We worked remotely for a month and lived to tell the tale

by Jobbatical October 20, 2016

Um… Where did everybody go?

It’s just another day in the office. At the desk next to you is the comforting presence of the lady from HR with the great hair. People are laughing in a meeting room. You wish you’d been there to hear the joke, but it’s OK. It can’t have been as funny as that thing you said in that meeting that other time. All is well with the world…

…and then everyone goes away.

Cue tumbleweeds and Western music. Photo by elgad via Shutterstock

In September, team Jobbatical was scattered across the globe more than is normal even for us—startups, am I right? Now, as far as I’m concerned, remote work is all very well—for a week here and there, if it’s nice weather and newt season. But a totally distributed team? A month of trying to keep track of who’s in San Francisco and who’s in Sydney?


Well, people do it all the time, I thought. It can’t be that bad, I concluded.

“What’s the worst that could happen?” — someone, seconds before this happened. Image by muratart via Shutterstock

It’s October now, so it looks like I (and the rest of the gang) successfully made it through Remote September. The world didn’t explode (at least not literally). Work got done. Lessons were learned; discoveries were made.

Curious to find out how the rest of the team felt about it, I sent out a survey. The results reflect a truth (almost) universally acknowledged: remote work is great… in moderation. And it can throw a bit of a spanner in the works if you’re not careful. Here’s some wisdom from team Jobbatical—now seasoned remote working veterans—distilled from the survey results:

You gotta have a system

If your team is new to large-scale remote working, things will almost certainly be weird for a while. Before everyone takes off for their location of choice, make sure you—as a team—have the necessary structures in place to deal with it.

The more established (and firmly written down in easily accessible places) your team’s processes and practices are, the less emphasis you’ll have to put on instant responsiveness. This will take the pressure off big time, and you can expect to wake up to fewer messages of “X happened! What do we do?” because the team will know what to do if X happens while you sleep.

To oversimplify, you should be aiming for the “We have a Google Doc for that” approach and beyond.

Your communication is bad and you should feel bad*

There are a million creative ways in which humans can screw up their communication. We’re famous for it. We literally can’t stop misunderstanding each other and making all sorts of assumptions that make sense at the time.

When you communicate in writing, make it count. If someone’s been waiting for your reply half a planet away and is asleep by the time you respond, give them more than one bare-minimum syllable. You’ll save everyone the trouble of going over the same question again by being clear and thorough in the first place.

Slack, email, and all other forms of written and visual communication are undoubtedly a remote team’s bread and butter, but sometimes you just need to speak to people to understand what in the world they’re going on about.

So call them, maybe. Even if you don’t feel like it, just make more calls.

Yes, you’ll have to go through the whole “Can you hear me? Hmm, hold on. It was working fine this morning.” ritual more often than you might like. But it’ll pay off.

*I’m not trying to be a jerk; that’s a Futurama reference.

Those expectations aren’t gonna manage themselves

Adjusting your schedule is an inevitability when you’re dealing with multiple time zones. While this could mean early mornings and/or late nights, it can also mean longer breaks during the day. So much time for activities! The danger lurking here is the potential for misunderstandings about when things are getting done.

The pins we dropped over the course of September. That’s, like, at least SEVERAL time zones. (I’m bad with numbers)

Let others know when you’re going to be off the grid, and when you can be expected to be at your most productive. As nice as it is to live spontaneously, you owe it to the collective sanity of your team to keep your calendar as organized as you can, wherever you are.

Getting an early start on Friday so you can take off early for [insert exotic activity here]? On a plane all day and planning to catch up on work over the weekend? If you work at a startup, that’s probably going to be fine. But not if it’s a last-minute surprise. That’s not the fun kind of surprise. If you like surprises, send a fruit basket.

It’s all about dropping the F-bomb

I’m talking about freedom, of course. This is the one that really makes remote work worth it. In the “What’s the best thing about it” section of the survey, freedom was the most used word by far. As one team member put it: every evening is a holiday when you’re working remotely. But enough paraphrasing. Here’s what the people have to say:

“I love setting my own hours and not being constantly distracted.”

“Discovering new places, being inspired by new smells, new scenery, new and exciting lunch options.”

“I can choose my own distractions.”

“The freedom to see the world while remaining a productive member of society.”

“The flexibility of remote work makes me much happier as an individual. This, in turn, generally helps my work.”

Nobody mentioned this specifically, but there’s also the freedom to dress in a chicken suit: a Jobbatical chicken at Disrupt SF in San Francisco, CA. Although, granted, this was work-related. So #dontbeachicken and take a jobbatical!

Want to join our team? We’re hiring! Want to check out other cool teams to join across the globe? Head this way!

Got tips for working effectively as a distributed team? Leave a response!

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