Be more productive: Block distracting websites and apps on all your devices with Freedom - try Freedom today

Working Remotely – Chase Warrington & Freedom Matters

Chase Warrington Freedom Matters

The head of Doist’s remote strategy joins us to discuss why the future of work is remote-first


This week, we welcome Chase Warrington. Chase is the Head of Remote at Doist, a pioneer of distributed work that specializes in productivity software. He is responsible for developing and executing Doist’s remote work strategy, co-located events and advocating for the future of work on behalf of the company.

He has worked remotely for over 12 years, as one of Doist’s 100 employees in 35 countries. He is a regular contributor, instructor, and consultant to many of the leading remote work organizations and publications, as well as the host of his own podcast, About Abroad.

In this episode we discuss:

  • How the remote-first and hybrid businesses, are becoming widespread
  • The key principles for operating a remote organization
  • How to work asynchronously, successfully
  • Why hiring has to change for remote work
  • How remote work is about giving your employees both a great job and a great life.

For more, find Chase on LinkedIn, Instagram, and Twitter.

Host and Producer: Georgie Powell Sentient Digital

Music and audio production: Toccare Philip Amalong


Chase: We just all leaned into our work a lot. And so we found a huge peak in productivity because everybody was hyper-focused and like, “Well, there’s nothing else to do. I guess we’re just going to hone in on work.” And then a big drop off in terms of morale, some mental health issues, there was a dark period there for a little while. And not to over-dramatize it, the company was fine, we were all fine collectively, but people were suffering in their own ways. 

And with the isolation that comes with remote work, you had to be very cognizant of this for your direct reports. So, it was an interesting process to go through to recognize, okay, we’re great at working, but we need to make sure we’re disconnecting from work more than ever right now, and making time for ourselves and our families.

Georgie: Welcome to Freedom Matters where we explore the intersection of technology, productivity, and digital well-being. I’m your host, Georgie Powell. And each episode, we’ll be talking to experts in productivity and digital wellness. We’ll be sharing their experiences on how to take back control of technology. We hope you leave feeling inspired. So, let’s get to it. 

This week, we welcome Chase Warrington. He’s the Head of Remote at Doist, a pioneer of distributed work that specializes in productivity software. Chase is responsible for developing and executing Doist’s remote work strategy, co-located events and advocating for the future of work on behalf of the company. 

He’s worked remotely for over 12 years, and is a regular contributor, instructor, and consultant to many of the leading remote work organizations, as well as the host of his own podcast, About Abroad. 

This episode is the first in a new mini series, which considers the relationship between technology, productivity, and the future of work. Today, we’ll be discussing the growing movement towards remote work, and just how to do it well. Chase, welcome to Freedom Matters. It’s really great to talk to you.

Chase: Thank you so much. It’s wonderful to be here.

Georgie: To kick off, I asked Chase to share his background, his remote story, and what he does as Head of Remote for Doist.

Chase: Yeah, sure. So, again, my name is Chase Warrington. I’m the Head of Remote at Doist. We are the builders of two products that we’re most well-known for Todoist, which is a task manager and Twist, which is a team communication platform built specifically for remote teams. We’re a fully remote team of 100 people in 35 different countries in all time zones. And so remote-first is really built into our DNA, both the products and the company. 

So, my role currently is Head of Remote, which is to oversee our whole remote work operations and also be looking externally for how can we continue to improve, continue to stay on the cutting edge of remote work. It’s been such a big part of our success, we want to keep it that way. 

I have been working remotely for my entire career over a decade now, 12 or 13 years, I guess. And both in hybrid organizations, and as a remote employee, and now at Doist as a remote-first organization. 

And I’m an expat currently taking advantage of that location independence living in Spain, and then traveling during normal times a handful of months a year. So, maintaining that balance is super important to me, but wouldn’t be able to do all that without having some sort of productivity system in place. And so thinking about these things that we’re going to discuss today, as always, it’s right at the center of my life.

Georgie: That’s amazing. And so Todoist, when they started out, as you say it was remote-first from the start. I know there are more and more companies now that are choosing to do that, but that was an early decision. What were the thoughts behind that?

