The Secret Playbook of One of the Most Famous Remote Companies (ft. Chase Warrington, Head of Remote, Doist)

Let's dive in to discover the secrets playbook of one the most famous remote companies with Chase Warrington, Head of Remote at Doist.
Daan van Rossum
Daan van Rossum
Founder & CEO, FlexOS
I founded FlexOS because I believe in a happier future of work. I write and host "Future Work," I'm a 2024 LinkedIn Top Voice, and was featured in the NYT, HBR, Economist, CNBC, Insider, and FastCo.
November 21, 2023
min read

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Welcome back to the Future Work podcast. In this episode, I’m speaking with Chase Warrington, one of the world’s leading authorities on remote work. 

Chase is the Head of Remote at Doist, an async-first company that created the famous Todoist tool and has over 100 people distributed across 35 countries. 

Chase is a LinkedIn Top Voice for Remote Work and has been featured by Forbes, BBC, Fast Company, the World Economic Forum, and more. 

Today, we speak about what any company can learn from his fully remote company, how Doist keeps people consistently engaged online, but also, why his company is remote yet he loves getting together in person. 

Here are a few lessons I picked up today:

  1. Getting people together is a huge priority for Chase and the team. He’s a head of remote pushing for more synchronicity. They got so good at async communication that they forgot to connect on a human level. 
  2. So how do they do it? Doist helps people connect through mentorship trips, where a new hire gets sent to work with their mentor face-to-face for a week, a mini-retreat where direct teams spend a week together somewhere, and Doist Connect, a company-wide retreat. 
  3. Doist doesn’t see remote as a way to save costs on offices. In fact, while they had some budget cuts this year, they actually increased their investment in getting people together. 
  4. If you invest in retreats, you have to consider how they connect to your core values and how people will get value out of it. Doist purposefully uses them for connection, spending 20% on work, 30% on activities, and 50% on rest and relaxation. Chase found that in the 50%, that’s where the true breakthroughs happen. 
  5. Even if companies don’t go fully remote, they can learn from some best practices, like documenting everything. As Chase said, we should ask ourselves, are we designing for how we used to work or how we work today? 

We hope you’ll love this episode and can put these insights to good use. Subscribe on FlexOS, Spotify, Apple Podcasts, and YouTube for the latest Future Work episodes.

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You can find the full episode and transcript here:


Daan: Welcome to the podcast, I wanted to directly jump in and ask you about this world of asynchronous remote work—does it really work? I recently had Brian Elliott, the founder of Future Forum, and he said that getting together at least once a quarter is non-negotiable for him. How do you feel about that?

Chase Warrington: Well, I totally agree with Brian, and I love his work. I try to read everything that he puts out there so I would totally agree with him. It's one of the more challenging aspects, and I think this is why, somewhat interestingly, I'm probably one of the few head of remotes out there pushing for more synchronicity.

Less async, more sync, in our space because we kind of naturally fell into this trap over the years where we got so good at asynchronous communication and so bought into that messaging that we forgot that we forgot that we needed to actually connect with each other on a human level. 

We can get our work done, and we can have great lives outside of work in conjunction with that, great work-life balance, and integration. But there's more to it than that. We want to feel that team cohesiveness and connection with your teammates, and really that starts with how you work together. We also fully believe we're a team, not a family kind of mentality.

It's okay to accept the fact that how we work together drives those relationships first, and then we sprinkle in some of the human connection that you get in a more serendipitous personal manner. But I think one important factor there is that we put a lot of thought into how our people can connect with each other in the ways that we're working. Solving problems together and making sure that there are cross-functional opportunities to work together are core to how we work.

We put a lot of thought into that because we're remote first, and then on top of that, we have things like a pretty robust social calendar where we have activities going on every month that people can join virtually. We revamped our perks to, for example, help subsidize costs and to go meet up with teammates in person. We do mentorship trips where we bring people together. We do two retreats every year where we bring the whole team together for a week of communication, collaboration, connection, and all of that.

Daan: What are some of the ways that you help people get together? I read somewhere that you actually give individual people budgets to do so.

Chase Warrington: That's right! We do in-person meetups in a few different ways. First of all, this is especially important, we think, when you're first hired. So we do mentorship trips. A new hire will be sent for a week to work with their mentor face-to-face. 

During that time, it's not all work. It should be a lot of just getting to know each other and chit-chatting and hanging out, letting the mentor be a tour guide for a week, and letting that person get a great first impression of the company, but also getting settled into the workflows and things like that.

