How to Plan a Team Retreat That Is Unforgettable

As a fully remote team here at Designlab, we don’t have many opportunities to spend time together face-to-face. So when we do get the chance, we like to make the most of it!

We’re lucky enough to get together twice a year for an all-team retreat—most recently for 5 days in Barcelona, Spain. Planning these retreats can feel a bit like doing a 10,000-piece jigsaw puzzle. You need to give the details careful consideration before starting to put things in place, but the end result is well worth the effort.

Coming together for a team retreat can be beneficial for many reasons. For starters, they’re great for team-building. We’re not talking about the cheesy kind of team-building, with trust exercises and human knots—we’re talking about the kind of authentic interactions that build real relationships.

Read on for our top 7 tips for planning your own retreat. They’re based on our experiences (and mishaps) here at Designlab. We hope you find them helpful for your team!

1. Determine your team retreat objective

For our most recent trip, before we started planning any of our team retreat logistics, we first wanted to make sure that we fully understood our team retreat objectives. 

Some objectives are constant across all of our retreats: they are a time for us to form connections as a team, and to reinforce through activities some of our key company principles. As a team that doesn’t get to interact in person very often, simply spending time together is one of our most important objectives, and it is a reason in and of itself to hold our retreats.

Others are specific to each retreat, and depend on the projects and themes we are exploring as a team around that time. This September’s retreat aligned perfectly with our Objectives and Key Results (OKR) planning cycle, and so one of our major objectives was to spend time together refining these OKRs before the start of Q4. 💼

2. Understand your team members

Planning the perfect retreat is very dependent on having a good understanding of your team. There is no one-size-fits-all or gold standard for team retreats. Instead, it’s about making sure that you know your team well enough to build the right retreat for them.

I’ve learned that our team is not that great with early mornings (or even, perhaps, mornings at all), but they’re happy to continue going well into the evening once they’re on a roll. 

In general, we prefer the slightly more private setting of a large house rather than a hotel or resort. It also turns out that our team is too healthy to drink soda (with one or two honorable exceptions), but a bit of chocolate after dinner does not go unappreciated. 🍫

One of the more important aspects of planning a team retreat is ensuring that you know what your team is going to need in terms of space and time to manage their energy levels. 

Do you know what makes your team feel comfortable? Are they introverts that need some time to themselves, or extroverts who are looking for lots of group activities? Or, perhaps more realistically, a mix where you will need to meet a range of needs?

Be sure to ask your team these questions in advance of your team retreat.

3. Decide on a location that works for everyone

Our team is split across six different countries, and even more time zones. This was our first ever retreat outside of the US, where most of the team are based. While we do have one team member in Barcelona, everyone else needed to travel to Spain. 

Barcelona made sense for us for a few key reasons, which we deemed to be important: 

• The cost of flights was reasonable;
• Spain was accessible for most of our team without unnecessarily long flights, or lots of connections;
• The cost of living within the city itself was well within our budget;
• No team member had much of a time zone change to deal with;
• Barcelona was a city that our team had a strong interest in visiting.

For US-based teams, heading abroad might be much more cost effective than you imagine. We have found that the costs for team retreats within the US—including domestic flights—can add up quickly. ✈️

All told, our previous retreat to Utah back in March actually cost 50% more than this trip to Barcelona.

4. Define your venue and accommodation parameters carefully

We are still a small enough team that we were able to find a really big house that was able to accommodate everyone comfortably—although this likely won’t be the case for long, as we’re growing rapidly. 

We like the opportunity that staying in a house gives us to prepare our meals together, eat together, and connect with one another without any distractions. Finding the perfect house, which has enough rooms, space for us to eat and meet together without feeling cramped, and is an easy drive from a main airport, is one of the biggest challenges of organizing a successful team retreat. 🏠

We actively search for houses that can accommodate the energy and activities of our team retreats. We strive to have the type of environment that encourages interaction and allows for the team just to hang out, while at the same time offering enough time and space for those who need periods of quiet.

For now, we’ve found that VRBO.com is able to meet our needs, so our search starts there using a set of carefully defined parameters. 

5. Pay close attention to administrative details

Planning a retreat is a big undertaking and it takes a lot of time and a lot of attention to detail. Unless retreat planning is your full-time job, don’t try to do it alone. 