Chase: Yeah, it was really early on. It was about 12 years ago when Doist was formed. And we went remote-first from the beginning. And really, it was just at the time the idea was our CEO and founder was in Chile. And he decided he wanted to take this company to the next level and start hiring people. He decided not to just limit himself to Chile. So, he hired somebody on Elance, which is now Upwork, and then it just sort of went from there. 

He thought, “Well, this is working really well. I’ve got somebody in Poland, and why not hire this guy who’s in Denmark and this guy who’s here and there?” And then before you know it, we had a team of 100 people that were all sort of hired this way.

Georgie: And how many more companies are you seeing starting to make this transition and to launch in this way or to shift their business completely to remote?

Chase: It’s just exploded over the… The last two years have probably pushed us forward 10 to 14 years depending on which survey you look at. But it’s gone from being very much a niche to now 15 to 20% of companies will lean towards remote work as the default and then 75% of companies will be hybrid in some format or other during 2022 . It’s really quite amazing.

Georgie: Yeah. So, what I’m really interested in is what true remote is versus what has kind of become how now lots of companies operate with people working remotely, right, and they’re kind of quite different things.

Chase: Yeah, it’s a great point. Working remotely during a pandemic is not what remote work should be. So, the people that have had this experience of their organizations suddenly having to go remote, and figure it out from scratch, that means you have no best practices in place, you don’t have the right tools in place, you have all the models set up to support in-office work. 

And now you’re being asked to do that remotely. And not to mention during a world pandemic, when kids are out of school, when you’re possibly having to take on additional responsibilities, it was a mess. It was just put a bandaid on it, we’ll figure it out later. Now, it’s hey, this actually works. Our people are really happy with it. But there’s a future here. Now let’s figure out how to do it correctly. 

And so at the very core of how to make it comfortable for all people involved are a few key principles. One of them is leaning really heavily on asynchronous communication, which is a buzzword that’s thrown around a lot. But it really just means communication that doesn’t expect immediate responses. So, not expecting meetings as the default, as the go-to. That’s the most synchronous way you can meet up or that you can communicate. 

So, you’ve got teams that are used to saying every five minutes, hey, let’s have a meeting, throwing everybody into a conference room so that you can get anything done. Going in the opposite direction of that is what most remote teams have to figure out how to do, and that can be a big jump for a lot of people. 

A couple others that I try to push remote managers to do, which is always against the grain a little bit, is to really try not to go to some sort of security state. Trust is super important in a remote team. And that’s really easy to say. Nobody’s ever going to stand up and say, “No, we can’t have trust. Trust sounds really nice.” But really, the ideal situation is you don’t have to implement some kind of security tracking software, you don’t want to make sure people are moving their mouses around. 

You don’t want to push people into making them feel like being present is working, because that’s what will happen. People will just sit at their computer and move their mouse around and feel like they’re working. You want to optimize for deep work, you want to optimize for people being able to disconnect from their tools, and focus on what actually moves the needle. 

The last one that I’ll mention is transparency, keeping things in a transparent place so that conversations and documents and assets that are important to everybody don’t get trapped in these silos, which is a big pitfall that new remote teams fall into.

Georgie: On the trust part, I thought it’s interesting how one of Todoist’s most important pillars is how they think about who they hire. And hiring for remote is actually perhaps different for hiring for in-office. So, how do you think about that?

Chase: It’s so important to think about this. You have to rethink all your practices, like all the models that you have in place. For instance, in a remote environment, most of your communication, if you’re doing it correctly, is going to be written, it’s going to be asynchronous. It’s not going to be synchronous video calls, hopefully, you’re not making people sit on eight hours of Zoom calls every day. 

So, all of a sudden the paradigm shifts from what does this interview process look like? Is the face-to-face interview even useful? In a lot of ways it is, but at Doist we want to look at your writing. So, we’re really interested in how well you can write. And that means writing in a clear, concise, succinct way conveying messages in the fewest amount of words possible. Because if all the communication’s in the written form, more isn’t better here. 

So, it makes you rethink everything in the way that you’re going about hiring people. So, we’re really looking at great cultural fit. We’re only 100 people and we have access to the entire world to hire. So, we can be really picky, like, probably finding somebody that can do the job that we’re looking for isn’t really a challenge anymore. But what is the challenge is finding the right cultural fit. 

