Welcome back to The Digital Workplace podcast. Today our guest is Chase Warrington. He’s the Head of Remote at Doist. Hey, Chase. How are you today?

Neil, good. How are you?

I’m good. I’m a little cold. We are into January here in the midwest of the United States. And I’m in the farthest room away from our heater. So it’s a little bit chilly where I am.

I won’t talk to you about the weather here in the south of Spain then. I will not do that.

It’s okay, though. It’s good to know some people out there are having fun. It is sunny here, which we don’t always get. So it’s still good. Chase, we’re going to get into a lot of cool stuff talking today. You have a lot of experience with distributed work, remote work, we’re going to be talking about the products you guys do. But first, we need to make sure you are a real human and not just thrown out there as a robot to us. Your question is, what is one of your most favorite smells?

Oh, man, that’s a fun one to start with. I absolutely love, I don’t know if this is going to be a super boring response, but I absolutely love and genuinely spend time enjoying this every single morning. It’s one of my daily non-negotiables, the smell of fresh coffee in the morning. So I have a little coffee ritual. One of the things that I love about doing that is opening up a fresh bag of coffee and enjoying that, so one of my indulgences.

Yeah, it’s amazing. I’ve recently come into coffee. The smell of the grounds is even better than the cup, I think, just smelling the new fresh grounds like that. It’s amazing.

Oh, yeah, definitely. That’s part of the morning. Every morning for me, I have to enjoy that. And then I get to the coffee when I get to the actual cup. But the smell is what gets my day going, really.

Yeah, that’s great. All right. We’re going to say that’s a human answer. I think you could have been programmed.

A robot could have programmed that one. That wouldn’t take too much AI, I don’t think. I’m a boring human, but I’m a human nonetheless.

Cool. I really want to get into the meat of our conversation right away. So Doist has two main products that they’re most famous for: Todoist and then Twist, which is Todoist being a project management, task management system, and then Twist being more of a communication platform for folks that are out there. But if you go to the Twist website, immediately what you’re going to see is the word asynchronous. It’s going to be out there. It’s going to be big and bold. We recently did a review of Twist just to get into it and expose people to it and show it out there. But I want to get into the fact of you guys really have a bias to say that work, especially distributed work is best done in asynchronous environment. So first, just walk us through that. How long has that been the culture at Doist? And how did that come to be?

I’m glad that it resonates. And you’re right, it is a bold statement. I’m proud to say we were pretty bold about that from the very beginning, even when it was a word that nobody knew. Literally, you could track this in Google Trends and such. Nobody was looking at this word. Nobody knew what it meant. It did not perform well in case studies and surveys and things like this. But we felt very strongly about asynchronous work. I think what helps here is a little bit of context. Doist is a 100-person company more or less spread across 35 different countries. We have no offices. We don’t work at the same time. We don’t care when people work. We don’t track hours. We don’t hire based on location. Often we don’t even know where people are working from. But it works. We’ve been doing that for almost 15 years. We’ve been pretty successful with it. And we work highly asynchronously.

The thing was, though, is that we built the company on tools, like for instance, Slack. We were in on Slack for a long time, which is obviously the default communication tool for software teams and startups and things like that. That worked really well for us when we were 10 people, 15 people, 20 people. But as we started to grow past 50 and such and get up towards where we are now with around 100 employees, working asynchronously in Slack got very messy. It’s not designed to be an async tool. It’s designed to be a chat tool and it’s really, really good at that. Slack’s phenomenal. So they don’t need any compliments from me, but they’re really, really good at that.

But it didn’t work so well for async communication the way we really wanted it to. We didn’t want people to feel like they had to live in their chat tool. We want people to disconnect, focus on deep work, reconnect when it works for them and check in and that ways. So we built Twist with this in mind. We said we got to get away from Slack. We can’t find something that really serves remote async teams really well. Let’s build it ourselves. And so yeah, we leaned heavy into async and stuck our flag in the sand and said this is what Twist is all about. We built everything in the product, all the things that it does have, and a lot of the things it doesn’t have, are highly focused on asynchronous communication.

As you go through the tool, it’s amazing how baked in that whole, I’m just going to say it’s a bias towards async. You see it everywhere, even from the fact that when you hit return or enter, it doesn’t automatically put the message in. That just gives you a new line to write more, to think more, and to say, wait, there may be more. Some of the messaging you use inside the product suggests to people, hey, does this need to be an immediate message? Or can you post this somewhere else? It’s really well done, from our standpoint, just to be extremely clear about how you think work can be done best for those who want to work asynchronously. So my first question is, how’s that working for you guys? In terms of being very bold, and not just trying to say, hey, here’s the chat platform, use it to do all your chat. Instead, you’re saying, this is a communication platform for people who care really deeply about being asynchronous. Has that been something that’s worked well for you? Do you feel like other companies should embrace that model?

