Josh Rubenoff

November 2019 : The resilience of remote teams

For three years, I worked at a fully distributed startup called DOBT. It was my first remote job, and I really appreciated the books and guides out there1 that helped me get up to speed.

When discussing the benefits of remote work, most of these guides talk about the lifestyle improvements. That makes sense, because they’re easy selling points: you can skip your commute, maintain a flexible schedule, and live anywhere you’d like.

But when it comes to actually running a company, they frame the topic in terms of trade-offs and qualifiers. Remote: Office Not Required literally has an essay called “[It’s] still a trade-off.” Zapier’s guide to remote working has 22 (!) bullet points explaining how to create a “successful remote work setup.”

I get why they strike this tone. If you’re coming from an office job, it’s important to know the transition to remote work might not be easy at first. But on the whole, this doesn’t reflect my experience. After leaving DOBT, I felt like remote work required fewer trade-offs than I was led to believe.

When you ask someone about the advantages of working in an office, or why remote “just won’t work” for their team, they might say that:

These advantages are real and meaningful. Now that I work in an office, I appreciate having them.

But I’d also argue they’re less important than we think. They often serve to paper over larger cultural issues that can be toxic in the long term. Since remote teams lack these benefits, they’re more incentivized to resolve those larger issues. And if they do, that creates a healthier and happier team on balance.

Below, I’ll walk through each advantage of an office and discuss how its absence creates an opportunity to advocate for a more resilient culture.

Impromptu discussions

Let’s say you’re an able-bodied person who wants to talk to your colleague. In an office, you can just walk over to them and strike up a conversation. On a remote team, it’s a little more complicated.

First, you have to write down what you want to tell them, which requires more conscious thought than talking. Then, you’ll need to wait for them to reply. If you don’t understand their initial response, you might schedule a call to clarify things and suffer through any technical issues that come up. When you compound this over many conversations, it can feel really cumbersome and inefficient. (It can also feel socially isolating, which I discuss in another section.)

But less efficient communication isn’t always a bad thing. When your culture prioritizes impromptu verbal conversations, you’re making a few assumptions that are worth re-examining.

Verbal conversation is so important for building rapport, talking through half-formed ideas, or resolving conflict. It also just feels better. When you don’t immediately click with someone and can’t talk to them out loud, it can be uncomfortable and frustrating.

But feeling like you can’t focus, or that you’re constantly reacting to colleagues at the expense of your own work, can be equally frustrating. If you really need to talk to a remote colleague, you can ask them to hop on a video call. It’s harder to get an entire office to minimize interruptions if that’s their cultural norm.

For that reason, I’ve found it easier getting remote teams to encourage verbal conversations (whether by investing in a good VoIP solution, encouraging an overlap in working hours, or making sure everyone can access a quiet space for calls) than getting colocated teams to respect the need for focused work.

More expressive communication

Our bodies really help us communicate.

Your body language makes it easier to build relationships with colleagues and develop an unspoken shorthand with them. The tone of your manager’s criticism can determine whether you accept it in stride or stress out about it all day. If you need to resolve conflict with a teammate, everything from your tone to your posture determines their comfort level.

When working remotely, you feel the absence of these things acutely. It’s hard to judge a person’s mood based on the few words they’ve tossed off in Slack or email that day. It’s easy to misinterpret people when reading their writing. It’s even easier to take offense, to have a negative gut reaction. If you compound those gut reactions over months or years, you might begin to isolate yourself from others. You might feel like none of your colleagues understand you, or like you can’t reach out to colleagues when you’re struggling. It can put you in a really emotionally unhealthy place.

But it’s easy to feel isolated in an office, too! Alienation isn’t correlated with where colleagues communicate, but how they get their message across. And it’s possible to compensate for a lack of body language by building cultural norms around communication.

For example, at DOBT, we tried to hire people who were kind and empathetic to their colleagues and had sufficient emotional intelligence to express that kindness to others. After they joined, we created an on-boarding handbook to guide them towards healthy ways of communicating: asking them to assume positive intent when communicating, and treat others with grace. Most importantly, we told them we expected them to not be a stranger, to ask colleagues for feedback and proactively resolve conflict when they noticed it.

Some people are super uncomfortable asking for help or initiating difficult conversations. It’s so much easier to empathize with that discomfort on a remote team, since everyone feels the pain a little bit. Thus it’s easier to encourage remote team leaders to build up these cultural norms and teach their employees to become more empathetic communicators.

A sense of community

When you’re colocated, you spend eight hours a day physically next to your coworkers. That has a primal effect. Even when you rarely work with someone, you can still feel something in common with them, if only because you share the same space with them day after day.

When everyone eats together and breathes the same air, it’s also easier for leadership to feel like they’re building a cohesive team. They can see everyone enjoying the baseball tickets they paid for, the open bar they bankrolled for a product launch, or the birthday cake they brought to the office.

