The Extrovert's Guide to Working From Home
April 20, 2020

There are ways to bond with your team even when you only see each other over Zoom.


When I took a new job a year and a half ago that was 100% remote, I told myself I was going to gain a lot of productivity. However, I didn’t expect that I’d be losing something as well: namely, the ability to connect with my coworkers on a personal level. As many more of us have begun working remotely during the coronavirus pandemic, many managers may be coming to the same realization that I did.

My oversimplified view of remote work ignored a couple of key details. In the past, I would work remotely only one day per week at most. When I was only working from home for one day at a time, I could turn off Slack and email guilt-free and work heads-down. That’s not the case when you’re 100% remote. And more importantly, even if I thought I was going to be more productive, I wasn’t going to be around people. It wasn’t until I had been working remotely for three months that I started to realize how big of a problem this was becoming.

I spent the next year reading everything I could find on remote work and talking to the smartest minds in building remote teams. If you have questions about the nuts and bolts of remote management — running meetings, setting communication expectations, reporting best practices — read Remote by Jason Fried and David Heinemeier Hansson of Basecamp. It’s by far the best resource I’ve found on the fundamentals of running a remote team.

But honestly, the “work” part of remote work is pretty easy, and the early adopters of this work style have covered those best practices ad nauseam. Few experts talked about my problem — the people problem. As I thought about the differences between remote and co-located work, one thing kept standing out to me: Remote work is hard not because of a lack of productivity, communication, or coordination but because of the fundamental lack of trust it can breed when handled inappropriately.

When you work remotely, your coworkers can easily become two-dimensional (both literally and figuratively), and your relationship becomes more transactional. This degrades trust, and your brain starts to put coworkers in other, less generous buckets. Instead of putting your coworkers in the same categories as family members, friends, and cherished mentors, you are more likely to think of your coworkers in a negative light, ranging from annoyances to villains.

The disproportionate amount of work-related interactions could create a self-fulfilling prophecy.

Where your work-from-home biases come from

Your brain’s perception of one of your coworkers is tied to the sum of your experiences with that person. In person, you have a ton of friendly, casual, and nonwork-related interactions with your coworkers every day. You also have work interactions, which can be positive, negative, or neutral.

When you’re working remotely, you’re far less likely to have these casual interactions, which means that the percentage of interactions you have with every one of your coworkers will soon skew heavily into work-related territory. By its very nature, this means that the percentage of negative or stressful interactions versus casual, friendly interactions you have with your coworkers over time will likely increase.

The disproportionate amount of work-related interactions could create a self-fulfilling prophecy. The negative self-talk that “this person doesn’t care about me” can erode the relationship to the point where you as teammates no longer care about one another despite the fact that it wasn’t true to begin with.

This phenomenon is real, and it’s scary, and if you’re transitioning into remote management, it’s your responsibility to stop this pattern before it emerges. This is something I thought deeply about as I looked to hire and scale my remote team, and I realized that there were three in-office experiences that I needed to replicate if I was going to breed the culture of trust we needed to be successful.

This feels counterintuitive, but there are a ton of structural features that must be present for those serendipitous conversations with your coworkers to happen.

Creating serendipity to keep your coworkers three-dimensional

In an office, you probably walk in, sit down at your desk, and make some small talk while you get set up for the day. Then, you go get coffee and have some small talk with coworkers while you pour. Periodically, throughout the day, these nonwork interactions add up and help you form bonds with the people around you.

They’re not scheduled or planned. They’re serendipitous. These moments are incredibly important, but they’re the first thing to get cut in a remote environment. Instead of shooting the shit with your coworkers while you wait for the boss to show up to a meeting, you’re staring at a blank Zoom window that says, “Waiting for the host to start the meeting.”

Solving for this is hard because serendipity requires structure. This feels counterintuitive, but there are a ton of structural features that must be present for those serendipitous conversations with your coworkers to happen. You have to be in the same building, share a coffee pot, sit in the same room, or park in the same parking lot for those “chance encounters” to occur.

When you remove those structural features, you must replace them, or you’ll lose the serendipity they enable. And before you ask: No, shared Slack channels don’t solve this problem. (They do help with another problem, though. More on that later.) And no, asking about everyone’s weekend during your Monday morning standup will not solve this problem either. It’s way too small and transient an effort. So, what does work?

Scheduled, one-on-one, recurring, nonwork calls

Our team has tried implementing a dozen variations of friendly virtual chats, and most of those attempts have failed. This is the only solution I’ve found that works, and every one of those details is important, so let’s break them each down:

Pro tip: Scheduling phone calls during mundane daily activities (e.g., doing the dishes) can be a really great solution for both being productive and escaping work mode during these calls.

Finding your virtual ping-pong table

Okay, confession time: I’ve never worked anywhere without a ping-pong table. That actually includes my remote job because there’s a table in my basement.

Having a ping-pong table doesn’t magically create a fun company culture, but there’s a utility to the ping-pong table that I never understood until it was gone. Ping-pong was a centerpiece for relationship building that had nothing to do with work. It allowed people with different interests and backgrounds to bond over a shared experience, which then translated into closer relationships.

This is why I love going to sporting events with people who I’m just getting to know. By attending an event together, you have a built-in conversation piece. There’s no reason to fear awkward small talk because you can talk about the thing right in front of you.

Now, let’s go back to those one-on-one calls. Without some cultural centerpieces that you can anchor back to, you may struggle to find conversation topics. It may devolve into small talk about the weather and current events instead of an emotionally resonant conversation that brings you closer to the other person.

You need to find your virtual ping-pong table. More realistically, you need to find several because just like a real ping-pong table, there’s no one centerpiece that’s right for everyone. Here are a few shared, virtual activities you can do with other team members to bring people closer together:

Pro tip: Don’t do “virtual lunches.” We tried that, and it just turned into us watching each other chew food on Zoom. It’s awkward.

Giving high fives and head nods to boost morale

So, we were having regular one-on-one conversations with our coworkers about nonwork things, and we were using shared cultural centerpieces to bring us closer together. We’d almost completely bridged the gap between bonding in-person and bonding online, but there was still something missing.

In an office, when you walk past your work friends, you give them a head nod. When someone gets a win, you give them a high five. Those little interactions matter, and they’re really hard to replicate in a remote environment.

Slack is actually an amazing tool to solve this problem. I’ve read so many think pieces about the importance of gratitude in the workplace, and I agree with them. I created a #Gratitude Slack channel over a year ago, and since then, my colleagues and I have filled it with little things we’re thankful for, ranging from the hard work of others to things about our spouses and families.

Working from home takes adjustment, but if you add some structure to your work life to make up for the physical structure and proximity you’re losing, you can build personal connections, even in a remote environment. And who knows? Maybe you’ll never want to go back to the way things were.

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