The State of Remote Work w/Chase Warrington

EP10 - The State of Remote Work w/Chase Warrington

In this episode we're doing a deep dive on the state of remote work with Chase Warrington, Head of Remote at

We cover all of the hot topics of the moment including collaboration, communication, managing offsites, employee flexibility, and productivity paranoia.

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Voiceover (00:03):

Welcome to Leading Remotely, Helping Remote First Leaders Navigate, Survive, and Thrive in this new world of work. Let's make remote work.

Matt Hayman (00:16):

Hi, and welcome to Leading Remotely. I'm your host, Matt Haman. Thanks so much as always for taking the time to listen to the show today. In this episode, I'm gonna be chatting at Chase Warrington head of remote at Now, if you have an interest in remote work and spend any time on LinkedIn, you probably come across Chase. He has loads of insights, loads of experience when it comes to remote work, and that's what we tap into. In this episode, we're gonna be covering all aspects of remote work, all of the hot topics of the moment, including collaboration, communication, managing offsite, employee flexibility, and a phrase I love productivity paranoia. Chase was extremely gracious in sharing all of the insights and firsthand experiences of implementing some of the techniques we talk about on the show, and I'm hugely grateful for him taking the time to speak with me. Well, let's get straight to the interview with Chase Warrington at

Chase Warrington (01:13):

Matt, good to see you. I'm doing great. Excited to be here and nice to finally meet

Matt Hayman (01:17):

You. Yeah, likewise. You and I have been trying to find a date and a time that works for both of us, and I'm so thrilled that we were able to get this off the ground today. I'm really excited. Obviously you are, for people who follow the remote work space. You are, it seems everywhere when it comes to remote work, so I really wanna tap into some of those insights, so maybe ask some questions that others maybe haven't asked of you as well along the way. So thanks so much for coming on.

Chase Warrington (01:39):

Oh yeah, well you're welcome. And likewise, I love following the work that you're doing, so I'm sure I'm gonna learn a lot along the way as well. So yeah, I'm looking forward to it. Let's dive in.

Matt Hayman (01:50):

Excellent. So as we often do on the podcast, a little bit of an introduction to you, your head of remote at Doist. Could you maybe just unpack a little bit about the role that you have at Doist, but also for people who aren't familiar with the product? Maybe just explain a little bit about the work that Doist does

Chase Warrington (02:02):

As well. Yeah, sure. So my role is to lead our remote infrastructure and how we approach being a remote first team. So we're a company of about a hundred people in 35 different countries and we've been operating in a fully distributed environment for 15 years. So it's baked into the company DNA hardcore from very early on. That matches up really well with my career timeline as well. I've been working remotely my entire career and hybrid organizations and now remote first teams. And so it's my job to look at how we're approaching remote work holistically and see how we can level up. We feel like we're pretty good at remote work. Again, having done it for 15 years, we sort of know what we're doing. We've got good infrastructure in place, but that landscape has shifted rapidly with the emergence of so many new products, tools, services more companies out there sharing more about how they're approaching remote work, and we see an opportunity to continue to do this at a really high level. So I look outward and externally and gather lots of information and bring that back in and try to make sure that we're continuing to do remote at a super high level.

Matt Hayman (03:07):

Brilliant. And that's exactly the kind of expertise I want to tap into. I've been a user of Todoist for as long as I can remember. For those who aren't familiar with it, either Todoist or some of the other products that you offer, tell us a little bit more about Doist as a company.

Chase Warrington (03:20):

Yeah, thank you. It's, I'm glad you asked. So many people are often interested in us as a company, but we produce products as well, and that's always fun to dive into as well. So we have two products that we're really well known for. Todoist is a task management app arguably the world's leading task manager really built as a to-do list on steroids for you, but it's also applicable to teams and we use it internally, for example, to run all of our project management. So as a lightweight project management tool, it works really well for teams and we've specifically built that for our needs. So it works particularly well for other remote teams. And then we have another product which follows a similar narrative called Twist but it's in the communication space. And so it was really built as a Slack competitor or an alternative to Slack for teams who were looking for a little bit more of an asynchronous approach, which is how we approach all of the work we do. We're hyper asynchronous and we built Twist to serve our needs as a fully distributed team.

