Working remotely has a lot of advantages, but it’s far from perfect. Here’s what we’ve learned in our journey as a remote team.

Note: I wrote this post years ago (as you can see from the comments), but it seemed like a good time to update it as so many companies adjust to working from home. I hope you find it helpful.

Headphones.

They were practically all I could see.

An ocean of big, round, silver headphones attached to silent, focused faces that hadn’t said a word all day.

When my last company grew big enough, we did what startups in New York were supposed to do.

We rented a big, trendy SoHo loft to give our team a headquarters.

It was a wide open floor plan that gave everyone the opportunity to talk to one another and collaborate seamlessly.

It was an opportunity that few actually took.

At around 9 a.m., employees would wander into the office, pour themselves a cup of coffee, sit down at their desks, put on those big silver headphones and get to work.

And they’d stay in that position for the whole day.

We were productive, and we got along really well, but anyone looking at the scene above would see an army of headphones getting little benefit from sharing a physical space.

When I started Groove, I decided to go in a different direction.

To forsake the office and build a remote team.

Over seven years later, I’ve learned a lot about remote work.

About working from a home office, managing a remote team, and building a business where the employees hardly ever see one another.

Working remotely doesn’t have to be temporary.

Whenever the world gets back to normal, some companies will decide that working remotely actually has a lot of advantages—for founders, leaders, and team members alike.

Choosing to stay 100% remote isn’t the right choice for everyone.

But if you’re at the same crossroads I was at in choosing which direction to go, or if you’re looking for tips on being a more efficient, cohesive and productive remote team, then this post is for you.

The Good: Pros of Running a Remote Team

1. We have access to more and better talent, faster

When it was time to start hiring, I tried to contain my initial push for developers to the area surrounding Newport, Rhode Island, where I live.

Asking for referrals

Unfortunately, I couldn’t find anyone with the skills, experience and intangibles that I was looking for.

As soon as I opened up my search to include the rest of the country, I found the right employees very quickly.

Our first two engineering hires were made within the next few weeks.

We now have team members from all over the world—including Australia, Germany, Spain, the U.K., South Africa, and six U.S. states.

As I write this from my standing desk here in Newport, the closest Groove team member is over 800 miles away.

2. Our employees have lives outside of work

Yes, we’ve struggled with burnout from time to time.

Remote workers are actually more prone to overwork rather than not working enough.

But our quarterly employee surveys say that our team is happy, and one of the things we all appreciate is the freedom to spend time doing the things that are important to us beyond our jobs.

Every day, we have a 10-minute check-in call with everyone from the team.

Our team checking in from around the globe

It’s optional, but most people attend most days.

It’s our chance to chat, learn more about each other, and build the supportive culture we all appreciate so much.

On Fridays we go a little longer to share wins, and we have occasional “Show and Tell” presentations where a team shows off what it’s been working on lately.

Aside from those, our team works when and where they want to. And we all have other commitments.

Most of us are married or in serious relationships.

Many of our team members have babies or small children (read: second full-time jobs).

Another is engaged to a nurse whose schedule changes every week. Their lives are made a lot easier by the fact that he’s able to work the same hours as her (sometimes, that means early mornings, evenings or weekends) and get time off when she does (usually weekdays).

Personally, I love living next to the ocean. On more than one occasion, I’ve stopped what I was doing, grabbed my board and headed out for some mid-day surfing.

The good life

Would all of these things be possible if we worked in an office?

Sure, there are a lot of people who make it work.

But not spending two hours per day commuting, and having the flexibility to work when you prefer sure does make it easier.

3. We can respond to “oh shit” situations faster

When our server disaster hit, we were definitely caught off guard.

But being a remote team helped us restore service when we did—and not hours later.

When we learned of the issue, we didn’t have to waste time waiting for our team to assemble at the office.

Everyone had everything that they needed to get to work right away.

Sure, with VPNs, practically anyone can work from anywhere if the shit hits the fan.

But if you’re accustomed to working together in an office, working remotely is a workflow disruption to your team on top of an already high-stress crisis.

We were lucky that, as far as collaboration goes, things were business as usual and we were able to move quickly and without interruption.

4. Our overhead is lower

Office space isn’t cheap.

Neither is furniture, or electricity, or business-level internet access (at least here in the US).

