The Extrovert’s Guide to Working From Home

Hi. My name is Tim and I’m an extrovert.

When I say extrovert, I mean extrovert. I make golden retrievers look shy around new people.

All of the best moments in my career have come when I’ve been surrounded by awesome teammates I could collaborate with. All of my worst moments came when I felt isolated or on an island. I’m self-aware. I know what feeds my energy and passion. It’s about people, plain and simple.

That’s why so many of my friends and family members were puzzled a year and a half ago when I took a job that was 100% remote.

“It’s okay,” I told them. “I have always gotten the most done when I work from home. I’m going to be so efficient!”

This over-simplified view of remote work left out a couple key details…

1. In the past, I would work remote for one day per week at most, meaning I was still in-person with my teammates 4 days per week.
2. When I was only working from home for one day at a time, I could turn off Slack and email guilt-free and go heads-down. That’s not the case when you’re 100% remote.

The larger issue, however, was obvious to everyone but me… I wasn’t going to be around people. It wasn’t until I had been on the job for three months that I started to realize how big of a problem this was going to be.

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 remote work have covered those best-practices ad nauseam. Few early-adopters of remote work talked about my problem… The people problem. So, I had to create my own playbook.

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.

To understand why that’s the case, let’s start by thinking about the basic fundamentals of human relationships.

Our brains use mental models they’ve established throughout our lives to bucket the people around us based on the sum of the experiences we have with that person.

This is why “love languages” are so powerful. If your parents showed you love by buying you a new toy unexpectedly, you’ll be more likely to respond with affection when a co-worker who brings you a memento back from their vacation. Your brain is bucketing them in the same category as your parents as a mental shortcut. As a result, you’ll be more likely to trust them. You’ll give them the benefit of the doubt more often. Hell, you’ll probably accept more criticism from them without degrading the relationship. After all, your parents criticize you sometimes, but it’s out of love, right?

Now, what happens when those micro-expressions of affection are harder to come by?

Your co-workers become two-dimensional, both literally and figuratively, and your relationship becomes more transactional. This degrades trust and your brain starts to put co-workers in other, less generous buckets. Instead of bucketing your co-workers in the same categories as family members, friends, and cherished mentors, your brain more closely acquaints your co-workers with negative mental models, ranging from annoyances to villains.

But here’s what’s wild… Your brain is doing the rational thing.

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

When you’re working remote, you’re far less likely to have these casual interactions, which means that the percentage of interactions you have with every one of your co-workers will soon skew very heavily into work-related territory. By its very nature, this means that the percentage of negative interactions you have with your co-workers will increase dramatically.

So, if your brain’s perception of your co-workers is tied to the sum of your experiences with that co-worker, and 80% of your interactions are related to a work objective, you’re going to feel like that’s a pretty transactional relationship. You both will feel like the other person only cares about that business outcome, not about you as a person. This will likely cause both of you to be a little more closed-off with the other person, which will erode trust further.

Before you know it, a simple ratio: the percentage of interactions that are work-related versus non-work-related, 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 very 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:

• Serendipity and small talk
• The ping pong table
• High fives and head nods

Creating serendipity to keep your co-workers three dimensional

Close your eyes and think about the co-worker who sits next to you… Who are they? What do they like? What do they dislike? Are they more energetic in the morning or in the afternoon? Do they like going out for lunch, or do they eat lunch at their desk? What do they do on the weekend? What sort of interactions get them excited? What sort of interactions demotivate them?

If you work in an office, you probably have pretty good answers to all of these questions. In a remote environment, these questions get a lot harder to answer, and it’s not hard to see why.

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 to get coffee and have some small talk with co-workers while you pour. Periodically, throughout the day, these non-work interactions add up and help you form bonds with the people around you.

They’re not scheduled or planned. They’re serendipitous, and to the untrained eye, they look like magic.

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 co-workers while you wait for the boss to show up to a meeting, you’re staring at a blank Zoom window that says “Waiting for host to start the meeting.” Alone. In isolation.

Solving for this is hard because serendipity requires structure. This feels counter-intuitive, but there are a ton of structural features that must be present for those serendipitous conversations with your co-workers 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.

BEFORE YOU ASK:

• No, shared Slack channels don’t solve this problem. (They will solve a different problem later, though.)
• No, the Donut bot will not solve this problem. (It doesn’t mirror how we behave in real life, unless you spin a wheel every day when you show up to work to see where you’re going to sit.)
• No, asking about everyone’s weekend during your Monday morning standup will not solve this problem. (Way too little. Gotta work harder than this.)

So, what structural features can we put in place to enable more serendipitous conversations?

