How We Planned an Unforgettable Company Team Retreat and How You Can Too

Team retreats are valuable investments for companies looking to enhance their team’s connection, creativity, and overall performance. These retreats offer a unique opportunity for teams to step away from their daily work routines and immerse themselves in an environment that encourages collaboration, team-building, and growth. By providing a space for team members to connect, learn from one another, and develop new skills, they can have a significant impact on company culture, morale, and overall business success. 

In March, Databox held its first team retreat in Tenerife, Spain, which was a resounding success. More than 100 Databox Playmakers from around the world came together for five days of team-building, collaboration, and working on the future of our business. This was the first such event for us, and it was a big logistical challenge, but our team pulled it off flawlessly. 

In this blog, we will share our experience organizing and executing this event and offer tips for planning a successful company retreat. So, if you’re thinking of planning a team retreat for your organization, keep reading!

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1. Define the purpose of the company retreat

Before you dive headfirst into planning, it’s important to establish the foundation. The key to a successful retreat is aligning the objectives with the unique needs of your company and team. This ensures that every activity and session is intentionally designed to have a meaningful impact. Whether you want to improve communication, build trust, enhance collaboration, or develop new skills, setting a purpose and clear goals from the outset will make all the difference.

To identify specific goals and objectives, it is first important to gather feedback – this can be done by gathering insights from team members through discussions, surveys, interviews, or focus groups. Involving key stakeholders and leaders in the planning process can also ensure alignment with the overall strategy and mission of the company. For example, if communication is challenging, a goal could be to improve team communication through workshops and team-building exercises.

At Databox, we believe strong company culture is essential to success, and our team retreat was a crucial part of that effort. The fact the retreat was our first in-person gathering (our Playmakers come from 15+ countries around the globe) played a crucial part in our decision-making when we thought about the purpose of the event. In the first place, for us, the retreat provided an opportunity to connect, share ideas, and build relationships across all teams. Additionally, we also wanted to communicate our high-level mission and vision and unveil our exciting plans for the future. 

Of course, there were many other ideas and goals on the table, but we consciously focused only on the two – connect the team and inspire them for the future of our business.

2. Plan the logistics

The planning of a team retreat involves careful consideration of logistics, schedule, and team-building activities. At Databox, our People and Culture team led the planning efforts closely aligned with the leadership team. We began the initial activities, such as selecting a location and securing offers, around ten months before the retreat. Logistics planning included arranging transportation, flights, accommodation, and meals, among other considerations. 

To manage the project, we utilized the power of collaboration and technology to achieve our goals. To stay on track and manage our progress effectively, we turned to Asana. With this handy tool, we were able to divide responsibilities and track our progress with ease. 

Our Operations Manager, Rebeka, led logistics and finance, while our Brand & Culture Manager, Maša, took charge of communication, branding, and agenda. And let’s not forget about our talented TA specialists, Gregor and Urška, who led the morning and evening activities. To keep everyone in the loop and address any challenges that arose, we held regular meetings twice a week. These meetings were expertly led by our Head of People and Culture, Aljaž, who ensured that we stayed on track and tackled any obstacles as a team.

It’s important to highlight that our project wasn’t a solo effort by a select few. We collaborated with the rest of the leadership team to confirm group topics, but we were mindful of not adding any additional workload on them, only preparing for their presentations. Moreover, we actively engaged other team members in generating fresh ideas and helping with executing the retreat’s activities throughout the planning process and implementation. We recognized the significance of involving the entire team, as the retreat was ultimately for them. By doing so, we tapped into a broader range of talents and expertise, making the retreat a resounding success. Remember, don’t hesitate to involve your team and encourage their contributions – you never know what innovative ideas they may bring to the table!

It’s worth mentioning that when it comes to organizing a team retreat, hiring an agency is always an option. However, in our case, we decided to do most of the event ourselves and use the help of a travel agency only when it came to choosing the location, service at the hotel, and travel arrangements. We knew that this was our first retreat, and we believed that we knew our business and culture best. By doing it ourselves, we could tailor the experience to our exact needs and preferences. It also allowed us to keep costs down, ensuring that the retreat was both enjoyable and cost-effective. So, if you’re considering organizing a team retreat, don’t hesitate to explore different options. 

3. Choose the location

Choosing the right location for a team retreat is a crucial part of the planning process. At Databox, we considered several factors when deciding on the location for our retreat. 

Accessibility was a key consideration, as we wanted a location that would be easy to reach for team members traveling from all over the world. We also had to take the budget into account, as well as the activities available in the area. Most importantly, we needed a location that could accommodate a group of more than 100 people and ensure that everyone could stay in the same place/hotel.

After considering all the factors, we decided Tenerife was the perfect location for our team retreat. The island offered a range of accommodation options that could accommodate our large group, and flights were readily available from all over the world. Additionally, Tenerife provided a beautiful backdrop for team-building activities, with its warm weather, stunning beaches, and picturesque landscapes. It also offered various sightseeing opportunities, such as exploring the famous Teide National Park. Overall, Tenerife was the perfect choice for our team retreat, providing a productive and enjoyable setting for our team to come together and grow.