Yeah, it’s worked well, in a relative sense. So I think a little bit more context will help explain that answer. We built Twist thinking that this was a long-term play. Like I said, nobody was using the word asynchronous, even two years ago. Before the pandemic totally changed the way people worked, and we were not predicting that, like everybody else was not predicting that. So we thought this was a long-term play. And we didn’t have huge aspirations of this being the mainstream product of overtaking Slack or something like that from the get go. We really thought this is going to be for teams that, like us, had crossed that chasm past the love of Slack, just like us. We built the company on Slack, for the most part, and said, okay, we need something different.

When we talk to other remote teams, before the pandemic, we were getting a sense of that. We did a survey at one time of thousands of our customers and found that 99% of them were distributed teams. And that was several years ago before the pandemic. So as remote has become more mainstream and more teams are really interested in approaching their work in an async way, it’s picking up steam. So yeah, you could watch, you could look at the numbers over the last two years and watch them just skyrocket compared to where they were, compared to where we thought they would be, and especially since we rebranded the product and redid the whole thing from the ground up a couple months ago. But it’s working out well in those relative terms that we expected it to.

Do you think, has Twist had much of an impact in changing the culture of a team? Because when we were doing our review, we talked a lot about, your team already has a certain culture. If you already have that bias yourself as a team towards async and said, hey, this is what we really want, then a tool like Twist will help support that. But do you have it as part of your mission at all or idea behind trying to change the culture of a team that is a little bit synchronous, a little bit chaotic, a little bit always on to try to push back against that? Are you more just saying, hey, if you’re already an async, come in and we’ll help you with that?

We really think the future of work is remote. The only way to do remote correctly and properly in a sane manner that won’t just drive people to burnout is asynchronous. Even hybrid teams, we really think that they need to adopt remote-first principles if they’re to have success without the burnout. So yes, I do think that there is some part of our mission that says we would love to change the way people think about work. A really lofty goal within that is we would love for asynchronous to be synonymous with work. Can we change that on our own? Probably not. But we’d love to be a part of that conversation, definitely.

But I do think that it’s important for any team that’s thinking about using Twist, or even just thinking about going asynchronous, you can technically adopt asynchronous communication with a variety of tools. For instance, you could do it with Slack. You could technically do it with just email if you wanted to, or instant messenger if you really, really wanted to. But there are certain tools that are going to lend themselves to that a lot better than others. And so the idea in this case is, first, think about your culture. First, think about how you want your team to work. And if you want your team to work asynchronously, if that’s really important to the core values of the team, then a tool like Twist could help get you there. I think it’s probably the best tool to get you there if that’s what’s at the core of what you’re trying to do. But if you’re not, if it’s on the periphery, then I think you need to really think about what your values are in terms of what tools you’re going to and tie to those goals and values.

If somebody is listening to this, and they’re like, I really don’t know where we are. We don’t really have an opinion, I guess, about if we’re synchronous or asynchronous. What questions or how would you guide them through the process of figuring out what those values they have are?

Yeah, I’ve been lucky. In my role at Doist, I’ve had the chance to talk to probably hundreds of teams and leaders that are at companies going through this process. So first, I would say you’re not alone if that’s where you’re at right now, because I think a lot of teams are trying to make that transition. They’ve gone from the in-office space to the remote space. They’ve gone from working in a very synchronous environment, where literally, it’s like knock on the door, hey, do you have five minutes, or, hey, let’s all jump in a conference room together, or let’s respond to something immediately, to trying to figure out how to incorporate asynchronous communication into that world. There are two competing factors. They work against each other, synchronous and asynchronous. So figuring out where to go is a bit challenging.

What I would say is, think about your current reality, and think about your previous reality, or think about the reality that you would like to have. Then think about every little process. Go through the nitty gritty of your day to day and your week to week, and think about which activities really work best in that reality that you want, in a synchronous way, or an asynchronous way. So an example of that would be like, in the past, we always had a 30-minute stand up meeting in the office every morning. Everybody got up and said what they were going to do for the day. Now you’re fully remote. Now you want to adopt asynchronous communication. What is the best way to get the same result, whatever that result was, whatever you think you were getting from that, what is the best way to get that same result or a better result now that you’re in an asynchronous environment or a remote environment? Then go through each of the practices throughout the day, every aspect of your culture, and think which way is best to get the actual result that we want. A lot of times people start shedding those processes. They’ll notice that, actually, we were just going through these rituals that weren’t actually doing much good in the physical space. Now that we’re in a virtual space, it really doesn’t make sense.