So, you’re looking for somebody that really fits in from the way you work together, to the way you socialize together, somebody who’s comfortable working autonomously and alone and at distance. And then is also a really good communicator in the written form, and then piecing it all together to see who is the right person to join the team.

Georgie: I thought it’s so interesting because you see in hiring the move towards AI to filter CVS and actually what you’re doing is totally the opposite. That first curation is the most important thing you’re doing for the rest of your company culture really.

Chase: Yeah, it is super interesting because we actually switched. We did go in the opposite direction. The CV will get you past people ops just to say if the hiring committee even wants to take a look at you, which is a pretty thin filter, really. 

And then after that what we’re looking at are the answers to these questions. We ask you a series of questions that you have to write a response to, and what you write is important, but how you write is equally as important, which I find pretty interesting.

Georgie: One of the things I’ve observed amongst friends now working from home is that now that most of the interaction between colleagues is scheduled around Zoom calls or other meetings, the informal conversations, which usually take place in an office around the water cooler, or whilst getting a coffee fall away. This can lead to employees storing up issues and feeling disconnected with company purpose. I asked Chase, how can we keep all these valuable lines of communication open?

Chase: It’s of the utmost importance, and you have to create exclusive space for these kinds of things. So, you have to actually build this into the workday very intentionally. And intentionality is another word that I think might get tossed around a little bit too much when we talk about making this transition, but I think it’s super important. 

So, this is a great example, you have informal communication. It seems simple on the surface, but well, we just create a water cooler channel in our Slack account, or in our Twist account, or we allow people to join a happy hour and chit chat on Zoom. It’s not the same, it takes a little bit more than that. 

So, you have to create dedicated spaces for people to connect, you have to allow for radical candor, open trust and honesty and transparency around feedback. These kinds of things have to be baked into the company DNA in order for the remote organization to actually thrive.

Georgie: I’ve talked to a lot of people recently about how productivity is not about sitting at your desk for eight hours a day, and how all the people who do great work understand that and they step away. And that’s when they think and they do something creative, and they have rest, and then they come back and they do really awesome deep work in an hour or two. And that’s what actually moves companies forward. 

How do we get that change in psychology through to business leaders that it really isn’t about how many hours you sit at your desk? This isn’t just about remote, this is about a better way of working, full stop.

Chase: It is, yeah. And I know, it’s something that both of our organizations feel very strongly about that, yeah, it’s no longer about how many hours you’re sitting in a place. This is a very archaic way of thinking. 

And when you look at data that reflects that people who have the ability to disconnect from their chat tools and focus on deep work in the place that they really truly want to work in and work from, which may be an office for some people, by the way. I’m not somebody that says like, that just totally can’t work. It’s remote or nothing. You need to have autonomy and the ability to choose where you work from. 

And then just focus on the results. If the leaders will start looking at results and not the inputs, like hours, hours in front of the computer and number of calls made, but instead look at the outputs that actually move the needle forward, then I feel like it speaks for itself. I’m not sure why it’s such a hard leap to make for a lot of organizations. But for those of us that have we, see the light, and I think you’re starting to have more people seeing the light.

Georgie: Yeah, I hope so. It’s really interesting when you see companies like Goldman Sachs that are forcing everyone back into the office again. Why do you think companies are doing that?

Chase: I really struggle to understand it fully. There’s people out there that jive to conspiracy theories that it’s all about control. And that could be it. I think it’s just change is hard. I think it’s very hard for a company of 50,000 employees to flip a switch and say, we’re going to go in a different direction from what has been working. It’s much easier, much safer to say we’re going back to what’s worked for us for the last 100 years. And I think a lot of it just comes down to that. 

I think it’s a short-sighted approach. There’s a lot of… some of the big four accounting firms are now switching to going fully remote and saying we’re going to do it and we’re going to do it right. And that will pay dividends for them over the years, I think, in terms of attracting talent, and plenty of other benefits. But I think it’s just that people don’t like change. It’s simple and easy and less risky to just kind of sit back and stay put, at least in the short-term.

Georgie: So, let’s move back to async because as you say, this is a really key part to working remotely. I had never experienced it until I started working at Freedom, and it’s completely revolutionized the way that I work. It’s just gold. And I think it genuinely is because everything is task-based. 