Matt Hayman (04:19):

As I say, I'm a huge fan of Todoist, an app that I recommend to anybody who's interested in productivity. It's super lightweight and personally massive fans, so great Connect <laugh>. So let's circle back to your work's head of remote then. This is a relatively new title. I think the role has been around for a while in different companies, but to be labeled as head of remote, that seems a fairly new innovation. What does a head of remote mean? What does the role entail for you at

Chase Warrington (04:45):

Du? That last part of the question I think is really the interesting bit because I've talked with most of the people out there that are in a similar role at other organizations and the funny thing that we've all kind of come across is that there is not a whole lot that looks very similar between our roles at these different companies. So new, it's very dynamic, it's very cross-functional by nature. You're kind of working alongside a lot of different departments within the company. So it just looks really, really different depending on so many factors of where your company is on the remote spectrum and then also where you are on the timeline of converting to or better establishing yourself as a remote organization or distributed organization. So it looks very different depending on who you talk to. At DUIs, my role is split about 50 50.


If you look at the job description, it's 50% focused on our internal infrastructure. And in reality that's probably where I spend 80% of my time, at least right now. And then the rest of the time is spent more so on what we would call remote advocacy. Our mission as a company is to build the future of work. Obviously that's through our products, but it's also through building in public and sharing how we're doing this as a fully distributed team. We, we've learned a lot from other teams that paid it forward and built in public in the past. And so we want to continue paying that forward and sharing what we're learning along the way. So I do a lot of that as well get to talk to great people like yourself and share the journey and some of the best practices that we've learned along the way. And so that fills out the other supposedly 50% of my time, but it's more like 20 30% at this point.

Matt Hayman (06:24):

Excellent. I'm not looking for you to reveal any state secrets here, but I'm curious to know what some specific challenges are that are top of mind for you in that role.

Chase Warrington (06:32):

When I first came into this position, and I guess I should preface it that you know mentioned before the roles existed for a while in some capacity or another, but it's been recently formalized into a title that people can resonate with. And so I guess for several years before that I was sort of acting as this person anyways, but we didn't have it formally set up. And so now that I've moved into the role formally about a year ago or so, we started defining what are some actual priorities that we wanna hone in on. Interestingly, I think for us the top priority was human connection. We were already pretty good at the work part, but we needed someone to really take the reins and think about how do we help our team connect during the pandemic, We hired a lot, we had some turnover. The great resignation hit everybody.


So we had quite a few new faces and everybody going through some challenging times. We weren't able to host the retreats that normally that we've been doing for many years. And so when I moved into the role, we were sort of coming out of that phase and the top priority for us was human connection. So as a hyper asynchronous organization, as a hyper productivity focused organization in the tech space that's distributed across all time zones, that piece can be kind of challenging. And so for me, that's been my top priority the past year has been how do we build stronger relationships? How do we and foster more trust and care and connection with our team and that is challenging in a distributed environment. So that's one of my challenges. And I think alongside that being that we're so focused on asynchronous communication, infusing a bit of synchronicity in there while so many other teams are trying to figure out how to cut out synchronous time and focus more on async kind of doing the opposite, which is sort of weird.


And so yeah, I've been having a lot of fun with that. And then beyond that, there's lots of initiatives that we're looking at. We're looking at how we approach payments and salaries when you're distributed across the world. We're looking at our benefits and perks and the tool set that we're using and what we can do to level up in those areas. So like I said, it's very cross-functional by nature, and so my hands are of in a lot of different things at one time and that's what keeps it fun and dynamic and interesting every day.

Matt Hayman (08:46):

Excellent. And we're gonna definitely get into that connection piece later on in the show. And also I think speaking to other remote leaders as well, those issues are top of mind across the board. Those are a fairly universal in the current situation. So let's think about myths and myth busting. I wanna do a little myth bust around with you. I was thinking about this in advance of the call and there are a couple of things I've read recently that I wanted to just throw at you and get your hot take on. So I'm gonna throw three myths at you. I wanna get your unique perspective on these. Somebody says to you, remote work, it's a fad, it's temporary, we're all gonna be back in the office in 12 months time. What do you say to that person?

Chase Warrington (09:20):

<laugh>, I have had people say this. I would say to look, this is a funny thing to entertain because there's plenty of data out there to showcase otherwise. So it's not hard to debunk this myth. 75 to 80% of companies in 2023, we'll identify as hybrid in some form or another. So just by pure definition, you're already talking about 80% of companies being defined as distributed in some way or another. Five to 10% are gonna be remote first. So this is the new way of working and adopting the quote future of work is sort the only way forward. You can't put the genie back in the bottle at this point. So I find that myth fairly easy to debunk

Matt Hayman (10:01):

<laugh>. Excellent. So here's another one for you then. A remote workforce is an unproductive workforce.