Yeah, that’s been such a big thing for us as we’ve been talking to people is just how much that digital world reveals what was going on before. We would have kept doing those 30-minute stand up meetings perpetually, forever, and not really realize that there is maybe a better way to do that in some situations.

I see a lot of teams, even in the virtual world, still doing them. When you ask, if you talk to the CEO of that company, and say, why do you guys do that? I’m not judging, just curious. Why do you do that? A lot of times, there’s not really a good answer. It’s like, oh, well, it’s just what we did. It’s the best way for everybody to know what’s going on. You say, is it 30, 45 minutes every single day, collectively, you’re spending 20, 30 hours of man hours on that? Is that the best use of your time? Could you write it down and send it asynchronously and get the same thing done in five minutes each? So that’s what I talk about, just pressure test these things and go, what are we doing and why are we doing it? And is there a more effective way asynchronously? For us, for instance, at Dosist, we’ve literally never had one stand up meeting. We don’t have daily, weekly, anything like that. We’ve never brought the whole team together in a virtual sense, to have 100 people on one Zoom call. We get all of those things done asynchronously. And yes, we still managed to have culture and close friendships and things like that. That works as well. But it’s interesting to test these things. That’s the point.

I’m going to come back to your culture in a second. But I want to close up with one one question about this culture and your preferences again. Tell me the difference between a company with a very strong async culture, like they really believe it, they’ve developed best practices, they follow that, but they’re going to use Slack, but they’re going to use something that tends to be a little bit more synchronous. What is the selling point for somebody who has that really tight, internal culture, to push towards needing to change tools? I guess, which one wins in the end? Is it the tool and the infrastructure behind it? Or is it the culture of the team that’s going to win out?

The culture of the team undoubtedly. Because I think we built a pretty sizable business on Slack, and it was possible. We just were also beating our heads against the wall and finding less people burned out, finding people not really being able to focus. I felt like we were wasting time. We’re a productivity company. We didn’t feel like we were being as productive as we could. So we had the values in place and we did fine with that. We just weren’t succeeding at the level that we really wanted to. So I think the culture and the principles and exhibiting those principles. The most important thing is, yeah, you can have these awesome ideas, and I’ve been inside, literally inside companies’ Slack channels and looked through their accounts and you see that they talk a lot about, hey, we’re going to work asynchronously and we’re going to allow people to disconnect, and all the same things that a lot of the very successful async-first companies talk about, but they weren’t exhibiting it. Often from the top down, they’re saying, hey, we’re gonna jump into a call in 15 minutes. Here’s the link, lots of things like this that cause people to feel like they always had to be connected to their tools. So having your principles is one thing, and actually living by them is a whole other. Then what can push you over the edge, I think, is the right tool.

Good point. Chase, let’s shift a little bit. Part of your role as Head of Remote is, what a lot people may not realize, with a fully distributed company like yours, is that culture and in-person events are still a big thing. So let’s talk pre-pandemic. How often did you guys connect, like everyone is in the same location at the same time? How often was that normal for you?

Yeah, so pre-pandemic, we were meeting up twice a year, and then another time individuals would meet in one place at one point, and then about six months later, we do individual team meetups, which we call mini retreats. In fact, we’re actually trying to start reigniting those in Q1 of this year with the mini retreats. Omicron is throwing us some curveballs. But nonetheless, we do think it’s important. It’s actually a core function. My job is Head of Remote at Doist and this falls directly in my department. So we actually see colocation as a very, very firm pillar in the remote infrastructure of the team, which is cool, I think. But that’s just one of the ways that we actually connect as a team. Throughout the other 50 weeks of the year, we have tons of activities going on in a virtual sense. A lot of what we base these on is we actually feel like we can bond really well around our work. It doesn’t mean that we’re just workaholics and we just focus on work. But we actually use work as a way to unite people and not try to force a lot of awkward social situations that don’t always make sense. But the colocated events are so key to us jiving as a team.

When you only have that limited amount of time to be in the same space at the same time, what are the activities? What are the outcomes? What are the things you want to make sure happens during that time? If this next one comes up, and it may be the first one you’ve had in several years, you have a lot of new people, what are your non-negotiables when it comes to, if we’re in person and we got to get this done?

