote work, so no restrictions there at all.
[00:15:36] Matt H: That's counter to some of the conversation that I've heard around, especially around junior developers specifically. The need for them to be in office with other, maybe, more senior people, and interesting you mentioned that. I also probably think that when you bring on a junior developer, especially with remote work, you can probably mold them and train them to process in remote work. Maybe they don't have that bias that they came in with before, if they worked remotely previously. It's interesting that you mentioned that.
[00:16:01] Gonçalo Silva: Yeah, for sure. Biases can be troublesome, although, if I'm honest, the truth is we don't hire junior people often.
[00:16:08] Matt H: Oh, okay.
[00:16:08] Gonçalo Silva: So, we do have some people in the team who joined as juniors, and they have been highly successful, but it's not a common occurrence. If you look at our job listings, we are usually looking for people with some experience in the fields, so ...
[00:16:22] Matt H: Right.
[00:16:23] Gonçalo Silva: That's our experience.
[00:16:24] Matt H: Right. Speaking with the hiring process for you, now, youmentioned that you look for people that have had projects outside of their regular day jobs. Do you give people projects to work on, as a part of the hiring process? Because I know that's pretty common amongst some tech companies that will give them a project like a two week thing, and then see how that goes, and then work through the hiring process from there. Is that something that you do in Doist?
[00:16:44] Gonçalo Silva: Yeah. We've done this for 10 years now. So, we definitely have this as part of the hiring process where we have a small test project. It's usually somewhere between eight and 12 hours of work, and of course, we're looking at things like code quality and how the final product actually works. But I would say the thing we are most interested in are the compromises that people make. So, these projects are usually just a little bit too big for the timeframe you are given, and in general, we are very interested to see what compromises you make because work, longterm, is all about compromises. And it's very important that people pick the right compromises to make, and of course, sometimes this is subjective, other times it's very objective. This has been very insightful for us within the hiring process, besides the regular interviewing.
[00:17:35] Matt H: Right. Part of that process, is that how they communicate with you as well? I'm assuming the answer to that is yes. Because I find that some people have mentioned to me that hiring process or the things that they look for is not necessarily the product itself, but how theyhave communicated their issues going forward and throughout the process, and struggles do pop up as you mentioned, how they've dealt with it. And theother thing I've heard as well is writing especially is important, especially within a remote team. Do you find that quality writing is something that you look for in your team?
[00:18:04] Gonçalo Silva: Yes, definitely. It's actually the first thing we check. So, we have this requirement where every candidate has to write cover letter, and we use this in a traditional sense so we want to make sure we don't get a generic cover letter. We want to make sure the candidate has done their homework, but we also look at how good the writing is. And duringthe interviews, we also look at how good spoken English is. The truth is, this is the language we use throughout the company for everything, and going back to the core values I mentioned before, the five core values. One of them is communication, and of course, this has many angles but you also need to be proficient in communicating.
[00:18:44] This is crucial to successfully collaborate, although we have hired people in the past that were not excellent at English, and we do have a perk, internally, where you can spend basically money on your education. I know we do recommend that people who are not great at spoken or written English use this education perk to improve, and we have seen massive improvementsinternally. Truth is, nowadays we are a little bit more demanding with this particular aspects, and right now, we definitely look at how good someone's English is before hiring them.
[00:19:17] Matt H: Interesting. So, going back to a little bit of a team dynamics within your sphere there, with the engineering side, is there difference in terms of processes for you being a remote team specifically, that wouldn't necessarily come into it when you're in an office, and how have you dealt with those things? I would just be curious to hear about or learn about your process, the engineering side specifically.
[00:19:39] Gonçalo Silva: So, one thing that applies here, and I would say it applies to many of the other fields, but it's specially important in engineering is, in general, you should keep a backlog of things to work on. Because of our synchronous nature about the way we communicate, and the way we work, it's very common to get blocked on things. So, you need input from someone from design or from products, and you don't have it right away. You need to be able to counter switch, and you go work on something else. This is entirelydifferent, from my experience, from the way most companies work, specially non-remote companies.
[00:20:16] And we have also found that this change in the way we work is one of the most challenging aspects of a new engineer joining the company. Make sure you always have more than one task at hand, so that you can switch between them while you wait from input from others. This has definitely been one of the things we had to adapt.
[00:20:34] Another aspect I think is, because we are remote, we generally areunable to do pairing sessions where people develop together, and they learn from one another. So, one other thing we have invested quite heavily, internally, are code reviews. So, pretty much every team has a very strict code review process and while this might look like an evaluation, it's more of a shared knowledge that you want someone else to read the code, how it works, understand it. The ownership of this knowledge then also becomes distributed, and it's a great way to learn from others as well, since you just can't sit right next to them.
[00:21:13] Matt H: Right. And with the product development side of things, is there any specific timeframe that you work amongst the other design aspects of it, other components of the product development? Do you have standing meetings throughout the month or throughout the process of developing a product, and how does that change within a remote team?
[00:21:32] Gonçalo Silva: That's a good question. Honestly, the way we do product development, I would say does not change significantly from the fact that we are remote. So, like most companies, we have a longterm roadmap. Like most companies, we try to break this down into smaller actionables that fit within our monthly cycles. And then, the squads that I mentioned before, they do have something we call the weekly snippets. So, this is not a stand up meeting because it is a sync, but it's just a thread where the squad discusses what they have been working on last week, anything they might beblocked or need input in, and what they plan to do for the following week. ButI guess never this, except for this part where we swap out what could be a stand up meeting for a more synchronous workflow, everything else I would say is pretty standard.
[00:22:22] Matt H: So, as you grown, I just want to take a step back and talka little bit about scaling a remote team as you have because you've obviouslydone this successfully, and your retention rate is high, the product is great. So, what has been the biggest challenge for you, in remote work? Is there anyprocess that you've put in place to meet that need?
[00:22:40] Gonçalo Silva: Well, one of the challenges we've faced since forever and it's unfortunately not something we have figured out yet is we hire very slowly. So, from the time we decide that we need someone doing a certain job to the time we on-board someone new, many months usually go by. Actually, we have a specific position that has been opened for over a year,and this takes a huge toll on the team because sometimes we are not quick enough to react, and we may have a certain team that's understaffed, and if it's takes over half a year for us to be able to hire someone, then it can be a very frustrating experience for that specific team, for any other teams that depend on it, etc.
[00:23:25] And honestly, we have not figured this out yet. We know how other companies are hiring, for example, it's not uncommon to set a deadline,get candidates throughout the time and then decide on who person will be hired for this position. But in general, we don't want to compromise, so we just keep looking until we find the right person for the role. But despite getting a lot of applications every single day, sometimes this takes a long time. Yeah, it can be a very frustrating process and I'm unsure what else we can do to improve here.
[00:23:58] Matt H: Yeah, that's interesting. I think it's a struggle, I'm guessing, with most teams remote or otherwise, that want to continue to maintain their culture and build on the team that they have already but also meet the need of the teams, and make sure that people aren't overloaded if there's another person that's needed. So, that's interesting, and again, I don'tthink that you're unique in having that struggle but it seems like you've prioritized making sure that you're hiring the right person as opposed to just filling seats, and making sure that the teams have the number of parties that they think they need so I don't think that you're alone there, at least.