We also subsidize the costs for people who want to meet up. For example, I happened to just be in Greece recently, and I had a teammate that was nearby, and she and her husband came down and visited and used the meetup perk, the Doist Meetup Perk, as we call it, to subsidize that trip and do some fun things together. So that perk encouraged us to hang out together and spend a week together.

Then, we do these two retreats per year. One we call a mini-retreat. It's with your direct team. So like the Apple team or the marketing team, they go to a place for a week and spend a week together working, but also just hanging out and getting to know each other a little bit better.

Then, about six months later, we do what we call Doist Connect, which is our company-wide all-hands team retreat for a week. And that's the one we just returned from after a week in Italy, which was fantastic out in Tuscany. I really enjoyed that.

Those are some of the ways we're doing the in-person aspect. We believe in this mentality of being remote first, but not remote only. That aspect of how we work together is completely crucial and was a huge game changer. We started doing those retreats back in 2015, which I believe was the first one. And complete game changers for us as an organization.

Daan: That sounds amazing, but it also sounds quite expensive. One of the benefits that we often hear about remote work is that you save money on office space. So in your case, do you end up spending those savings on retreats? 

Chase Warrington: Yeah, you do. I think we look at it as reinvesting those funds back into your people, and we're not remote first for the cost savings, I guess you would say. It's a benefit in a lot of other ways.

Depending on where you're located, those numbers will look a little different. If you're trading out Times Square office space and going remote first, you could probably do about 10 of those retreats before you cut into those savings.

But for the average team that maybe had just a bit of office space here and there, I would say you're probably breaking even, you need to budget. For one retreat, you need to budget several thousand US dollars per person for a 4- or 5-day retreat. 

Depending on to what degree you want to do certain things, there are a lot of levers you can pull, but in our case, it's a big investment. But one of the interesting facts I think is that this past year, we tightened the belt a good bit, like a lot of companies. 

With the recession looming and just not knowing what was over the horizon, we tightened the belt, we cut a lot of things, we went on a hiring freeze, but we actually increased the amount of money we were willing to spend on our retreats, which I think was pretty fascinating and speaks to how important we think this aspect of remote work is.

Daan: Yeah, for sure. It's very interesting. I'm sure that, besides money, it's also a big investment in time.  Who ensures that the logistics are done well and that there's a great payoff on the investment of getting people together?

Chase Warrington: It falls on me. It's a core part of my job, and fortunately, I love travel logistics and the planning of events.

I'm actually someone who's in a head-of-remote role that you might think is very focused on the virtual experience. I am a huge fan of the in-person human experience and what that does to support the greater future of work. I'm fortunate that it's a core part of my job.

I get to handle the logistics. I do hire people in the localities that we're going to and get some assistance from local vendors and such. We thought about outsourcing this. There are companies out there that you can outsource the whole process to, but our CEO is a big fan of the idea that this is a core part of how we build our culture. 

There are certain things that you outsource, and certain things that you don't. And just to be clear, this is not a broad stroke for everyone out there. 

It just happens to be that in our case, we like the idea of keeping this internal and keeping it very much in line with everything that Doist is about, both in the way that we approach work while we're there and the way that we approach the stipends that we give people to travel and the travel logistics in general, the communication, all of that.

It actually just works better for us to keep it internal, but you're right. It is a huge undertaking. And I think it has to be a very strategic decision for a company to decide: should we keep this internal or should we outsource it to someone who does it really well? Because, yes, it is a core part of your culture, and there are some benefits to having an internal person plan it, but everything's a trade-off.

My focusing on that aspect of how we work is pulling me away from other things that I could be doing. And so if it wasn't a strength or if it wasn't something I enjoyed, there's certainly vendors out there that could do a phenomenal job and take that off your plate, and I would certainly suggest evaluating that as an option if your company is going down this path and trying to decide which route to take and thinking really carefully about that.

Daan: That speaks to the idea that this is a huge investment. How do you go about planning for a retreat like this? If you don't see your people that often and you get them together and make that investment, you better not miss it. How do you make sure that these retreats are valuable?

Chase Warrington: Yeah, that's a great question. I get a lot of questions coming in from somebody, like the common narrative around this would be, “Hey, Chase, I'm the head of accounting, or more often, it's like I'm the chief of staff or the head of people ops. And, as I've just been tasked with, we have to do retreats now because everybody's doing them remotely, and Hey, I got to do a retreat.

