Designing a People-First Remote Strategy with Chase Warrington, Head of Remote at Doist

Chase Warrington is one of the leading experts on remote-first strategy and global distributed teams. We had the privilege to talk with him about remote-first work, prioritizing employee well-being, and why mental health is just health. Part of our ongoing People-First Experts interview series!

Meet Chase Warrington

To put it simply, Chase is passionate about making remote-work, work. He's the Head of Remote at Doist (the creators of Todoist & Twist) which supports 40M+ customers and over 100+ remote-first employees spread throughout 35+ countries and every time zone. He is also a regular contributor to many of the leading remote-work courses, conferences, and publications including Forbes, Running Remote, wrkfrce, RePeople, The Remote Times, Remote-how, The Remote Future Summit, and Work From Anywhere, amongst others.

For starters, tell us about your job title. What is a "Head of Remote" role and why should every org have one?

The "Head of Remote" role at Doist is probably different than it is at many other companies. I've talked to most of the folks in a similar role, and that's one thing that I've found––we all have very different functionalities that are each tailor-made to fit the needs of the company. [The role] is still very new and evolving.

At Doist, we define the role in two different ways. It's split 50-50 on the job description. The first half is marketing, advocating for the future of work and building in public, and sharing how Doist is building a remote-first team in today's age of remote work. The other half is all about tweaking and refining our remote-first infrastructure. I'm looking at all the different ways we can improve how we're working, collaborating, and connecting. That might mean looking at the tools that we're using. It might mean looking at best practices and how we can refine them. Or it may mean looking at the different ways that we connect as a team. These are the elements that are important for us to have at Doist!

If you have any remote element, and specifically for those companies that are hybrid or distributed, you'll probably want someone that is leading the charge. You want someone that's holding the whole company accountable and doing it at a really high level. In this day and age, it's inevitable that 85-90% of companies identify as remote in some way or another. It's crucial to have somebody lead that for you if you want to design a really high-functioning product––the product being the company and the employees being the users.

When you’re designing a remote strategy, where does employee well-being factor in? Is it too "squishy" to be included?

I would like to think that employee well-being should always be factored in and that remote work is just one aspect of how we work. I would consider Doist people-first before even remote-first. We put our people first. The cliché goes that your people are your greatest asset. I think we take that to heart and we really, really want to build a sustainable model of work with people that we enjoy working with. We want to be a part of the team for a very long time. So that's key for us from the very beginning. It's almost like talking about why water is important to drink. Well-being just is for us.

Remote workers do have a high tendency to burn-out or overwork themselves. There's all this data out there showing that remote workers are more likely to burn themselves out than they are to underperform. We have all these managers out there worried that their teams are going to underperform. So this paradox of forcing people to work too much and people being naturally inclined to work too much is a recipe for burnout and disaster.

We want to put in a lot of safeguards to make sure that people have plenty of time to disconnect for vacation, health reasons, themselves, their families, whatever the reason may be. Parental leave is really important to us and we try to go above and beyond there. The whole concept comes down to recognizing that people have a life outside of work. We don't want work to be their life. We want it to be a nice piece of their life that fits well into whatever it is that they want to accomplish.

You touched on a great point earlier. There's this ongoing debate about whether remote work is "good" for us. Do you think remote work helps or hurts the mental health of employees?

I think it can go either way. I think remote work done poorly can be really detrimental to the mental health of employees. I witnessed this at a younger age. My mom was the first remote worker that I ever knew. She somehow managed to turn her nursing job into a remote job, long before it was even a thing anywhere else. But it was horrible. They tracked all her clicks. She didn't have a good ergonomic setup. It was a terrible experience. It was horrible for her mental health and physical health.

Remote work can be detrimental if not done well, but if it's done really well, it gives people the space to disconnect, to focus on themselves, to build a life outside of work, to have great social relationships, and great family dynamics. I think a key piece of that is not just the remote part, which is about where you work, but embracing the non-linear workday and asynchronous communication. I think those two married together are when you get to the sweet spot, that's where the magic happens. It can be hugely beneficial for people who crave that flexibility and crave that ability to build their work around their life and not the other way around.