[00:24:26] Gonçalo Silva: Yeah, but we have definitely not figured this out. We have tried different things, and we can make smaller improvements, but this is one of those things where you need a 10X improvement to really makea change, and we're still looking at that.
[00:24:40] Matt H: Right. Because I know there's a lot of engineers out there that are listening to the podcast, and you obviously have quite a bit of experience in hiring and working with different teams. So, what would you say is a skill that every engineer should know, especially getting to a remote role or wanting to work for a company like Doist? Is there a skill that maybe isn't necessarily intuitive, that you think that everybody should master beforeapplying for a job at Doist?
[00:25:07] Gonçalo Silva: That's a great question, and yes, I do, from experience. It's actually not directly related with engineering but we have found that engineers might struggle with this a little bit more than other people. Communication is key. The fact that you're not sitting in an office with50 other people who can just touch on your shoulder and ask what's up, makes it a little bit difficult to keep people in the loop and be proactive in terms of communication. This is a very important aspect of working remotely,how well and how often you communicate, and of course, how efficiently. Don't want to spam your colleagues. And this is a very important skill to keep things running smoothly over time, and it's very important to master this, andit's something we definitely value very highly.
[00:25:54] Matt H: Right. I also wanted to ask with the isolation thing that you mentioned or the issue of isolation within remote teams, what do you do outside of just communicating as effectively as possible and making sure thatpeople are part of stand ups? Is there a process that you guys do specifically, that might not be intuitive to other teams, to make sure everybody's getting that face-to-face time and getting to know people within the company?
[00:26:17] Gonçalo Silva: Yeah. So, besides the stuff you mentioned and theyearly retreats.
[00:26:22] Matt H: Right.
[00:26:22] Gonçalo Silva: We are, generally, very open about this topic, andeven other complicated topics such as mental health. So, we have this thing where we discuss a different mental health issue every month, from isolation to imposter syndrome, and we have these very, very open conversations where people join in and they share their experiences, and their views on these topics. And I think these have been highly efficient in terms of avoiding taboos. In terms of isolation outside of work, because this also happens, right? Working remotely, you might sit at home every day. Longterm is a very dangerous path.
[00:27:00] We generally try to be very proactive about time off, about our work week. We work 40 hours a week, and we don't want people to overwork or burnout, ever. We are very proactive about this. We have 40 vacation days per year and we monitor this so that people do take their time off, and rest, and recharge. So, yeah, I guess there's not a huge thing we do. There's just a bunch of small things we continuously do to make sure people don't isolate themselves and don't burnout, or become depressed. But it's definitely a challenge, and something we are still improving as time goes by.
[00:27:37] Matt H: Right. For you specifically, what does a day look like for you? Because I'm sure that there's a lot of people out there that are curious as to what a CTO does on a daily basis. I, myself am included in that. How do you maintain your work life balance and what does a day look like for you?
[00:27:51] Gonçalo Silva: Well, my days are honestly very, very different. So, obviously, my priority number one is supporting other people. That is, after all, my job, but depending on the time of month, it can be very different.For example, in the beginning of the month, we are usually very focused on the beginning of the sprints that I mentioned before. So, there's a lot of planning going around. I spend a lot of time talking with the team heads about what's possible, what's not possible, what is too much, what is too little, etc. Usually, in the beginning of the month, I also have my one-on-ones with people I manage. So, obviously, that's a time for more personal conversations. Having said that, we have a very strong culture of being what we call doers, so I program, and everybody has some kind of groundwork thatthey do on a daily basis.
[00:28:41] So, I also block out my time to do deep work, to code a little bit. Ofcourse, I don't have any specific team so I'm usually landing a hand to any team in need. But, yeah, my day usually looks like this. It's just a normal day like everybody else. I probably have a few more minutes than most people, and I spend a bit more time thinking about ... in terms of a high level review of the company, our engineering, our products, how things are going, and how are we going to meet our longterm objectives. But like everybody else, I do spend my time doing my own share of coding.
[00:29:15] Matt H: Right. Do you work only at specific hours or do you shut off at a specific time, or is there tools that you have that make sure that you do shut off, that you focus on those deep works other than, of course, your own products? But is there a certain type of day that you shut off, typically?
[00:29:28] Gonçalo Silva: Yeah. I'm probably the worst guest you will have for a long time around this topic because-
[00:29:34] Matt H: I don't know about that.
[00:29:36] Gonçalo Silva: The truth is I am very unstructured person and my creative process, my work process is very chaotic, and I've honestly spenta lot of time of my life trying to become more structured and balanced. But I have found out that is usually is ineffective, and it just makes me more frustrated. So, what I've been trying to do instead is, I use this app called Rescue Time, which just monitors how much time I spend working, and I keepa close eye on it. And if for example, there is a week where I go a little bit overboard, I will just scale down next week. I will do a proactive effort to ... next week, I'm going to have shorter week or a more lightweight week to compensate for this one.
[00:30:20] I don't really follow a strict schedule any day. My days are all different but I know this does not work for most people, so I'm not in any way advocating that anybody tries this. It's just like I've always done it this way, it worked great, and honestly, only after starting a family, I've had a son recently.
[00:30:38] Matt H: Oh, congratulations.
[00:30:39] Gonçalo Silva: Thank you. But only then, I really started thinking more about this balance and about the structure, and trying to incorporate it more into my daily life. But it honestly has not worked that well. So, in this area, I'm just more reactive. I keep track of what I do, and then I react accordingly later on so then, things balance out.
[00:30:58] Matt H: Right. I think that was the most honest answer to that question, that we've received. And actually, Rescue Time has been mentioned a few times so shout out to them. They're obviously helpful. Do you recommend that your employees do that as well? Do you talk with an actively, if for example, like you said, if you go over for one week, do you talk with your team and say that, "Hey, if you spend too much time during this week, you should pull back next week"? Are you intentioned about communicating that to your team?
[00:31:22] Gonçalo Silva: Yeah. For sure. To be honest, I do try to communicate that people should have as much structure as they can, which goes against what I, myself, do. But the truth is, even as I observe other people around me, most people deal very well with a more fixed and stable schedule. So, I try to adapt that to my own teams, assuming that most peoplewill do well with a more fixed and stable schedule. Now, we have totally flexible hours at Doist, and I think it's one of the huge perks that we provide, and something that remote work easily enables, but we definitely are very mindful of how much effort people put into things and then try to adapt, balance things out as we were saying.
[00:32:05] For example, I mentioned the monthly cycles. We do this every year, but we actually have three months per year. In August, because of vacations, December, because of the holidays, the month of the retreat, which is usually April, May, where we have something called the do breaks. During the do breaks, people actually have total freedom on what they want to work on. They can literally spend a month learning something new, and this is another way where we can balance out the stress. So, the monthly cycle, you finish one, you start another, and you keep going and going and going. But the truth is every two to three, four months, you have a break, a full month to focus on something else you want to work on, learn something new, etc.
