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Organising a Company Retreat For Your Global Remote Team

This April, our ShieldGeo team come together in Phuket for a five-day retreat. Our HR manager, Stella Huang, along with our founders, Tim Burgess and Duncan Macintosh, organised everything from flights and accommodation through to company awards handed out on the final night. The trip gave us valuable time to connect, enjoy shared experiences and receive training as well as plenty of Thai food, massages and dips in the pool. 

The Benefits of Bringing a Distributed Team Together

For our distributed team, coming together in Phuket meant an opportunity to see people face-to-face who we’ve potentially been working with virtually for years.

“I’d read about and spoken to founders and employees of remote companies who gave great reports of the value of getting everyone together,” says Tim.

“I remember Claire Pettitt who was at YouCanBookMe at the time (now at Bumble) spoke of how they had a “post-retreat high” that lasted for months.”

This has definitely been the case for our Shield team as well.

“Initially, I wasn’t convinced that the cost would be worthwhile, but I was proved totally wrong,” Duncan says.

“Simply having everyone meet each other [and] share a meal was enough in itself to warrant the cost — but we all got so much more out of it too.

“[It improves] how everyone communicates between individuals and teams, it engenders ‘buy-in’ from our employees, builds rapport, provides an environment to discuss how we can improve things and our vision for the future.”

The retreat also provided an opportunity to roll out company-wide initiatives and training in a unified way.

“Everyone’s there, everyone’s present and everyone gets the same message that you’re only delivering once,” Stella says.

 “It seems to be difficult to deliver such important content virtually.”

If a message is delivered via slack, there is a risk it could get overlooked, or not taken as seriously as is necessary. Email isn’t much better, with everyone’s inboxes always full of urgent tasks.

“We wanted to take this opportunity to make sure everyone’s getting the same message,” Stella says.

Amy Schwartz has been running Unleash, an annual surf retreat, with her partner John for two years. The retreat invites anyone interested to join for a period of coworking, living and surfing in Huanchaco, Peru. Over the past two seasons, she’s seen an array of people participate from journalists, videographers and digital marketers to owners of apparel companies and Shopify experts.

“About 80% of our clients are people who can work remotely and the other 20% maybe even 30% are people who’ve come to an agreement with their employer,” she says.

While initially, the idea was to fill a gap in a scene that seemed to favour partying and country hopping, Amy has seen fantastic growth in her cohort that was somewhat unexpected.

“People that I would least expect to say this have said that they become more creative [as a result of their time with us]. Just being in a different place with a different place to live, different places to eat, their brain just starts to function a little bit differently,” she says.

“From the perspective of an employer that in itself is worth its weight in gold. All you have to do is pay a couple thousand bucks to get your employee out of the office for a month and they kind of get rejuvenated in their work – I mean that is priceless in a lot of ways.”

Tim agrees with the sentiment saying, “I look at it now as really cost effective. If we hired one person for a full year to try to get people connected and motivated you couldn’t deliver as much as we got from those few days.”

Choosing a Place To Go For Your Remote Company Retreat

For Unleash to be everything Amy and John wanted it to be, there was a fairly significant list of prerequisites.

In addition to great surf and high-speed internet, the pair wanted to ensure their clients had good rental apartments with all the essentials like kitchens and bathrooms and access to great places to eat and technical help in the event of a broken computer. They also wanted a walk-friendly city so that trips from the office to the ocean could be frequent and simple to organise.

“In some senses, we have a high maintenance style of client,” Amy says. 

“[They are all] uniformly, really laid back, lovely and interesting people but if you need to work every day and you also want to make sure you get better at surfing, you want your lessons to fit into your schedule. But then also you need good internet and your equipment to work almost as easily as if you were at home. So, we’ve got a lot that we need to be taking care of for our clients.”

For a shorter trip, you’ll more likely be in a hotel and happy to eat at restaurants, but it won’t change your need for fast internet, especially if you plan on working throughout. A walkable city negates the need to organise transport (which helps with large groups) and gives people a bit more freedom to explore.

Planning a Remote Company Retreat

When planning our retreat, Stella started with research. She read as much as she could but still found there wasn’t an easy step by step process to follow.

“I guess the only way to do things is to jump in the deep end,” she says.

The most important consideration was visas. Some of the first correspondence with the team was to gather information about whether they would need to apply for a visa for the trip.

Luckily, Thailand has a list of 22 countries that are visa exempt if you are going for less than 90 days for a holiday. This meant most of our team didn’t need to worry about visas.

Stella found TypeForm questionnaire’s a great way to gather necessary information about everyone attending the retreat.

“A lot of people are really busy, and email is how they often communicate with their clients so I was afraid if I sent too many it would either clog up their inbox or get lost,” she says.

Using TypeForm allowed Stella to gather personal information like passport numbers, home addresses and full names necessary for purchasing flights. It also helped to get the public opinion on group activities and any allergies or health concerns.

Flights and accommodation are obviously the most significant parts of planning any trip, let alone one for 26 people.

Initially, Stella asked everyone to send through three potential flights they’d be happy with the guidelines of an “economic and reasonable” journey.

However, this proved challenging to implement as flights fluctuate so often. In the end, Stella had to do the research herself and pick the flights she thought worked best.

“What we wanted was for people to tell us what flights they wanted and then we would buy them for them, but there was a little bit of disconnect there,” she says.

“In the future, the better way to do it might be just to get people to buy [flights] themselves and reimburse them.”

Duncan and Tim both agree the process needs refinement.

“Flight booking was 100% an issue and took so much effort from Stella. We can be much clearer with people about the dates and deadlines to give them time to get organised,” Tim says.

“[In the future], we’d use a bit of technology to put the onus on those booking the flights and to control the budget,” Duncan says.

For accommodation, Stella used lastminute.com which allowed her to submit a proposal detailing a budget and requirements (including 26 separate rooms!). This was sent to a group of hotels on the lastminute.com network, and then interested parties would bid, like an auction, for the opportunity to host.

“Once I chose the place, they put me in direct contact with the hotel – I called them up a few times we signed a contract, they sent an invoice, it was pretty easy,” Stella says.

How Long Should a Company Retreat Be?

The Shield retreat spanned five days. We asked everyone to arrive by Sunday to ensure at least one night’s rest before starting the structured portion of our retreat on Monday morning. Some came early in the day and had time to sightsee or enjoy the resort amenities, while others arrived at night trickling in on our group dinner which lasted hours. We had three mornings, Monday through Wednesday, of conference time, followed by a group lunch and then free time for activities and work. Thursday was free time until whenever each person’s flight was scheduled. Some team members opted to stay longer at the beginning or end (or both!) of the retreat to make the most of their time in Thailand.

Upon reflection, Stella would recommend a longer timeframe of at least five working days.

“If possible, a longer retreat would be nice,” she says.

“We’re not shutting down the company – people still have work to do, clients still have requests and cases that they want, and it was a little bit stressful for people to juggle making sure that gets done, attending the group meetings that we had and have fun.”

By making the retreat longer, Stella suspects there will be more time to fit in everything. People won’t feel they need to go to every activity if they have work to do but equally won’t feel as though they are missing out.

“Our aim there wasn’t to get everyone together to work their butts off together. It was sort of to collaborate together. Work on things you wouldn’t necessarily work on, with people you don’t work with on a day-to-day basis, and to also have fun,” she says.

Amy from Unleash tends to agree with the longer time frame.

“We do a season from February to May, and we have options for people to come for two weeks, a month or up to 3 months.”

She says, “most people stay about a month.”

– Bree Caggiati April 2019

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