Chase Warrington (10:08):

<laugh>. Funny enough, I'm writing an article about this right now and some of the productivity highs and lows that we see throughout this distributed journey. Where do you start? I mean, put it very simply, when each of your employees is able to craft their perfect workday, embracing non-linear work and working from the place that's best suited for them, not defined by the organization, whether that be the office itself or the geographic location or taking into account the time of day that people really choose to work. When you fully embrace remote work and the non-linear work day and asynchronous communication, you're empowering people to build out their most productive day, extrapolate that across the year and across your whole team, I think it's easy to see how it can be productive. The counter argument to that is, and what's often used is the, to hold up that myth is a lot of data related to people who aren't doing remote very well. I mean it's pandemic remote, it's knee jerk reaction remote to a worldwide phenomenon that we're all having to deal with. Nobody or very few companies we're set up to do that very well. So separating from the experience that most of us had and looking to what other companies are doing, setting up the right infrastructure to make this work, that's what we should really be focusing on and that's how it can be productive.

Matt Hayman (11:26):

Fantastic. Last one then. Remote work disconnects us from our colleagues.

Chase Warrington (11:30):

Oh, this is my favorite one, <laugh>. This is my absolute favorite one. As I said, it's been my top priority the past year is building that connection. So actually a very similar answer to the previous one. If you do it poorly, if you don't put the infrastructure in place, it is lonely and it will be a poor experience. But the companies that invest in it actually, they really give their teams an incredible opportunity to connect, build real deep relationships, and at the same time have the freedom and flexibility that 80 to 90% of employees want. So it can be the best of both worlds if you're willing to be deliberate and intentional and put the infrastructure in place to support

Matt Hayman (12:07):

It. So let's think about collaboration then specifically, let's move away from some of the myths and focus on collaboration. Do you think remote working is actually redefining what it means to collaborate at work? Or are we looking to replicate what we used to do in person?

Chase Warrington (12:23):

I think some fundamentals of work will have not changed as much as we want to believe they have. But I do think that it's a common fallacy to just take what we were doing in the office and replicate that In the virtual world, it's sort of a yes and a no. Sometimes I get asked by leaders, I don't know how to be a good manager at a distance. And when you dig deeper into that, I mean you really find out being a good manager is just being a good manager. It's being a good, just good person. There are some things you need to tweak and maybe some different practices you need to put in place or some bad habits you need to break. But a lot of this is just we're looking for a lot of the same outcomes and results. We're just going about it actually in a little bit more of an intentional, a more productive way. So putting the right systems in place, using the right tools, giving people the opportunity to embrace elements of work like deep work instead of presenteeism for example. These are all things that are slightly different, but actually when you really think about it, it's giving people an opportunity to succeed at a much higher level. I do think it's a little bit of yes and no as a more direct answer, but ultimately I feel like you can get to a more desirable end result if you embrace this new reality that

Matt Hayman (13:40):

We're in. It's funny you mentioned deep work. I had a conversation with Sebastian Marshall from Ultra working the guys behind the work cycles principle. It was, I think remote workers thrust us into a world where these are more available, these options are more available, this ability to work with people globally is more available. But I think being remote, it's forcing us to think about how we structure our day, how we work productively, and how we collaborate with other people.

Chase Warrington (14:03):

And I mean think the thing that people want to go to very quickly often is our two things. I think one is like the water cooler. Oh, how are we gonna have those serendipitous conversations? And then the other one is the brainstorming, the aha moments, the energy that you get when you throw 10 people in a room and see what comes from the brainstorming session. And so when we think about collaboration in those terms, it's very easy to create this narrative around that where we simply can't recreate that in the virtual world. So we've lost, this is a huge failure. The other way to approach that is to say, yeah, those things can be true. We may have lost a little bit there, but what do we have to gain from collaborating in a slightly different way? For example, confining a brainstorming session to a one hour meeting with 10 people in that conference room is very limiting in a lot of ways.