[00:32:47] Matt H: That's great. Have you noticed that you see a spike in innovation during those times?
[00:32:47] Gonçalo Silva: Yes, for sure. I have actually an example. Recently, (Piater) , one of our Android developers, showed a demo to the team. You take a photo with your phone, of a to-do list on paper, just a regular list, and it gets imported as a Todoist project.
[00:33:09] Matt H: Wow.
[00:33:10] Gonçalo Silva: This was pretty cool, pretty out of the box thinking, and obviously, it's something very hard to do when you're just goingfrom cycle to cycle within the roadmap. So, kudos to him.
[00:33:21] Matt H: Yeah.
[00:33:22] Gonçalo Silva: And this sort of ideas can really spark when you have total freedom to do whatever you want.
[00:33:27] Matt H: Yeah, that's super interesting. So, when you say that heycan work on anything and learn something new, can they work on their own side projects or is it specifically to do with Doist, and products that are going on within Doist?
[00:33:38] Gonçalo Silva: We don't have any restrictions what people work on, although, I mean, obviously, we expect that everybody has Doist in mind. Like I'm learning something because it will be useful to me, or even if you're working on a side project for yourself, that's fine. If you can use the learnings or you can use the side project itself in the future, for Doist. So, we usually say we're all adults, so there is not a strict list of things you can do.
[00:34:02] Matt H: Right.
[00:34:03] Gonçalo Silva: But of course, we expect you to keep the company interests in mind when doing so.
[00:34:08] Matt H: Wow, that's fascinating. Taking another step back with the management side of things, I'd be curious to know, because it sounds likeyou gradually grown within the company and you've (inaudible) CTO within Doist, starting as an Android developer like you said. Is there any management techniques or skills that you've had to develop again, that you took you off guard, or what was the most important management skill that you've had to learn you've grown within Doist?
[00:34:30] Gonçalo Silva: I think the most important thing, and honestly, it was one of the hardest things for me to figure out, is that as a manager, your number one priority is not to be an individual contributor. So, u need to become an enabler for the people you manage. That needs to be your top priority. It's like how can you make them better individual contributors.
[00:34:52] Matt H: Right.
[00:34:52] Gonçalo Silva: And honestly, since, as you said, I grew internally within the company, from a developer to a manager of a team, to a CTO. Thishas been a gradual evolution and something I have struggled with at times, because I've always a lot on my own individual contributions, and this shift, I think, can be very hard. Not only for me, also for other managers that we have grown internally. Your own role as an individual contributor needs to diminish so that you can truly focus, empower, and enable the people you're managing.
[00:35:26] Matt H: Yeah, that's interesting. It makes so much sense. From my perspective, when I see the CTO role, it seems like that would be heavy inthe technical side and it would be product driven, and seems like what you're saying is that it's mostly focused on getting the best out of your employees, which I think is fascinating.
[00:35:43] Gonçalo Silva: Now, I mean, every management role I would say is about people.
[00:35:46] Matt H: Right. I know that your time is valuable, Gonçalo, and I really appreciate you coming and spending some time to talk us. I have a couple of closing questions before you go. What is your favorite unplugged activity outside of work? So, what do you do to unwind?
[00:36:00] Gonçalo Silva: Yeah. I mean, these things change over the years,and of course, I'm a father and I love spending time with my son. It's something I, again, remote work enables this, I get to do every day for long stretches of time. When I am not with my son, something I have started doingrecently, about half a year ago and I've been having a great time, is learning the drums.
[00:36:21] Matt H: Oh, nice.
[00:36:21] Gonçalo Silva: So, an instrument. It's something I had never done as a kid. I always wanted to but never really took that step. It was funny, one of the times in my life where I felt the most stressed with how much I had to do. New person in the family, a newborn, I had this role within the company that obviously demands a lot of attention and focus, and it just felt like the right time to start something new, and put things into perspective. So, I've been having a great time drumming and I think doing something that's physical, and that demands your total focus and attention, ithelps immensely, relieving stress and making me feel good about myself, andall of that. Because when I'm drumming, I cannot be connected to anything else. I need to be playing the instruments, so that's really, really a great feeling, and I highly recommend people have some sort of activity in their lives where they need full attention.
[00:37:18] Matt H: Yeah, and I found that as well, with myself. I think it's a good practice to have something outside of work and family life, that it demands your attention because it does allow you to leave everything else aside, and really unwind in a focused way, so I think that's really interesting. The next question I have for you, do you have a favorite remote work tool that you use outside of your own products, potentially?
[00:37:38] Gonçalo Silva: Well, we build tools for remote teams, so it's really hard not to pick one of our tools or both of them. But I would say that inmy day-to-day things that are directly related with remote work, it is Rescue Time for me, so it's the way I keep track, and I keep myself in check. I don't really use anything else, specifically for remote work, although of course, there's Zoom for meetings. Amazing tool, which would probably not be needed on co-located company. Of course, things like Dropbox, we share a lotof files and documents, so it also enables a lot of the work we do.
[00:38:14] Matt H: Nice.
[00:38:15] Gonçalo Silva: But yeah, I mean, nothing too special I would say.
[00:38:18] Matt H: Interesting. All right, I have one more question for you, and again, take this in whatever direction you want but what is the best advice that you've ever been given? And this can be work related or outside of work. You can take that in whatever direction you want to.
[00:38:34] Gonçalo Silva: That is a hard question.
[00:38:35] Matt H: I know.
[00:38:36] Gonçalo Silva: I've gotten so much good advice over the years, from so many people.
[00:38:40] Matt H: Yeah.
[00:38:40] Gonçalo Silva: I don't want to pick favorites, honestly, so something I will do is I'm going to mention the best advice I have gotten recently.
[00:38:47] Matt H: Okay.
[00:38:48] Gonçalo Silva: So, recently a co-worker told me to do less things,and I think this applies to a lot of people in a lot of fields, doing all kinds of jobs. The truth is, the more things you do, the less ability you have to do deeply focus on something, the less ability you have to take a step back and have a higher level vision on what you're working on, and in general, just the less dedication and the less time spent thinking on a particular thing. And thetruth is some of our best ideas don't come immediately, they come when youleast expect it. So, if you're juggling a lot of things at the same time, it's very,very hard to have that background processing in your brain happening without you noticing, on a particular topic.
[00:39:32] So, recently this was an advice given to me and I think it was extremely insightful, very timely, and I think it might also apply to other people out there. So, yeah, I'm definitely going with that one.
[00:39:44] Matt H: Nice. That's a good answer. I think that was one of my favorites so far and I know that I just threw that onto you at the last minute, so well done. All right, like I said, I really appreciate you taking the time. I think that was super valuable for our listeners. Was there anywhere that you wanted to send people, to learn more about Doist or to learn more about you,or is there anything that you want to point out?