How can leaders fight against mental health stigma and ensure more folks have access to necessary resources and support while remote?

One thing is to consider mental health as just health. We take health really seriously. Most companies have health days or understand when people need to go to a doctor. If somebody calls in sick, we accept that. If they break their foot, we accept that. But then for some reason when somebody says, “Hey, I'm suffering from depression or menopause or I'm unable to function today because I'm in a dark place," we don't take that as seriously.

It's equally as relevant. Perhaps even more relevant in today's knowledge-worker space. If I break my ankle, I'm pretty capable of continuing my work. But if I'm having a bad day mentally, I'm not really capable of being a knowledge worker.

Building awareness and getting people on board, especially executive leaders, with seeing mental health as health is extremely important. From there, we can connect those dots between mental health, the people on your team and how that equates to your output as a company. Happy employees, engaged employees, satisfied employees are the ones that are going to not only stick around, but they're also going to produce. In terms of retention and satisfaction and productivity, you're doing yourself a service. If you put an emphasis on this as a company, it can actually be a bottom-line booster too.

What are some of your favorite remote work or well-being hacks?

There's a huge amount of opportunity to humanize remote work. We put a ton of emphasis on terms like productivity, output, communication, and collaboration. But what we lose with remote work is this sense of community and connection with other humans. You could go hyper-synchronous, where you're doing lots of in-person and virtual meetings, but that doesn't really optimize well for high-quality, remote asynchronous work. There's a lot of space in there to optimize for team-building connection with your teammates.

A lot of our hacks are focused on that. We're looking for ways to create organic connection between our teams wherever we can and put extra emphasis on whatever we might take for granted if we were in an office environment together. It's looking at every little thing we do and saying, "Is there a way where we can build in an opportunity for people to connect? Could we do more things in public? Provide people with a platform to speak up about how they connect with other teammates on things inside and outside of work?"

A good example of this is that we try to democratize everything. We form what we call "squads" for work-focused things or "crews" for non-work focused things. That gives people a natural space to connect. So we might be working on a project and we invite people to volunteer to work on that project. If it calls to you, then you're naturally connected with a few other people that are going to work on a sprint together for let's say, four or eight weeks. They're working together around something that they're all really excited about. On the flip side of that, we might have something like planning the company retreat where four or five people are going to collaborate on that, and they're all excited about this. So we're forming a crew around that activity and they're working together on that.

It's just giving people an opportunity to connect wherever you can and building out a series of activities that people can participate in, both virtually and in person, synchronously and asynchronously.

And finally, help us leave readers with a gift! What are some books/podcasts/resources you’d recommend to remote leaders?

There's some great remote books out there:

• Running Remote just released one called Remote is the Way by Iwo from Remote How.
• We are big fans of all the books by the Basecamp guys.
• One that might fly a little bit under the radar, but I'm a huge fan of, is the Culture Map, which I think is really useful for teams that are dispersed across the globe. If you are working with people from a lot of different countries, the Culture Map is a fantastic read for getting better at dealing with people from different parts of the world and understanding how we all interact and approach problem-solving, praise, conflict, and all of that in different ways.

Podcasts:

• I'm biased, but I might recommend listening to my podcast "About Abroad!" Though it's more about global mobility than strictly about remote work.
• “That Remote Life” is really interesting by my friend Miko Kovski.
• “The Remote Show” by Tyler Sellhorn is great.
• “Remote-First” by Daphne Lak is wonderful as well. Would definitely recommend that one.
• And there's so many more, but I'll stop there.

Resources:

• You can't go wrong with the GitLab Handbook.
• Also, I think our Twist Async Newsletter is awesome, curated by Becky Kane from our content team. Absolutely incredible stuff all about async communication.
• Our Doist blog is also pretty great as well. We've built up with tons of content and there's a whole remote work section there that can be really useful as well. 

Are you or someone at your organization struggling with burnout? You're not alone! Check out our free mental health resources for remote teams.

Chase Warrington is a wonderful expert to follow on LinkedIn. Check out his profile.

Leaders can get started with Kona, the employee wellbeing and support platform in Slack, for free! Leave a comment or email yen@heykona.com to get started.