The costs of running a virtual team are minimal in comparison. Our “office” expenses are subscriptions for the SaaS tools we use to function:

Slack for constant communication: $8/person/month

Zoom for company meetings and customer demos: $14.99/host/month

G Suite for email, collaboration, and sharing files: $12/user/month

Trello for project management: $9.99/user/month

Calendly for scheduling: $8/user/month

Every dollar we save on rent is a dollar we can reinvest in the growth of the business and our employees.

The Bad: Cons Of Running a Remote Team

1. A great startup employee doesn’t necessarily make a great remote startup employee.

While the talent pool certainly gets bigger when you’re hiring from around the world, your hiring needs also change drastically.

We can’t just hire good startup employees, because we’ve found that that simply isn’t enough.

There are a lot of people who don’t have the organization, focus and motivation to be productive working remotely.

It’s not that they can’t. It’s just that they haven’t had to.

Successfully working from home is a skill, just like programming, designing or writing. It takes time and commitment to develop that skill, and the traditional office culture doesn’t give us any reason to do that.

We had some early hires—very talented people—not work out, only because they had never worked remotely before and we were unsuccessful at helping them develop that skill.

Now, we don’t just look for good startup employees, but we look for good startup employees with experience working remotely.

Everyone on our team has either worked on a distributed team before, or been a freelancer or entrepreneur in the past.

2. You have to work harder on company culture

There’s a lot more to startup culture than having an office. At the end of the day, culture is about shared values and goals.

But having everyone in one place makes it a lot easier to build that culture.

The more exposure team members have to each other, the more developed and defined that culture becomes.

Simply by virtue of being remote, that exposure is necessarily limited.

We’ve done a pretty good job at working on culture through close contact in Slack, team culture exercises, and ensuring that new employees are a good fit through trial periods before we hire.

An average day in Slack

But it’s still, and I suspect always will be, a challenge.

3. Communication gets harder.

With team members in different time zones and on different schedules, there are very few times when everyone is available.

Most of the time, this isn’t an issue.

Outside of our weekly call, our team primarily uses Slack to talk, as it keeps everything in one place and saves chat messages for when a user gets back online.

But sometimes, you need an answer now.

Maybe a customer needs an urgent fix and the developer you need is coding away in full-screen.

Maybe there’s a question about a blog post that needs to go out today, but the only person who can answer it is three time zones away and won’t be up for another two hours.

In an office, if someone isn’t responding to an email, it’s easy enough to stop by their desk and get what you need.

On a distributed team, that’s not really possible.

Of course, in a truly urgent situation, we won’t hesitate to call.

But for everything else, it means we have to be organized and diligent about tracking what we need from each other. And if getting that information or deliverable is an obstacle, we need to be able to switch tasks until we can get it.

It’s not the most efficient system.

While I think there’s a net positive impact on productivity from working remote, the communication barrier can, and sometimes does throw a wrench in the gears.

4. It’s (practically) impossible to transition to an office.

At this point, whether or not I was wrong about going the remote route doesn’t really matter.

Switching to an office-based team would mean either a) moving everyone to one place, or b) laying off the team and starting over.

We have an amazing team, and they’ve got deep roots all over the place.

Neither of those options are on the table now, nor will they ever be.

So in the practical sense, the fact that we can’t switch isn’t a challenge, since it’s not happening.

But it’s a challenge in that I always wonder whether it was the right move.

Would we have grown faster if our team was in one place?

Would we have been taken more seriously by press and potential business partners?

Would we have been more productive and efficient by working elbow-to-elbow?

We’ll never know.

We’ve Still Got (Remote) Work To Do

Although we’ve tackled a lot of the hardest challenges of working as a remote team, and reaped many big rewards from it, I’d hesitate to call us a remote success story… yet.

We’ve still got work to do, and much of that revolves around developing and protecting our culture and collaboration as we grow.

Some of the ways we’re going to be doing that include:

Retreats to bring the whole team together in person (it’s crazy to me that I’ve never actually met a couple of the people I work with).

More defined systems for onboarding new employees to our remote “office.”

Hiring employees in more time zones to improve our support coverage and development cycle.

I hope that our experiences help you make up your own mind about whether remote is the right way to go for your business, and if you’re a remote team, I hope you’ve learned something new.

This is an important topic to Groove, and we’ll keep writing about it as we learn new things and grow our team.

But first, I’m going surfing.



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