[00:40:04] Gonçalo Silva: Well, I would definitely recommend that people took a look at our blog. We blog a lot about topics we care about and the values we uphold, also about how we work. So, it's also a good way to keep track and get some insight into how we do things, and my direct messages over on Twitter are open. So, any questions, I'm happy to take them. I'm happy to discuss anything with anyone. And of course, thanks so much for having me. I've enjoyed thoroughly this conversation, and I hope we can do this again.
[00:40:34] Matt H: Yeah, no, for sure. We'd love to have you back on, and I can attest to the blog, I think it's a great source for people, especially who arelooking to get into remote work or best practices, and just the Doist company in general. Follow them on Twitter and we'll have all that stuff in the show notes as well. Gonçalo, thanks again, and we will talk soon.
[00:40:50] Gonçalo Silva: Thank you very much.
[00:40:51] Matt H: Thanks so much again for listening to the show today. Besure to check out weworkremotely.com for the latest remote jobs, and if you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do. As always, if you have someone that we should talk to, advice you have, or if you'd like sponsor the show, please reach out to us at podcast@weworkremotely.com. That's podcast@weworkremotely.com. Thanks so much for listening and we'll talk to you next time.
[00:00:25] My guest on today's show is Gonçalo Silva. Gonçalo is the CTO of Doist, the company behind the well-loved Todoist and Twist products. Doist is a bootstrapped, profitable and fully distributed company with over 50 employees. I encourage you all to check out what they're up to at doist.com. They have great blog full of remote work content that is super valuable. Gonçalo, thanks so much for coming on the podcast. We really appreciate it.
[00:00:48] Gonçalo Silva: Thank you for having me.
[00:00:49] Matt H: All right. So, why don't we start of with just going over how you got started because you are Doist's CTO. So, where did you get your start and how did things go when you first started?
[00:01:00] Gonçalo Silva: Yeah. The start is actually interesting because I was a freelancer, and actually, pretty much everyone except the founder from Doist was a freelancer in the beginning. So, in a very special way, we were already a remote company from the start. Of course, as the product wasbuilt up and it grew, we figured out this was not going to scale so I got hired, a lot of other people got hired as well in that beginning, and I was head of Android for a few years, and that evolved into the CTO role that I have today. So, short story.
[00:01:32] Matt H: That's great. How long have you been CTO for?
[00:01:35] Gonçalo Silva: About two years.
[00:01:36] Matt H: Two years. Nice.
[00:01:37] Gonçalo Silva: Right now. Yeah.
[00:01:38] Matt H: Cool. So, Doist runs two products. You've created two products. Do you have your hand in both of those products, as CTO, or is that something that you focused on one or the other?
[00:01:47] Gonçalo Silva: Well, the thing is I'm going through a transition actually right now, from less product development into a more technical side of things. I was more focused on Todoist throughout the past couple of years, that's my original product, and also the way we approached building a new product within the company was to ... I know this is a bit cliché, but we tried to create a small startup within the startup, and shield this team from outside noise and pressure. And that team has had full ownership upon roadmap development, etc.
[00:02:24] Now, we do keep things open so of course, me and everybody elsehas participated in a lot of the discussions, the brainstorms, etc. But this team has held the final say in most of the things so far.
[00:02:37] Matt H: Great. Just so people are aware, you started with a to-do list, and then you built out the Twist app.
[00:02:44] Gonçalo Silva: Yeah.
[00:02:44] Matt H: The communication and productivity app. Is that correct?
[00:02:48] Gonçalo Silva: Yes, yes. So, back in 2007, Amir, our founder, had a side project of his own. It was Todoist. He just basically wanted a to-do list for himself, and he was not a fan of any of the offers in the market at the time, so he built Todoist. That's how we started off, and for many years, that'sall we had. Although, as the company grew and we also adapted our mission statement to what we have now, which is we want to build the future we want to work in, we realized how important communication is, and we were also very angry and skeptical about the current offerings in the market, and the way they work. Things like Slike and Microsoft Teams, and all of the constant presence, always being online, FOMO, notifications everywhere, andwe always had a very different stance on this so we decided to build Twist for ourselves and obviously for other teams who think like ourselves. And the truth is, we truly believe this way of communication is the future. It's not what most teams are using right now.
[00:03:54] Matt H: I see. So, you obviously have had some success with that. You mentioned that there's quite a number of teams that are using Twistat the moment and share that vision. Was there any trouble getting started with that product or what was the pushback there, and how are things going within the Twist app?
[00:04:10] Gonçalo Silva: Yeah. I mean, to be honest, there is always, I think, a lot of pushback when you build something new.
[00:04:16] Matt H: Sure.
[00:04:16] Gonçalo Silva: And bring it to the market. So, we obviously had alot of pressure to make Twist more like Slike and the like. We have had many numbers of requests to do things like adding online presence indicators and synchronous communication workflows, and it's always very tough to balanceour vision for what a product should be, and what people expect from it. The truth is, we have been scaling down on many of the things that people are actually requesting us to add.
[00:04:32] Matt H: Oh, interesting.
[00:04:32] Gonçalo Silva: So, it's been quite a challenge because I think ourbiggest struggle, and this will be the case for many or at least I expect so, is that Twist is not only a new tool, it needs a mentality change so people need to approach communications, people teams, companies, etc, and this, obviously, always takes a long time. We need to prove, slowly, that this is better than what is already out there.
[00:05:15] Matt H: Right. You mentioned your mission and changing the way people communicate, and people work. What is the end goal and what would you consider to be success for Twist and also Todoist, just in terms of your mission and your roadmap?
[00:05:29] Gonçalo Silva: So, although the missions for both products are different, they collide in the whole mantra of we want to build the future we want to work in.
[00:05:36] Matt H: Right.
[00:05:36] Gonçalo Silva: For Todoist, in general, our feeling is that most people in the world don't use any productivity system, and the thing is, of course, we humans, we are incredibly smart and capable, but we just can't keep track of everything at all times. And one thing we have found is that most people who start using a productivity system and of course, we promoteand develop Todoist, over time become just a lot more capable of managing their life and their work. In the end, they just become more productive and have more time for what really matters.
[00:06:11] For Twist, there is a little bit of a difference because it's more focused on teams. It's focused on communication and in general, we are huge fans of a synchronous communication. The reason being that we do our best work when we are truly focused, what's so-called deep work, and the way to achieve this is to block uninterrupted time to work on something. And if you have something like Slike or Microsoft Teams, or whatever else you're using, pinning you and distracting you all the time, this is something that's very difficult to do. And even if you control notifications and for example, reserve time slots to catch up later on, when you have a single stream of information, it becomes very hard to catch up and some discussions will probably be over by the time you get there, and that generates FOMO, etc.
[00:07:01] So, what we're really trying to do with Twist is provide a platform where a synchronous communication is key, where you are totally in control of your notifications and where we also don't let the discussion topics just slide up into some kind of a history log where you'll spend a lot of time catching, and in general, might not even be able to bring it back on. So, I guess we could see this as just making communication much more efficiently and people more productive.
[00:07:30] Matt H: I think that's definitely something that I've heard before with remote team specifically is, both from the management side of things aswell from the employee side of things, is that people often trying to figure outa way or a process to make sure they have time devoted to specific things, sothey can really dive into it, really dig in whatever they're doing and focus specifically on that.
