Centaur Stage Season 2 Ep.8 - Building a Remote-First Team with Chase Warrington

Updated: 5 days ago

Centaur Stage is a weekly video series produced by Cosmic Centaurs, and this second season is all about the magic of teams. Each Thursday afternoon, on LinkedIn Live, at 3:30 PM UAE-time, Marilyn Zakhour, CEO & Founder of Cosmic Centaurs, is joined by incredible guests who share insights, opinions, and perspectives about what makes teams cohesive, high-performing, and happy.


The second season of Centaur Stage is divided into four chapters, and this episode is in the second chapter all about building teams. Marilyn hosted Chase Warrington, Head of Remote at Doist, and in their conversation, they covered what helps remote teams thrive, in terms of communication, tools, and team dynamics.


Watch the full episode here.


About Chase Warrington

Chase Warrington is the Head of Remote at Doist, a pioneer of remote work that specializes in productivity software. Doist created the award-winning task management app Todoist, and Twist, an asynchronous team communication platform that combines long-form discussions and chat messaging into one. Collectively, Doist supports 25 million people globally to stay organized and productive.


Chase has worked in both hybrid and remote-first environments for over 12 years, managing teams spanning all timezones as one of Doist’s 100 employees in 35 countries. He is a regular contributor, instructor, and consultant to many of the leading remote work organizations and publications, as well as hosting his own podcast, About Abroad. He is currently based in Spain and is fluent in English and conversational in Spanish.


About the Topic

Building remote-first teams is a complex task, with 75% of employees working remotely experiencing burnout symptoms according to a flexjob survey, and 40% of remote workers stating unplugging after hours is one the biggest downsides of remote work according to remote.co. There are a lot of different components that need to be kept in check: the structure of teams, the work design, the tools that keep everyone connected and performing, people’s mental wellness and the management of loneliness, as well as others.


Remote Teams 101

Marilyn kicked off the session asking Chase how he defines a remote team. Chase answered that being remote-first (from Doist’s perspective) means hiring completely independently from location. It doesn’t matter where the team member is, as long as the work gets done.


Marilyn then asked about the advantages of working in remote teams, aside from traveling around the world, which she knows is a great interest of his.

Chase’s perspective on the advantages of remote work has changed over time. When he was younger, the idea of traveling fascinated him, as he couldn't stand the idea of just sitting in a cubicle, but he also wanted to build a career. Early on in his path, he really enjoyed having a variety of adventures, which he still enjoys in certain aspects in his life. Today, he is very appreciative of how remote work gives people more choices, and has seen first-hand how people’s lives have drastically changed as a result of it.


“Remote work might seem like a minor thing on the surface, but when you start digging deeper, you see how heavily it impacts real people in very real ways”, Chase said. “For example, it has significantly helped people who live in countries with crumbling economies who have had the chance at making money online, couples who live in different places to visit each other, and those who live away from their aging parents and were able to spend their last years together…”


Agreeing with Chase, Marilyn added that we underestimate how important sometimes it is to just have access to work. She referenced a previous episode of Centaur Stage with Rama Chakaki,who spoke about how working remotely can create more opportunity for refugee talent.


There are of course benefits at the organizational level. Chase added that remote work benefits the bottom line as well, because there is no cost associated with location.


Chase also believes that hiring and building a culture that brings people from multiple perspectives into one room adds to the team’s diversity: “We're collaborating with people who are coming from different backgrounds, different education systems, different thought processes, and we get the best of all worlds in that way”.


The Ideal Remote Team Member

Marilyn asked Chase about the specific traits or skill sets of really great team members in remote teams.

Chase emphasized on the skill of writing, as he hasn’t met any remote team leader who wouldn’t put that skill in their top three when asked the same question. Another important skill for him is the ability to shift gears from one thing to the next, and to be an autonomous worker. He said, “While it’s true that asynchronous work can slow things down, one needs to have the confidence and empowerment to move to another task if the one they are currently working on is blocked, and those who can unblock it are not available.”

Marilyn asked him how he does that in the hiring process, “How do you find out whether someone is a self-starter or not?”


“By the time someone gets to an interview, they've responded to a few questions that indirectly ask this. We ask for examples of ways in which they've exhibited certain things, or about how they’ve approached certain situations. We look for what’s underneath the dirt there. The answer to the question is one thing, but the way that one responds and the autonomy they exhibit is something we explicitly look for,”Chase answered.


Remote Team Tools

Marilyn then spoke about how in the past, the main channel for engagement to happen would be the office, or a physical space. But today, we can’t talk about remote teams without discussing the tools that support them. Mentioning the tools from Doist, Todoist and Twist, she asked Chase about the arsenal that needs to be available to remote teams.


