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Disasters or Dreams: How Does the Size of Your Team Affect Remote Work?


With the rise of remote work (which is well documented by how much platforms like Workfrom are growing!) situations like mine are becoming so much more widespread.

I work for Deekit, the world’s most collaborative online whiteboard for remote teams. We’re a small, remote-friendly team. We are super flexible about work too and understand that people are most productive in all sorts of ways. This kind of approach is allowing me to be on the island of Koh Phangan in Thailand while most of the team are in Tallinn, Estonia!

I see first hand that people are working in teams of all shapes and sizes on the road. From freelancers to creative teams to businesses with several hundred employees. People from all walks of life are making the be-productive-anywhere lifestyle work for them.

But what makes our experiences different? Does working for a smaller startup change remote work? Or do distributed employees in larger organizations have a similar experience?

Let’s dig in.

Teamwork always makes the dream work, regardless of how big you are

Despite our team at Deekit being eight people strong we often work with external stakeholders, increasing the size of our team. On the other end of the spectrum I work 1-on-1 with team members on specific projects. It’s the same across all companies. Regardless of team size or structure, we’re all using similar business tools like Slack, for example, to communicate instantaneously.

The core needs of a remote worker are the same

Stable internet and a workplace that meets whatever criteria we have. It’s pretty simple, but we all have the same requirements to some extent. Everyone’s idea of the perfect workspace is different. For me, it’s an office while for others they love nothing more than curling up in the corner of a coffee shop. But we all need the holy grail of remote work—a stable internet connection!

Smaller remote teams can afford to be more flexible

When there are fewer people to organize, you have increased flexibility. Because our team is small, we don’t feel bad moving things around by an hour here or there. It’s pretty typical for us. I can imagine that larger teams lose this sort of flexibility. As in any business, more moving parts mean more organizational backbone needs to be in place. That’s not saying smaller remote teams are unorganized, but if a little adaptability is required, it’s not the end of the world for us. On this count working in a smaller remote team wins hands down.

Job types makes a difference

On my travels I’ve met some interesting remote workers. Apart from pushing communications for releases, my role as a growth marketer is relatively fluid. I can work whenever I’m most productive without a set time. However, I’ve met systems engineers and customer support folk who have to be around at certain times. Interestingly, most of them have worked for larger organizations. In smaller teams, I’ve seen everyone being a little more hands-on in different departments. We chip in all over the place.

Unusual work hours are a part of everyday life for us all

Despite the differences, we all have to work some odd hours occasionally. I’m currently four hours ahead of most of my colleagues, so it’s not too bad. But I’ve got co-workers in Beachub, the co-working space I’m in right now who are working with associates in the US. A 12-hour difference pretty much means a reversed work schedule. Calls at 2 AM? Sometimes they’ve just got to be done!

We all have to communicate like pros

There’s no way of getting around this one, regardless of the size of your team. To make remote work viable, you have to communicate like a pro at all times. It sometimes means over-communicating. Things feel even more transparent online; everything is traceable. If you mess up, you can’t hide, and if you make incredible progress, you should tell others about it and share it. It doesn’t matter what your company looks like; it’s crucial you consistently communicate!

In conclusion…

In my opinion, the size of the business you work in has some impact on remote work, but for the most part we all share many of the same benefits and problems. Every remote worker I’ve spoken to has a different scenario. They all seem to have different ways of working in their respective companies and work arrangements. But we all need reliable internet, a good workspace and a steady supply of coffee—or maybe that’s just me!

To learn more about the world’s most collaborative online whiteboard, visit us at Deekit.com. You can use code DEEKITLOVE to get $10 off any of our plans if you want to get more out of your whiteboards too!


  • Thanks for the feature guys! 🙂

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