Working Without Borders, S01E04: Brenna Loury on embracing an async remote culture at Doist


How an asynchronous remote team is different from a remote team where everyone has a 100% time zone overlap? What are the advantages and pitfalls? In a team organized around not being interrupted, who responds when there's something urgent? These and other questions were the subjects of our conversation with Brenna Loury, Head of Marketing at Doist (maker of Todoist and Twist).

With the transition and opening to remote work during 2020, many companies are considering to maintain this modality in the future, and are willing to go out and look for talent where it is. The biggest challenge for these companies accustomed to synchrony is to embrace a new style of communication: the asynchronous.

Doist is one of the first totally asynchronous remote teams, and they take it seriously. Being a globally distributed team, they have a well-defined and documented culture around their communication channels, always being asynchronous first.

 🎧 Listen to the podcast below (Audio in English, also available on Spotify and Apple Podcasts) 🇬🇧

👉🏽 Here are the main ideas that came out of our conversation with Brenna:

  • In relation to asynchronous communication, it has taken them 10 years to iterate through trial and error to see what works best for Doist as a company.
  • Setting expectations and creating a culture around asynchrony, and understanding what that means is the key to success.
  • At Doist they have a remote communication pyramid, where at the base are asynchronous tools like Twist, Figma, or Google Docs, and at the top is Telegram, only for immediate and urgent matters. 
  • Transitioning to asynchronous communication should be discussed openly with your team, and it should be well-documented. For example, define the times, or how much is a 'reasonable time' to respond. Everyone should be 'on board' with this. It can't be an overnight decision.
  • Changing what would normally be a synchronous meeting to something based on a written form of communication (asynchronous), so that people don't have to be all connected at once, requires a lot of coordination at first, and mutual understanding, but it is very important. 
  • The main pillar of managing a remote team and ensuring that everyone can prosper in an asynchronous way is trusting people. You can't work asynchronously - or remotely - if you don't trust your team members.
Read the transcription of the interview below, lightly edited for clarity.


Sergio: Welcome to this 4th episode of Working Without Borders. Today I have an awesome guest. She's Brenna Loury. She's head of marketing of Doist. Brenna thank you so much for being here.
Brenna: Thank you so much for having me Sergio, it's nice to talk to you after so many years.
Sergio: It's been so many years. Brenna and I met in Chile back in 2012. It’s been a long, long time. First of all, I’d like you to explain to our listeners what does Doist do, exactly?
Brenna: That's kind of a tongue-twister, right? What does Doist do (laughs). Doist is the parent company. We develop software that helps people be more productive and balanced in their day-to-day life, so we are the company that builds the productivity app called Todoist. Todoist has around 25 million users and that's kind of our flagship app that has existed since 2007. Then, in 2017, we launched another app called Twist, which is for team communication, and it's marketed pretty heavily towards remote teams because Twist is like an asynchronous-friendly and thread-based communication app. So that's what we do at Doist, and, if those of you who are listening don't know, we are a fully-remote company of 79 people at this point, in 36 different countries ­– if I'm not mistaken. We've been doing this since about 2010, a decade exactly.
Sergio: Wow, a decade. Surely Doist is one of the pioneers of remote work and, actually, one of the things that caught my attention initially was Twist, and the kind of culture — this async culture — that Twist promotes in the very tool.
So, I want to talk about async in general and how async communication and asynchronous working is so different from the remote work that most people are experiencing right now. They’ve only been experiencing this flavor of remote, which is the pandemic one, which mostly replicates the schedule and dynamics of a co-located workplace, so how would you describe the difference between this way of doing remote and remote in an asynchronous organization?
Brenna: I guess it's important to add to the context that we have been doing this for the last ten years, so we've taken ten years to iterate with trial and error and see what works best for us as a company. I honestly have a ton of empathy for people who are dealing with this situation, with the pandemic: one day to the next having to go remote, because it's probably so foreign to a lot of people, and companies are scrambling to try and figure out what to do, and you know they're doing all these crazy things, like putting tracking software on people’s computers... My neighbor spends like seven hours a day on Zoom meetings every day,  I'm not really sure how most people are able to get things done right now. So, I really feel for people who are going through that. It must be really hard.
But for us at Doist we have been remote since the very first person that we hired. Amir, our founder, and CEO, was working in Chile and he hired David, who was our first customer support person —I think he was hired in 2011 and David was in Poland and Amir was in Chile— so, being remote has always been part of our DNA. And we've always kind of had this asynchronous mindset because we always have had such a breadth of time zones. So, we haven't really been in many scenarios where synchronous communication has been our default, but we have sort of tipped the scale much farther towards asynchronous communication since we launched Twist. But for us that works really well, because like I mentioned — we’re in 35-36 different countries, and it would be totally impossible if people were having to respond to messages at the moment, right?
Sergio: Yeah, and I was curious about what obstacles did you have to sort out as a team during this decade-long journey?
Brenna: Yeah, that's a great question. So to give you —and our listeners— a little bit of additional context: before we created Twist,  in the very early days of Doist, we were using another tool that we have developed called Wedoist which was kind of similar to Twist but it had a lot of other additional task management features inside of it. So, ultimately we decided to deprecate Wedoist —I think in 2014 or 2015 — and we started using Slack.
Honestly, in the beginning, it was super cool for us, because this was before our first company retreat as well, so personally, for example, I had been with the company for two or three years at that point, and I had only met Amir and Alan who are the COO and the CEO. So Slack kind of gave us a new life in the company and allowed us to connect on a much more personal level. 