You've boxed it in so many different ways. The people that are present, the people who are gonna have access to that information later the time period that people have to really think the fact that most people identify as introverts and aren't gonna really shine in that moment, the loudest idea is probably gonna win. There's all these downsides to it too. So everything is give and take. There's pro and con to both sides of this equation. And we can't just focus on one or the other. We have to take the good and the bad and then figure out how to make the best outcome in the end given both realities.

Matt Hayman (15:27):

So if we think about communication, it's a, seems a fairly obvious question, why is effective communication so important among remote teams? But I suppose the question behind it really is what is it that's unique to remote working that encourages or forces us to be better communicators

Chase Warrington (15:43):

When your work is living in the written form? For us, 99% of what we do is written in in twist, and it's there for forever <laugh>. And that is a good thing and a bad thing. If it's not approached in the right way, the bad can shine through really strongly. But that alone, just the idea that you're going to be putting something out there that isn't just gonna be passed by in a meeting, not anybody in the entire company can peer in on what you're talking about and what you're saying, what you're suggesting that forces you to be a very clear communicator. And that forces us to have real conversations about things that are important to the company and those things that aren't get left to the side. So I think just by nature, it's the fact that everything's or most work is done in the written form think's important.


There is the culture that you build around that, right? Cause you can't have this culture where people are terrified to present ideas. You can't have this culture where people are thinking one line at a time and just thinking they need to be present and respond very quickly and be online at all times. That discourages deep work. So you have to build out this culture that encourages failure, it encourages people to make mistakes. You don't have to be perfect when you present an idea in the written form, but we do want well thought out, clear, concise, thoughtful communication. Those are the things we focus on most when we're hiring, for example. That's like priority number one. And then we move to culture fit just soon after that. So yeah, this is massively important.

Matt Hayman (17:13):

<laugh>, I really wanna tap into, if you can, sharing some maybe examples of how you do that as part of the recruitment process. Some specifics for maybe new remote first leaders who are looking for some inspiration about what they can do today and tomorrow as they're recruiting.

Chase Warrington (17:27):

Yeah, sure. So mean, we actually went back and a couple years, several years ago and reviewed the way we were hiring, onboarding different aspects of the business because even though we were always built as a remote first organization, you can't help but adopt some practices that are just more commonplace. How do you recruit? You just do the same thing that everybody else is doing. How do you onboard? You just do the same thing everybody else is doing. So we've tweaked those things over time and one of those areas of the business was how we went about hiring. We wanted to match that more to the way that we worked, which and the way we work is hyper asynchronously with a lot of written communication, very little focus on meetings. Recently ran a survey that in our company, 95% of our company is participating in less than five hours a week of meetings and 60% are participating in less than two hours of meetings per week.


So we have very, very few meetings. We run this company almost completely asynchronously. And so our hiring process should mimic that. So for instance, before you even get to an interview, you will have answered a long series of questions. We wanna see as much as we're looking for what you're writing, the content itself, we're really looking at how you write, how you present that. Can you be thorough but concise and can you deliver it in a clear message. I've seen some amazing cvs come through with people applying for positions that they're way overqualified for, but they don't put a lot of thought into the questions that we're asking and the way that they're presenting that communication. They think that their skill set stands on its own, but the skill set is just a piece of it. We wanna see how you write and communicate. So that's been really important to us. Another piece was adding early on in the process a test project which involves a little bit of communication between us, some collaboration in a transparent space and seeing how you get work done and how you approach problem solving in an asynchronous way. And then we're getting to interviews after all of this so you can see that it's kind of been inverted and we're putting a lot more emphasis on how you communicate in the written form. That's been a huge game changer for us actually. And

Matt Hayman (19:30):

What's been the feedback from people that you have hired That process?

Chase Warrington (19:33):

I recently got some amazing feedback. I shared it on LinkedIn actually cuz I was just so proud of this. But a new hire came in and told us, I've never been through a more thoughtful, thorough and well thought out interview and onboarding process. This basically she was saying this whole process has just been so seamless and so well thought out and intentional and she really appreciated that and we really appreciate that feedback because we're obviously trying to tweak it and make it a great experience for all. But there's certainly room for improvement. I mean we are constantly improving, but so far the retention rates speak for themselves that we really don't lose. Many people once we get them in our retention rates have hovered in the 90 percentile, 90 to 95 percentile, even through some trying times. So we feel proud about once we get talent in the door, we've screened the right people, we've gotten them in, and then we usually retain them.

