Remote Retreat Ready: How to Plan a Company Retreat (+Ideas)

Remote Retreat Ready: How to Plan a Company Retreat (+Ideas)

Our company retreats were legendary. As a remote team spread across 5 continents, hosting company retreats has always been a significant part of our company culture and a way for us to invest in strengthening relationships and the social fabric of our international team.

Introduce COVID-19. For two years, we replaced our retreats with quarterly virtual retreats.

And while we were happy with the results, it wasn’t the same.

Finally, in May 2022, we were able to host an in-person company retreat. In that time, our team had more than doubled in size. We had new team members from even more distant parts of the world that hadn’t met any other team members.

How did we overcome the challenges of creating a meaningful company retreat? And how can your remote team design a company retreat that’s engaging and productive for everyone involved?

Let’s find out.

What is a Company Retreat?

A company retreat is a time for the entire team to get together in person, brainstorm, and develop their personal relationships. For remote teams, a company retreat is an essential time for team bonding and employee engagement.

The Goal of a Team Retreat

When planning a corporate retreat for a remote team, we strive to set clear expectations: This is not a normal work week. Instead, we create an intentional agenda with two main goals in mind:

  • Create business alignment. That means talking about the current situation of the company and the areas of focus that are most important for the entire team over the next year. This requires prep work from the leadership team prior to hosting the retreat.
  • Strengthen the social connections of our team members. This means creating an intentional agenda and environment that encourages organic interactions between team members. Whether this is through working, activities or sharing meals, think about each moment as an opportunity to develop and strengthen relationships. Ultimately your team culture will benefit.

Our goal when we plan a retreat is to provide a meaningful, enriching experience that is valuable for both the individual and the company. We want everyone to grow in their relationships with team members and invest in our greater goal of building a house we want to live in.

Who Plans a Company Retreat?

The planning process of a team retreat touches many different departments. At Close, our People Operations team are the main planners and facilitators of our company retreats.

Who Plans a Company Retreat?

It’s important to designate a person or core team who will handle the finer details of the retreat planning process. They can ensure everything runs smoothly and problem-solve whenever unexpected challenges come up (which is guaranteed to happen).

Want to see how our planning process works? Download a free retreat planning timeline template to use and adapt to your next company retreat:

GET YOUR FREE RETREAT PLANNING TIMELINE TEMPLATE →

How to Plan a Remote Company Retreat in 4 Steps

Make it fun! Retreat planning can be a stressful and overwhelming experience. But when your efforts are in the right places, the results can be overwhelmingly positive. It’s often one of the most rewarding projects the People Ops team undertakes in the year.

Why do we say that? Because of responses like these from the team:

“Having everything so structured and organized was incredible. I was never confused or lost on what to do. You guys did an AMAZING job with that. Overall an incredible retreat! You all should feel super proud with what you created for the team.”
“My huge appreciation to the ops team for not only organizing this retreat in such a seamless way, but looking out for all of our individual preferences and happiness during the week. You are a very special team and I'm so happy and thankful that you work here.”

Here are the four main steps you’ll take in the planning process.

1. Build a Budget

While it may not be the most interesting topic, it’s often the most necessary planning factor that will determine how the retreat is designed.

Figure out how much you can spend per team member to get an overall estimate of the entire retreat cost. Some of the main items to include in your budget may include:

  • Transportation to, from the airport and during retreat (flights, shuttles etc)
  • Accommodation (single vs double occupancy rooms)
  • Food & Beverage
  • Activites
  • Meeting space & AV

Become familiar with the travel & event planning industries. Take advantage of perks and understand the variables. For example, a resort may have a F&B minimum that should be considered within your budget. Oftentimes onsite meeting space fees can be waived based on other requirements.

Download this free budget calculator for your next company retreat:

GET THE COMPANY RETREAT BUDGET CALCULATOR →

2. Decide on a Company Retreat Location

We start our retreat planning process at least 10-11 months in advance. Choosing a location is always one of the most exciting yet challenging decisions. We recommend partnering with a company like RetreatsandVenues.com which is a great way to optimize your teams’ efforts and receive the best competitive rates.

