How to plan the perfect workation for your team

First of all, what is a workation? For The Remote Company, the workation is a special time of the year when the entire team gets to see one another IRL and get things done. It is the perfect blend of work and play in a location of our choice. It is also another we stay productive and collaborate with our remote team in a meaningful way.

Let’s talk about expectations, how to choose a destination and create a program for your team’s success.

#1. Inform people about the trip as early as possible

Anticipation is a source of free happiness. A valuable emotion.

Research shows that people can reap substantial enjoyment from anticipating an upcoming event even if the event itself is not entirely enjoyable. People who devote time to anticipating enjoyable experiences report being happier in general. 

From the moment you will reveal the destination and the date of your workation your team will start planning. Some of them might stay longer or travel around. Perhaps their family and friends may come along too. Others will have to make arrangements, such as childcare or pet hotels, for their time away from home.

Another great benefit of planning workations is that you can mention them in your job ads. This might increase the chances of people applying because they are eager to join a unique company culture and meet their new hybrid or remote team in Panama City or Bali. 

At The Remote Company and MailerLite, our top rule is to provide all the necessary information about the trip at least three months before and invite all team members who have worked for more than three months at the company.

#2. Involve as many people as possible to create a program

With over 8 years of experience, we are very particular when it comes to planning our workation.

90% of what makes a gathering successful is put in place beforehand. (Priya Parker)

#1. Workation is a business trip from Monday through Friday

Workation is the best way for us to meet and work together. We take it very seriously and expect everyone to attend it (the last two years were exceptions. If people feel unsafe, they can stay at home)

People can buy flight tickets for any dates that include the workation. Team members usually plan their vacation with family and friends before or after the workation.

#2. Mix work-fun-work

On Monday evening, we welcome everyone with drinks. 

Tuesday is focused on work - presentations, discussions and workshops.

Wednesday is a Creative Day full of fun activities. 

Thursday is usually for planning sessions and time to reflect before the goodbye party. 

After breakfast on Friday, we all say goodbye until the next time.

#3. Food brings people together

Our team takes food seriously. First, we have breakfast and lunch in the hotel to save time.

However, when it comes to dinner… that’s a different story. We plan dinners with 6-8 random people every night, allowing everyone to connect with people they might not work directly with. The conversations and topics vary a lot, and it's a great way to get to know everyone.

#4. IKEA effect

Finally, we ask everyone to contribute to the workation. This could mean organizing workshops, selecting restaurants for dinner, or planning a goodbye party; the more people are involved, the more engaged they are. We call this the IKEA effect.

#3. The destination should be a place that makes people excited

And also accessible.

In 2022, we planned a MailerLite & Vercom workation for 140+ people from 30+ countries. I started the process by googling ‘European airports with the most connections’. And this is how we chose Istanbul. 

Another important aspect is the accommodation. It can make or break the trip. 

Fast internet, on-site conference facilities, easy access to the airport (max one-hour drive) and walkability to restaurants are non-negotiable for us.

Previously, I asked remote teams to share their favorite places and collected a list of 20 destinations & approved hotels with activities nearby.

Planning your next workation? Join our email list and gain access to our exclusive list of 20 destinations & approved hotels to make your planning easier.