Making remote teams work

This essay originally appeared on STET.

Last year saw both a clampdown on remote working at Marissa Mayer’s Yahoo! and the publication of 37 Signals’ Remote, an occasionally breathless but largely convincing treatise on why and how to work remotely.

I’ve worked on remote teams for four years now, and interviewed over a dozen remote workers on teams both large and small in preparing this essay. And I’ll be the first to admit that remote work is not a panacea for all that ails the modern workplace, nor is it suitable for everyone. It’s just as possible to have a dysfunctional remote team as it is to have a broken and unproductive office space.

That said, in the tech community today, remote work has some clear advantages. For the employer, it enables hiring from a more diverse set of workers. Yahoo! may be unwilling to hire an engineer who lives in Kansas City and isn’t inclined (or able) to move to Sunnyvale or New York, but another team may be more than happy to accommodate her. Remote teams also don’t incur the costs associated with expensive campuses and their roster of caterers, laundromats, buses, and gyms, making them more appealing to smaller and leaner organizations. (And, since those perks are usually designed to keep workers at the office, employees could be said to benefit from their absence.) For employees, remote work can permit a flexibility and freedom that is especially valuable to those with less-than-perfect home lives. Caring for children or elderly parents, or contending with an illness or physical or mental disability, may all be made easier with the flexibility to work when and where it best works for you.

This last point is, in some ways, the most damning criticism of Mayer’s policy at Yahoo!: a mother with a full-time nanny may find no difficulty in making it to the office every day, but most parents are not so well-supported. Of the remote workers I spoke to, a recurring theme was the ability to time-shift one’s day to meet their kids’ schedules (as were various techniques for insulating the workspace from tantrums, about which more in a moment). Remote working holds the promise of adapting work to fit our lives, rather than requiring that we twist and bend our lives to fit the space that work demands.

But only if it’s done well. Remote working is a different way of working, with different constraints and practices. It undoes decades of management policies and, given its relatively recent uptake, there’s scant information about the best way to proceed. What follows is some advice, drawn from my own experience at Editorially, with guidance from others about how to make remote teams work—and which pitfalls to look out for.

Say it once, say it again

Perhaps the most persistent bit of advice I gathered—and in some ways the most counterintuitive—is the need for remote teams to over communicate. That runs against the prevailing theme of efficiency that marks many discussions about workplace best practices: most teams have evolved to consider efficient communication one of their primary concerns, and a range of tools and platforms have arisen to address that very need.

But efficiency has its limits. On a remote team, opportunities for misunderstanding between teammates distributed across both time and geography magnify. The best way to avoid that terrible realization halfway or further through a project, when one person says, “Wait, I thought we agreed on X?” and the other replies, “No, it was Y, wasn’t it?” is to communicate decisions and plans redundantly.

For example: a remote team may brainstorm ideas over a video call, then share notes from that brainstorm via email, then discuss it further amongst themselves over chat and instant message, then post revised and updated notes to an internal wiki. At each point of communication there’s opportunity for questions and clarification, plus a recording of the discussion, all of which can be referred back to later. The repetition serves to ferret out confusion and make the teams’ goals abundantly clear to everyone.

Further to that, there are different kinds of communication with different needs for redundancy. Sometimes sharing information is as simple as getting a byte of knowledge from one person’s head into another’s. “What time is tomorrow’s meeting?” can be swiftly and efficiently delivered by an invitation that automatically updates everyone’s calendar. But much other communication within a team is less about delivering basic morsels of information than it is about collective thinking. Making decisions about a product direction, brainstorming new features, and evaluating various marketing strategies all involve communication, but are not straightforward knowledge handoffs. That kind of communication benefits immensely from repetition—the opportunity for a team to collectively noodle on an idea or explore it from different angles, across different mediums and platforms.

While efficiency is a laudable goal for much of our work, it isn’t the only goal. Over-communication is a key skill for remote teams.

Remote by default

A second recurring theme among my conversations with remote workers was the need for the entire team to change: many teams are partly or only occasionally remote, with a core team in an office while remote workers are scattered about; or else, some workers split their time between being in the office and working remotely. It’s easy under these circumstances for the remote team members to end up as second-class citizens, always a step behind their in-office counterparts. Many remote workers I spoke to voiced anxiety about being neglected, simply because their colleagues naturally prioritized the needs of the people they could see face-to-face each day.