But then it became this kind of nightmare situation — the honeymoon period was quite short.  I'm one of the few people that moved to the US in 2015 and I would wake up and have like —I don't know — hundreds of messages to try and sift through, kind of banter between these serious topics, and everything was getting mixed together. Decisions were being made while I was still asleep, and everybody started to kind of experience this sensation of having to be on all the time, and not missing messages. That was a huge inflection point for us. While we were experiencing this is when we decided to create Twist because we knew that Slack would be the downfall basically of our company culture.
So, yeah, that was a big obstacle for us, realizing this. And what we did is we kind of created like a minimum viable product in Twist — just a really bare-bones version of the app — and then we shut off Slack and quit cold turkey, basically. That was a big deal for us and that plays into a lot of the narrative behind Twist, because working synchronously is not sustainable, if you're a remote company spread across so many time zones.
Sergio: Don’t you ever miss the immediacy of working in sync? I'm not saying that you miss video calls, but... how this async culture substitutes this kind of live instances, like pair programming, or brainstormings, or all-hands... How do you deal with that?
Brenna: We are async-first and we are very explicit in our company culture of defaulting to asynchronous and over-documentation and over-communication. But that's not to say that we don't do any synchronous communication. For example, we never do company-wide all-hands meetings —except for when we meet together in our company retreat once a year— but we do have specific Twist channels that are dedicated to more serious announcements, and Department updates.
For example, every Department will share a monthly marketing update, or a monthly front-end update, so that everybody in the company can know what's going on with everybody else, but they can read that on their own time. And then we have —specifically on the marketing team— we have one monthly all-hands meeting, which lasts for about an hour, and then I personally do monthly one-on-ones with all of my direct reports.
Honestly, I think on the marketing team we tend to have more overlap in terms of time zones because many of our first language is English, which means that many of us live in North America. So,  we are very much async-first —that's not to say that we don't DM each other sometimes, but it's an important balance, and having that explicitly laid out for everybody —especially new people to the company— I think it's really important. Setting expectations and kind of creating this whole culture around being asynchronous-first, and really understanding what that means — I think that's key to making it successful.
Sergio: You mentioned something important that I'm really curious about. How do you avoid that people start to work together with people that shift then to share their time zones? How do you make sure that collaboration happens between people that might be in really different time zones and might have zero overlaps?
Brenna: Yeah, that's a great point. For example, one of the illustrators that we work with really frequently on the marketing team, he's based in Taipei, so we have literally no overlap at all. So, in those types of scenarios it's so important —like I mentioned before— to over-communicate, and instead of just typing one line like ‘hey Jen, how's it going? Do you think you could help me with a blog post illustration?’, like going much farther above and beyond, and sharing a creative brief, and giving him examples, and making sure that when he wakes up he has all of the information to be able to start working on the task, because, if you don't, then the lag time can be so long —if there is like 12 hours of distance between you two— it can take a really long time to do anything.
So, if you're not over-communicating and sharing all of the details that the other person would need, that becomes super problematic. But I think the nature of our company at least, we never require that people be in a specific time zone, so, that's never really been part of our company culture or DNA. Just kind of like where the cookie crumbles – where the people are from that are going to do the best job, so that's why it's so important for us to make sure everybody is on the same page of being async-first, and documenting everything, and assigning decision-makers who can make decisions while other people are asleep and things like that.
