• The Big Bet
  • Posts
  • "Deep work is where the real work gets done"

"Deep work is where the real work gets done"

How Doist's 100 Remote Teammates Work Async Across 35 Countries

Here at Almanac, we love talking to people who are passionate about making remote work, work.

Twenty-five years ago, Chase had a lightbulb moment: his mom was working a fully remote job with a four-day work week.

She could work from home and advance her career, without sacrificing one for the other.

It was the best of both worlds, and Chase wanted the same.

So when it came time to start thinking about his own career, Chase knew that a traditional job in finance wouldn't cut it.

He wanted to travel and push his career forward, and he didn't want to have to choose between one or the other.

So he set out to work remotely from day one.

After six years with his first company and a gap year of travel, Chase landed at Doist (the remote company behind Todoist & Twist).

Now, he's been with the company for over seven years and serves as its Head of Remote.

At Doist, Chase is responsible for maintaining and improving the company's remote work infrastructure and best practices, and for advocating for the future of work internally and externally.

He's a self-proclaimed remote work nerd, and is full of hard-won insights that he shares regularly on Twitter and LinkedIn.

He's an expert when it comes to organizing co-located events, maintaining cultures of documentation and asynchronous collaboration, and implementing emerging technologies on distributed teams.

I'm excited to share my recent conversation with him, because it's full of practical advice that will help your team thrive in a remote- and async-first culture.

In our conversation, Chase talks about:

  • How an async culture helps your team move faster, even if it means individuals move slower.

  • Why you should answer every question with a link if you're trying to get your documentation effort off the ground.

  • Why you should constantly reinvest in your infrastructure if you want to move your company forward.

You can catch our full conversation below, or on Almanac's YouTube channel.


Walk me through your early years. What shaped the path you're on today?

I've always been a remote work nerd. I just didn't know it early on. I was born to a pilot and a flight attendant who took me on 30-something planes before I was 30-something months old.

Once I got to college, I got really interested in traveling. I wanted to explore more of the world–I wasn't interested in sitting in a cubicle. I aspired to do more than just get a degree and land a job with a good paycheck.

I thought that maybe I would go into finance, and that I would have to sacrifice my career aspirations for the ability to have freedom and location independence. But I gradually started to realize that remote work offered me the best of both worlds.

It's funny–my mom was the the first remote worker I knew. She turned her nursing career into a remote job about 25 years ago. And she also managed to finagle a four day work week at the time, which was totally unheard of back then.

But her experience with remote work was terrible. Her company did all the things you'd tell remote teams these days not to do. But watching her work from home, for four days a week, got my wheels spinning. I wanted to push my career forward, and I wanted to travel, so I chose to optimize for location independence and remote work. I chose to make working remotely my priority.

What was your first remote job and how did that experience inform your decision about where to work next?

I worked for an awesome, forward thinking company in the risk management / insurance sector of the finance industry. I worked from home, and I didn't have to go into an office. Well, except for one day a week during my first six months, which was enough for me. I got to travel ten to fifteen days per month, which was exciting. I was a road warrior, but I got to work with cool international companies, like Lloyd's of London.

This first experience with remote work gave me an interesting perspective on something we talk about a lot right now–which is the challenge of hybrid work and how to best manage proximity bias and other things like that.

I was working in this hybrid within a hybrid model. My team was completely distributed–we had fifteen people in fifteen different locations. I was the only one based out of the city where the home office was, so I got more access to the CXOs in our company because I would go into the office one day a week.

After a year, I left my initial hybrid position to become a fully-remote team member. So I continued to broaden my perspective on what it was like to be a remote team member in an office-first company. And even though there was a lot of emphasis put on the remote experience–we made up about ten percent of the company–we still felt a bit like outsiders when we came to visit the office.

But I felt like I was still winning. I didn't have to go to the office every day. I basically took one step back to take two steps forward. It was a really interesting dynamic, and I absolutely learned a lot from it.

How did you end up at Doist?

So with my first remote job, I worked remotely, but I had to live within the US. I had a strong desire to get out and explore other places, so I tried to finagle a way to take my job international. And the company was very forward thinking–they strongly considered it–but ultimately we just couldn't make it work.