Chase began saying he is very biased towards asynchronous work, and would aim for any tools that work asynchronously. He said that emails and instant messaging tools (such as Slack) could be asynchronous depending on how we use it . Certain tools embrace the asynchronous approach better, and for Chase, the one that does that is the product they built - Twist. Another engaging tool is Yac, which has asynchronous voice communication. It’s helpful because it conveys more than written words can, and allows you to express yourself through videos and voice as well. There are other great tools such as Google Docs and Dropbox that aid transparency, as opposed to email chains that make it hard to include someone new in the thread. .


Culture & Values

Marilyn then took a question from the audience about Doist’s company values and how they were uncovered. Marilyn also asked about the activities and team rituals they have and how Chase brought in culture in a remote-first team.


Chase answered that Doist figured out the work part well, with an eight figure business and 100+ people in 30+ countries, now it is really about the human part and how individuals connect. Chase recently published an article on the company blog discussing the ins and outs of humanizing asynchronous work where he makes it really clear that socializing isn't how you build culture.

“Culture is about how we work. We subscribe to the idea that we're a team and not a family, and so we really do bond around our work. We use work to connect us”. He elaborated saying in his team, they take on opportunities to connect because building team cohesion and culture is very important to them.


Chase shared some examples of activities they do to connect as a remote team. Before the pandemic, they met in locations and spent the week there for company get- togethers. They also do synchronous virtual meetups, and asynchronous games, using bots and quizzes.


He highlighted, “Those activities are part of the workday. Leadership has to exhibit that. It's not added on top of your work, because if you give everybody the choice between doing their work and doing a one hour casual hangout, you're probably going to choose your work. It takes intentionality and leadership from the top down saying that it's important”, Chase said.

About Asynchronous Work

Knowing about Chase’s strong stance on asynchronous work and his avoidance of synchronous work, Marilyn asked more about that. For her, his stance is a bit extreme, as she is an extrovert who feels the need to see people at least once a day.

Chase answered that being an extrovert as well, he is also responsible for creating the ways in which his team interacts both outside and within work. He has to incorporate this in real life by creating curated events for them to actually get together virtually and in-person. He doesn’t think requiring people to be on camera for elements of work which could be done asynchronously is very efficient.


“What I suggest teams do, is to pressure test every single activity that they do internally, and see if it could be done better asynchronously. The answer may be no, but every team is different. If the daily standup adds value to the team, that is great. But it doesn’t work in teams with significantly different time zones.”, Chase said. He added that synchronous work takes a lot more time than asynchronous work.


Marilyn added, “The element of testing is really important in knowing which one works for you, getting a sense of the range a team can take.”

“That's what we mean when we say you should intentionally test each one of your processes. If you're going from an office space to remote, that would be an intentional way to go about creating your remote culture. The teams that have made that transition successfully have gone through that process meticulously”, Chase said.

Conflict in Remote teams

Marilyn asked Chase about how he manages conflict in his fully asynchronous team.


“Not asynchronously, honestly! It’s a great moment to interject asynchronous activity”, answered Chase. He explained that in general, seeing conflict is a good opportunity to build in some synchronous connection.


Marilyn shared that in her experience working in a team that was distributed across time zones, conflict would be very hard to approach, as she would wake up sometimes confused by seeing a very long message about what her team did was wrong.


Chase shared why it’s important for asynchronous teams to have radical candor. “It opens the door for everybody to give feedback and express their thoughts in a very deep and thorough way. The feedback can be difficult, but if you have a culture that embraces that type of feedback, it has to be delivered correctly.”


He continued, “One of the real benefits of asynchronous communication is that you take away a lot of the emotion. When you see the comment in written format, you have the time to think of an answer. I think conflict approached asynchronously in a culture that embraces it can actually be done in a really good and healthy way. But when you get to an impasse and things are just getting heated, it's time to go synchronous.”


Intentional leadership in remote-first settings

Before continuing the conversation about trust and radical candor in teams, Marilyn switched back to the topic of intentionality. Reading questions from the audience, she asked Chase, “What tips would you give leaders to think more intentionally about having team members interact virtually in a valuable way? What behavioral patterns should leaders be keeping an eye on? What questions should they be asking themselves to make sure their team's interactions are productive, meaning even if it's about disagreeing with each other, but the endpoint is creating value?”


For Chase, it starts with leaders setting a good example for their team. They should make time for the social life within their teams, show that it is important to disconnect from work, and exemplify how to do deep work and synchronous work. He also noted that it’s important not to go too far in terms of crafting moments of serendipitous conversation, because to him, these things happen naturally. “You have to be intentional about creating this space, and creating the right balance of good quality activities that actually add value and allow people to connect”, he said. Chase noted that there are lots of ways to do this and maintain the balance, with tools, best practices, company culture, and leadership.