By contrast, remote work can feel lonely. When you don’t see colleagues in person, it’s harder to feel like you’re part of a bigger team. When everyone’s spread out, it’s impossible to build communal traditions like a happy hour outside of team retreats.

But our positive memories of these experiences make it easy to overlook how they, by themselves, can’t create a healthy or safe culture. If a company rewards and promotes assholes into leadership positions, a baseball game isn’t going to make them less abusive. Even if managers have good intentions, these things can feel discriminatory if an employee can’t take advantage of them. For example, a happy hour isn’t great for someone who doesn’t drink.

When it comes to feeling a true sense of community, what matters most in the long term is feeling like you have something in common with them beyond just sharing the same room. It helps to establish strong, authentic company values and hire people who embody them. When your colleagues share your values, it’s more likely you’ll enjoy working with them. And when conflicts do arise, it’s more likely you’ll be able to reconcile your differences. If you’re a conscientious, thoughtful leader, you’re more incentivized to do this on a remote team, where you don’t have the benefit of a shared space to prop up your assumption that the team will naturally gel together.

As a remote leader, you might also be more thoughtful about building systems to make sure everyone feels seen and included. At DOBT, we had purely social team check-ins and lunches on top of our regular stand ups, and elaborate retreats that helped us bond.

Shared space

An office, in and of itself, is an incredible collaboration tool. Whiteboards let you sketch ideas collaboratively. Walls let you hang up project documentation, giving the team shared points of reference. Conference rooms are a great venue for group synthesis sessions, where the team can write and rearrange Post-Its to make sense of a large data set.

Remote collaboration tends to be more awkward. Using Figma as a shared whiteboard feels less natural than sketching with your hands. Emailing a link to a Google Doc doesn’t guarantee that others will read it. You can synthesize a large data set in tools like Airtable, but it’s not as intuitive as moving around pieces of paper.

But we tend to overlook how a shared space’s benefits diminish when our meetings end. If no one’s carefully taking notes, it’s easy to try to remember a meeting the following week and mischaracterize the discussion. If someone does take notes, but doesn’t show them to participants during the meeting, each person might walk away with a different interpretation of what they just talked about.

When you hang documentation on the walls, you might assume that everyone in the office can now access a single source of truth. But you have no idea whether they actually understand what you hung on the wall, or feel comfortable referring to it when you’re not around. And the minute someone needs to work outside the office, whether they’re at a conference or taking care of a sick kid, consolidating all of your organizational knowledge to a physical space discriminates against them.

Shared workspaces are only effective alongside strong facilitation, communication, and organizational skills. Ironically, those are exactly the kinds of skills that remote teams are incentivized to cultivate, because they’re painfully aware their time together needs to count.

For example, at DOBT, we tried to keep our digital tools more organized than our average office. We used as few apps as possible for collaboration, so that we’d only need to search in a few places to find a given document or conversation. As the team grew, I even wrote a guide to which communication channels are best suited to different types of work, making documentation even easier to find and reference. We screened for strong written communicators in our hiring process, and ended meetings by reviewing the notes to ensure they made sense to each of us.

Co-located teams can also build these skills, but they take real work to acquire, and thus there has to be a top-down mandate to do so. Otherwise, people will take the easy route and rely on their incomplete memory of a collaboration session, or tap someone on the shoulder to construct a patchy memory together.

On a remote team, you don’t need anyone telling you to build those skills: you feel the pain if you don’t have them, and you’re motivated to learn them and seek out help if you want to succeed.

Cross-pollination

Offices also increase the chances of serendipity. From striking up a conversation in the break room to glancing over at a colleague’s screen, they provide plenty of unplanned opportunities to learn from colleagues in different disciplines. These encounters can inspire you to form connections between unrelated ideas, or bond with people you otherwise wouldn’t have a reason to talk to.

On remote teams, this won’t happen naturally. Since remote workers are async by default, they’re responsible for reaching out to each other if they need to talk. It’s unlikely they’ll have an unexpected / surprising conversation with a colleague during the work day.

That is, unless it’s not left to chance. The truth is, even “accidental” office encounters happen by design. For example, Steve Jobs designed Pixar’s headquarters with a huge open lobby and one set of bathrooms, a forcing function to make everyone run into each other throughout the day. He understood that cross-pollination is too important to leave it up to your teammates’ comfort level with new people.

Since remote teams are always hungry for ways to feel more connected to their colleagues, they’re more incentivized to be thoughtful in solving this problem. At DOBT, we used recurring 1:1’s between people of unrelated disciplines to encourage cross-pollination. Other remote teams adopt a culture of internal transparency: for example, Wordpress uses P2s to help people understand and get inspired by other teams’ work without needing to set up a meeting.