It’s necessary for everyone on a team to adapt to remote work, even those who continue to commute to a traditional office each day. For example, at Editorially, on the occasions when the entire team was in the same room together, we still prioritized chat as a mechanism for communication. More than once I actually forgot that a colleague (usually thousands of miles away) happened to be sitting next to me and was startled to hear him laugh when someone shared a particularly astute gif. You could interpret this habit as an unhealthy reliance on tools that intermediate our relationships; or you could see it for the positive effects it produces: our communication is no less real for its delivery via pixels rather than sound waves, and the remote-by-default habit ensures no one is disenfranchised.

The best way to guarantee this habit is to make sure that every team member is at least sometimes remote. There are exceptions, of course—the office manager needs to be in the office to accept deliveries, for example—but preferably everyone on a team would spend enough time as a remote worker to develop effective habits as well as empathy for the role. Teams with fixed in-house staff and roving remote workers may discover an inevitable clash between cultures.

Put another way: ensure your in-house staff communicates as if they are remote, because to somebody else, they are.

Managing time zones

Technology can bring together remote team members from as far apart as Australia and New York. But while information moves at the speed of light, our bodies remain subject to the usual constraints of the circadian rhythm. You may technically be able to make a video call from one end of the world to another at any hour, but the realities of scheduling work at 5am in one timezone and 8pm in another will get old, fast.

To put it mildly, time zones are a bitch.

Different teams and workflows will have different tolerances for the amount of time their team members need to overlap. In Remote, Jason Fried and David Hienemeier Hansson advise at least four hours of synchronous time between team members, which is certainly a reasonable baseline. At Editorially, we averaged a bit more than that, and found that every minute counted. In practice, that meant we could hire within the continental United States (and across those same time zones to the North and South), but that adding a team member in Europe—whose day would not much overlap at all with our West coast staff—would have been tough.

Of course, there are possible exceptions: a night owl living in Berlin may be perfectly happy to shift her day to align with her American counterparts. Or the American arm of a European-based team may be delighted to start work in the wee hours, and take the afternoons off to watch the kids play fútbol. But it’s worth some caution, in that those kinds of extreme day/night shifts can be disruptive in the long run. A remote worker needs to not only find her life in concert with her team members, but also balance time with her friends and family.

Ultimately, the decision about how geographically distributed a team can be comes down to the needs of that team: how much of the work requires—that is, really requires—synchronous time among team members? And how much can be handled asynchronously? If your team is considering the switch to remote, it’s worth evaluating any currently synchronous processes to ascertain whether or not they really need to be handled that way. Then any work that does require real-time collaboration needs to be prioritized in those few hours when everyone is available.

Tools of the trade

A variety of tools and platforms have emerged in recent years, some aimed directly at remote teams, others providing support to office-goers and remote workers alike. Which particular tool you use is a topic big enough for another essay, but understanding the taxonomy of tools that make up a remote workflow can help you and your team members adapt.

Chat

Every single person I spoke with referred to the team chat room as their primary gathering place. Developer-oriented teams tend towards the free IRC protocol, which can be accessed through any number of third-party tools, such as Colloquy. Many other teams rely on 37Signals’ Campfire (now sunsetted) or the new-but-seemingly-ascendant Slack. These tools not only enable group conversation—both of the productive and animated gif varieties—but often also support direct messaging and topic-segregated channels, as well as a wealth of integrations with other services. One of the keys to encouraging a remote-by-default workflow is to grow the team chat room into a full-fledged watering hole: on the various teams in which I’ve worked, information about system status, support tickets, commit messages, and more were all piped into the main chat room. This makes the chat room not only a good place to catch up with one’s coworkers, but also a prime resource for understanding the work as a whole.

A few things are required to make the team chat room effective: First, it should be permitted for team members to turn away from it to work quietly when they need to. That means that whatever tool is being used needs to have robust transcripts available, so a team member who was out for a while can catch up on the happenings while she was away. (This is one of the ways in which a remote workflow can be preferable to an in-person one: if you have to step away for a little while, you can catch up on the chatter when you return. That’s much easier when said chatter is written than when it’s spoken into the air.)