Sergio: How do you deal with truly urgent stuff? –and I know that the word "urgent" is usually inflationary, and people tend to overuse it for everything, and most of the time it's just anxiety speaking– but when things are truly urgent, like ‘there's a bug in production and users are suffering’ or I don't know. Do you have shifts or how do you deal with this time-sensitive stuff?
Brenna: That's an awesome question. So, Twist, for example— we do all of our team communication 100 % in Twist for the most part. So, in Twist we have threads, and there's a UI of direct messages— so for example, we have one company direct message where sometimes we'll send the message to everybody in the company like, "yay, we were featured in the App Store!", something like that. Or we also have DM chat room –I guess you can call it– it's not a chat room, but it's a DM with all of the support people; and so this DM channel —I guess you could call it, or is called Expanded Support—, is usually the first stage of things. If there is a bug or if there's downtime— say somebody will post in this channel like ‘who's awake? who can help me with this?’  then we'll kind of triage from there; but if there's something that's like crazy urgent —which I'm not even sure how many times this has actually happened, probably we can count them on one hand—  we do have a Telegram group with some of our back-end developers, and front-end developers, and our CXOs.
This is the major red flag. If somebody sends a message in Telegram —it's kind of required for people who are in this Doist Telegram group to have their notification turned on —which is otherwise very a no-no at Doist basically— but in this particular instance, writing in the Telegram chat is such a red flag that people need to know about it, and get up to speed immediately. And we actually have a kind of a cool blog post about this, I think it's called the pyramid of remote communication, where we talk about: our base is Twist and then we have collaboration in Figma or Google Docs or Paper, and then we have Zoom or Meet and then at the very top of that triangle is Telegram, for the most urgent things.
Sergio: So, the key is having these urgent channels but seldom use them, right? Trying not to use them at all.
Brenna: Really knowing what is urgent and what is not urgent is very important –I think– and being mindful. The great thing about Doist in spanning so many time zones is that usually, somebody is awake. So, you know, if somebody posts in this Expanded Support DM then it's pretty frequent to get a relatively quick response there because it's not a DM that's updated all the time, so I think knowing where to look for these more or less "urgent" states is really important, and having that hierarchy of communication so that people really know when it's important and when it can wait.
Sergio: Awesome. You mentioned earlier that you and your team tend to be concentrated in North America and that gives your team a sort of an advantage, and I'm curious about how companies that share a single time zone, or that have high overlap, can benefit from async —it's our case in Get on Board, actually, we tend to share a great deal of overlap because everybody is in the Americas. So, for a company that doesn't necessarily feel the need to ditch time zones at all —and I think it's probably going to be the case of most companies going remote these days — how such companies can embrace async and benefit from it?
Brenna: I love that question because like you mentioned, and kind of what I mentioned before, even though a lot of the Marketing team is based in the Americas, we are still very much async-first. There are very few instances where we collaborate in real-time, but I think if companies are facing the situation, and are recognizing the importance of asynchronous communication —in terms of being more productive and sane—, I think the first place to start is definitely having this conversation with your team in the first place. You can't just decide one day  ‘oh, I'm gonna be async-first. I’m not going to respond to any of my messages until I want to’, then your team is going to be like ‘what? what is happening here?’.