Matt Hayman (20:28):

Hey, it's Matt again. Do you lead remote teams but struggle with spontaneous communication and collaboration? If so, I'd like to invite you to check out our platform a virtual workspace where teams can connect, collaborate and grow working side by side from anywhere. For a limited time only podcast listeners can use the discount code L r P 30 to get 30% off your first three month subscription or annual plan. Head over to, start your free trial today and use the discount code l r p 30. Now back to the interview. So thinking about the hiring process, particularly around flexibility. So we came across this study from McKinsey a couple of months ago showing just how important it was for the workforce to have flexible working in whatever that means to them. Is that something that you see at Doist? Is that something that is very, very important to people who are coming in through the door, that idea that they have a lot more flexibility, a lot more autonomy in the work that they

Chase Warrington (21:33):

Do? What's interesting, Matt, is like before remote was a commodity as it kind of is today almost. When we think about distributed work being identified by 80 to 90% of companies at this point in some form or another, even though some are maybe less distributed or less flexible than others. Before we reached this point, it was the key driver for us attracting talent. And I don't know that that's necessarily changed a ton. I still think people are very attracted to the flexibility, but that talent also has other options now. And so I think what's important is to recognize that A, it's becoming more of a commodity. So that means people are expecting it. It's no longer a perk, it's an expectation. And if you're not offering that, then be prepared for those eyeballs to start looking elsewhere. And so for us, we're already far on that spectrum.


We're already location independent. You live and work wherever you want from wherever you want in the world. We fully embrace the non-linear work day. So literally you don't clock in, we don't know when you're working, you just get your work done and we're satisfied with that. How can we continue to make that even more flexible? And even I, there's a point where, what else can you offer? But our job now is to make this the best experience overall that you can possibly offer in the future of work fully remote settings. So yeah, absolutely. People still value it, they just look at it in a different way. It's not so much an extra anymore, it's a must have and you have to do it at a really high level.

Matt Hayman (23:05):

I'm interested at a cultural level why you think there has been this shift towards flexibility, why this has become so much more important for people over the last couple of years, just culturally think's going on there.

Chase Warrington (23:18):

I feel like it's one of those things where when you didn't know that it was possible or you didn't expect it, it wasn't something that you put a lot of emphasis on a as in terms of have to have I can speak for myself, I always wanted remote work. When I came outta university, I specifically wanted to find remote work. This is 13, 14 years ago. It was not exactly a normal thing to find and I had to make sacrifices in order to get remote work to find some flexibility. But I really valued that. But it wasn't location independence, it was still geographically confined, but I didn't have to go sit in a cubicle every day and that was the ceiling for me, that was as high as it would go. And then as things evolved and I started to wanna stretch my wings a little bit further and I really desired location independence, I sought that out and I found this really weird company called du, and I think it's a funny kind of story.


My wife found the company in a Pinterest post that something on Pinterest where there were 72 companies hiring from anywhere and 70 of those 72 jobs were engineering roles and one of them was not with dus in a capacity that fit my background a little bit more. So that was seven years, almost seven years ago now. And so when I think about that shift that we've had since that seven years when literally there were 72 companies in the world that we're hiring from anywhere and now there's hundreds of thousands or millions of companies hiring in this way and the explosion that that's caused in terms of interest. Once people know that this is the reality and that they can actually earn a great income, have a productive career, have that sense of belonging to a team and a company and a purpose that you're really aligned with, but also have a bit of flexibility, spend more time with your family, choose to go eat lunch when it's best for you or work, do your deep work when it's best for you. Once you know can have these things, it's really, really hard to go back. And a lot of people got to taste that when we were all forced to work remotely. And again, I think a lot of them got a bad experience. They didn't even see what it really could be. But once you've had that taste, it's really hard to, as I said earlier, put that genie in the back in the bottle. So I think that has a lot to do with

Matt Hayman (25:27):

It. So one of the consequences of this shift towards a lot more flexibility, a lot more freedom in the work that people do is what I recently heard described as productivity paranoia, <laugh>. And this was the Microsoft study where they found, I think it was 85% of leaders were saying that the shift to hybrid working has made it hard to be confident that employees are actually being productive. But yet when you speak to employees themselves, 87% were saying that they're performing just fine. So there's this real disconnect between the employer and the employee's perception. Why do you think there's such a pronounced disconnect?

