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8 Tips for Hosting a Remote Team Retreat

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Whether first-hand or through the experiences of others, the past two years have demonstrated that teams can be just as effective working remotely as working in person. However, this doesn’t mean that you should be losing out on the benefits of some of the more traditional office activities ⁠— like team retreats.

Team retreats provide the opportunity for your company to get together, talk business, socialize, and have fun outside of the usual work environment. Data shows that talented, loyal employees want benefits ⁠— beyond free coffee and paid delivery lunches. A team retreat in a desirable location is just one way to incentivize your hard-working employees.

In fact, with remote work and hybrid arrangements now the norm across the workplace, team retreats have become a necessity. Work is built on relationships, and investing in those relationships is a proven strategy to improve collaboration within your organization. So, if you’re considering hosting a remote team retreat, make sure you’re set up for success.

1. Survey Your Team

To start, it’s important to understand your team’s thoughts about the possibility of a remote retreat. Some may have busy schedules, and others might be uncomfortable with the concept of overnight business travel. It’s also worth checking in with your contract employees and extending the same benefits to them.

Surveying your team, however, isn’t just about gaining their initial impressions. Lead by example and demonstrate that your employees have a say in the decision-making process. Your survey should gather information on desired destinations and which part of the year they are available.

In many cases, a dedicated remote team retreat partner can even help you during these initial stages to organize and analyze feedback from your team.

2. Consider Your Company Goals

After surveying your team and making your decision, plan your team retreat with your company goals in mind. As you plan, you might work with your leadership team to determine which areas you’d like to focus on. Are you looking to cultivate more community and culture within your teams? Do you hope to focus on the business and inspire your employees to meet their KPIs? Or, are you simply rewarding your employees for their efforts over the past year?

While every remote team retreat will combine multiple goals, deciding which objectives you’d like to focus on while planning your retreat will help you narrow down the location, activities, and overall experience of the event.

3. Identify a Location

In choosing your location for your remote team retreat, you’ll need to strike a balance. It’s essential to find a location that offers ample space to create a comfortable and social atmosphere that encourages a combination of relaxation and productivity.

Is your team willing to travel? Would you prefer something local? A remote location far from the stress of the workplace (or even something to pull people out of their daily routine) can facilitate mental changes across your organization.

There are many companies that have curated experiences across worldwide locations. If you decide to choose a remote team retreat partner, make sure that they have established spaces for retreat activities and a history of executing successful team retreats.

4. Reserve Lodging

Wherever you plan your retreat, your team will need lodging – be it house rentals, hotel rooms, or other overnight arrangements. If your lodging isn’t the same as your retreat location, confirm that your retreat center is nearby. You won’t want your employees to feel like they’re commuting, especially on a remote retreat.

Find a location that can accommodate all of your team and also offer benefits. If you’re able, book a space that embraces a coworking mentality so your employees can network with other remote workers and develop lasting relationships.

Once you’ve found this, set a budget and book! Now you can focus on planning the events.

5. Choose a Catering Provider

Food, like location, is one of the major motivators behind any retreat. If you’ve decided on an overseas retreat, plan on sampling the local fare. This will give your employees and team members the opportunity to experience some of the culture on location. Check local listings on TripAdvisor or Google to discover restaurants that accept large volume preorders, or choose a dedicated caterer to work with your team within your retreat venue.

As you’re exploring your options, determine which meals you’ll serve to your participants. Only breakfast and lunch? Only lunch and dinner? All three? While you’re planning, you may also want to give your team members the option of going out on their own or with others to explore local fare.

No matter which option you choose, ensure that all dietary restrictions and allergy needs are met. Doing so will help keep morale strong within your organization and demonstrate that you care about the (very literal) health of your employees.

6. Find Group Facilitators

During a remote team retreat, organizers and executive leadership should be equal participants in the activities. By having group facilitators present at your event, not only will the executive leadership team benefit from many of the activities on the agenda, but also be on the same footing as everyone else in the company.

Presenting your executive team in this way can have many benefits for both senior management and employees. Workers may be able to bond with leadership in a way they haven’t been able to during hectic day-to-day routines, and leadership can gain a deeper understanding and appreciation for their employees’ different personalities and perspectives.

Additionally, group facilitators can also hold discussions or mediate conversations on difficult topics, providing a neutral presence at your retreat that can help facilitate better cross-team dialogue and communication.

7. Design Team-Building Activities

Not surprisingly, activities in a team retreat should appeal to a broad range of people. As the retreat planner, be sure to plan these activities after deciding on the goals of the retreat. Additionally, consider whether or not the venue will suit the types of events you’d like to host. Some venues include team-building activities in their programs, which can help reduce costs overall.

Most importantly, during the events, your retreat participants should feel challenged but not isolated. This is a delicate exercise and requires knowledge of your team’s personalities and preferences. When planning events, consider the following as a starting point:

  • Hire dedicated presenters in your company’s field of expertise
  • Find a motivational speaker who is relatable to your employees
  • Plan creative events like cooking classes, painting, or yoga
  • Split into teams and play physical sports or mental strategy games
  • Seek out mindfulness practitioners to facilitate meditation sessions

Unfortunately, you can’t please everyone, even at a team retreat. But by offering a range of activities, your employees will walk away feeling as if they have learned something and bonded with their team members.

8. Learn With the Locals

If you choose to have a remote team retreat in a foreign country (or even a part of the city your company is not familiar with), it’s helpful to foster relationships with local communities to gain insider knowledge about the area.

Wherever you choose to hold your team retreat, make sure to network with locals or long-term visitors to gain initial impressions and trusted recommendations for any services you and your team may need. Look into teaming up with WhatsApp groups, Facebook groups, or even connections through your own networks to build out local events that will leave a lasting impression in your team’s mind.

Obviously, there are many ways to plan and host a team retreat. With such an investment in your team at stake, it’s not always easy to decide how to proceed when first exploring your options. A dedicated team retreat partner can help alleviate some of the pressures or anxieties around planning and executing.

Find the Right Partner

Our partner, Outsite, offers 20+ locations across four continents in urban, alpine, and coastal locations to make it easier than ever for companies to offer their employees a remote retreat experience. All Outsite locations are designed with remote work in mind: they’re comfortable, social, and optimized for work, and their locations are designed to make company offsites easy.

Their retreat programs can scale according to any team’s needs and offer a variety of options, including caterers, event coordinators, group facilitators, and local guides.

At Esteemed, we’re committed to attracting, retaining, and rewarding top talent. A remote team retreat is one of the best ways to showcase yourself as a leader in a forward-thinking, remote-centric environment. If you need help planning your retreat, get in touch with us today.