So I think that you really need to have a transparent conversation with people to make sure that people are on the same page and setting these norms that are so important. For example, defining a time frame, or what is an OK time frame to respond. Usually, for us, it's 24 to 48 hours, but what does that look like for your team? Giving people space and time to disconnect is really important, too. Making sure —especially as a manager— that you're not saying like ‘OK, I don't see you logged in. What are you doing?’ That’s just the worst (laughs). And I don't know if that means having people block off time in their calendars, or shifting what would usually be a meeting to something thread-based, or a written form of communication so that people don't have to be all connected at the same time. I think it requires a lot of coordination in the beginning –and mutual understanding– but it's so important. 

I hope more people can transition to asynchronous communication because I just can't imagine what it's like having to spend your whole day in Zoom meetings, and then, where does that information go? Like, nobody is writing it down or I don't know if people are recording things, but then, people have to go back and sift through the recordings...
Sergio: I cannot agree more, and this leads me to the next question. First, leading an async team, which you do, and leading a marketing remote team, which you also do— I'm asking because most tools that come to mind when thinking about distributed work tend to be optimized –or created– for  Dev teams, and code writing. So I'm curious about how this Marketing function that tends to be more reliant on creativity, and ideas, and strategies work in remote, specifically in an async setting.
Brenna: The first pillar of managing a remote team and ensuring that everybody can thrive asynchronously is trusting people. I mean, you can't work asynchronously –or remotely– if you don't trust your team members. That's huge for us.
We really are meticulous about hiring people who display these qualities, making sure that they have all the tools to do their job also so that they're not having to ping you all the time and ask like ‘where's this document?’ or like ‘where can I find more information about X-Y-Z?’ Like really being mindful about setting people up for success and giving them all of the resources that they need to basically get on the job and start flying solo, because if you have to do so much handholding, then that kind of defeats the purpose of being asynchronous.
And in terms of marketing, I think asynchronous works great for us because a lot of the marketing that we do is content-based, so we really focus a lot on long-form blog posts which you can't do – I mean it's almost impossible to write something coherent when you're getting messages all the time – so being able to disconnect and write for a couple of hours it's really important. Personally, I do a lot of work on our landing pages, so being able to disconnect and get in the flow of writing the copy and thinking about how the sections work together...I don't really see how that would be any different than a developer team.
But there is one instance that I am thinking of – in terms of what I do personally – if I'm creating a landing page, sometimes we do work kind of synchronously with our designers to say like ‘oh you know this will go better here or here. This is what I'm thinking for this section’ but we also do that in Figma –and we use Loom sometimes as well. There are so many tools out there that can really facilitate a healthy remote and asynchronous environment, no matter what area of the company that you work in.
Sergio: So, you mention a couple of tools including Figma –and obviously Twist, which is your workplace. I'm curious about where you store your knowledge. Which tools do you use to store what you are learning as a team? The rules of the company, and the culture, and all that.
Brenna: Yeah, that's an awesome question because we have a few different spaces for that actually. I mean Twist is an amazing tool for teams who can really adapt it properly because, for us —we've been using it since 2015 or 16—all of those conversations, and all of those threads and all of those decisions are perfectly crystallized in their original form. So, I can go back and do a search and say like ‘Twist logo’, for example, and I can find the exact channel and thread where we discussed what the twist logo was going to look like and it's not polluted by any other conversation.
Twist is a huge source for us and then, on a more formal level –I would say– we have a Handbook that we update in GitHub. So that's kind of the basics of the company: what are our perks? and our vacation policies? what does the career path look like at Doist? So, a lot of the official documentation is in GitHub but before we reach any of those conclusions, we always have those conversations in Twist. And then, obviously, we have Google Drive and Dropbox, Paper and so, but our single source of truth is our Handbook in GitHub or Twist –where you can see the whole decision-making framework leading up to something that was added into the Handbook– that makes sense.
Sergio: Amazing. So, to finish, I wanted to ask you about a project of yours, it's called We are async. Can you tell us a little bit about it, and what's the purpose of it?
Brenna: Sure! At Doist we have this really cool opportunity that’s called personal dues, so that means that anybody in the company can spend one month out of the year working on a project that they're passionate about, so I spent the month of July working on this project called we are async, and it was amazing I am not a designer, or by any means but I pulled out together this website I did it all by myself and it was a huge learning experience for me. And basically, the premise of this is a community for people and companies who are advocates of async communication. And it's a way for people to learn more about the benefits of asynchronous communication.
I have a job board of the member companies so you can see what asynchronous-friendly companies are hiring, and then you can take this cool questionnaire that has a handful of questions that will ultimately tell you how asynchronous you are on a scale of 1 or 50 to 100 –I can't remember. It was a really cool process to go through, and it was amazing to see how excited the other companies were to join this community.
I kind of went into the project with not that many expectations but –you know– Buffer and Help Scout, and Zapier, and Toggle, and Gumroad, and all these big companies signed on, so I was definitely feeling the pressure during the project. So, anybody who is interested in learning more about asynchronous cultures at work can check it out, and if you're interested in joining as a company, there's a way for you to kind of apply to do that there as well.
Sergio: Amazing, for sure. I will definitely take the test I'm really interested.
Well Brenna this has been an amazing conversation. Thank you so much for all the candor, and the insights. I think it's been really illuminating. Not every —not too many companies are working async the way you are doing it, so I thank you so much for your insights and for what you said today.
Brenna: Yeah, thank you so much for having me. And it was a pleasure to chat about like our little corner of the world, and hopefully, more teams and companies can get excited about this because it's a really great way to work and live and –you know– we're not all stressed out and crazy and stuff at Doist, so I definitely recommend that.
Sergio: Absolutely, thank you so much, Brenna.
Brenna: Thanks, Sergio!

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