So one of the first things that I try to focus on is actually less is more. So having a fully packed agenda where people are in meetings all day, every day, and forced into brainstorming sessions, and things like this, really actually don’t work well. My thought is we do the work really well in a virtual sense. I get to go to my office every day or my favorite place to work. I design my perfect schedule around my day and my energy levels. We’ve got remote work down pretty well. We actually do the work better in our normal everyday environment. What I think is when we get together, that’s the time to bring people together for bonding team camaraderie, getting to know each other, and a lot of that happens over just organic conversation.

So making space in the agenda, A, for people to connect just on a human to human level and get to know each other and see what conversations come from that is one thing. But then also providing people with the opportunity to recharge and step away from work is really important. So first I focus on let’s make sure that we don’t have an agenda that’s just packed full of meetings. We usually spend a couple hours a day, usually in the morning, on work stuff. Those can be brainstorming sessions. Those can be presentations. They can be breakout sessions. They could be team-only sessions, things like that. But then we spend a majority, probably 70%, 80% of the time, in more of a social setting, free time activities, sightseeing, fun meals, and things like that.

Excellent. I think that that’s such a good thing to remember as people get together is that that in-person time is often what makes everything else work so smoothly, too. I find that that’s the biggest reason why I like to get together with folks is to feel like in the midst of the asynchronous conversations you do have where you don’t get as many signals. So if somebody types something that I could interpret badly, I might do that unless I know them. It’s like, hey, we hung out, I know how they are. This is what they’re like. So I find that those in-person times really smooth out those communication processes, too.

It’s so vital. I mean, when I joined Doist, I was there for five, six months before we had our first retreat. I got to “meet” people in the virtual world and got one impression of them one way or the other, just we jive or we don’t. Then we got together in-person. We went to Iceland, to Reykjavik in Iceland, and spent a week together there. I walked away just blown away by some people that were super introverted online were very extroverted in person, super extroverted online were very introverted in person. Some people you could connect with really deep in the virtual world and not so much in person, and then vice versa. So it was just really awesome to see that come together. You round out people’s personalities when you get to collaborate with them in both senses. So it’s a pricey endeavor to bring 100 people together from around the world, but we’ve decided, as a team, it is absolutely vital for us, and well worth every penny. So if any team, however big you are as a remote team, if you’re on the fence about whether or not it’s worth it, I can guarantee you, it absolutely is.

Nice. Chase, what’s your favorite thing to say to people when they say, hey, digital culture is not working? My culture is falling apart because we’re all remote. We can’t make this work. How do you respond?

I like to say, “What’s your email address? I want to send you this article I wrote.” Because I really love this conversation. And I get it. I’m actually the kind of person that really, I worked remotely at a hybrid company before. And the company was very big on bringing people together, doing events. They have tons of happy hours and the classic ping pong tables, and things like that. It was very inviting in that way. I actually loved a lot of that. I didn’t necessarily want to have to be in an office and I didn’t want to have to live in a certain place. But I enjoyed a lot of that. And so I understand the person who comes and says you can’t make friends without being able to go out for a drink together after work, or play, workout together in the mornings, or something like that.

But I think we’re one of many now, one of many teams that showcase that that’s not the only way to build culture. I said it earlier. I think a lot of the culture in a team is actually built by how you work together, not how you play together. So we build culture in a lot of different ways. We build culture with the way that we communicate, the way we collaborate, who we hire and fire, the conversations that we have in a personal space, the virtual events that we create, the asynchronous games we create, the in-person events, all these things connect us in different ways. You have to get creative with remote work and asynchronous work in particular. I think you can’t just apply old methods to new ways of working. But there’s absolutely a way to create team unity and bonding and real friendships in a remote sense.

So contact me if you want to discuss it further. I’m happy to. I also did just post an article on this about all the different ways we’re doing this at Doist, which you can get on the Doist blog. And yeah, hopefully, it helps inspire some people. I draw a lot of inspiration from other teams. I’m constantly looking at what other remote teams are doing to figure out how to do this in a virtual world.

Yeah, excellent. Where else do you want to direct people if they want to learn more about what you guys are doing?

Yeah, sure. That place I just mentioned is probably the best place, blog.doist.com. There’s a remote work section. There’s also a section for asynchronous work and Twist and Todoist. There’s lots of individual spots, you can go there, depending on which part of the conversation interests you the most. I’m available on LinkedIn, pretty active there talking about remote work and asynchronous work. And recently reengaged on Twitter as well, so @DCWarrington if you’d like to tweet at me, if that’s how you say it.

I think they still say it like that. I’m not sure. Well, cool. Chase, thanks for being on the show. We look forward to staying in touch and talk with you again soon.

Yeah, thank you, Neil. Enjoyed it.