Chase Warrington (25:59):

I feel like a lot of this has to do with the fact that most people that are in that managerial situation, they built their careers for many, many years on managing people in a certain way, which involved a high level of presenteeism, a lot of hands on in the same space. Let's hop in the conference room and iron this out together. And when they're robbed of all that, it's understandable that they feel uncomfortable with it. I don't think it's completely fair to fault somebody who does feel a bit awkward about that shift. It's drastically different from what they've built an entire career perfecting and mastering. So I think a lot of it has to do with that. The focus in the office space world is on inputs, it's on showing up. You get a ton of credit just for walking through the door door in an office.


There's plenty of studies that show you might actually work what, maybe two and a half, three and a half hours a day during an eight hour day in the office, but you're getting credit for being there for those full eight hours. So, and there's plenty of other little stats to throw around in that space, but I think that's what it comes down to, right, is like you, you've built this career seeing people, managing people being in a certain situation with your team and now all of a sudden you're having to do that at a distance. And it is quite different. On the flip side of that, you have employees who again are working where they're comfortable, they're not distracted by meetings and they're not distracted by employees and they're finding their groove in their new work setting that's set up perfectly for them and they're feeling a lot more productive, but they're focusing on the outputs, not the inputs while the managers focusing on the inputs and not the outputs. And so we need to invert that paradox a little bit and help managers get to the point where they're just focusing on results and not on buts and seats.

Matt Hayman (27:46):

I listened to a podcaster, the Seth Godin podcast a couple of months back now, and he was talking about the origins of the office, the history of the office, and how that feeds into this idea of presence of this is my interpretation of a sense of ownership of you are in the office space now, we own you for that time. Now you go and do the other things in your life that matter to you. Whereas when you're working remotely, there maybe isn't that sense of I don't own your time. There are all these other demands that are calling on you and there's a sense of relinquishing some of that control perhaps.

Chase Warrington (28:14):

Yeah, I think that that word control is so important and it's not to demonize, again, I don't think it's useful to demonize it and say like, Oh, it's this big bad corporate managers that are just spying on their employees that or want that hardcore control. There's some of that for sure <laugh>, and I've seen that firsthand and how detrimental that can be. But I think for the majority of people it's a sense of losing control and they need to be guided to a place where they can recognize they still have some of the control, but by relinquishing some of that control, they're actually gonna get what they're seeking, which is better results in the end but they have to educate themselves on how to get there and work in this new reality.

Matt Hayman (28:56):

And where does tech come in? I mean obviously you have skin in the game. We have skin in the game with both platforms that enable or help to facilitate this, but to what extent do you think employers in some cases are leaning too heavily on tech as a way to gain some of that control back calendar availability, monitoring presence in Slack? This crazy thing I saw the other day where you can buy this device that will move your mouse so that it shows that you're on Slack, it's gone crazy. How do you think about all of that?

Chase Warrington (29:23):

Yeah, if you don't mind, I'll share a story cuz I just kind of alluded to it a second ago. But the first remote worker that I knew was actually my mom who converted her nursing career into a remote job, which is pretty crazy to think about how do you do that? And we're talking 20 something years ago. She was sort of a pioneer in that way, but she managed to do this. She worked from home, she did nursing over the phone and anyway, but she worked in that type of environment. She worked in one where they didn't trust that this could work and so they were tracking mouse clicks. She had to ask to go to the bathroom. If her mouse didn't move every 10 seconds, then her boss was pinging, her boss would ping her constantly to say, Hey, are you there? Just answer me back so I know you're there.


These all the cliche kind of things that we just cringe at now. So I have a very strong inclination towards not doing that and not using tech to award presenteeism because again, I think just being present isn't the key here. That doesn't actually put any results in our pockets. So we have to think about this in a totally different way. And I think who was it catalog and get GitLab produced this great report about digital presenteeism and not focusing on that and how companies are spending and wasting so much energy and time just invested in trying to track employees without ever thinking about what actually matters is what they're producing at the end. Who cares if it takes someone eight hours or four hours to produce something if in the end you get the result that you're looking for. And so for some reason we've skipped by this step and we're using tech as the way to track results, but the results aren't really, the results that they're tracking aren't really what we're interested in. So I'm very much against this, obviously it goes without saying, but I think we have to find this healthy balance between using all this awesome tech that's emerging to facilitate remote work and at the same time not using it for the wrong reasons, like creating some ridiculous surveillance state to monitor our employees.