4. Set the Schedule and Agenda

When setting a schedule and agenda for a team retreat, it’s important to consider a balance of activities that includes team building, skill development, and relaxation time. At our retreat, we carefully crafted the schedule and agenda to include various activities that catered to all of these areas.

Some of the activities that were included in our team retreat agenda were keynote speeches, workshops, team-building exercises, and social events. To ensure that the agenda was relevant and meaningful to our team, we chose specific topics to address in keynotes and workshops that were important to our team and aligned with our company values. We also invited a guest coach to facilitate the entire program and run the workshops agilely.

In addition to the structured activities, we included morning and evening activities in the schedule to allow for some unstructured time for team members to bond and connect. Every activity was chosen mindfully, taking into account the purpose of the retreat and closely aligning with our company culture and values.

How we did it:

• To kick off the retreat on the right foot, we reserved Monday and Friday for arrivals and departures, giving everyone time to settle in and prepare for the exciting days ahead.
• We recognized the importance of balancing work and play, so we dedicated two days to business and learning and one day entirely to sightseeing. This allowed us to explore the local culture and scenery while also gaining valuable insights and knowledge to bring back to the office.
• A successful retreat requires a healthy mix of scheduled activities and free time, so we made sure to include both in our itinerary. From morning and evening activities to plenty of opportunities for relaxation, there was something for everyone to enjoy.
• We understand that work comes first, so we made it mandatory for everyone to participate in the scheduled activities between 9 a.m. and 4 p.m. However, we also recognized the importance of flexibility, so we made the morning recreating and evening programs optional for those who wanted to participate. This allowed everyone to strike a balance between work and leisure, ensuring that everyone had a memorable and productive retreat experience.
  

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5. Incorporate Company Culture and Values

Incorporating company culture and values into the team retreat agenda is crucial to reinforce the organization’s identity and purpose. It also helps team members align with the company’s mission and vision and understand how their work contributes to the bigger picture.

One way to incorporate company culture and values into the retreat is through team-building activities specifically designed to align with the company’s values. And another way to do this is by incorporating workshops or sessions focusing on the company’s mission and values. This can include keynote speeches or panel discussions highlighting the organization’s history, values, and goals. 

How we did it:

• On Tuesday, the second day of the retreat, we shifted our focus to strategy and company culture with inspiring keynote speakers from our leadership team. As part of the keynote, our CEO, Pete Caputa, presented the company strategy and plans for 2023, and our founder and CPO, Davorin Gabrovec, walked us through some of the early Databox stories and product strategy for 2023 and beyond. Following this, the team of Databox leaders shared their perspectives and plans for all departments, including marketing, sales, customer service, product, engineering, people, and culture. 
• In the second part of day 2, we started with a talk about our company culture and the role of each team member in cultivating it, presented by Aljaž and Maša from our People & Culture. We discussed how we plan to develop our teams and leaders further, followed by a workshop on exploring our values and initiatives to shape our future.
• Next up was our guest spiritual coach Simona Majerska with her presentation and challenge with practical work on the topic of How Conscious Breathing Can Help You Find Inner Peace & Balance. This keynote, as well as our choice of morning activities, were all closely connected to one of our values, “Balance work with life”.
• On Thursday, the entire day was focused on building high-performing teams. After a short keynote by our program facilitator and agile coach Matej Golob, the team was divided into cross-functional groups to identify specific challenges that hinder the creation of such teams. Each group presented its findings, providing insights for discussion. Then, groups brainstormed initiatives to address their challenges. We also envisioned Databox in 2030 and simulated interviews, which were both thought-provoking and fun. These workshops were insightful and provided valuable takeaways for our daily work.

6. Plan for team-building activities

As the saying goes, “teamwork makes the dream work,” and what better way to strengthen the team’s bond than through a memorable and productive retreat experience? That’s why we made it a priority to include team-building activities and free time during our recent retreat. Not only did this give us a chance to recharge and unwind, but it also helped us foster a sense of camaraderie that carried over into our work once we returned to the office.

To make the most of our retreat, we planned a full-day trip that took us on a culinary journey through the unique gastronomic culture of Tenerife. From a culinary class where we prepared the traditional mojo sauce to wine tasting, we immersed ourselves in the flavors and sights of the local culture. We also took the opportunity to explore the stunning landscapes of Las Cañadas Del Teide, which provided an unforgettable backdrop for the photo memories.

Speaking of team-building, we made sure to include plenty of fun-filled morning and evening activities led by our team members. From Breathwork and meditation sessions to sports activities and trivia nights, there was never a dull moment. We even had a few karaoke nights that brought out our inner pop stars! Ultimately, the combination of team-building activities, free time, and unique experiences made our retreat an absolute success. 

7. Brand the experience

Creating a strong brand and slogan for the event can help build anticipation and a sense of unity among team members. By reinforcing the company’s culture and values, well-designed retreat branding can make the event even more memorable.