When choosing a company retreat location, here are some things to consider:

  • Logistics: Where is your team currently located, and how will they arrive to the location? If your team is spread across the world like ours, you’ll need to consider proximity to a major international airport and how your team members will get from the airport to your retreat venue.
  • Accessibility: How accessible is this location for your team? Is there anyone on your team with specific needs or disabilities that should be considered? What about visa requirements for international team members?
  • Lodging: Planning and activities are always easier when the whole team is hosted in the same space. As part of your budget and location scouting, decide if attendees will be sharing rooms or have private accommodations.
  • Retreat venue options: Does your lodging venue have conference rooms for meetings? (We highly recommend onsite meeting and breakout rooms). Are food services onsite, or will you need to hire a catering service? What restaurants and amenities are nearby?
  • Activity ideas: What does this location offer for activities, both onsite and offsite? Is there a good variety of activities to choose from? Is there space in the venue to host activities for the whole team?
Decide on a Company Retreat Location

It’s also important to know what your team is interested in. For example, our last retreat survey showed us that the team was interested in a more nature-based retreat (rather than, say, endless happy hours in a bustling city), with more open spaces in a less populated destination.

Prior to signing a contract, we send someone from the People Ops team to visit for at least one overnight. This ensures we are comfortable with the venue and area before making a large financial commitment. We recommend doing a site visit if you’re hosting more than 30 people. During the visit, it’s a great time to also check out some of the activities, tours and restaurants that may be part of the retreat experience.

Our company retreat locations have included Montreal, Park City (Utah), Lisbon, Dublin, Berlin, Venice Beach, Charlotte, Lake Tahoe, and Santa Barbara. We try to host between North American and European destinations since our team is mainly distributed between these locations.

3. Pick a Relevant Theme

For the entire team to be aligned coming into this offsite event, we recommend choosing a theme.

For example, at our 2017 retreat in Dublin, Close CEO Steli Efti decided on the theme “Getting Back in Touch With Our Core Customers”. The week was focused on how we could make our product, customers, and company more successful by serving our end-users better.

Our May 2022 retreat had a very different theme, based on one of our core values: “Invest in Each Other”. After two and a half years of not seeing each other in person due to the pandemic, we wanted to deepen our relationships within the team and get to know each other better, especially since this was the first time many of our team members were meeting in person.

Pick a Relevant Theme for Your Team Retreat

To choose a theme for your company retreat, consult with the leadership team and talk about these questions:

  • What are the main business challenges we’re facing as a company right now?
  • What are our most important goals for the next year?
  • What personal or professional challenges are the individual team members facing?
  • What does the team need right now to walk away from this retreat feeling motivated and aligned with the company?

4. Create Your Company Retreat Agenda

For a small team that’s generally located in the same area, a one-day retreat may be feasible. But for most remote companies, it makes sense to organize a 3 to 5 day event.

Your agenda for these days will obviously vary depending on your goals, but here are some of the key pieces you should absolutely include:

  • Presentations from leadership
  • Working time for the different departments to spend together
  • Shared meals
  • Fun activities and team-building exercises
  • Space for team members to have free time

Company Retreat Agenda Template

Our last company retreat agenda looked like this. At first glance it may look overwhelming but it was thoughtfully designed to ensure we optimized our time together:

Company Retreat Agenda Template

Here’s how it worked, broken down by day:

  • Sunday: Team arrivals, with an optional welcome event with drinks and pizza. This was very casual, and gave people who were arriving at different times during the day the option to meet team members and get settled in.
  • Monday: Our first day of business alignment started with a kickoff meeting and presentations from our CEO, Steli, as well as the Sales, Marketing, and Product teams. In the evening we had our all-hands dinner together at the lodging.
  • Tuesday: This was a day for retreat activities, including horseback riding, trap shooting, side-by-sides, and hiking tours. In the evening, each department went to dinner together at local restaurants.
  • Wednesday: This was a day for collaborative sessions with each department. Additionally it was an opportunity for managers to host 1:1 walks with their direct reports. As part of our theme, “Invest in each other” we hosted a relationship-building card game that gave storytelling prompts.
  • Thursday: Another day for retreat activities, including mountain biking, yoga, a wine tour, and a low-key hangout time for team members who wanted some pool-side space. For our last night, we hosted another all-team drinks & dinner to finish off the week.
  • Friday: After breakfast, the team went their separate ways and traveled back home.
Pro Tip: Ready to create your own team retreat agenda? Use our company retreat agenda template to get you started!

GET YOUR COMPANY RETREAT AGENDA TEMPLATE →

Company Retreat Ideas: 17 Team-Building Activities to Build Camaraderie & Have Fun

From remote startups to larger companies, arranging fun activities as part of your company retreat is a great way to build teamwork and help the whole company get to know each other and grow together.

Wondering what to do? Here are 17 ideas for your next company retreat.