Scheduled, 1:1, recurring, non-work calls.

Our team has tried a dozen variations of “virtual people time” and most of those attempts have failed. This is the only solution I’ve found that works, and every one of those words is important, so let’s break them down one-by-one:

• Scheduled: “Show me your calendar & I’ll show you what you value.” If you don’t put it on the calendar, it won’t happen. Plain and simple. Furthermore, don’t schedule these at times when you’ll be focused on something else. These calls never work if you or the other person is thinking about your big client meeting in 30 minutes.
• 1:1: Group calls are really hard. There’s lag, you can only hear one person at a time, and people aren’t as vulnerable in front of groups as they are individually. 1:1 works well because you can, to borrow a phrase, stop being polite…and start getting real.
• Recurring: If you don’t make these meetings recur on a regular basis, you’ll forget about them. Your cadence shouldn’t be the same with everyone… Direct reports and close colleagues may be a weekly call whereas someone in another department that you don’t work closely with may only happen monthly. Regardless, make sure they’re set to recur so you don’t forget.
• Non-work: ABSOLUTELY. NO. WORK. TALK. ON. THESE. CALLS. If you’re talking to your direct-report, this rule is EVEN MORE important. If you’re spending 30 minutes on this call, you have to make up for an entire week’s worth of lost interactions. Make this time count. If you use this to check-in on projects, you’ll undermine what makes it work.
• Calls: Video or phone both work fine, but no Slack. This can’t be over text. This has to be a conversation where you hear a real person’s voice.

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. Here’s what I’ve got: I’ve never worked anywhere without a ping pong table. That actually includes my remote job, because there’s a table in my basement.

I’ve talked at length about how having a ping pong table doesn’t magically create a fun company culture, and I still believe that’s true, 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 1:1 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:

• Play video games together online while talking on the phone. Some of our favorites include Killer Queen Black and Mario Tennis.
• Host a “virtual coffee” or “virtual happy hour” where everyone brings a beverage of choice. Preferably they should take the video call somewhere that’s NOT their home office. Change of scenery can be a conversation starter.
• Watch a movie, TV show, or other video together and live-stream your thoughts in a Slack channel.
• Play online games/apps together asynchronously. (e.g. Words With Friends)
• Host a virtual book club.
• Set up a #Pets-of-[COMPANY NAME] Slack channel and post pictures of your pets regularly.

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 really weird.

Giving high fives and head nods to boost morale

So, we’re having regular one-on-one conversations with our co-workers about non-work things and we’re using shared cultural centerpieces to bring us closer together. We’ve almost completely bridged the gap between bonding in-person and bonding online, but there’s 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.

Here’s a list of my favorite Slack tricks we’ve used to boost morale:

• Create a #Gratitude Slack Channel: 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.
• Use Zapier to Automate Positive Events: This is really common, so your team is probably already doing this to some extent, but it’s even more important when you’re remote. When a meeting is booked, have it push to a Slack channel. When a new deal closes, have it push to a Slack channel. Invite the whole team, especially those in other departments that may not see the inner-workings of what your team is working on.
• Assign Team Members a Doppelganger or Thematic GIF: So, this started on accident and it’s now my favorite thing. My first hire for my team looks EERILY similar to Jack Black, so I told him for every meeting he booked, I would post a Jack Black GIF in our #sales-prospecting channel. My second hire looks EERILY similar to Conan O’Brien. Rinse and repeat. Next thing I know, the team had started assigning doppelgangers for everyone, and would post GIFs of that celebrity any time they got a win. It’s SUPER fun and adds some personality to celebrations that emojis can’t capture.

Pro Tip: Use Giphy with caution. If you accidentally send the wrong GIF, you could get HR called on you fast.

So, fellow extroverts, take heed.

Working from home is an adjustment and, if you get your energy from other people, it will require changes for you to adapt. You will need to introduce some structure to your work life to make up for the physical structure and proximity you’re losing, but if you think about the problem systemically, you can strike a great balance.

• Build in structured 1:1 calls with teammates to talk about non-work stuff. If you can, plan these for times you’re doing other activities like washing dishes or cooking dinner. The less formal, the better.
• Create cultural centerpieces for your team that allow people with different interests to come together and bond over something they can share.
• Find unique ways to celebrate wins and give your team high fives for hard work. The weirder and sillier, the better. Also, show some sincere gratitude for good measure.

If you do those things, it may not matter how extroverted you are, you’ll thrive in a remote environment. Who knows? Maybe you’ll never go back.

What questions do you have about managing remote teams? Tweet at me and let me know.

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