HomeResourcesBlogWhy We Do a Team Retreat Every Year (And Where We’re Going Next)

Why We Do a Team Retreat Every Year (And Where We’re Going Next)

Years ago I was a digital nomad and for 5 years traveled to over 60 countries.

During that time I started and grew NinjaOutreach and it was a goal of mine to meet as many members from the team as possible. 

Meeting people in person is so much different from online

Personally, as a very terse and direct writer, I come across much more human in person. 

I was able to meet close to a dozen team members, but, because NinjaOutreach was sold after 4 years and the team was totally remote; we never had the opportunity to get the entire team together on a retreat. 

With Shortlist, I wanted to finally realize that goal and get as many people as available out of the office and hanging out. 

After all, there were people on the team who had never been on an airplane or left the country. As someone who has traveled more than 99% of the world and benefited from it tremendously, I really wanted to incorporate that spirit into Shortlist’s culture.

Hence came the annual team retreat.

Embarking on a Journey Together

Every year, as we gear up for our team retreat, it feels like we’re starting a journey together that goes beyond our usual work routines. 

Our retreats are more than just team-building; they’re about creating lasting memories in different parts of the world. We explore new places and cultures, and the connections we form during these trips stick with us long after we return to work. 

The special energy and understanding that comes from being together in person are hard to match. 

Exploring Past Retreats

2019: Bodrum

The first retreat was in Bodrum, where my business partner David lives. Bodrum is great because it’s inexpensive, relatively close to Macedonia, and has a cool beach vibe. 

In addition to being practical, the choice of location was also sentimental as it marked our team’s first face-to-face meeting

Petar reflects “We did a lot of workshops which brought the team closer and improved our communication and collaboration.”

Even though Bodrum’s beachy vibe was awesome, we learned that trying different places each year keeps things fresh, so the following retreat we traveled to one of Europe’s most famous capitals…

2021: Barcelona

In 2021, we had our team retreat in Barcelona after taking a break in 2020 due to COVID-19. It was bigger this time, with more people and new faces from the company

Marko remembers Barcelona as a truly unique experience. “We did an axe-throwing competition and paddling in the sea. Some of the guys went to see a football match at Camp Nou,” he recalls. “But most importantly, all of this came during the Covid era and a whole year of quarantines and lockdowns. So, the team retreat in Barcelona was a refreshing way to reconnect.”

But it’s important to balance team retreat entertainment with some structured learning. This is really my only time to be face to face with the team, so we spent a full day diving into the economics of each service and brainstorming ideas for improving them. 

It was also the first time as a company that we defined our core values as well as where we came up with the wishlist idea for company benefits.

2022: Rome

In 2022, we decided to do a repeat of European capitals and went to Rome. 

Due to flight logistics, the retreat lasted from October 2nd to October 9th, making it our longest one so far. We had some awesome new team members like Konstantin, Jana, Marija, and Ana joining us for the first time as well as people who flew in from different parts of Europe, like Monika from Croatia and Viktor with Marina from Sicily. 

For Konstantin, the team retreat was, “my first time going to another country with people that I didn’t really know that well outside of the office.” And what was it like meeting the boss? “I also got to meet Dave for the first time, and I must say I was nervous. However, after the meeting, I had a really positive impression of him. All in all, the team retreat in Rome was a 10.”

Like Barcelona, we tried to balance the cultural must-dos with more org-dev activities. One such activity, courtesy of David Henzel, has each person indicate pivotal moments, both good and bad, in their life, and then share those with the rest of the team. In doing so, you learn more than just the skills the person utilizes day-to-day at work, but what actually shapes and drives them. 

2023: Bodrum

In 2023, we decided to go back to Bodrum to celebrate the company’s 5th birthday. New team members like Katerina and Ivana joined us, and luckily due to David’s expansive property and multiple guest houses, we were able to accommodate everyone on his ranch. 

This was Ivana’s first team retreat, who notes, “The stunning coastal backdrop of Bodrum created a perfect balance, enabling us to share our ideas and collaborate on strengthening our bond as a team. It was an exhilarating experience, and I just wish we could have spent one more week there!”

Windsurfing, horseback riding, and a boat cruise were some of the highlights, but I personally enjoyed coming up with a new vision for Shortlist with the department heads and introducing it to the team.

Planning an Effective Team Retreat

Having our entire team based in Europe makes team retreats cost effective, but make no mistake, they’re typically still ~$1k per attendee.

So, we have to make them valuable from a strategic standpoint

I meet with each person individually (which up until recently I was not doing). Together, we plan out the company’s goals and refine its mission, vision, and values. 

One of my important takeaways is that it’s not possible to please everyone. Everyone has a different vision of how they want to spend their time. 

We try to accommodate various wants and needs through a democratic approach to picking activities and restaurants, but at the end of the day, it isn’t possible to plan a work trip that everyone is going to enjoy 100%. 

Here’s a completely logical question, “If everyone’s on a team retreat, who is doing the work and handling the clients?” 

Typically we set aside a few hours of the day for people to handle anything urgent and keeping-the-lights-on type of activities. 

In preparation, people will often put OOTO autoresponders on or proactively let clients know. We also try to avoid scheduling meetings during this time. 

It’s sustainable for a few days, but people often return to work with a backlog. 

Nevertheless, the team retreats are always an inflection point for us, making the trade off worth it.  

Where the Wind Takes Us Next

As we gear up for our next team retreat, there’s a buzz of excitement about where we’ll be heading this time. 

We love the idea of exploring new spots every year, and the journey is just as exciting as the destination itself. 

When it comes to choosing where we go next, everyone gets a say. It’s a fun tradition that’s worked well for us. Our team’s diverse preferences make sure we end up in a spot that feels right for all of us.

But if it’s up to me…I choose Greece.

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