Work-life Balance and Remote Work

Marilyn then mentioned that knowing Chase favors working remotely because it allows him to travel and have adventures while building his career, there's also many people who feel like remote work doesn't give them an opportunity to compartmentalize. “Not everybody thinks working from home is the holy grail. What are your thoughts on that? Do you ever recruit people who don’t think remote work improves their work-life balance?”, she asked.


Chase noted that lots of people experienced remote work for the first time on the onset of the pandemic, which isn’t a great example of how remote work-life balance can be done correctly. He then explained that remote work isn’t for everyone, nor for every company or organization, and admitting that is a good first step. At Doist, they try to screen for that during the hiring process, although sometimes people they hire who haven’t worked remotely before do great. On the organizational level, they provide a co-working stipend, which Chase uses when he goes to a co-working space. Similar to many, working during lockdowns was very difficult for him.


“We had this big spike in productivity because there was nothing else to do. Everybody just worked really hard. There was a big burnout phase following that, and signs of depression and morale going down. So, you know, extrapolate that out. We're a team that's used to working remotely, a lot of us have been working remotely for over a decade. All of a sudden, we're experiencing what a lot of people were saying about the downsides remote work”.


For him, on the organizational level, leaders have to help people disconnect, and create a culture that embraces that disconnection. In fact, he always shares with his team when he’s working and when he is not, and includes everything in his calendar so that people know when not to book his time. “It's about knowing what’s the perfect workday for you, what times and places work best for you. If the company embraces that you shouldn't be working all the time and that you need to disconnect in order to show up as the best version of yourself every day, then you can make remote work work, even if you're not naturally a remote work person”, he concluded.


Although Marilyn thinks what Chase shared is great advice, she noted that as much as there should be pressure on the organization to enable everybody’s choices, there should also be pressure on everyone to communicate their preferences. “I think it's always important to strike a balance, which everybody is co-responsible for. If you're not actually communicating your individual preferences, then you shouldn't get too upset if they're not heard, because then people can't get everything that you need.”, she said.


Trust

This observation brought Marilyn to the topic of trust. She pointed out one of Doist’s values, which is to trust everyone on the team by default. “There are different kinds of trust: affective trust, which is based on feelings generated by the level of care and concern the person has been showing, and cognitive trust, which is based on the person’s reliability, dependability, and competence. How do you develop these different kinds of trust within your team?”, she asked Chase.


Chase answered that trust and transparency go hand in hand for them. At Doist, they over-communicate and are always very explicit in their communication. Instead of having daily stand-ups, they report back in writing what each one of them is accountable for for the day.


For Chase’s team, being very transparent about what they're doing on a weekly, monthly, semi-annual and annual basis, is at the core of the way that they work. This allows them to understand where they might have fallen short on, and embrace their mistakes together. “That creates trust. It's not about explicitly saying, ‘I trust you to do this and you trust me to do this’, but it creates a company culture where people aren’t scared to admit mistakes”, he elaborated.


Chase added, “It's also really important to empower your teammates in a remote environment. We give people the ability to make decisions, in a cross collaborative way.” This process creates new project managers every single month, and as team members are empowered by their sense of leadership, when they fail it’s forgiven as it’s part of the journey.


Marilyn observed that as this answers her question on the cognitive side of trust, but she was also curious about affective trust, and raised a question from the audience about how to communicate emotions through email. “How can I know that my teammate cares about me as an individual, and not just because we both contribute and can perform well? How do you create that interconnectedness between the humans on the team?”, she clarified.


Chase answered that this is very challenging in an asynchronous work environment. It can work by being intentional in creating spaces for those connections, having conversations outside the scope of work. They do that in his team through many different activities.“We have spaces where people can go to spend time together and chat about things that they're interested in. We created what we called ‘crews’, which are similar to volunteer committees for people to tackle things within the company that improve the employee experience, such as diversity and inclusion. People can connect on things, and really get to learn about what makes each other tick, and what they can unite around outside of work. Trust gets built through these kinds of activities”, Chase said.


🔥Rapid Fire

The one thing every team needs is…”Strong leadership”

The one thing a team needs to avoid…”Synchronous meetings”

A good team leader is…”A leader by example”

The best book on teams is…”The Culture Map, by Erin Meyer”

What’s your favorite team ritual? “Ask Doist! One of our teammates frequently comes up with simple yet hilarious questions, which we choose to answer or not. They can be very thought provoking, or very simple. It’s nice to see the difference in answers across the 35 countries we are in.”