Matt Hayman (31:23):

Excellent. So I don't wanna spend too much time on the downsides of the negatives of remote. I feel like we spent a little bit too much time on this. I wanna talk about the positive. One of them in particular that I know you are quite passionate about is offsites or retreats. Are you actually involved, Are you responsible for designing an organizing offsite cert du?

Chase Warrington (31:39):

Yeah, it's kind of a weird thing. My job is is head of remote, but the only non remote aspect of my role of our company is actually falls under my jurisdiction I guess. So I always think that's kind of a little bit funny, but it comes back to that idea that the short answer is yes. And the reason for that is we think that offsites retreats, as we refer to them at DU, are a core part of our remote infrastructure. If we're gonna do this at a really high level sustainably over time, we don't need to be together five days a week or one week a month or even one week a quarter. We do two meetups per year and that sustains us for the year. It helps us build strong relationships and collaborate on things that we can't do as well virtually and focus on connecting with each other. So that's really, that's done very well in person and we see that as a core part of how we're gonna build the future of work, which I mentioned earlier is our mission. So yeah, that's why it falls to me and I'm happy to do it. I love this aspect of remote work. I love bringing people together and seeing what comes from that and it's a lot of fun and a lot of work, but something I take a lot of pride in.

Matt Hayman (32:45):

So you kind of alluded to a couple of these already, but I wanna just dial in on these a little bit. What do you think are some of the key desired outcomes for the retreats themselves?

Chase Warrington (32:52):

There's a couple things that I think are really important. One is for each team, they should define their why. There's a great book which you probably have read or heard of it called The Art of Gathering by Priya Parker. And she talks about really diving into what is the reason for this gathering, and that's something that's often overlooked. I've talked with hundreds of people now that have suddenly been thrust into this job of, Hey, I we're a remote team all of a sudden and my boss told me I have to create an offsite, I have no idea what I'm doing. I'm thinking of going to Lisbon and renting a hotel. What do you think? And it's like, well why are you gathering? What's the point of this? And when you stop and think about that, you can reverse engineer what the goals are for your team.


So you have to first define your why. For us, we really want to focus on three things. One is connection, which is very broad, but generally speaking, we really want to build out the connection bit of our company. So we want people to feel like they're connected with their teammates even though they're working across all time zones. So we put a lot of emphasis on that. That means de-emphasizing work. In a lot of cases we're focused more on connection. Then secondly, what we wanna do is focus on our mission statement, reinforcing the mission statement and then thirdly, reinforcing our core values. So the retreat should always be serving those three functions in everything that we do. And so we'll check that against the itinerary, against the activities, against the plans, how does it serve those needs? And then build around

Matt Hayman (34:19):

That. And so from your perspective then, how would you say a retreat has been a success? How would you gauge whether or not it has been a

Chase Warrington (34:26):

Success? Quantifiably, we've run some surveys throughout the year and then afterwards specifically about the retreat, but then also just pulse check surveys throughout the year so we can track how things are going overall. So you can definitely see spikes in these sorts of things when in terms of engagement and happiness, level satisfaction, things like that. But specifically I survey the team after the retreats and ask, Do you feel more connected to your teammates? Do you feel more aligned with our mission statement? Do you feel more aligned with our core values? Many, many data points. And it's very easy to say yes or no. We do that survey anonymously and ask for very har, We encourage really harsh criticism. We're all about radical candor, so we encourage harsh criticism. It's done anonymously and we take that to heart. But I can honestly say when you look at the data, it speaks for itself. People really feel engaged and more aligned with the company once they've been to this, especially new hires. So it's well worth investing in.

Matt Hayman (35:24):

So pen, ultimate question from me. Very conscious of time pen. Ultimate question then in terms of Doist, you, you've been at the company for quite some years, is that

Chase Warrington (35:32):

Right? That's right, yeah. Almost seven years I guess, which is a lifetime in startup world, right? <laugh>

Matt Hayman (35:38):

Definitely is multiple lifetimes. <laugh>. In terms of what you've seen in terms of the progression towards remote, would you say there are any particular moments, standout moments in the development of remote at Doist that you'd share with the audience moments when there was a significant leveling up about how you guys think about and address remote work?