So I decided to leave. I took a year off, during which my wife, my dog, and I traveled. I helped my wife run her e-commerce shops and learned a lot about e-commerce. During this time, I found Doist.

I've been here for seven years now, but at the time, Doist was one of the only companies I could find that was hiring fully location-independent, non-engineers. And that was important, because I'm not an engineer! It was the perfect role for me at the time, and I've been with Doist ever since.

How did Amir (Founder/CEO) and the rest of the Doist team know that remote was such an optimal way to work or run a company?

It's interesting, because I think it happened by accident at first, and then it just became an obvious way of life.

So Amir started Todoist, which is the product we're most known for, as a side project. He just wanted a better task manager for himself. Then, before he knew it, he had a business and needed to hire people.

At the time, he was living in Chile working on a project in Start-Up Chile. He started hiring people on Upwork, which at the time was Elance, and then just realized that this was the way he wanted to build his team.

He learned a lot from the guys at Basecamp, and borrowed a lot from their books. In fact, a lot of their books became mandatory or suggested reading for new hires at Doist.

What's been the biggest benefit of being a fully remote company?

Now, it's hard to imagine Doist as anything but a fully remote company. Although, at one point, we sort of became a tiny bit hybrid, because there was a group of people working out of the same co-working space in Portugal. But to his credit, Amir, our CEO, intentionally broke that up.

Every single thing we do is optimized for being remote first. We want to be really good at operating as a remote first company, and we don't budge on that. Even when not-budging is a bit painful, we really try to stick to completely asynchronous, remote first principles as much as possible. I can't imagine operating in any other way.

What are the biggest benefits to asynchronous, remote work?

At Doist, we're a people-first organization. That's why we adhere so strongly to the async- and remote-first principles, because they allow people to embrace the nonlinear workday, and optimize every little bit of the day for a personal schedule.

Every practice and principle that we have in place is built around not having offices and letting people work from wherever they want. So our people can live wherever they want and work whenever they want–at times that are most conducive to their personal energy levels or family dynamics.

What are some of the challenges with asynchronous work?

Everything comes with tradeoffs. We're not naive to the fact that at times, asynchronous communication moves slower than synchronous communication. We know that sometimes, the quickest possible way to resolve a problem is just to hop on a call.

And sometimes, we do want to execute a little faster. But that's tough to do when you also tell people, "We want you to disconnect and you don't need to show us when you're online," or "We don't need to have meetings to move things forward."

So these conflicting dynamics are definitely real, but part of our growth as a company has been learning to accept these trade-offs and figuring out how to work around them.

On a macro level, has asynchronous worked slowed down your company's velocity?

I wouldn't say async work has slowed us down, but I would say that we could be moving quicker. We could optimize for faster execution if we all worked the same hours and were available for immediate response. But our work-around is to have really good documentation systems.

We have really good practices around asynchronous communication, so people aren't blocked when teammates aren't available. At Doist, often times you don't need to seek approval in order to move something forward. So even though we work asynchronously, our documentation has kept us from feeling some of the stronger pain points that other remote, async teams might experience if they don't have strong cultures of documentation.

How has being remote-first impacted your company's growth?

Being remote-first is our superpower. If we were in a more synchronous environment, then we might gain a little bit of speed, but we'd give up a lot of deep and high impact work.

Sometimes it feels like we move a little bit slower because we work async, but that's because a specific task or project might be blocked or something isn't moving at the speed that we'd like it to.

And on the contrary, we might have eight or ten of those projects being worked on 24/7, which is a really impressive rate. So the key difference here is that individual work might feel slower, but on the whole, the company is moving faster.

Tactically, how do you enable deep work at Doist?

We dropped Slack and moved to our own tool, Twist, because Slack was pulling us out of deep work and creating a lot of distractions. People felt like they needed to be online at all times or else they'd miss something. The notifications were distracting, and there was always a constant flow of chat.