And so you come to task and you pick it up in the… I don’t have emails to go through, I don’t have Slacks to go through. I just go to my task, I pick it up where it was left off, and work on it deeply for a few hours and put it away and then go and do something else. I mean, there’s just… 

Chase: It’s hard to imagine going back, right? 

Georgie: Never. I literally could never,

Chase: This is not a secret anymore so it does make you wonder. You go, “People know about this, why don’t other people do this?”

Georgie: Yeah, yeah. So, I mean, in your own words, what is async communication, and how is it best done?

Chase: Sure. In a nutshell, it’s just communicating in a way where you don’t expect an immediate response. So, there’s a full spectrum here. So, the most synchronous thing we could possibly do would be meeting together in the same co-located spot. We have to be in the same place at the same time. And when I speak to you, I’m going to expect that you speak right back to me. 

On the other end of that spectrum is completely asynchronous where, like we communicate at Doist, I send a message to a colleague and I don’t expect a response back for 24 hours. Of course, I could get a response back faster, but my expectation when I send it is that I may wait 24 hours to get a response. Then there’s everything in between. So, everything from chat to email to Zoom calls, all these elements play in between those two points. 

And so at Doist, for instance, we are Uber asynchronous, and we optimize for async because we want to allow our teammates to disconnect from their chat tool. We kind of have this mantra that chatting isn’t working. So, if we want our people to be at their best, then they shouldn’t be addicted to their chat tool. They shouldn’t have to feel like if they’re not online, then they’re not working, because we see the opposite. 

If they’re online, then they can’t really be focused on deep work, right? So, we need them to be focused on whatever mock up they’re designing, whatever product they’re fixing, whatever support ticket they’re working on, that’s the core of the work. And then reconnect to communicate with colleagues as needed. It takes a lot of autonomy, it takes a lot of trust. But if you build your culture around those things, then it can be hyper successful. 

We do have strict standards around like, if I was to be working on a Saturday and left a bunch of stuff in Twist and then Monday morning, my colleagues came in, they would be like, “Why were you working on Saturday? What’s going on?” As opposed to the opposite, where maybe in a lot of cultures, you would be praised for something like that, you would be slapped on the wrist here.

Georgie: Yeah, that’s a really significant culture change, I think as well, which is really hard for people to navigate. I feel like it’s ingrained in me. You know, I used to work in management consulting, it was always how hard you work, it’s like a badge of honor. How have you personally moved away from that?

Chase: I come from a similar background. I mean, I grew up in the US and I went to business school. I went into that world, in the finance industry at first where… I mean, it was a work hard play hard mentality and the early bird gets the worm kind of thing. And we praise the people who come in on the weekends, and who put in the extra hours. There’s a lot of emphasis on the inputs there, the butts in seats matter in that mentality. And showing up and being present, is seen as, like you said, a badge of honor. 

So, I have never really understood that. And I’m lucky at v, it’s very much so a part of our company culture that you don’t get any credit for that. We don’t track hours at all. And like I said, a little bit ago, you actually will get slapped on the wrist if you were, for instance, working on the weekends, if we can see that you are working a bit too much, if you’re working when you’re on paternity leave, on vacation, things like this. 

So, that’s a big part of our culture and I think the reason is, because we are plenty productive at work during the time that we are working. Because of the way we’re set up and the optimization for productivity and remote-first and asynchronous communication, we don’t really need to squeeze more out of people by asking them to work on the weekends. Instead, we need to put some bumpers on the sides and kind of make sure that people don’t get outside those working hours and overwork. 

That’s what most data will show is that most remote workers are more likely to burn out than they are to underwork, which is kind of interesting, because most managers at first, really want to try to figure out how am I going to know that they’re working? How am I going to track their work now that they’re working remotely? 

But all the data shows you they’re probably just going to burn themselves out because they’re going to work too hard. Because they don’t have those limits and those boundaries in place, they don’t have you looking over their shoulder, they’re not getting credit for just being in an office. So, they’re going to want to prove to you that they are working by overworking.

So, it’s your job as a manager in a remote organization to keep the team in line in that regard and make sure that they don’t burn out. So, I think that’s really why we’ve baked that into the culture is that it’s really important for the long term gain of the company.

