How to organize IRL events for your remote team

How to organize IRL events for your remote team: tips by Headroom Executive Assistants

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Stand up paddling on Amsterdam’s canals, finding our Ikigai, learning about resilience in the workplace and tasting delicious wines from the Valpolicella region… What a week we had at Headroom!

As a remote and people first company, we always ask ourselves “how can we build an inclusive and engaging culture while ensuring a flexible work-life integration for the entire team?”

We’re sure that’s a challenge many other people-oriented companies face – especially after a two-year long global pandemic. 

That’s why we decided to get the whole team together at our HQ in Amsterdam for a week of learning and team building.

This was the first time since Headroom started expanding to the US that we organized something on such a big scale and IRL. Luckily, we’re an Executive assistance service! This means we have a team of admin pros and creative travel planners ready to step in and make sure everything runs smoothly and all details are taken care of.

Is your company organizing an IRL event with your remote team anytime soon? Read on and get inspired.

1. Bringing the team together in Amsterdam

With the team spread across two continents and multiple countries, the first thing to agree on was a meeting point: it goes without saying, Headroom headquarter in Amsterdam was the obvious choice.

What better opportunity for our remote team to get together where everything started, and learn a bit more about our unapologetic Dutch roots?

Booking flights & transports

What’s the most important thing when booking long-distance flights? Comfort. At Headroom we’ve been booking our fair share of trips and flight tickets for executives and we wanted to make our US team’s trip as smooth as possible. They were flying from different areas across the country: Texas, New York and Atlanta. When researching travel plans in advance it was important to find a non-stop flight, with a Comfort Plus seat to survive the eight-hour flight. Public transportation in the United States is not as great as Amsterdam, so prior to arrival, they were all set on Ubers.

“Throughout the week, me and the visiting colleagues commuted from/to the hotel in one Uber, which definitely helped with our bonding and connection. Next time we might try Dutch bikes!” shares Simone, one of our Houston-based Executive Assistants.

For our European colleagues living outside of the Netherlands, we arranged for a comfortable train ride the weekend before L&E kick-off. As these things usually go, a nation-wide train strike was announced for that same week. But that’s a story for another time!

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The Headroom team attending a workshop on making the Executive Assistant career future-proof. With EA coach Dana Venema.

Choosing The perfect Accommodation

Accommodations are everything when it comes to a week long vacation. Finding a hotel that includes breakfast, light-speed wifi and a lounge area to do work when needed was important when researching for our stay. The accommodation we chose also had a handful of resources in walking distance. In this way, we didn’t have to trouble calling an Uber for basic day necessities.

2. Welcoming everyone at the office

For the first time since opening, our HQ was set to host the Headroom team in (almost) its entirety. To mark this special occasion and make sure we could accommodate everyone, we went through the following check list:

  • Prepare a signing spreadsheet for everyone who will be at the office throughout the week. This will inform decisions like how much food and drinks to order, how many desks and monitors to set up…
  • Share a timetable of planned activities with the team
  • Test the wifi to ensure it can handle a full team connecting to it
  • Allocate an office host for each day. They would take care of opening up the office in the morning, and setting up lunch and lunch-break activities
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The Headroom Team attending a workshop on resilience and energy in the workplace

Arranging Lunch and dietary requirements

Fuel is everything and lunch is a perfect moment to get together and reevaluate the day. We placed a big, varied order of healthy food, drinks and snacks. The L&E team prepared lunch every day, with vegan and gluten free options so as not to leave anyone out. We also made sure that there was prepping and cleaning time scheduled to prevent any delays for the rest of the day. 

Ordering Equipment & props

To make every activity as engaging as it could be, the L&E team had to ensure all the right equipment and props was available. To do so, we put together a list of what we needed for each day and activity, along with quantity needed and projected costs. In this way, we made sure we didn’t go over budget.

We took care of:

  • A 90’s photo-booth created with fun props
  • The right AV equipment
  • Headroom gift bags for the entire team
  • Gifts and flowers
  • Tripod, microphones, ring lights & video equipment.

3. Helping each other

At Headroom, we’re organized in EA squads of 3-4 colleagues each. This allows us to share knowledge and workload, take over each other’s executives whenever needed and provide our members with a seamless, top-quality service.
During L&E week the squads showed an enormous amount of team work. For example, they made sure they took care of the executives of any team members who were off for personal reasons or PTO.

Setting expectations with members

When running a service company, you can’t simply pull the plug for a few days. In fact, we had to make sure we provided enough support to our executive members. While at the same time allowing the team to join our L&E activities.

The main goal was to communicate the importance and value of a learning and team-bonding week for EAs to members.

EA Simone shares that “during L&E week I informed my US members that I wasn’t going to be online at all business hours and not as responsive as usual. This was so I could attend the team activities. My executives were excited for me! I have a great relationship with them. So they encouraged me to take the time to enjoy myself and connect with my colleagues.

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Conclusions: would do it again

Our follow-up survey results speak for themselves! The team gave a whopping 8.5/10 satisfaction score. Moreover, we all shared the feeling that we’ve gotten closer with each other. Now we’re already thinking about how to make our next L&E week even bigger and better.

“L&E week was a great experience for me. I got to connect in person with people I chat with on a daily basis but never met face-to-face. This brought an unexplainable burst of joy. Since I made friendships with other EAs, I’m even more excited for the next L&E week!”

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