Our First Remote Company Off-Site: What Worked, What Didn’t, and What We’ll Do Differently Next Time

In the open-source community, when a problem is solved once it doesn’t have to be solved a second time. In that spirit, we wanted to share some of our learnings from our first-ever Flagsmith off-site in Amsterdam. 

We’re a fully remote team with employees across the world (spanning from London to Bolivia and from the US to South Korea). We decided to get everyone together because great things come from people being together in the same space. We wanted to meet colleagues that we’ve spent years working with as heads and shoulders in Zoom calls, just to check if they were all 7 feet tall. 

As is often the case with building a COSS (Commercial Open-Source Company), there’s no guidebook—that we could find—for getting a worldwide team together. There are a lot of things we wish we’d known before we started planning our first remote company off-site. 

What Worked

In short, it was totally worth it. It was amazing to realise that we’ve gone from two people pushing code in GitHub to having a global team on a boat in Amsterdam sailing down the canal. 

10 Minute Life Stories Were the Best Part of the Week

On day one, we all shared a 10-minute presentation about ourselves. People shared travelling photos, embarrassing outfit footage, family albums and stories about their lives. It was wonderful to meet each other as people—not just coworkers. 

You learn a lot about what’s important to someone when they have ten minutes and can choose what they’d like to talk about.

Working in the Same Room for the First Time Was Hugely Valuable

As a remote team, this was the first time we’d all been in the same space. This led to: 

• 100% alignment between teams—and within teams 
• Accountability to each team member (it just feels different when you’ve spent time together) 
• A tonne of ideas and momentum. So many ideas came from getting teams into the same space with undivided attention

Standups Are Just Not the Same—In the Best Way

We know each other as human beings now! Standups feel so much different as a result. Also, we know how tall we all are. 

What Didn’t Work

Visas and Travel are Depressingly Hard 

We underestimated how much work goes into getting people together from four continents. The logistics get real very quickly. Some hurdles we came up against: 

• Visas are tough - Choosing a location that would work for everyone was no small feat. One coworker couldn’t get through the visa process in time. One of us had to leverage local government connections from a previous job to get a coworker to the Netherlands. Simply put, it wasn’t easy. This was a wake-up call to those of us who had grown up in “the West” and had no real concept of how hard it can be just to get a travel visa.
• The flights were crazy expensive - Converging in Amsterdam from so many different places was not cheap! 

We Should Have Done More Location Research

One of our coworkers has a house in Amsterdam and it helped to have a central base to work from, lunch from, and meet at. 

There are a lot of logistics (and costs) that go into coordinating a travelling team. Next time, we’ll do more research into logistics and locations to make this process smoother. We might even look into a dedicated travel agent to manage these details.

Timeframes are Tough to Gauge

It’s hard to know how long to set aside for an off-site. We were coming from different corners of the globe so people had different jetlag levels. We wanted to set aside enough time for people to get over their tiredness and enjoy the perks of being abroad. We also wanted enough time to be productive, get momentum, and spend time with each other.

On the flip side, travelling takes up a lot of time; people also have lives and families back home that need to be considered, too. It’s hard to get the balance right.

What We Would Do Differently Next Time

Some things we want to try next time:

• Finding somewhere outside a major city - Staying in a major city can rack up costs fast. We’d like to try staying outside a major western city but with good facilities. We still need to figure out where to meet next!
• More agenda-setting - We had an agenda, but there was so much that came from each session that it was easy to run over and lose track of time. Next time, we’ll set a clearer agenda that leaves room for that. 
• Offer people to stay on - We’d like to create an official policy that lets people adjust their trip to add time before or after the work days. Some of the team travelled a long way, and this flexibility would be a good thing; we need to find somewhere cheaper for that to happen though!
• Use a travel agent - This would help a lot—both for costs and headache reduction!
• Work on the visa situation earlier - This process took a lot of time and was not straightforward. Next time, we will get a headstart on it earlier. We will also reach out to local officials to get the ball rolling and get immigration advice so we have a clear plan. 

Our first remote company off-site in Amsterdam was absolutely worth it. There are things that we want to do differently next time, and it was definitely a learning experience, but it was a huge win overall. We're already looking forward to our next gathering, wherever it may be!

If you're also building a company and have put together off-sites, we'd love to hear your learnings.