But I love the conversations, and I'm happy to keep those going. I feel bad for someone who gets tasked with this when it's not what they were hired to do. It's not what they enjoy doing, and it's not their strength. They could be living in their little individual zone of genius in another space, but they're being tasked with doing this.

Therefore, they're focused a lot on finding a venue, creating an itinerary, and getting everybody there, and if you can do that, then you've done 70 percent of the work, but you've missed a big opportunity in terms of how this retreat can really serve your business needs.

That's where the key to this whole thing comes in. Yes, you're going to do it. Yes, everybody's going to have a great time. You want to get everybody there. You want to make sure they're safe, fed, and entertained, and that some work gets done. 

But how does it connect with your company's core values? How does it help you solve your greatest challenges? How do you make sure that people are getting a real, meaningful connection out of it? And it takes thinking very strategically about that.

In our case, there were a few things that we decided. First, we stepped back and thought about our retreat strategy. Yes, we're doing this, and we're going to invest in it, and we know we're going to do it. But how does it serve our business needs, and what do we really want to get out of it? 

One of the key determinations that came out of that is that we don't see these as a great space for getting a lot of work done. We're actually purposefully built as a team to optimize our workflows for asynchronous communication, working across time zones, deep work, and things like that.

Retreats aren't great for any of that; being in person doesn't facilitate any of that. So we kept going on these sometimes and trying to get a lot of work done, but really finding that juice wasn't worth the squeeze. 

We were just not getting a lot out of them. We were getting something. There was some value there, but it wasn't worth spending all the resources that we had just to come together and try to solve one problem when we probably could have done it just as well asynchronously and remotely.

What we decided was that, while it might seem like a huge investment on the surface to look at these as just a space to connect on a personal level, that's really what they serve the best purpose for. 

We rebranded our event to Doist Connect. We use the word connect the team; the whole company voted on it, and it could have been Doist Work or collaborate, or something like that. 

But we feel like the focus is on connection. So we've got this formula that we try to live by, which is that our itinerary is built up of 20 percent work, 30 percent activities, and 50% R&R, rest and relaxation. And I find that in that 50%, that's where the true breakthroughs happen.

That's where the real conversations, the serendipity, and the real deep connection come from. This is backed up by lots of data. It's not just an opinion. So, in a nutshell, the strategy is to recalibrate for what we think these work well for. We still have some work to do. When we're doing that, 20% is hyper-focused.

We do it really well. We put a lot of effort into it to make sure it went well. There's still always room for improvement, but it's about finding the right balance for you and figuring out how these major investments serve the needs of the company. And not just thinking through it; let's just get people there because this is what we need to do. There's a deeper meaning behind it, for sure.

Daan: Is there another side to the success of those retreats if people only see each other twice a year and it's a great experience? Is there ever the sense that let's see each other more often? Maybe even a discussion about having some office space in certain places?

Chase Warrington: I've asked the team this, and we've landed on two: about every six months is the right amount. We've offered to potentially host more retreats, but I think everybody likes the balance of two. I think, if I recall correctly, around 80% said two is the perfect number; about 17 or 18% said we could go to three; that would be the maximum. Then, a few said I'd prefer just one.

One other thing is that we make these all optional, and then by introducing the Meetup Perk that I mentioned earlier, we give those people that want that extra Meetup an opportunity to do, although not in a team setting, they can do that sort of thing.

I'm looking at, though, is perhaps doing something along the lines of a pop-up co-living sort of situation. So it would be, 3-4 months after the team retreat, we would have co-living rented out that you could optionally just come stay for a week or something, hang out, and work. There wouldn't be a lot of activities planned, but your costs would be covered to go do that, work with your teammates, hang out in the evenings, and things like that. So we may go to 2.5.

Daan: It sounds you're giving people a lot of ways to get together, but also that you're getting the team very involved in deciding the approach. Is that correct?

Chase Warrington: You're right. There's a few key pillars of communication and collaboration at Doist. One of them, I would say, is that we're very intentional with how we work. So you can see there's a lot of intentionality put into not only how we're creating these events but also how we communicate with each other and such.

Another one is transparency. We've got a pretty democratic approach to work, and you have to be careful with this because if you go too democratic, we've gone too democratic before, and when you've got too many cooks in the kitchen, things get a bit messy and can be slowed down. So you have to find the right balance.

But with very key decisions, we at least like to ask the question to make an informed decision based on what the team wants and needs, and of course, you know what we can afford and what aligns with the business objectives.