[00:07:50] Gonçalo Silva: Yeah.
[00:07:50] Matt H: But there's also part of it too that you do want to have some accessibility, and you do want to be able to ping somebody on a projectbecause otherwise you do feel a bit isolated. So, how do you balance those two things? How do you balance allowing for deep work but also allowing for some level of openness and approachability in your daily work?
[00:08:09] Gonçalo Silva: Well, if I'm fair, we don't. So, what happens is we truly focus on a sync and then, we have different processes for when people can do face-to-face, and they can synchronize. For example, all of our teams have weekly meetings where they all get together and discuss deadlines for that week. All of the leads have one-on-ones with everybody on their team. We have a yearly retreat where everybody gets together face-to-face for a week. But the truth is, on a day-to-day basis, we don't really count on having people online and synchronous at the same time. The reason being, we don't really believe this is feasible at scale. We are over 60 people in over 25 continents. We pretty much span all timezones you can imagine, and actually, in some teams, we have all of the world covered. So, what this means is even the team meetings that I just mentioned become increasingly complex, so anything else on top of that can just be very frustrating. So, it's something we try to avoid and just have a better overall process to achieve that.
[00:09:19] Now, you mentioned something that I find very interesting, and I think would pay a lot of attention to this, which is isolation. Something we do is 99% of our conversations are public. I mean, even our head channel which has all of the team leads, that's a public channel so all of there are discussions there are public. Now, people are not notified about them because that would spam, but they can go there anytime they like, and see what's being discussed. So, we keep, basically everything open. From product development to leads discussions, to the groundwork on each specific feature, etc.
[00:09:56] Matt H: That's interesting. I think Doist is probably the largest organization that I've been able to learn about through this podcast, but that's really interesting. One of the questions I was going to ask, with being so large and growing, and scaling as you have, how have you come up with an effective way of disseminating information amongst the teams, and how do you make sure that the people who need to know the information get the information and that sort of thing? So, I think it's interesting how that stays open all the time. Did you start that way or is that something that evolved as you grew, or how did that go?
[00:10:27] Gonçalo Silva: This has been constantly changing. In the early beginnings, I think up until the point where we were about 20 people, we didn't have any kind of formal process. Things just happened and we were comfortable with it, which was nice but of course, as you grow, this is not always the case and we had to adapt. I think we do a lot of things to make this happen. So, I will just focus on two which I think are the most important. We use a work system called The Do system.
[00:10:54] Matt H: All right.
[00:10:55] Gonçalo Silva: And within this system, I think we could say we have one month sprints, but the really interesting thing about this is that we assemble squads of people from different teams to work on a specific topic. We borrowed this idea from Spotify, but the really great thing about this is that people who never would work together end up working together, and we switch things up every month to keep things fresh. And because we have this system, we have, of course, in the beginning of each month, we distribute thework, we detail the work and so, everybody who will be working on something has the information necessary to be working on it.
[00:11:35] Yeah, so, I guess that's the number one thing we do. Something else we have started doing more recently is these monthly updates, company-wide updates. We do these per team but we also do it per topic. So,for example, we have a monthly Todoist update, the stuff we've been workingon, the stuff we plan to work on, what's the longer term roadmap, how are things changing. We do the same for Twist, but we also have monthly updateson people ops, so who are we hiring? Why are we hiring them? Who joined the team? Etc. And these, I think, have also been very effective in aligning everybody behind the common pillars of how we operate.
[00:12:18] Matt H: Yeah. It's interesting you bring that up. I think the peopleops side of things, and we can go back to the engineering side, which is obviously your area. I was interested in how people within, especially larger distributed teams, manage to build a company culture and how you keep thatculture maintained as you grow, and what do you look for in people that will fit well within the team. And I did a little bit of research before the show, and Isaw that your retention rate for your employees is crazy high, and I think they said that there is only one person that left voluntarily or something like that, that might've changed, but how have you managed to do that and maintain those crazy high retention rates for your employees?
[00:12:58] Gonçalo Silva: I think we pay a lot of attention, and we really focus on having a workplace that is inspiring for all of us. So, I know for example, Amir, our founder, he spends a lot of time thinking, and you can hear actually a lot of comments in this direction like if I was an employee here, how would I feel about this? And this is an exercise we do very often. When we are looking for people, when we're hiring people, we have these fivecore values we uphold throughout the company. We talk about these all the time, we try to look at everything through the lenses of these five core valueswhich are independence, mastery, communication, balance, and impact. And for example, when we are hiring, we look a lot at the candidates and see how they match around these values.
[00:13:46] Let me give you an example, there's a very high correlation between the success of the hire, and this particular aspect, are side projects. People who have side projects, they maybe have a podcast or they wrote a book, or they stream online, gaming or even coding, or they just maintain a library, an opensource library. The truth is that if you are doing any of these things, you are showing independence, you are showing mastery, in some cases, you are showing that you are good at communication, especially to deal with other people in the case of opensource. So, we look for these thingsand try to have the best match possible.
[00:14:25] Now, the truth is, it hasn't worked all the time. We have honestly had people who struggled in the beginning, and despite our best efforts, in the end we parted ways. I personally maintained contact with a few of them, and the truth is they found a local job afterwards, and they are really happy right now. So, in a way, remote work is not for everybody or at least that's what we've been finding, but we can definitely make it work most of the time.
[00:14:50] Matt H: Right. Do you look for people that have worked remotelyprior to coming on-board or is that something that you require, or how does that work?
[00:14:59] Gonçalo Silva: Not at all, actually.
[00:15:00] Matt H: No. Okay.
[00:15:00] Gonçalo Silva: I would say we are very excited to have newcomers to remote work and be able to help them make the shifts. We have a process in place that helps with this, so for example, every newcomer has a mentor for three months, with whom they are expected to maintain a constant conversation to help them sort out not only how the company operates, but also how to approach remote work and change any habits around this. We also have a trial period. We have a very tight feedback loop system. So, we are eager, honestly, to introduce people to remote work, so no restrictions there at all.
[00:15:36] Matt H: That's counter to some of the conversation that I've heard around, especially around junior developers specifically. The need for them to be in office with other, maybe, more senior people, and interesting you mentioned that. I also probably think that when you bring on a junior developer, especially with remote work, you can probably mold them and train them to process in remote work. Maybe they don't have that bias that they came in with before, if they worked remotely previously. It's interesting that you mentioned that.
[00:16:01] Gonçalo Silva: Yeah, for sure. Biases can be troublesome, although, if I'm honest, the truth is we don't hire junior people often.
[00:16:08] Matt H: Oh, okay.
[00:16:08] Gonçalo Silva: So, we do have some people in the team who joined as juniors, and they have been highly successful, but it's not a common occurrence. If you look at our job listings, we are usually looking for people with some experience in the fields, so ...
[00:16:22] Matt H: Right.
[00:16:23] Gonçalo Silva: That's our experience.
