How to do remote work right, from the teams that know it best

What are the most important things to get right about remote work? What needs to be prioritized?

With more and more teams being thrown headfirst into remote work, I spent a few weeks talking with some of the people who know the topic better than just about anyone: the founders and execs who’ve put countless hours into making remote work … work.

Some of these companies — like GitLab, Doist, Zapier, Mattermost, FlexJobs and YouNeedABudget — have been working fully remote since their earliest days. Others, like Twilio, had been partly remote for years but found themselves shifting gears to expand remote work to a team of nearly three thousand people.

Looking for the highlights? I’ve pulled out some of their tips and collated them below for easy reading. Want the full interviews? You can find those here:

Write down everything

It was probably the thing I heard most from all of these teams: Write. Things. Down. Make it a habit.

Outline your company values. Document decisions — and how decisions are made. Take meeting notes. Track project progress publicly, and keep roadmaps transparent.

“One of our biggest core values is communication, and especially written communication,” says Doist founder Amir Salihefendic. “People really need to be good writers; they need to be able to convey ideas well. It doesn’t matter if you’re a designer, or a developer … we have a ton of content. Internally, everything is documented.”

Writing things down by default keeps everyone on the same page and helps teams work across time zones with fewer misunderstandings and less work duplicated accidentally.

“You have to make sure that you’re documenting your work, you have to commit to writing things down.” Zapier CEO Wade Foster tells me. “You just have to write this down, you have to document that, you have to share this out. And you have to commit to that discipline, otherwise it doesn’t work.”

“Context, in a remote company, is probably the most important thing,” according to Mattermost CEO Ian Tien. “You can’t just go and say, ‘Let’s figure this out over lunch’ … you have to provide really good context, all the time, so that people can align.”

Have a hub for key information

All those written things need a home.

Some teams build special tools just to keep track of their documents. Others use Notion or Dropbox Paper. Others just have a big ever-evolving Google Doc of links to other Google Docs.

Whatever you use, you need somewhere that your team can turn to to find the latest information on any given topic without digging through Slack. When major events happen — like, say, a pandemic that completely changes your team’s workflow — give people a place in the documentation to find all of the key details immediately.

“We have a Google Doc inside the company,” Twilio CEO Jeff Lawson tells me. “It’s essentially our COVID-19 status page. And there’s a change log. So every day, any new things that are arising … there’s a daily change log at 5 p.m. Pacific. Everyone knows that is one place you go, just leave it up in your browser, and go back to it to see what changes there are.

Embrace Async

Beyond just keeping everyone on the same page, writing everything down also paves the road for a more asynchronous workflow — one in which people can work (and respond to emails/messages) on their own schedule, rather than feeling like they have to be always online and always responding instantly. It helps to grow your potential hiring base by making it easier to work across time zones. Even if your entire team is in the same city, it can help to make people feel less tethered to their screens. Making people feel like they can never disconnect is a quick path to burn out.

Not all work can be done asynchronously. In case of emergencies (like, say, your server is down or your site is getting hacked) you probably want the relevant folks all online. But a lot of things don’t have to happen in real-time. Maybe the product feedback session works well enough over a Zoom call … but would it work just as well (or better!) in an email thread where people have time to really think things through?

Going async is a company-wide shift: The person receiving the message has to feel like they can answer at their convenience, and the person sending it has to know an immediate response isn’t guaranteed. Consider reserving immediate methods of communication — like direct, out-of-the-blue phone calls — for emergencies, so the person on the receiving end knows when the phone rings, it’s going to be important.

“It’s basically a pyramid,” Salihefendic tells me. “At the top, we have phone numbers of everybody. I’ve actually never used the phone numbers to call anybody — but in extreme cases, we have phone numbers and can call people. We also have a Telegram group that I use … This is our ‘red alert’ — like, ‘You need to come online right away.’ This is used a few times per year, I’d say.”

Iterate to find what works best

If something isn’t working about your workflow … change it! With more teams going remote than ever, more and more companies are focusing on building tools just for remote work. Sometimes what works today with a team of five won’t work nearly as well when you’ve grown to a team of one hundred, or two hundred, or three thousand.

“The one thing I’d say is it’s about iteration.” Tien tells me. “When you go remote, some things are going to work, some tools are going to work … but you want to change them and get better.”

Consider trying new tools with just a handful of folks at first to figure out their strengths and weaknesses; if it seems better than what you’ve got, you can shift everyone else over later.

As you grow bigger, consider building tools in-house that fill gaps your team sees.

“The more you can customize what you do and make it your own and make it really fit what you need it to do — it really helps you accelerate,” says Tien.

Hell, sometimes the gaps you see are ones that plenty of other teams have as well — and ones they’ll pay to fix. Doist built Twist in-house when they couldn’t find an asynchronous communication platform that fit their needs. Now it’s one of their main products.

Don’t be afraid to undo what doesn’t work

Doing a test run with a handful of people helps weed out pain points, but sometimes issues don’t rear their heads until you bring more people into the mix.

Once you’ve made the decision to move to a new tool, it’s easy to feel locked in to it. Yeah, maybe it has some issues … but you’ve already switched everyone over. Won’t they be mad you wasted their time?

