5 ways to maximize your company retreat

Planning a company retreat can have various benefits for team building, employee morale, and overall company culture. At Expensify, we’ve been doing our team retreats, called Offshore, since 2009, and we’ve seen the benefits it has brought to make our team more productive, more communicative, and more engaged. So if you’re considering a team building retreat for your company, read on to learn more!

What is a company retreat?

A company retreat is an organized event where members of an organization get together outside of the regular workplace for a specified period, ranging from a few hours to a month. Retreats are typically held at offsite locations, away from the office environment, to provide a change of scenery and create a more relaxed and conducive atmosphere for the planned activities. A company retreat can also be referred to as a team retreat, corporate retreat, or team building retreat.

Why should your company organize a team retreat?

Ultimately, an engaging, memorable, and well-executed team retreat can increase trust, morale, and communication amongst the team, and even push big projects forward in a sprint-like format. While these may feel like small, disconnected endeavors, ultimately it can create long term positive currency between team members when they return home to an online-only engagement format.

So, whether you’re planning your first or fifteenth retreat, here are my top seven tips for maximizing the effectiveness of your next company retreat.

1. Figure out the Why

Since joining Expensify in 2016, I’ve attended and/or planned many team retreats. Our goal has always been to foster closer relationships between employees, which increases trust between team members who are located all over the world, from many different cultures and backgrounds. 

The most important thing to remember when planning a team building retreat is to ask yourself: what is the goal? Some reasons could include:

• Increase interpersonal relationships to enable collaboration to offset the “coldness” of online communication

• Create an opportunity for in-person work in a sprint-like fashion to meet a deadline, establish team trust and collaboration, and ship out a product?

• Team-specific goal-planning, or executive team retreats are common as well to align company leadership 

Once you understand the purpose of the retreat, logistics like location, budget, duration, activities, and more will become more clear.

2. Make it an adventure

Every year at Expensify, we pick a foreign country to work from for 3 weeks — we find that bringing people together in an unfamiliar environment creates more moments for connection simply by experiencing something new together with your colleagues. Each week is a different city, and typically, these weeks are standard work weeks. 

The advantage of doing it this way is to encourage employees who might not normally spend time together to, well, spend time together. This strategy may not seem like a typical “team-building retreat”, but we have found that bringing people together outside their routine and obligations creates more authentic moments to discover something new together, which turns into shared experiences that can last a lifetime.

Past locations include: 

• Perugia, Alghero, and Bari, Italy

• Lagos and Porto, Portugal

• Quebec City, Quebec

• Santiago de Compostela and Cadiz, Spain

• Ubud, Bali 

• Punta del Este, Uruguay

We specifically opt for smaller cities simply because (1) they are not cities one may normally visit, so there’s a higher chance employees haven’t gone there, and (2) it means there’s a bigger chance that employees will run into each other while walking around, and link up with colleagues they may otherwise not think to spend the day with. 

Of course, it is impossible to completely avoid the large cities, but when picking a larger city, I highly recommend choosing a specific neighborhood so that your team can all be close by, increasing the likelihood of hanging out and/or running into each other.

3. Make it a family affair

Taking time for a company retreat is always a trade-off, especially for those with families to take care of or other larger time commitments that make it hard to be away from home for too long. Not only can you encourage employees to come by choosing unique locations, consider policies that allow employees to bring their partners and/or families.

The key to balancing family and work is to make sure your team understands that they need to set expectations with their partner and/or family on what your availability looks like. It might be a fun vacation for them, but for you, this is still a work trip. Setting expectations ahead of time allows for minimal confusion, and possible frustration or even resentment on the trip. That said, we’ve seen that the benefits of making our team retreats family friendly outweigh the cons — some partners bring their work with them and become a part of our #workfromcafecrew, while most others simply are thankful that they have the opportunity to visit somewhere new for the first time, which in turn, helps us cultivate a more inclusive culture at Expensify.

4. Make it #social with shared chat groups

Before each trip, we set up specific workspaces in New Expensify — one for #announcements, and another for #social events so employees can share what they’re up to and invite others to join in. To further incentivize meeting and connecting with colleagues who you may not have much overlap with, we’ve also provided “social budgets” in the past where, if you invite others to a planned activity by posting it in a #social channel chat on New Expensify, you can get part or all of the cost of that activity reimbursed. 

While this may just sound like a fun perk on the surface, we have seen this pay dividends post-retreat, when employees are back at home and working remotely. As a remote-first company, we rely on Slack and New Expensify for most of our collaborative communication, which means that tone can sometimes be misconstrued when in a particularly deep thread about a controversial topic. We’ve seen that the relationships and trust forged on the streets of Hoi An or in a Perugian cafe become extremely important in these moments — employees are more likely to assume best intentions and be collaborative rather than combative, because of their shared experiences.

5. Make sure to plan at least one big event

Everybody loves a party. We’ve found that hosting a large team-building event allows for everyone to get excited during the trip and it gives them something to look forward to.  The best types of events are those that can only be experienced in unique locations.  Plan something memorable, hype up your fellow employees then surprise them with an experience that coworkers and their families will never forget.  Some examples from our travels include:

• A maple farm on the outskirts of Quebec City.   

• Italy, 15th Dancing outside the remains of a 15th century castle in Italy

• Dining on a dirt road outside a famous chef’s restaurant in the countryside of Uruguay.   

Learn more about Expensify’s company retreat. If you’re interested in joining the team and travel the world with us, head over to we.are.expensify.com to view our open positions.