[00:16:24] Matt H: Right. Speaking with the hiring process for you, now, youmentioned that you look for people that have had projects outside of their regular day jobs. Do you give people projects to work on, as a part of the hiring process? Because I know that's pretty common amongst some tech companies that will give them a project like a two week thing, and then see how that goes, and then work through the hiring process from there. Is that something that you do in Doist?
[00:16:44] Gonçalo Silva: Yeah. We've done this for 10 years now. So, we definitely have this as part of the hiring process where we have a small test project. It's usually somewhere between eight and 12 hours of work, and of course, we're looking at things like code quality and how the final product actually works. But I would say the thing we are most interested in are the compromises that people make. So, these projects are usually just a little bit too big for the timeframe you are given, and in general, we are very interested to see what compromises you make because work, longterm, is all about compromises. And it's very important that people pick the right compromises to make, and of course, sometimes this is subjective, other times it's very objective. This has been very insightful for us within the hiring process, besides the regular interviewing.
[00:17:35] Matt H: Right. Part of that process, is that how they communicate with you as well? I'm assuming the answer to that is yes. Because I find that some people have mentioned to me that hiring process or the things that they look for is not necessarily the product itself, but how theyhave communicated their issues going forward and throughout the process, and struggles do pop up as you mentioned, how they've dealt with it. And theother thing I've heard as well is writing especially is important, especially within a remote team. Do you find that quality writing is something that you look for in your team?
[00:18:04] Gonçalo Silva: Yes, definitely. It's actually the first thing we check. So, we have this requirement where every candidate has to write cover letter, and we use this in a traditional sense so we want to make sure we don't get a generic cover letter. We want to make sure the candidate has done their homework, but we also look at how good the writing is. And duringthe interviews, we also look at how good spoken English is. The truth is, this is the language we use throughout the company for everything, and going back to the core values I mentioned before, the five core values. One of them is communication, and of course, this has many angles but you also need to be proficient in communicating.
[00:18:44] This is crucial to successfully collaborate, although we have hired people in the past that were not excellent at English, and we do have a perk, internally, where you can spend basically money on your education. I know we do recommend that people who are not great at spoken or written English use this education perk to improve, and we have seen massive improvementsinternally. Truth is, nowadays we are a little bit more demanding with this particular aspects, and right now, we definitely look at how good someone's English is before hiring them.
[00:19:17] Matt H: Interesting. So, going back to a little bit of a team dynamics within your sphere there, with the engineering side, is there difference in terms of processes for you being a remote team specifically, that wouldn't necessarily come into it when you're in an office, and how have you dealt with those things? I would just be curious to hear about or learn about your process, the engineering side specifically.
[00:19:39] Gonçalo Silva: So, one thing that applies here, and I would say it applies to many of the other fields, but it's specially important in engineering is, in general, you should keep a backlog of things to work on. Because of our synchronous nature about the way we communicate, and the way we work, it's very common to get blocked on things. So, you need input from someone from design or from products, and you don't have it right away. You need to be able to counter switch, and you go work on something else. This is entirelydifferent, from my experience, from the way most companies work, specially non-remote companies.
[00:20:16] And we have also found that this change in the way we work is one of the most challenging aspects of a new engineer joining the company. Make sure you always have more than one task at hand, so that you can switch between them while you wait from input from others. This has definitely been one of the things we had to adapt.
[00:20:34] Another aspect I think is, because we are remote, we generally areunable to do pairing sessions where people develop together, and they learn from one another. So, one other thing we have invested quite heavily, internally, are code reviews. So, pretty much every team has a very strict code review process and while this might look like an evaluation, it's more of a shared knowledge that you want someone else to read the code, how it works, understand it. The ownership of this knowledge then also becomes distributed, and it's a great way to learn from others as well, since you just can't sit right next to them.
[00:21:13] Matt H: Right. And with the product development side of things, is there any specific timeframe that you work amongst the other design aspects of it, other components of the product development? Do you have standing meetings throughout the month or throughout the process of developing a product, and how does that change within a remote team?
[00:21:32] Gonçalo Silva: That's a good question. Honestly, the way we do product development, I would say does not change significantly from the fact that we are remote. So, like most companies, we have a longterm roadmap. Like most companies, we try to break this down into smaller actionables that fit within our monthly cycles. And then, the squads that I mentioned before, they do have something we call the weekly snippets. So, this is not a stand up meeting because it is a sync, but it's just a thread where the squad discusses what they have been working on last week, anything they might beblocked or need input in, and what they plan to do for the following week. ButI guess never this, except for this part where we swap out what could be a stand up meeting for a more synchronous workflow, everything else I would say is pretty standard.
[00:22:22] Matt H: So, as you grown, I just want to take a step back and talka little bit about scaling a remote team as you have because you've obviouslydone this successfully, and your retention rate is high, the product is great. So, what has been the biggest challenge for you, in remote work? Is there anyprocess that you've put in place to meet that need?
[00:22:40] Gonçalo Silva: Well, one of the challenges we've faced since forever and it's unfortunately not something we have figured out yet is we hire very slowly. So, from the time we decide that we need someone doing a certain job to the time we on-board someone new, many months usually go by. Actually, we have a specific position that has been opened for over a year,and this takes a huge toll on the team because sometimes we are not quick enough to react, and we may have a certain team that's understaffed, and if it's takes over half a year for us to be able to hire someone, then it can be a very frustrating experience for that specific team, for any other teams that depend on it, etc.
[00:23:25] And honestly, we have not figured this out yet. We know how other companies are hiring, for example, it's not uncommon to set a deadline,get candidates throughout the time and then decide on who person will be hired for this position. But in general, we don't want to compromise, so we just keep looking until we find the right person for the role. But despite getting a lot of applications every single day, sometimes this takes a long time. Yeah, it can be a very frustrating process and I'm unsure what else we can do to improve here.
[00:23:58] Matt H: Yeah, that's interesting. I think it's a struggle, I'm guessing, with most teams remote or otherwise, that want to continue to maintain their culture and build on the team that they have already but also meet the need of the teams, and make sure that people aren't overloaded if there's another person that's needed. So, that's interesting, and again, I don'tthink that you're unique in having that struggle but it seems like you've prioritized making sure that you're hiring the right person as opposed to just filling seats, and making sure that the teams have the number of parties that they think they need so I don't think that you're alone there, at least.
[00:24:26] Gonçalo Silva: Yeah, but we have definitely not figured this out. We have tried different things, and we can make smaller improvements, but this is one of those things where you need a 10X improvement to really makea change, and we're still looking at that.
[00:24:40] Matt H: Right. Because I know there's a lot of engineers out there that are listening to the podcast, and you obviously have quite a bit of experience in hiring and working with different teams. So, what would you say is a skill that every engineer should know, especially getting to a remote role or wanting to work for a company like Doist? Is there a skill that maybe isn't necessarily intuitive, that you think that everybody should master beforeapplying for a job at Doist?
