Cultivating a thriving remote culture: Lessons from a decade of remote work

Maintaining a company culture when everyone is co-located is hard. Doing it remotely is even harder. But it's far from impossible.

As someone who's been working on remote teams for the past decade, here are some things I've learned about how to keep remote culture great. Hint: it starts with leadership.

Remote companies need the right employees

Let’s be honest, for a lot of people, remote work seems ideal. They'll have some autonomy not always afforded in an office environment, freedom to work hours that are more conducive to their lifestyle, and pants aren’t (always) required.

But is it right for everyone? Probably not. It takes so much self-direction and self-motivation to do remote work well. And if this isn't something you're heavily screening for during the interview process, it could end up in unhappiness for both sides. Obviously, previous remote work or independent work is ideal, but you won't find that in every candidate. So you have to make work expectations clear: yes, they'll have some work flexibility, but they can never miss meetings, and they'll still have to work a full day, they need to be in frequent contact with their team, etc. Speaking from personal experience, my previous company, Compose, took a chance on me. It totally worked out.

When new people do come on board, you'll need a way to make work visible. Allowing people to work silently in the dark can be a nail in the coffin for employees and your company. At Vercel, we gave everyone an onboarding buddy to help navigate working at Vercel and get used to how we work, and helping them find an advocate with in the team.

Companies also need to decide if remote is right for all positions. Even in a remote-first company, there may very well be a geographical need to mind. If you have a tech salesperson, it’s pretty important that salesperson live somewhere near a tech hub. Does your management team need regular meetings to hash things out? If so, they need to be in compatible time zones.

These are things to consider to make sure your culture works.

Communication is key

In an office, employees gather around the water cooler, grab lunch together, go out for events or drinks, and have opportunities for less formal communication with one another.

In a remote-first or remote-only environment, those water coolers don’t exist. You have to create a way for your team to chat. When you work remotely, Slack becomes your virtual office. I've had Slack Workspaces with a #team-chat channel for the team to talk, #misc channel for random junk, #music channel for sharing music, #coffee for coffee snobs to talk and show off, and #standups for daily standup checkins. And we used them. Not only that, I invest heavily in adding emoji reactions and having a good gif on the ready.

These kind of channels give your team a place to connect with one another based on common interest, not just because they’re on the same team. It’s a great way to breakdown silos that naturally pop up.

Willing to try (and fail)

When something doesn’t work, the team has to be ready to have tough conversations, come together, and shift focus. You can’t do that without taking chances and being willing to fail. An idea may sound amazing on a call; when implemented, it may be just as awesome, or it may fall short. You don’t know until you try.

When I was at Vercel, we were big Notion users. We tracked our projects outside of Notion in GitHub. As we grew, we hired people who weren't use to GitHub or markdown. We moved to Linear for tracking and played to our strengths - we would document everything in Notion and link to it from Linear. It was great. But we tried a few things before landing on this workflow.

No substitute for face-to-face

Tools like Slack or Discord make communicating remotely so easy. We can get real-time feedback, collaborate, and get ideas right when we need them. But if that’s the only way we communicate, we’re going to fail at building relationships, our teams, and our culture.

I find it important to make video chats mandatory for meetings, and to use Zoom or Google Meet just to talk casually now and then. I've worked places where we were connected with a random employee for a coffee chat. I got to meet people I may otherwise not work with. Shortly after I joined Serverless, one of my teammates invited me to a 1-on-1 video chat just to get to know one another. I've chatted books, weight lifting, Christmas, the arts, friends, family, movies, music, hometowns. I made some friendships in these calls that have lasted for years.

On a more “business” level, successful teams have all had regular All-Hands meetings to hear from leadership about how the company is performing, updates that affect the team, and callouts from different parts of the company. I also schedule weekly 1:1 calls with each member of my team and with my boss to checkin. These meetings belong to my team - they build the agenda, telling me what they've done that they're proud of, where they need help, and anything else that's important to them. We'll then haev a team-wide call at least bi-weekly. During our All Hands, every team member builds a slide where we share some good things that have happened in our lives over the last two weeks and any challenges we’ve faced.

All of these things are great when it comes to building a team, but nothing replaces team retreats.

Most teams I’ve worked on had meetups. At Compose and Serverless, we had company-wide offsites in places like Portland and Lake Tahoe. At Influx, we paired team get togethers with events we were hosting. At Vercel, we did smaller, team-specific meetups. What was common across all of these companies was our goal – to both build meaningful connections with our team and plan. We would strategize, refine or rethink our objectives, prioritize projects, and build a shared vision for how we all helped grow our business. We also have team building activities like Battle of the Air Bands, and down time to sit and chat over a meal. We get the chance to visit and share with each team member, and develop real relationships that help us to better understand who we’re working with, what’s important to them, and how to better communicate. We would always leave with a clear plan for what’s next.

Feedback is a must

One last thing to think about when building and maintaining a culture with a distributed team is giving everyone a way to provide feedback. I read a book that I liked called Radical Candor. It had some great ideas. I've seen it work and I've seen it fail. For it work, everyone has to be committed to hearing and learning from feedback. That means management and employees. By giving room for honest feedback, you build trust and will have a culture wh open dialogue between all levels of the company.

To make this work, you need buy-in, and wholehearted participation, from the leadership. Companies succeed when they take feedback from employees on what is working, what isn’t, and what could be done better. Teams succeed when managers listen to what employees need. It helps everyone. And that feedback must be acted on. When leadership listens, everyone feels like they have a voice and a stake in the company, which pushes each person to do more to guarantee success.

A remote-first culture isn’t easy to define, is tough to build, and takes constant nurturing to maintain. But at the end of the day, you have the opportunity to work with people from around the world, with diverse backgrounds and viewpoints, all coming to together to make what you’re building that much better.