This is a key part. We want to know what the team prefers. After the retreats, I sent out a pretty lengthy survey, gathering a lot of data. I think it resulted in 13 pages of data that I have from this most recent one. So anybody could bore themselves to death with that, but I find it fascinating.

These are some of the key principles that came out of it. People will like it for about five days. Six days is a little too long; it cuts into their weekends. Four days feels a little too quick, especially for people flying all around the world. Another one that has emerged is that we've gone for a more rural setting outside of major cities.

We used to go to major cities like Santiago, Chile, and Athens, Greece, for example, and now we're going to more rural settings where we feel like we own the space for the entire week.

These are some things that are emerging. Then the other one is that two seems the right number. I've heard of some teams that do quarterly meetups, and some teams that do them even monthly, four or five times a year. 

For us with our distribution, bringing people in from Australia, Japan, the south of Chile, and all over the world, it gets very cumbersome for them, and there's some added expense, not just financially, but time, energy, and such, that those people have to put in. Two is the right number for us. 

Daan: We talked about these great retreats and meetups where people find each other, but what happens in between them? What does work look like at Doist, and what are some practices other companies can get inspired by even if they're not fully remote?

Chase Warrington: This is an interesting point, I think, because, as I mentioned before, we're a team of around 100 people in 35 countries. We're working completely remotely, with no offices, and predominantly asynchronously, and a lot of people would tell you those elements can't work.

I see headlines all the time. This doesn't work. You can't do it like that. But we're in a very competitive industry. Our two products, Todoist is a task manager, and our biggest competitor is Microsoft, and in that regard, you may have heard of them.

Our other product is Twist. Our biggest competitor is Slack, with our second biggest competitor again being Microsoft, with Microsoft Teams. We're managing just fine as a bootstrap team of 100 people competing against some of the most powerful companies in the world. I would argue vehemently that it can work.

And just because you haven't done it doesn't mean you can't do it. But it takes, again, a lot of intentionality. It takes a very disciplined approach to how you work and how you separate work from the rest of your life.

For us at Doist, we bought into the async-first model, meaning that all of our workflows and communication practices are built around being asynchronous first. So we have very few meetings.

On average, people have less than two hours of meetings per week. That includes our executives and CEO, who loves to share screenshots of his calendar, where he's got 45 minutes of meetings a week. Follow him on Twitter if you want to see those. It's hilarious.

Daan: That should be your entire employer's branding. All your employer branding should basically just be that screenshot of the calendar with only two meetings on it.

Chase Warrington: This is the funny thing. As people say all the time, you have to get in the office to do your meetings and work, and then I see people, everybody, saying, I hate meetings.

You see all the data that says people are not getting much value out of them, and that 50% of meetings that people are invited to, they would automatically decline if they felt empowered to do so. We just thought through this and said, of course, we're distributed around the world, which makes it logistically challenging.

But also, why are we continuing to force ourselves to do these meetings? What if we just focused hard on doing things asynchronously, doing that really well, and built out a robust documentation system? We've got a 1200-page handbook that we've just completely revamped that people can reference.

We want to be able to reference every question, and there's a link for that. So here we've got a link for that in our handbook. We do all of our communication, 99% of it on Twist, which is our team communication platform. All our project management into Doist, which is built for individuals first but now manages, can help teams build really complex projects and manage task management that way.

We're doing this each and every day. For us, it feels like second nature now, but it's funny when I look outside of our echo chamber and see companies really struggling with some of this. People sitting in 18 hours of meetings a week and being returned to office mandates coming in, and this is actually possible if you're willing to put the effort into doing it.

Daan: Right. For companies that would want to put in the effort, what are some principles that you would recommend they definitely put into place?

Chase Warrington: I think it's a wonderful question because so often the challenge that people face with remote work, the reason that my friend that I met referenced before had such a horrible experience during the pandemic, is because a lot of managers were suddenly asked to switch their way of working.

They built a career operating under one model, and 25 years into it, they're suddenly, at the snap of the fingers, expected to shift and do things completely differently, and applying old ways of working to new methodologies is just a recipe for disaster.

But a lot of people were left with no other option. They weren't given the training. They weren't given the right tools. They were just asked to do something. And so it's no wonder that a lot of people had pretty rough experiences. So, I think where this starts is by looking at it from a slightly different angle. The managers they're managing are very important.