[00:25:07] Gonçalo Silva: That's a great question, and yes, I do, from experience. It's actually not directly related with engineering but we have found that engineers might struggle with this a little bit more than other people. Communication is key. The fact that you're not sitting in an office with50 other people who can just touch on your shoulder and ask what's up, makes it a little bit difficult to keep people in the loop and be proactive in terms of communication. This is a very important aspect of working remotely,how well and how often you communicate, and of course, how efficiently. Don't want to spam your colleagues. And this is a very important skill to keep things running smoothly over time, and it's very important to master this, andit's something we definitely value very highly.
[00:25:54] Matt H: Right. I also wanted to ask with the isolation thing that you mentioned or the issue of isolation within remote teams, what do you do outside of just communicating as effectively as possible and making sure thatpeople are part of stand ups? Is there a process that you guys do specifically, that might not be intuitive to other teams, to make sure everybody's getting that face-to-face time and getting to know people within the company?
[00:26:17] Gonçalo Silva: Yeah. So, besides the stuff you mentioned and theyearly retreats.
[00:26:22] Matt H: Right.
[00:26:22] Gonçalo Silva: We are, generally, very open about this topic, andeven other complicated topics such as mental health. So, we have this thing where we discuss a different mental health issue every month, from isolation to imposter syndrome, and we have these very, very open conversations where people join in and they share their experiences, and their views on these topics. And I think these have been highly efficient in terms of avoiding taboos. In terms of isolation outside of work, because this also happens, right? Working remotely, you might sit at home every day. Longterm is a very dangerous path.
[00:27:00] We generally try to be very proactive about time off, about our work week. We work 40 hours a week, and we don't want people to overwork or burnout, ever. We are very proactive about this. We have 40 vacation days per year and we monitor this so that people do take their time off, and rest, and recharge. So, yeah, I guess there's not a huge thing we do. There's just a bunch of small things we continuously do to make sure people don't isolate themselves and don't burnout, or become depressed. But it's definitely a challenge, and something we are still improving as time goes by.
[00:27:37] Matt H: Right. For you specifically, what does a day look like for you? Because I'm sure that there's a lot of people out there that are curious as to what a CTO does on a daily basis. I, myself am included in that. How do you maintain your work life balance and what does a day look like for you?
[00:27:51] Gonçalo Silva: Well, my days are honestly very, very different. So, obviously, my priority number one is supporting other people. That is, after all, my job, but depending on the time of month, it can be very different.For example, in the beginning of the month, we are usually very focused on the beginning of the sprints that I mentioned before. So, there's a lot of planning going around. I spend a lot of time talking with the team heads about what's possible, what's not possible, what is too much, what is too little, etc. Usually, in the beginning of the month, I also have my one-on-ones with people I manage. So, obviously, that's a time for more personal conversations. Having said that, we have a very strong culture of being what we call doers, so I program, and everybody has some kind of groundwork thatthey do on a daily basis.
[00:28:41] So, I also block out my time to do deep work, to code a little bit. Ofcourse, I don't have any specific team so I'm usually landing a hand to any team in need. But, yeah, my day usually looks like this. It's just a normal day like everybody else. I probably have a few more minutes than most people, and I spend a bit more time thinking about ... in terms of a high level review of the company, our engineering, our products, how things are going, and how are we going to meet our longterm objectives. But like everybody else, I do spend my time doing my own share of coding.
[00:29:15] Matt H: Right. Do you work only at specific hours or do you shut off at a specific time, or is there tools that you have that make sure that you do shut off, that you focus on those deep works other than, of course, your own products? But is there a certain type of day that you shut off, typically?
[00:29:28] Gonçalo Silva: Yeah. I'm probably the worst guest you will have for a long time around this topic because-
[00:29:34] Matt H: I don't know about that.
[00:29:36] Gonçalo Silva: The truth is I am very unstructured person and my creative process, my work process is very chaotic, and I've honestly spenta lot of time of my life trying to become more structured and balanced. But I have found out that is usually is ineffective, and it just makes me more frustrated. So, what I've been trying to do instead is, I use this app called Rescue Time, which just monitors how much time I spend working, and I keepa close eye on it. And if for example, there is a week where I go a little bit overboard, I will just scale down next week. I will do a proactive effort to ... next week, I'm going to have shorter week or a more lightweight week to compensate for this one.
[00:30:20] I don't really follow a strict schedule any day. My days are all different but I know this does not work for most people, so I'm not in any way advocating that anybody tries this. It's just like I've always done it this way, it worked great, and honestly, only after starting a family, I've had a son recently.
[00:30:38] Matt H: Oh, congratulations.
[00:30:39] Gonçalo Silva: Thank you. But only then, I really started thinking more about this balance and about the structure, and trying to incorporate it more into my daily life. But it honestly has not worked that well. So, in this area, I'm just more reactive. I keep track of what I do, and then I react accordingly later on so then, things balance out.
[00:30:58] Matt H: Right. I think that was the most honest answer to that question, that we've received. And actually, Rescue Time has been mentioned a few times so shout out to them. They're obviously helpful. Do you recommend that your employees do that as well? Do you talk with an actively, if for example, like you said, if you go over for one week, do you talk with your team and say that, "Hey, if you spend too much time during this week, you should pull back next week"? Are you intentioned about communicating that to your team?
[00:31:22] Gonçalo Silva: Yeah. For sure. To be honest, I do try to communicate that people should have as much structure as they can, which goes against what I, myself, do. But the truth is, even as I observe other people around me, most people deal very well with a more fixed and stable schedule. So, I try to adapt that to my own teams, assuming that most peoplewill do well with a more fixed and stable schedule. Now, we have totally flexible hours at Doist, and I think it's one of the huge perks that we provide, and something that remote work easily enables, but we definitely are very mindful of how much effort people put into things and then try to adapt, balance things out as we were saying.
[00:32:05] For example, I mentioned the monthly cycles. We do this every year, but we actually have three months per year. In August, because of vacations, December, because of the holidays, the month of the retreat, which is usually April, May, where we have something called the do breaks. During the do breaks, people actually have total freedom on what they want to work on. They can literally spend a month learning something new, and this is another way where we can balance out the stress. So, the monthly cycle, you finish one, you start another, and you keep going and going and going. But the truth is every two to three, four months, you have a break, a full month to focus on something else you want to work on, learn something new, etc.
[00:32:47] Matt H: That's great. Have you noticed that you see a spike in innovation during those times?
[00:32:47] Gonçalo Silva: Yes, for sure. I have actually an example. Recently, (Piater) , one of our Android developers, showed a demo to the team. You take a photo with your phone, of a to-do list on paper, just a regular list, and it gets imported as a Todoist project.
[00:33:09] Matt H: Wow.
[00:33:10] Gonçalo Silva: This was pretty cool, pretty out of the box thinking, and obviously, it's something very hard to do when you're just goingfrom cycle to cycle within the roadmap. So, kudos to him.
[00:33:21] Matt H: Yeah.
[00:33:22] Gonçalo Silva: And this sort of ideas can really spark when you have total freedom to do whatever you want.
[00:33:27] Matt H: Yeah, that's super interesting. So, when you say that heycan work on anything and learn something new, can they work on their own side projects or is it specifically to do with Doist, and products that are going on within Doist?