Georgie: Yeah. So then individually, what would you say to people who are struggling to find that balance who kept on feeling like they’re getting caught up in the cycle of work and work and work really by their own doing than anyone else’s?

Chase: Yeah, yeah. We do see this pretty often, especially with new people that joined the company who come from other backgrounds. I actually fell into this trap the same exact way when I got here. I got here really excited, dive right in, I’m ready to apply kind of old mentality to work here and just hit the ground running. 

And it’s pretty easy to spot you kind of stick out when this is happening. If your manager is in a good position to view this, they can step in and say, “You know, it’s a marathon, not a sprint.” We have some rules in place. We have a project management system where it’s easy to have an overview of what everybody is working on. 

And therefore, we can say, okay, this is probably going to be too much on your plate. We also allow people and we encourage people to say no a lot. So, if you get asked to work on a project, you have first right of refusal to say, “Nope, can’t do that. I’m going to be way too busy that month,” or “I’ve got a week of vacation planned. That won’t work for me. 

And we’ll never ask you to move your vacation, or move something else in your personal life around so that work can take precedence. We’ll always move the work obligations. So, I think being unapologetic about these things and just sticking to our guns in a way has really helped everybody feel comfortable saying, “Okay. I’ll settle into this culture.” And then once you get into it, it’s hard to imagine going back.

Georgie: Yeah, for sure. And if someone’s working part time, how does that work?

Chase: I think about like, when you buy a car, there’s a price for the car, right? You’re not like, well, how many hours did it take to make this car? And how much did this person work and that person work? No, you just buy the car. So, the same for you, for instance, or for our translators, I would love to be like the work that you do is 1,000 a month or 2,000 a month or whatever it may be. Sometimes it’ll be a little more, a little less, but I would love to get to that. 

Georgie: Yeah, [inaudible 00:21:14] on output rather than hours in. Yeah, I love that, really important. 

Now I know you kind of, as your company started to grow, and you’re all working remotely and async’ly, you felt like some of the rails fell off a little bit, and the cadence and the productivity of the company started to dwindle a bit. Can you talk a little bit about what happened there, and then how you got things back on track again?

Chase: Yeah. So, we had a really interesting period at one point. One of the leaders in the company wrote this open thread in Twist sent to the whole company saying, ‘Have we gone off the deep end’. 

And interestingly, what it was referring to wasn’t so much about productivity, it was actually about the other side, which was more the social aspect, the culture that we had gone so far… so deep into leaning on asynchronous communication, and this mentality that meetings are toxic, and never need to see each other. 

And we had our one annual retreat per year and that was really the only time we would see each other. That was great. But then we had the other 51 weeks in the year. We just weren’t prioritizing anything other than productivity for a little while. And we had to backpedal a little bit and rethink some things and make room for that human element. 

Georgie: So, what kind of things have you done? 

Chase: So, we’ve implemented quite a bit to address the social side or the human element of remote work. They range from some being synchronous, like in-person activities. For instance, we have our once a year company retreat, where we bring everybody together in one place for a week. We have about six months later, we have mini retreats, which is your individual team gets together in a co-located place. 

And then we started introducing some one-off perks, I guess you’d call them. So, we send a brand new hire will be assigned a mentor on the team. They’ll go live alongside their mentor for a week and train with them, have some fun, go out, see where they live, work. It’s a nice bonding experience for a new employee. 

We started reimbursing people for meetups if they wanted to go meet up with a colleague. I went and recently met up with a colleague of mine up in France and spent a weekend together and the company reimbursed the travel expenses for that. 

We built out some asynchronous games, we added some bots to Twist that will prompt people with questions. So, “Hey, what did you do this weekend?” Or, “What’s your favorite holiday?” Or, “What’s something interesting about the country you live in that nobody else knows?” 

And then we’ve even got a bunch of things baked into the onboarding process to get people to talk about themselves so that we can build some bonds early on with new employees. We created a bunch of chat spaces so people can talk about things that they’re interested in, like coffee or travel or working out, or parenting or gardening or book club.

We’ve got 25 different spaces where people can go. But I don’t think how we socialize is how we build culture, it really is about the work. That’s what actually unites us. But there’s a piece of the pie that was missing and we filled that in with some of these activities.