This time, we formed a committee and divided up the work between us. Specifically, our committee teams were: team retreat logistics, meal planning, and outings & activities. 

The high-level team retreat goals and the overall agenda were the responsibility of our executive leadership team. This approach worked well for us, as it meant that no one person had to carry the full weight of organizing a retreat alone.

When it comes to travel—and international travel in particular—attention to detail is essential. At a minimum, you will need to collect the full legal name, date of birth, and closest airport location from each team member in order to plan their travel. This information needs to be collected and stored securely. 

In addition, if you plan an international retreat, you’ll likely need to collect passport numbers and country of passport origin. Some European countries require you to submit this information upfront in order to calculate and pay a tourist tax. You’ll need to research visa requirements for the team retreat location for all nationalities that will be attending. 

We try to book our international flight tickets 4-5 months in advance, as that’s the time frame we’ve found gets us the best prices. Because this is so far in advance of the retreat, we insure each of the tickets we buy so that we can cancel for a full refund if our plans change.

Look into travel health insurance for your team in your retreat location if this is not already covered by your company health insurer. It often doesn’t cost that much, but might make a big difference if something does go wrong. 🏥

If anyone on your team will be helping with driving at the retreat location, check whether they will need an international driving permit. These are really easy to get as long as you do so a few days in advance of leaving the country. You can get one in minutes in the US at AAA stores. There are also a few online services, like the International Drivers’ Association, which you can use to get your permit delivered to your door.

6. Leave space in the itinerary for flexibility and down-time

Our past team retreats have had very structured agendas, as we’ve tried to make the best use of our face-to-face time and explore some big themes and ideas. This time, we decided to try a slightly looser structure with a lot more informal coworking time. And our team loved it!

Over the last quarter, we’d spent a lot of time working on refining our roadmap to focus on the few things that we believe are most important for us as a business and are in line with our company vision. This retreat became an opportunity to collaborate closely on moving those efforts forward. 

There’s something special about being able to turn in your seat to ask a question, or share a moment with a colleague nearby, when it is not something that you can do every day. This retreat we tried to create opportunities for more of those moments. 

In general, we use the team retreat time together to achieve things that are hard to do via video calls, and so we deprioritized passive activities like presentations, in favor of hands-on sessions and face-to-face discussions. 💭

Be prepared with an agenda, but also build in room for flexibility. You need to take each opportunity to read the room and decide whether to extend a session that is adding value or perhaps cut a session that could happen at a later date. 

Don’t cram your agenda so full that you don’t have time to leave your venue and explore your location. It can be really intense to spend so much time together as a team when it’s not normally part of your daily routine. Make sure to plan a few outings that will prevent your team from going stir-crazy. We went on two outings during the course of our four-day retreat, which gave us some welcome time at the beach!

7. Pro tip: strategic meal planning is the key to success!

We are a diverse team with a wide variety of dietary needs and preferences, which can make meal planning one of the greatest challenges of team retreat logistics. On top of that, there is an additional complication when you host an international retreat: shopping in unfamiliar grocery stores!

Our meals needed to be vegan; as well as dairy, tomato, onion, seafood, and nut free; with optional additions for our non-vegans who in turn are a mix of meat eaters, pescatarians, and vegetarians. 

Meals are really important: underfed or badly-fed teams are generally grumpy teams, and grumpy teams don’t collaborate well. 

This year, we had a committee that helped plan our retreat logistics. Our front-end developers, admirably took on the job of meal planning, working with the team to find recipe ideas and menu options. 🍽

Once we arrived in Barcelona, we divided into teams and took turns to cook for one another. In general, we ate well and had plenty of options to go round—although our breakfast teams were often a little bleary-eyed when reporting for duty. 

* * *

We had an amazing time in Barcelona. We came away with loads of ideas to make our next retreat even better—with more co-working time, and later start times being at the top of that list.

There are, of course, already less than six months to go until our next retreat, and planning is already well under way! If you’re planning your own trip, remember to get started early. 

We’ll let you know how our next trip goes. Thanks for reading!

Enjoyed reading about this retreat? Check out the write-up from our trip to Colorado last year!