At Running Remote, Chase Warrington — Head of Remote at Doist — moderated a panel entitled: Do You Need a Head of Remote?

The panelists went deep on how companies benefit from a dedicated executive/management role whose specific mandate is to manage the shift from office-based to remote work.

In some cases, where companies have always been remote or made the shift a long time ago, the role of a Head of Remote is more about the preservation, maintenance, and growth of a strong, permanent remote work culture.

We caught up with Chase in the week after Running Remote 2022 to dive deeper into his insights about remote work leadership.

Chase is Head of Remote at Doist, a company founded in 2007 and a pioneer of remote work culture. Doist specializes in productivity software, like task management app Todoist, and Twist, a team messaging tool designed for async work. These products are used by tens of millions of users worldwide.

The panel was, by its very nature, very "pro-remote". So in the follow-up, I wanted to ask Chase to address some remote work objections head-on, as there are indeed strong critics of the philosophy (like Elon Musk...!).

Curtis Duggan: What are the top objections you hear from leaders who are skeptical about remote work?

Chase: I think what they say — and what they actually fear — are two different things. Some leaders say they are concerned employees won't be able to handle the autonomy. That they will slack off while working from home, or maybe their team culture will dissolve.

What I think they actually fear, though, is change. Change is hard, and there are some extremely ingrained practices in the way that we work, which date back to the Industrial Revolution and earlier.

People have built their entire careers on managing people in a physical office. By providing flexibility and autonomy they render themselves less useful in the modern workplace.

Understandably, there is skepticism, but those who don't work through this will find themselves obsolete, one way or the other, so it's important for leaders to convert this skepticism into an optimistic outlook, and view remote work as an opportunity.

You have been with Doist since long before the pandemic. To what extent did you experience any synchronous fatigue (Zoom, meetings, etc.) during the pandemic?

We were fortunate during the pandemic, in that our working habits didn't change much, if at all. At Doist, have been remote-first since our inception as a company 15 years ago, and we operate in a hyper-asynchronous work atmosphere.

If anything, we intentionally tried to infuse a bit more synchronous activity into our day-to-day, to help support teammates on a deeper level while they were starved for social outlets.

Our biggest challenge was trying to prevent teammates from overworking during the pandemic, as we all turned to work for purpose when the world shut down.

You mention that culture is really important to remote/async teams.

Who a company chooses to hire is a big part of the culture that emerges.

Do you ever run into situations where a candidate is absolutely stellar for the job — but there is evidence that they simply aren't attuned to remote culture, and therefore you don't make the hire?

We hire for culture-fit and perhaps better said, value-fit, over all else. There are a lot of excellent marketers, designers, and developers in the world, and fortunately, due to our structure, we have the entire world as our hiring pool, since we are operating as a global team.

Finding talent is rarely a challenge. We're fortunate to have an amazing group of talented people in their respective fields. What unites us though is our value fit, and that is our top priority as we expand the team.

How long do you think it will take for remote work to be synonymous with work? Ballpark where we are at in 2024 and 2030?

While our day-to-day experiences didn't change over the past two years, our outlook on remote work did. Managers discovered that they could run things fairly well with a distributed team, productivity increased and their staff was actually happier at home. That's what has led to this worldwide remote shift. Necessity drove us all to innovate and adapt, and we have done that fairly successfully. The "future of work" became the "now of work!"

As for what the next 10 years will look like: we are already in the Great Resignation. People now have more choices than ever, and the pandemic and climate change are forcing us to evaluate what is important.

Knowledge workers everywhere who have the opportunity to choose where they want to live and what they want their lives to look like are taking that opportunity seriously. Remote jobs are in very high demand, and companies that do not permit people to have that flexibility will have some challenges as a result.

Can you talk more about retreats and off-sites? How do you mesh these in-person retreats and offsites with remote team members who are passionate on principle about avoiding in-person modalities?

For example, a team member who says: "I never want to have to physically be somewhere — I don't want to do an offsite."

We make everything we do optional by default. You don't have to attend a meeting about work if it doesn't align with your schedule or priorities, so we're certainly not going to require you to attend an in-person event. If you do attend the event, then we also make nearly everything within the itinerary optional by default as well.

I go into more detail on how to plan and prepare for a remote team offsite in this Forbes Business Council article.

Readers can also learn more about our previous retreats to Athens, Menorca, Azores, and Singapore here.

What do you think is the biggest misconception people have about remote work?

It's less pronounced than a few years ago, but there is still a misconception amongst some that remote work isn't real work. Elon Musk's recent comments about people pretending to work at home are a good example of this.

Regardless of what his true intentions were with those comments, it speaks to some truth about what some leaders believe about distributed work.

Going beyond that first misconception, another classic objection that "you can't build team culture in a remote environment" comes in at a close second place. I am always happy to help debunk this myth — I would make the argument that a team can build a thriving culture because of their distribution, not despite it.

Case in point: Doist has been remote for over 15 years and last month at Running Remote, we were awarded Most Vibrant Work Culture at the Flexible Workplace Awards.

Curtis Duggan
Curtis Duggan
Founder of Wayviator.com. Curtis co-founded a digital health company in 2016 and sold it to Virgin Pulse in 2020.
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