So we built our own tool to get rid of all that stuff. In Twist, there are no read receipts or presence indicators. And at Doist, there's no expectation that you're online at any given time. We don't have set schedules.

We have this mentality that if you're chatting, you're not working. It's the opposite mindset of the boss who says, "when I ping you, you better ping me back in X minutes." Our reaction is kind of like, why do you want to hang out in chat when you could be doing real work? 

You could be coding, designing, writing, or whatever it is that you do. Deep work is where the real work gets done. And I realize that shift is very drastic for some people, but that's the foundation of how we work.

How did you overcome the cold start problem of getting your documentation efforts off the ground?

Well, I have to say real quick, the whole reason we moved over to Almanac is because we feel the need to up-level our approach to documentation. We think Almanac is how we get there.

The key to solving the cold start problem is just to start. I know that sounds so basic and useless, but I see so many leaders try to formulate a plan or come up with this or analyze that before they even put a pen to paper.

We borrowed this idea from GitLab, but you should try to answer every question with a link.

If you don't have a link to share, then you need to create that link. We have this idea baked into everything that we do. If somebody asks a question, and I can't send them a document or a Twist thread with the answer, then we have to create a link.

And it's important, too, to make it clear that everyone can contribute to your company's documentation in some way or another. Now, how you go about doing that is very nuanced, but it's important to create a culture where everyone can take ownership of the documentation.

It's also super important to continuously improve your documentation and to invest in it. Documentation is the key that unlocks your remote team and helps them work in a distributed fashion. Not being willing to invest time or effort into documentation is like not being willing to have internet in your office. It's just not going to work.

How do you create a culture of trust on your remote team?

This is my favorite part of the job: building a culture of trust on our distributed team. It's a very real challenge, and one that a lot of companies got wrong during "pandemic remote." Most of those companies just had a knee jerk reaction and said, "We're going remote. It's all about work. Here's your Zoom account. Go for it."

None of them thought about how to rebuild trust, connection, or psychological safety at work. They never asked how their people could have those water cooler talks and build relationships with other people at work. These things are important, too, and have a real impact on the overall health of the business.

It's important to recognize that culture isn't about Zoom happy hours. And it isn't about retreats (which we happen to invest a ton into at Doist). Culture is about how you hire and fire, work together, onboard, and collaborate. The work that we do brings us together.

At Doist, we're intentional about opportunities that help people connect over work. We have this rotating system of projects called the DO (Doist Objective) System, which gives people the opportunity to work on new projects with different people from across the company. It's very much a part of our culture to have this space within our company where people can build lasting relationships with each other.

And then, kind of like the side dish to the main course, we have a bunch of activities that we run. We have an opt-in social calendar full of fun and interesting activities that are mentally stimulating, collaborative, and fun. People can take part in these activities virtually, asynchronously, or synchronously. And we also have retreats twice a year. We bring people together for a week each year, which has really gone a long way in building trust across our team.

Group pic from a Doist team retreat in Austria.

What advice do you have for other remote leaders?

Reinvest in your infrastructure. Whether you're coming into the remote experience from a more office-based experience, or you've been at this for a long time, it makes sense to ask yourself, are we optimized for today's working world? 

A lot has changed. You (Adam) just said our documentation was in an amazing state, but we're redoing it completely because the world has changed. There are now tools, like Almanac, that help us document better than the way we were documenting before.

So it's important to reinvest in your infrastructure, tools, and practices. Make sure that you're really set up for success in today's world. Don't say, "oh, this is what we've always done. This is what we'll keep doing." Because what got you here might not get you there. There's always room for reinvestment.

Next Week on The Big Bet: Vignan Velivela, The Co-Founder and CEO of AtoB

Vignan Velivela is the Co-founder and CEO of AtoB, a trucking-focused fintech company that’s modernizing the payments infrastructure for companies with vehicles and fleets of vehicles. AtoB is backed by prominent investors like Y Combinator, General Catalyst, and Bloomberg Beta, and was a member of the Forbes 2022 Next Billion-Dollar Startups list. My full conversation with Vignan is coming to your inbox next Thursday.

Join the conversation

or to participate.