Chase Warrington (35:58):

It's very top of mind right now because we're just talking about retreats. But once we incorporated an I l in real life element to our remote setup, it changed things dramatically. We started doing that back in 2015 and it's united the team in a way that we couldn't be united otherwise. So that was a huge inflection point. Another was redefining the way that we're going to approach connection and tempted to say collaboration, but it's not the right word, but let's just use connection. We basically, we're starting to go down this path of we're only ay, meetings are toxic. We don't need to meet, we don't talk, we just need to get our work done and then go have our lives. It was based on this mindset that we don't really need those things to get our work done and the sooner we get our work done, the sooner we can go live our real lives.


That worked I think for a while and people really appreciated that. But we also really wanna feel like we're a part of something. I think a lot of people experience this through the pandemic remote. It's like, okay, this is great. I can work from home or I can work from wherever I want, but I don't feel as connected to my team and I enjoy that. That's what you get in an office. So I think, or you can get in an office, at least for us, we redefined that. We came back and we said, Okay, we are gonna focus on the fact and agree to the fact that we're gonna bond around our work first. We subscribe to that mentality. We're a team, not a family, and we're okay admitting that, but that's what we're gonna do. But then beyond that, there's a big space between just doing that and having a culture built around lots of meetings and lots of Zoom, happy hours and things like that.


There's a big space in between. And so taking that seriously was very important and a big inflection point for us where we were already good at the work, we could do the work, but we needed to build out that personal connection bit. And if you don't mind, I'll mention one, a third one, which was we built our own project management system, not, we used Todoist as a tool, but I mean more like the processes. We were using OKRs, KPIs and all Sprint. We were testing other systems that were built for other companies, but they weren't built for Doist. And we created our own system, which we call the do system several years ago, and it's been tweaked and refined over years, but that really tailoring that to our needs as a remote team and the tool sets that we use and the mentality that we have about work was a huge game changer for us. So those three points are kind of those inflections over the last six or seven years that I think have made a big difference.

Matt Hayman (38:37):

I love those a lot that we could unpack, but sadly we are, we're running short on time. Last question, then I ask this of all guests now. What's the one tool, app solution, whatever it might be that relates to remote work that you could not live without and why?

Chase Warrington (38:51):

Well, it sounds totally, but I'm just be lying if I said otherwise. Everything happens in Twist at du. we have hundreds of thousands of interactions going on there at all times. Again, it sounds totally self-serving, but I'm being 100% honest when I have to go work in Slack for instance, I find it very chaotic and frustrating and I can't imagine us going back to that world. So I'm very grateful for the product that we built and that we've tailored it to our needs and it would be hard for me to go elsewhere after experiencing what I have there. That said, I know it's not for everyone, so I'm I'm respectful of the fact that there's differing opinions, but that's mine.

Matt Hayman (39:31):

Okay, fantastic. Chase, I've really enjoyed this conversation. Super, super grateful for you making the time to talk to us today. How can people find out more about the work that you do and the work of Doist?

Chase Warrington (39:41):

Yeah, thanks Matt. This was awesome. Those are some really great questions that I'm still pondering and wishing I had better answers for as we speak. So thanks for the thought provoking questions and for having me as well. If people wanna follow along. My work personally, I'm pretty active on LinkedIn talking about remote work, so you can just find me Chase Warrington on LinkedIn. I've tried to do a bit of tweeting as well, but less so than I am there. I'm too long form for Twitter. Those character limits hit me hard, so I found a little home there. From a work standpoint, we do a great job with our blog, has some awesome remote work content, productivity content, things like that. And we have a fantastic new AY newsletter, which you can find by Googling Twist ay newsletter. And you'll get some amazing content from our twist content team there, which I contribute to that about quarterly. So anyway, yeah, those are some great places to follow along. And I also host my own podcast called About abroad, where we talk about remote work. It's a show really about global mobility and some of the aspects of how that relates to the future of work. So about is another place to find me.

Matt Hayman (40:54):

Excellent. We'll be linking up to all of those locations and the show notes for everybody. Thanks once again for your time, Chase. Hugely grateful. Really enjoyed the conversation.

Chase Warrington (41:02):

Me as well. Yeah. Thank you so much Matt.

Voiceover (41:07):

Thanks for listening to Leading Remotely. For show notes resources, or to discover how you can make remote work for your team, head over to That's

The State of Remote Work w/Chase Warrington