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What we've learned from being a remote first company

Kurt Schrader

Editor’s note: This is the second post in our Distributed Joy series. When we began to plan this series out earlier in the winter, we did not expect so many people to be put in a position where they’d be working from home by necessity; we simply wanted to share our own experiences building a remote first company. 

Things are different now, of course, and considering the spread of COVID-19, joy may seem like the wrong word to use when describing distributed work. Many people in the world are facing panic, fear, and illness; is this truly a time to talk about joy? We believe it is. Even in bad times — especially in bad times — it’s important to seek out joy wherever you can find it. Ensuring your employees and co-workers have a good remote work experience can, at the very least, keep from piling added stress on top of everything else. 

Lots of companies have suddenly become (at least temporarily) distributed this month. Shortcut is already a remote first company, but things have even changed around here as the folks in our New York HQ are now working from home too.

Our experience with remote work means we’ve had plenty of opportunity to learn what works and what doesn’t. We’ve succeeded. We’ve failed. We’ve gotten fairly good at managing teams spread out across the world. And we have a few tips here that we could have used when we were just starting out.

If you put any of these tips to use in your own org, remember to explicitly tell your teams and colleagues to do these things. More than once. Remind them. Remind them again. Be forgiving if they don’t immediately adapt. This stuff may seem obvious, but these are new habits that people need time to build.

Write everything down 

You can no longer rely on other employees overhearing something you’re saying and jumping in to add their perspective. Have most of your conversations in public Slack channels and within Shortcut Stories (or in your lesser PM tool of choice) so that your colleagues can see and engage with them. No one is going to overhear your good idea at lunch, at least not so long as lunch consists of eating soup on the couch next to your cat.

Every meeting is now a remote meeting

Every meeting invite should go out with a video conference link attached. If people don't have Zoom licenses, then buy them for them. If you don’t want to buy Zoom licenses, use Google Hangouts. Just ensure you’re set up to have a (fairly) reliable video meeting experience so that people aren’t wasting five minutes trying to get connected every time they meet. Record and share larger meetings if possible, so that information doesn’t end up siloed.

Make sure employees have the tools they need 

You need a good pair of headphones, with a high-quality mic. So does everyone else. If your company can afford it, provide them to employees. Straining to hear co-workers over the sound of dogs barking at mail carriers or garbage trucks crunching piles of trash is a good way to turn an otherwise valuable meeting into an exercise in frustration.

Related to the above, make sure that you have a good internet connection. Plug in to power and ethernet if possible. Regularly cutting in-and-out during a meeting is one of those little annoyances that can quickly become a big annoyance.

Set aside time to sync

Make sure that teams have set times to sync. Some of our engineering squads have a fixed time to check in on Slack everyday with what they're doing. Don't put people in a position where they feel like they're off on an island for days at a time.

Don’t rely on individuals to set up these meetings. Make it company or team policy and create a set schedule. If people begin to feel isolated, they may become even less likely to schedule meetings of their own, making them even more isolated.


Over-communicate and over-clarify. When you're all in an office together, people can ask their coworkers to clarify things that were said in meetings or come to you later for more information. They cannot do so in a remote setup unless they want to surprise you with phone calls over Slack.

When we were first getting started as a remote team we found it helpful to let people know (in a dedicated slack channel) if we were away from our keyboard during the normal work day. This became less important as we adjusted to asynchronous communication, and will likely become less important for you over time too.

Build more dashboards and radars

This is the perfect time to work on your dashboards and information radiators as a company. You can't walk over to people and ask for status updates anymore, so find ways to push information out about how things are going. Don’t assume anyone knows what’s going on and find ways to automatically make them feel connected and informed. This will be valuable even when your company returns to business as usual, since it’ll continue to make employees feel more connected and informed even if they’re in the office every day.

There are a lot more small things that make remote work easier over time, and we’re going to continue to talk about them in this series. Let us know if you have any questions or have any tips of your own.

As always, we’re here to help. And also to project manage. But mostly to help.

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