Optimizing your hiring practices for getting people in the door that are built to do remote work that function in a highly functioning way in an asynchronous first environment They're really good writers. They're really good communicators in written form. They're succinct, but thorough.

They're the type of people who are going to take a problem and walk away and figure out how to solve it themselves before needing to hop into a conference room, virtual or in person, and need to figure it out with other people, especially those that really work well in a deep work environment. A lot of managers were given a team that preferred working in an office, and they preferred or were trained to work to those standards.

At Doist, we were very fortunate because we had been optimized to work this way for many years, and when the pandemic hit, we didn't really have to change anything. A lot of teams weren't given that advantage, and the managers they're managing were also given the short end of the stick in that regard.

So I think there's a lot to be said for that. Then, I think making sure that people are given the right tools, the right practices that their share, they're pointed to leaders in the space who can help mentor them as a great thing. I found a lot of unbelievable resources, a lot of companies who believe in building public and sharing their learnings.

I'm a part of the running remote community, which is a fantastic space for people to share their learnings and challenges in a private space, pretty thorough with, “Hey, this is something we're facing with our remote team, and does anybody have any challenges, answers, or similar questions that they're trying to work on, because maybe we can work through this together?"

I think giving them those resources and making sure that you've set up your hiring practices will get them the right type of people on their team. And then, thinking back through everything that the company does and all the workflows that you have in place, Are they built for the way we used to work, or are they built for the way we're working today?

A lot of teams don't even ask that question. They never challenge it. They just armed everybody with a Zoom account and went for it, and that's setting the managers up for failure, I believe.

Daan: Definitely. As we're getting to the end here, both as the head of remote at Doist and also generally as someone who's speaking to a lot of company leaders, what are some misconceptions that people still have about remote?

Chase Warrington: One of them, I think, is what we referenced earlier: that remote first means remote only.

You hear people saying all the time that they'll beat up remote work because you lack human connection or you never get to see your teammates face-to-face. 

I know very few teams that are operating under this model that never meet face-to-face, and I would venture to say that the intentional time that they're spending together during their few weeks together is equally or much more powerful than four or five days in the same setting every single day.

All year, every year. I think that is one misconception that people are coming around to, but you still hear that narrative quite a bit. Connected to that is the fact that you can't build culture and cohesion in a remote environment. 

I think Malcolm Gladwell's comments last year about “What a miserable existence. You're just sitting alone in your bedroom with your underwear. Is this how you really want to live? What have you done to yourself?” 

That sounds pretty miserable. And, to be honest, I think that is the worst form of remote work that can be true. I know people who have had that experience.

On one side of the coin, you could say that there's a misconception out there that those statements are completely false. 

On the other side, you could say that there's a misconception that those statements are true. I think acknowledging both sides is really important because acknowledging what the worst form can be and that people have had that experience gives us some answers and some challenges to solve.

But also looking at the other side and saying, “You know what? There are plenty of teams out there that are building incredible cultures where people have really tight bonds and relationships with their teammates and true friends that they work with.”

I think that those are some of the things that are still TBD for a lot of teams out there, but for many of us, we're already seeing that it's totally possible to have them and work in this model.

Daan: Amazing! I think companies can take away so much from what you shared over the course of this interview.

We're getting to the end, and I wanted to ask you one final question. It's the same one that I ask everyone.

For the future of work, what is one big wish that you have or one thought that you would put on a big billboard?

Chase Warrington: That's a great question, and I realized when I was speaking earlier that I accidentally referenced another podcast totally unrelated to our subject here.

I am a big American college football fan, and there's a podcast that I love tuning into, “The Late Kick with Josh Pate,” to give him credit, and he says, “Just because you haven't doesn't mean you can't.”

And I said that earlier in this conversation, and I think it's very true. I talk to people every single day who haven't done something with remote work in the future of work, and they say they can't. In their minds, it's framed as I can't do this.

And I would challenge anyone: when you're thinking through your business infrastructure, considering this remote hybrid spectrum, just because you haven't done it yet doesn't mean that you can't.

Do the research, figure out what your objectives are first, do your research, and then see if it's a possibility, because I think you'll find there are a lot of teams out there that have and are continuing to do it.

Daan: Wow, I think we could not have asked for a better call to action at the end. Chase, thank you so much for being on.

Chase Warrington: Yeah, thank you. This was a lot of fun. I appreciate it.

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Future Work

A weekly column and podcast on the remote, hybrid, and AI-driven future of work. By FlexOS founder Daan van Rossum.