And, importantly, the tool needs to support superficially silly things like sharing animated gifs and emoji. Lest you think I’m kidding about that, let me be very clear: I am serious. The variety of expression available to team members across a medium like chat is considerably smaller than that achievable by people in a room together; images (even and especially frivolous ones) serve to fill in that gap and ensure productive and fun conversation. When your team can discuss a complicated topic and arrive upon a decision together using only animated gifs, you will know you have succeeded.

Video

Of course, chat is just one way of communicating, and sometimes the speed and efficacy of face-to-face conversation is warranted. If a discussion in chat gets particularly hairy and feels like it isn’t coming to a quick resolution, bouncing to a video call can be very effective. The shift across mediums (remember the point about over-communication, above) can help, as can the improved ability to measure colleagues’ feelings when you can see them.

Among the people I spoke with, Skype and Google Hangouts are the most commonly used tools for quick video calls. The Editorially team hosted a brief standup via Hangout each day at noon Eastern time; that Hangout serveed as a quick check in and preview of the day’s work, as well as a chance to feel like we were all in the room together. Likewise, I held weekly one-on-ones with each member of the team over Hangout, and we routinely got the whole team together to discuss product direction, taking advantage of both video and screen-sharing features in Hangouts. And we closed out each week with a Hangout in which we each talked about our work that week, shared things we’d learned, or just caught each other up on our lives away from the screen. Those end of week Hangouts—appropriately titled “The Week”—were usually accompanied by a few beers.

Project management

There are almost too many project management tools to count these days, and most of them are not designed with remote workers specifically in mind. But that hardly matters. Any tool that allows team members—whether sitting right next to each other or separated by oceans—to record information or check in on a project’s status is likely to be useful. In my conversations with remote workers, all-purpose tools like Basecamp and Trello were cited most frequently. Likewise, Dropbox, which serves as a central repository for a team’s assets, has become a critical service for remote and in-house workers alike.

The important thing to remember about project management tools is they are personal and circumstantial (which may explain why there are so many out there). The best advice I can give is to experiment with different tools and see what works for you, keeping in mind that what works for a given circumstance may not work for another (and that’s OK).

Wearing pants

The cliché image of the remote worker is a disheveled pajama-wearing bro slouched on his sofa with empty five-hour energy bottles strewn about his feet. But in chatting with many remote workers, I found nearly all of them had dedicated workspaces within their home, or else they regularly ventured out of the house to cafés or co-working spaces. Those who worked from home emphasized the need to keep a regular schedule and wear pants, so as to provide some separation between their leisure and work lives. Remote workers with kids were especially strident in their need to carve out kid-free space at home, with at least one worker actually building an office whose only door led outside (making it difficult for tantrum-happy kids to rush in).

Co-working spaces were also popular (in fact, more than half of the Editorially team worked from shared spaces in their respective cities). That said, while big cities like New York and San Francisco offer a variety of co-working spaces, smaller towns seem less likely to have many options for remote workers. Several remote workers I spoke with voiced interest in co-working, but had so far failed to find any resources near their homes. That said, as remote work gains in popularity, small town remote workers may find their numbers grow sufficiently to support shared spaces. In my own experience, a good co-working space need not reproduce the frills of a typical office so much as provide a quiet, convenient location to work and foster a community.

IRL

Finally, while remote work can enable a flexible and productive team, it doesn’t preclude gathering face-to-face. If your team is spread far and wide, plan on getting everyone together in the same room at least a few times a year. The frequency and duration of those visits will vary team by team: too much travel can be exhausting, too little and you risk alienation among distant team members. Team gatherings should privilege the kind of work that’s hard to do over the tubes: brainstorming on a whiteboard, long casual conversations over meals, longer-term thinking that you may not make time for day-to-day. Be sure to set aside time for just hanging out. And just as importantly, schedule at least one solid block of time each day for quiet; the introverts on your team will thank you.


One of the most unexpected things that I’ve learned from working remotely is that it isn’t just about accommodating different lifestyles or taking advantage of technology’s ability to compress long distances. Remote working encourages habits of communication and collaboration that can make a team objectively better: redundant communication and a naturally occurring record of conversation enable team members to better understand each other and work productively towards common ends. At the same time, an emphasis on written communication enforces clear thinking, while geography and disparate time zones foster space for that thinking to happen.

In that way, remote teams are more than just a more humane way of working: they are simply a better way to work.

Related books

Remote

Jason Fried & David Heinemeier Hansson

A breezy and utilitarian introduction to remote working.