But branding isn’t just about logos and catchy slogans. A well-crafted welcome package can also play a big part in building excitement and a sense of belonging among attendees. Whether it’s branded T-shirts, hats, or water bottles, the swag you choose should align with the company’s mission and values. Not only does this create a sense of appreciation for team members, but it also reinforces the company’s culture and values, helping to build a more cohesive and motivated team. 

What we did:

• We selected the ideal slogan, ‘One Team, One Spirit,’ which effectively encapsulated the essence of the event, and our talented graphic designers, Gašper and Aleks, skillfully crafted a vibrant visual brand to complement it.
• We placed a welcome package for every Playmaker on their bed at the location of the retreat.
• The package included: personal accreditation, neck strap, t-shirt, backpack, notebook, pen, rubber bracelets (in different colors and messages – aligned with our values and leadership principles), pop socket, value cards, and leadership cards with Databox and leadership competencies.
• We didn’t forget about the graphic equipment of the room in the conference hall – slide decks, balloons, and posters that communicated our values and leadership principles were also branded.

8. Communicate. Over-communicate!

Effective communication is key to the success of any team retreat. It is essential to over-communicate everything from the logistics to the agenda to ensure that all team members are on the same page. 

At Databox, we created a dedicated Confluence space where we uploaded all the information related to the team retreat. We also regularly updated the Q&A section, where we addressed all the questions and concerns of the team members. In addition, we had a team retreat newsletter where we communicated all the updates and details. 

To build excitement before the retreat, we also had our “Friday Countdowns” activities, where we prepared Tenerife trivia, travel services called “Exploring Tenerife with Gregor,” and language lessons, “Spanish for Playmakers 101.” 

Communication is also important on the location itself – for all the logistics, updates, and also to running the activities such as workshops. Here we chose to go with the WhatsApp group – for the entire team and an additional one for the organization crew, as we called it.

9. Make memories 

Capturing memories is an important aspect of any team retreat. Not only does it serve as a way to remember the experience or a recording for the members who could not join the event, but it can also be used for future promotion, employer branding, and social media. 

It’s important to think ahead and plan for how you will capture the event. By taking the time to capture the event, you can ensure that the memories and impact of the retreat are preserved for years to come.

What we did:

• We designated our Playmaker, Robert, to take photos and videos and hired an additional videographer. We call them our “media crew”.
• We recorded all of the keynote speeches – for the team members who could not join the team retreat and for our archive.
• Our media crew took tons of photos and videos. During and after the retreat, they produced daily videos and a longer promotional video for external communication.
• We opened a Google photos album where all the Playmakers could share their photos of the retreat.
• We chose and communicated our social media hashtags to the team and regularly reposted their posts during the retreat.

10. How much does it cost?

Organizing a team retreat requires meticulous planning, and one of the crucial aspects is budgeting. We wanted to provide our team with a memorable experience, but we also wanted to make sure that we didn’t go overboard with the expenses. Initially, our primary budget for the team retreat was around 250k, and we anticipated that everyone would be able to attend. However, we later faced some unforeseen circumstances, such as cancellations due to medical or family reasons and visa issues, which resulted in adjustments to our budget. Despite these setbacks, we were able to negotiate with vendors and carefully budget our expenses, resulting in a final cost of just under 200k for everything, including the hotel, flight tickets, transfers, trips, and more.

We were fortunate that our company covered all the costs of the retreat, and we understand that not every organization can afford to do so. It’s important to note that unexpected events can impact the budget, and as a result, we had to be flexible in our planning. Additionally, we made sure not to burden our team by requiring them to take vacation time for the retreat. At the end of the day, it’s important to find a balance between creating a memorable experience for your team and being responsible with the budget.

11. Don’t forget the retrospective

After a successful team retreat, it’s important not to forget to conduct a retrospective to reflect on what was accomplished during the event. This includes analyzing the outputs of the workshops and discussions and making plans on how to implement the key takeaways in the future. Keep the momentum going and regularly remind the team about the agreements and ideas raised at the event.

Additionally, it’s a good idea to conduct a survey after the retreat to get feedback from the team and gather ideas for improving future events. A retrospective and survey can help to ensure that the team retreat was not just a one-time event but an ongoing part of a company culture that helps to build stronger teams and achieve business goals.

Make the best investment in the future of your business

In conclusion, planning and executing a successful company team retreat can be a lot of work, but the benefits are truly worth it. By taking the time to step away from the daily routine and connect with colleagues on a deeper level, you can create a stronger, more cohesive team that’s better equipped to tackle challenges and achieve success. 

From our own experience, we can say that the rewards of planning a retreat far outweigh the effort involved. By aligning your objectives with the needs of your company and team, incorporating team-building activities and free time, and creating a strong brand and sense of belonging, you can help build a thriving and motivated team that’s ready to take on the world. 

As for us, Tenerife 2023 has been conquered! But where to next for the daring Databox Playmakers? The world is our oyster, and we’re already buzzing with excitement to see where our next adventure will take us. One thing we know for sure is that we’ll be more than ready for whatever comes our way, thanks to the unbreakable bonds and sense of belonging we’ve forged during our epic team retreat.