Consider how much time you’re wasting by pushing them to use a tool that just isn’t working out. Be mindful not to stick with changes out of stubbornness or pride.

“We like to use the term ‘two-way door,'” GitLab’s Darren Murph tells me. “If you make a change and it sucks … revert and try something else! It’s a two-way door. We try to do things that are two-way doors; before we press “Go,” do we have the ability to walk back through this thing if it sucks? Do that.”

Understand that no one is running at top speed right now

Absolutely nothing is normal right now … so we probably shouldn’t be gauging anyone’s performance as if it is.

“Know that everyone’s dealing with a lot of crazy shit right now,” Lawson tells me. “We have to roll with what we have and do the best we can … but first and foremost, treat our people well and look out for the welfare of our people.”

“I think the biggest thing we do is listen, pay attention and recognize plans may change,” he adds. “That’s just the nature of the world right now.”

The editorial team of TechCrunch has been largely remote for many years … and even in our case, nothing is normal. Parents have kids at home. People have medical issues that are harder, and scarier, to address in the middle of a pandemic. People are marching in the streets for justice, and just want to find ways to improve the world around them. It has to be acknowledged that nothing is normal right now, and that has to be okay.

“Think about the context around us,” says FlexJobs CEO Sara Sutton. “If everything is optimal, I want to be an A-player every day. I even would like to be an A-player when it’s not optimal! But when it’s really suboptimal, when it’s pretty darn hard … and you know what, you’re still performing pretty well? In my book you’re an A.”

Give new people buddies and time to settle

Joining a new team can be tough. Doing it when you can’t actually meet anyone is even tougher … especially for folks who’ve never worked remote jobs before. You’re diving headfirst into a whole new work flow and into a team with established relationships and inside jokes aplenty. How do you catch up? How do you ask questions without feeling like you’re distracting everyone?

GitLab’s Darren Murph tells me they use a buddy system to make for a smoother landing.

“Everyone at GitLab gets another person from the company, outside of their department, to join them as a dedicated one-on-one contact through their whole [onboarding] journey,” he tells me. “This person shares their Zoom link and their Slack, and the new hire has full permission to ping them as many times as they want so that they’re only ‘bothering’ one person.”

“This person connects all the dots for them,” he adds. ‘It makes [the new hire] feel like part of the team and it also lowers their anxiety. They’re not like ‘I don’t know who to reach out to … do I just spam the whole Slack channel?’ Like, no, just go to this one person.”

YouNeedABudget uses a similar buddy system, and founder Jesse Mecham tells me that he encourages people to take their time catching up.

“I also try to tell them not to worry too much about getting up to speed really fast or doing something superhuman,” he says. “Once we’ve hired them, we know they’re right. They’re not on trial anymore. They’re not trying to prove themselves; they’ve already proven themselves. They can relax and just know they’re part of the team and we’re in this for the long haul.”

Pick the right communication platform for each purpose

Of all the tools used by remote teams, the best known is probably Slack.

Slack is great for a lot of things; it can help make a team feel more connected, and seeing coworkers chatting away can make people feel a little less alone. The direct messaging system is also great for quick, casual, one-on-one (or small group) conversations.

But don’t make the mistake of feeling like you have to use Slack, or Microsoft Teams, or any other real-time chat platform, for everything. These chat systems have their weaknesses; amongst other things, it’s easy to leave for an hour or two and come back to a wall of text and a million notifications spread across a dozen channels, the key bits you actually need to know buried within a billion GIFs. GitLab, for example, specifically uses Slack solely for nonwork stuff; if something is “work,” it gets started (or moved) into their internal, purpose-built tools.

Figure out what tools work best for the different types of communication your team does, and divvy it up accordingly. It can feel weird to use multiple different platforms and a handful of apps just to talk — but eventually it becomes second nature. And if someone starts something in the wrong place or a topic evolves into something bigger on the wrong platform? That’s okay! If you use Slack for casual chat and say, Yammer for longer, threaded “actual work” topics, make it normal to bump a conversation from one platform to the other.

Like most things remote work, what works will change as you grow. It’s easy enough to use chat for everything with a team of five people. With a hundred? Less so. 3,000? It’s just a big pit of noise.

And remember: Not every topic needs to be a meeting, and not every meeting needs to be via video chat. It’s nice to see your team’s faces … but being on video all day can be exhausting. People like to mill about, or do their thinking without feeling like all eyes are on them. Consider sticking to voice only sometimes.

“It’s something to consider, because you hear a lot more [on the phone]. There’s less distraction. And there’s something really valuable about the phone,” says Sutton. “I’m trying to encourage everyone who is a little overdosed on video to remember that there’s other mediums of communication.”

And for teams that eventually do start returning to the office, one final bit of advice that I heard from just about every team I spoke with: If anyone in a meeting is remote and joining via video, act as if everyone is remote. Give everyone their own camera view, rather than putting five people in a meeting room with the sole remote person dialing-in. It puts everyone on equal footing, with the same opportunity to speak, hear and be heard.