Georgie: That’s amazing. And then you said there was a wobble in the pandemic as well.

Chase: Yeah, in the pandemic, we went back in that direction a little bit, I think. We were fortunate in a lot of ways because our business was not really disrupted. Sure, some changes happened and people’s lives got shaken up a little bit, but we kept working the way we had been working. 

The difference was, there was no outside distractions for many of us that ended up in quarantines and unable to travel, no real desire to take vacation when you can’t do anything. We just all leaned into our work a lot. 

And so we found a huge peak in productivity because everybody was hyper-focused and like, “Well, there’s nothing else to do. I guess we’re just going to hone in on work.” And then a big drop off in terms of morale, some mental health issues, there was a dark period there for a little while. And not to over-dramatize it, the company was fine, we were all fine collectively, but people were suffering in their own ways. 

And with the isolation that comes with remote work, you had to be very cognizant of this for your direct reports. So, it was an interesting process to go through to recognize, okay, we’re great at working, but we need to make sure we’re disconnecting from work more than ever right now, and making time for ourselves and our families.

Georgie: Yeah. And it’s harder to see that same, you know, if you see a colleague come into work in the morning, and you can tell they’re really tired or you know… It’s easier, isn’t it, to sense the mood of someone, what else they might be going through in their personal life than it is when you’re remote?

Chase: It comes back to that intentionality word again. As a remote manager, you have to actively try to engage in what’s going on in the personal lives of your direct reports. 70% of my communication with somebody on my team will be more about their personal life, what’s going on, their workload, trying to manage those elements, not so much looking for how do we get more out of this given project, or how do we strategize? 

It’s really just keeping your finger on the pulse of what’s going on in their lives. And personally, because you can’t see that you don’t have those physical context clues anymore. 

We forget, a lot of us, that what’s happening in our home country is one thing, but when you’re on a global team, everybody’s having different experiences. So, there’s an extra layer of empathy needed, and to really be cognizant of everybody’s situation.

Georgie: Yeah. And I think it takes a lot of compassion. And I heard some great recommendations about when interpreting communication to always assume the best, really, because there is oftentimes opportunity for misinterpretation, which I assume it’s one of the reasons why you pick great writers, but there are a lot of times when wires can get crossed.

Chase: Yes, yes. And it’s important to also encourage, like, when we talk about writing, it’s also about expressing yourself. Little things like using emojis and reactions and showing some character in that way. 

I mean, we’re not writing an encyclopedia here, we’re communicating with other humans. So, fostering this and embracing some of the fun sides of technology within your workspaces is really important to keep your finger on the pulse in that regard as well.

Georgie: Amazing. So, if you were going to paint a picture of the perfect remote working Utopia, the company, how would you describe it?

Chase: Oh, wow. This is a great question. First of all, where it all starts, for me personally, I won’t speak on behalf of Doist, just my personal opinion. What is the most important aspect for me is that everybody has true flexibility over when and where they work. I think that there’s so many reasons why that’s so important. 

But when people have the ability to choose where they work, when they work, and how they work, then they can produce their best work. But they can also really live the most balanced life. Which I think that’s what this is really all about is actually taking a step forward in terms of how we live our lives, and work is just a piece of that. And we can be really, really good at that piece and then also have the other pieces in place. 

So, a company that optimizes for that in the remote setting, and that may mean also having a co-working space or a co-located space where people who choose to go there can go if it’s set up with remote-first principles in mind. Meaning like asynchronous communication and decisions aren’t made in the office, but they’re made collectively as a group highly focused on transparency, and not defaulting to Zoom meetings and enforced Zoom happy hours as your only way of socializing. Then I think you have a nice recipe for success and for people to live very happy and balanced lives.

Georgie: Perfect. Thank you so much, Chase. Have a wonderful rest of week. Thanks for being [inaudible 00:28:58] We really appreciate it, and I hope to talk to you again some other time.

Chase: Enjoyed it. Thank you, Georgie. Have a good week. Bye-bye.

Georgie: Thank you for joining us on Freedom Matters. If you like what you hear, then subscribe on your favorite platform. And until next time, we wish you happy, healthy, and productive days.