Alignment

If you’re co-located, it’s possible to steer everyone on a team in the same direction through sheer force of will. It doesn’t matter how often you pivot, only how much you’re willing to sacrifice work/life balance. You can chase down a busy stakeholder late at night to get their stamp of approval. You can intercept someone in the hallway to ask if they’ve read your latest email. You can do a drive-by at someone’s desk to make sure they’re working on the right thing.

At one past job, this kind of thing took up 30% of my week: relaying crucial information between engineering, design and product in a deeply siloed company. It was super stressful, but also kind of exhilarating. I felt like this vital conduit that was keeping the company together through sheer force of will.

When I started working remotely, I was a little unsettled to realize these strategies no longer worked. When I noticed people having trouble coordinating or misinterpreting a shared strategy, it wasn’t practical to resolve it myself. Since my colleagues were spread out across time zones, I couldn’t bring people together or relay information in a reasonable amount of time.

After a while, though, I realized that I most appreciated my old habits for how they made me feel essential in my job, rather than their actual value to the team. On top of that, I think they helped distract me from systemic cultural dysfunction. At this company, the CEO discouraged designers and engineers from talking to each other, because he wanted the designers’ creative ambitions unsullied by technical constraints. I was too scared to confront the CEO and advocate for a change, so I chose to ferry information between the two groups instead.

I think this is representative of any case where two groups fall out of sync over and over again. Either you can mend each rift as it arises, or you can identify the root problem and try to fix it. Their managers might be in conflict with each other. They might be misinterpreting directions from a shared manager. One group might be preoccupied by avoiding the wrath of an asshole in their midst. Maybe they even have fundamental disagreements on the company vision or strategy.

In any case, it’s easier to identify and tackle root problems on a remote team than spend your days chasing down symptoms… if only because you don’t really have another choice.

Your manager’s peace of mind

I once had a boss who arranged the office so that, from his desk, he could have a clear line of sight to every employee’s monitor. That way, he didn’t have to pay for content filtering software, and could visually confirm that we were focused and hard at work.

It’s easy to call that behavior extreme, but it reflects a sentiment I’ve heard many managers express. Intellectually, it’s easy to understand you can’t measure someone’s productivity by how long they sit at a desk. But managers of remote teams can’t say for certain whether their directs are actually getting work done at any given moment. If that makes them anxious, they also can’t placate it by walking up to someone’s desk and asking them what they’re working on. If someone’s in a far-flung time zone, a Slack DM might not even elicit a same-day response.

That can feel super uncomfortable! And it goes both ways: it’s easy for remote teammates to feel anxious that their boss has no way of noticing their hard work. Earlier this year, Anne Helen Petersen wrote about “LARPing your job:” the performative work remote workers do to make colleagues remember they exist.

But this isn’t an issue with remote work itself. Rather, it stems from a lack of trust, accountability, and communication. If managers can’t tell whether a given project is on track, of course that’s going to lead to anxiety and a lack of trust. If employees can’t easily show their managers how hard they’re working, of course that’s going to make them feel pressure to “perform” their job over getting things done.

As Project Include suggests, managers can solve many of these problems by setting performance expectations during the employee on-boarding process. They might describe their expectations for:

They might also describe the specific consequences for the employee if those expectations aren’t met.

I think the examples above more accurately reflect an employee’s performance than their time spent sitting at a desk or logged onto Slack. But for a company to properly assess them, first they’d have to:

That’s a lot of work! If the leaders of a colocated team haven’t thought too hard about increasing trust and accountability in their culture, it might not seem worth the hassle to them.

But on a healthy remote team, colleagues have no choice but to trust each other, if only because async work grants everyone a certain amount of autonomy. In that environment, it’s easier to make the case that this effort is important.


I don’t think remote teams always have healthier cultures. Actually, I kind of feel like the opposite is true? When browsing through remote job boards, a good chunk of the job descriptions make them seem like pretty low-trust environments. An office with the discipline to solve the issues I’ve mentioned above will always be more effective than a remote team.

But most teams lack the discipline or self-awareness to solve these things. More often than not, when you join an organization, you’ll notice a major problem with the culture. Then you’ll have to make a choice. Is it mild enough to live with? Is it bad enough to make you quit? Or do you think there’s a chance that, if you speak up, you can fix it?

In the end, a healthy relationship with your job is like any other. You’ll feel happiest if you feel psychologically safe expressing what bothers you, and if your colleagues are willing to talk through it to help make things better. In many situations, the constraints of remote teams make your colleagues more likely to meet you where you are, working with you towards a culture with fewer trade-offs.


Thanks to Kari Mah, Kevin Barrett, and K. Tempest Bradford for reading drafts of this essay.

  1. This essay is intended to supplement the excellent introductions to remote work that are already out there. When I was starting out, I really appreciated Remote, The Year Without Pants, and Zapier’s remote working guide.