[00:33:38] Gonçalo Silva: We don't have any restrictions what people work on, although, I mean, obviously, we expect that everybody has Doist in mind. Like I'm learning something because it will be useful to me, or even if you're working on a side project for yourself, that's fine. If you can use the learnings or you can use the side project itself in the future, for Doist. So, we usually say we're all adults, so there is not a strict list of things you can do.
[00:34:02] Matt H: Right.
[00:34:03] Gonçalo Silva: But of course, we expect you to keep the company interests in mind when doing so.
[00:34:08] Matt H: Wow, that's fascinating. Taking another step back with the management side of things, I'd be curious to know, because it sounds likeyou gradually grown within the company and you've (inaudible) CTO within Doist, starting as an Android developer like you said. Is there any management techniques or skills that you've had to develop again, that you took you off guard, or what was the most important management skill that you've had to learn you've grown within Doist?
[00:34:30] Gonçalo Silva: I think the most important thing, and honestly, it was one of the hardest things for me to figure out, is that as a manager, your number one priority is not to be an individual contributor. So, u need to become an enabler for the people you manage. That needs to be your top priority. It's like how can you make them better individual contributors.
[00:34:52] Matt H: Right.
[00:34:52] Gonçalo Silva: And honestly, since, as you said, I grew internally within the company, from a developer to a manager of a team, to a CTO. Thishas been a gradual evolution and something I have struggled with at times, because I've always a lot on my own individual contributions, and this shift, I think, can be very hard. Not only for me, also for other managers that we have grown internally. Your own role as an individual contributor needs to diminish so that you can truly focus, empower, and enable the people you're managing.
[00:35:26] Matt H: Yeah, that's interesting. It makes so much sense. From my perspective, when I see the CTO role, it seems like that would be heavy inthe technical side and it would be product driven, and seems like what you're saying is that it's mostly focused on getting the best out of your employees, which I think is fascinating.
[00:35:43] Gonçalo Silva: Now, I mean, every management role I would say is about people.
[00:35:46] Matt H: Right. I know that your time is valuable, Gonçalo, and I really appreciate you coming and spending some time to talk us. I have a couple of closing questions before you go. What is your favorite unplugged activity outside of work? So, what do you do to unwind?
[00:36:00] Gonçalo Silva: Yeah. I mean, these things change over the years,and of course, I'm a father and I love spending time with my son. It's something I, again, remote work enables this, I get to do every day for long stretches of time. When I am not with my son, something I have started doingrecently, about half a year ago and I've been having a great time, is learning the drums.
[00:36:21] Matt H: Oh, nice.
[00:36:21] Gonçalo Silva: So, an instrument. It's something I had never done as a kid. I always wanted to but never really took that step. It was funny, one of the times in my life where I felt the most stressed with how much I had to do. New person in the family, a newborn, I had this role within the company that obviously demands a lot of attention and focus, and it just felt like the right time to start something new, and put things into perspective. So, I've been having a great time drumming and I think doing something that's physical, and that demands your total focus and attention, ithelps immensely, relieving stress and making me feel good about myself, andall of that. Because when I'm drumming, I cannot be connected to anything else. I need to be playing the instruments, so that's really, really a great feeling, and I highly recommend people have some sort of activity in their lives where they need full attention.
[00:37:18] Matt H: Yeah, and I found that as well, with myself. I think it's a good practice to have something outside of work and family life, that it demands your attention because it does allow you to leave everything else aside, and really unwind in a focused way, so I think that's really interesting. The next question I have for you, do you have a favorite remote work tool that you use outside of your own products, potentially?
[00:37:38] Gonçalo Silva: Well, we build tools for remote teams, so it's really hard not to pick one of our tools or both of them. But I would say that inmy day-to-day things that are directly related with remote work, it is Rescue Time for me, so it's the way I keep track, and I keep myself in check. I don't really use anything else, specifically for remote work, although of course, there's Zoom for meetings. Amazing tool, which would probably not be needed on co-located company. Of course, things like Dropbox, we share a lotof files and documents, so it also enables a lot of the work we do.
[00:38:14] Matt H: Nice.
[00:38:15] Gonçalo Silva: But yeah, I mean, nothing too special I would say.
[00:38:18] Matt H: Interesting. All right, I have one more question for you, and again, take this in whatever direction you want but what is the best advice that you've ever been given? And this can be work related or outside of work. You can take that in whatever direction you want to.
[00:38:34] Gonçalo Silva: That is a hard question.
[00:38:35] Matt H: I know.
[00:38:36] Gonçalo Silva: I've gotten so much good advice over the years, from so many people.
[00:38:40] Matt H: Yeah.
[00:38:40] Gonçalo Silva: I don't want to pick favorites, honestly, so something I will do is I'm going to mention the best advice I have gotten recently.
[00:38:47] Matt H: Okay.
[00:38:48] Gonçalo Silva: So, recently a co-worker told me to do less things,and I think this applies to a lot of people in a lot of fields, doing all kinds of jobs. The truth is, the more things you do, the less ability you have to do deeply focus on something, the less ability you have to take a step back and have a higher level vision on what you're working on, and in general, just the less dedication and the less time spent thinking on a particular thing. And thetruth is some of our best ideas don't come immediately, they come when youleast expect it. So, if you're juggling a lot of things at the same time, it's very,very hard to have that background processing in your brain happening without you noticing, on a particular topic.
[00:39:32] So, recently this was an advice given to me and I think it was extremely insightful, very timely, and I think it might also apply to other people out there. So, yeah, I'm definitely going with that one.
[00:39:44] Matt H: Nice. That's a good answer. I think that was one of my favorites so far and I know that I just threw that onto you at the last minute, so well done. All right, like I said, I really appreciate you taking the time. I think that was super valuable for our listeners. Was there anywhere that you wanted to send people, to learn more about Doist or to learn more about you,or is there anything that you want to point out?
[00:40:04] Gonçalo Silva: Well, I would definitely recommend that people took a look at our blog. We blog a lot about topics we care about and the values we uphold, also about how we work. So, it's also a good way to keep track and get some insight into how we do things, and my direct messages over on Twitter are open. So, any questions, I'm happy to take them. I'm happy to discuss anything with anyone. And of course, thanks so much for having me. I've enjoyed thoroughly this conversation, and I hope we can do this again.
[00:40:34] Matt H: Yeah, no, for sure. We'd love to have you back on, and I can attest to the blog, I think it's a great source for people, especially who arelooking to get into remote work or best practices, and just the Doist company in general. Follow them on Twitter and we'll have all that stuff in the show notes as well. Gonçalo, thanks again, and we will talk soon.
[00:40:50] Gonçalo Silva: Thank you very much.
[00:40:51] Matt H: Thanks so much again for listening to the show today. Besure to check out weworkremotely.com for the latest remote jobs, and if you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do. As always, if you have someone that we should talk to, advice you have, or if you'd like sponsor the show, please reach out to us at podcast@weworkremotely.com. That's podcast@weworkremotely.com. Thanks so much for listening and we'll talk to you next time.
← Back