  • Mountain Biking: If your team loves adventure, try mountain biking! When visiting a place that’s not familiar to most of the team, you’ll probably want to book a biking tour with a professional.
Company Retreat Ideas
Mountain biking during our last team retreat in Utah
  • Cooking Classes: Every team has a few hidden chefs (or at least some who’d like to become chefs)! Cooking classes are a lot of fun and get your team working together in an environment outside of the day-to-day work.
  • Sailing: Getting out on the open water is a great way to enjoy lovely weather and spend time with your team.
Company Retreat Ideas Sailing
  • Trap Shooting: This is a great sporting activity that our team has enjoyed together.
Company Retreat Ideas
  • Customer Visits & Interviews: While your company retreat is a time to get away from the day-to-day hustle of work, it’s also a fantastic opportunity to get to know your customers in-person. It’s really inspiring to walk into a customer’s office and see people actually using the software you’ve developed. It’s something you can’t replicate in a dashboard. Sometimes we’ll also invite customers to give talks or conduct Q&A sessions at the retreat. If there aren’t any customers in the city we’re visiting, we host a video call with a customer in the same time zone. These are great opportunities to learn from the people who use your product most.
  • Scavenger Hunt: A fun combination of competition and teamwork, use a scavenger hunt to help your team get to know each other and win prizes.
  • Team Sports: Whether it’s a friendly game of football (American or European), baseball, or volleyball, playing a team sport together can be a great team-building exercise while having fun!
Company Retreat Activity Ideas Volleyball
  • Horseback Riding: For adventurous remote teams, this can be a great way to get outside and see the world together.
Company Retreat Ideas Horseback Riding
  • Side-by-Sides: Of course, if you’re looking for a faster mode of transportation, side-by-sides are a great retreat activity for your team to enjoy. Definitely a Close team FAVORITE.
Company Retreat Ideas Activities
  • Hiking: Getting into nature and enjoying a walk in the woods is a nice way for the team to spend quality time together and talk (or goof off together).
Company Retreat Ideas
  • Escape Rooms: This has become an ever more popular activity for company retreats, and is another great way to build teamwork outside the work environment.
  • Yoga: Take a few deep breaths together and relax. Trust me, it’s worth it!
  • Game Night: At our last retreat venue, we had access to an arcade, and our team enjoyed getting to know each other over a bit of friendly competition.
Company Retreat Ideas Game Night
  • Tours: A remote team retreat typically takes the team to a place they’re unfamiliar with. Take advantage and schedule a tour of the area, whether through famous museums, natural sites, or a tour of the city.
Company Retreat Ideas
  • Axe-Throwing: This is another retreat activity that our team enjoyed in Montreal.
Company Retreat Ideas
  • Karaoke: Nothing bonds a team like singing loudly (read: badly) together.
  • Team-Building Games: At our last retreat, we hosted a relationship-building card game that far exceeded the team’s expectations. The prompts helped to create conversation and storytelling and has already been requested by many for our next gathering.
  • Icebreaker Games: These are especially important for remote teams who are coming together for the first time. Build this into your schedule early in the retreat so team members can get to know each other. We organized an Scavenger/Bingo icebreaker game that prompted everyone to find other team members who had things in common, and snap a picture to prove it. This helped the team open up and get to know each other (and the winners got a prize at the end).
Company Retreat Ideas Scavenger Hunt

Pro Tips for a Fun and Inclusive Remote Work Retreat

After 10 years as a remote company, we’ve planned retreats in 9 cities and 5 countries around the world. What started as a small retreat for six people grew into international retreats for almost 60 team members.

Through all of those experiences, here are some of the biggest lessons we’ve learned for a successful remote team retreat:

Understand What Your Team Wants and Needs to Feel Comfortable

During the pandemic, we stopped our in-person retreats and hosted virtual summits. In mid-2020 and again in early 2021, we sent out a team survey to gain a better understanding of what people were comfortable with in regards to COVID-19 and retreats.

These surveys helped us plan a retreat where our team would feel safe and comfortable, and where they would be able to enjoy the experience. From these surveys, we established our search parameters to help us decide on a location and activities for the retreat.

Inclusive Remote Work Retreat

Plan for Casual Social Times

Traveling and socializing can be taxing experiences. You should aim for your corporate retreat to be a low-stress event for all attendees. To make that happen, something we’ve learned is that it’s best to set a clear agenda, including any downtime or free space in the schedule.

Having casual times to get together without the pressure of an event is a great way for the team to develop stronger relationships. Whether it’s a S’mores night, cocktail hours, a casual pizza dinner, or a game night, these low-key gatherings are a great place for your team to recharge and learn about each other in a more relaxed setting.

Inclusive Remote Work Retreat

Communicate Well in Advance

Communication is an essential part of making sure everyone is comfortable before and during the team retreat.

At Close, we have a company-wide Wiki where we post all information about our upcoming retreats. We start these pages in the early stages of planning, and continuously update them as the time gets closer, sharing the final details one month before the retreat.

We also host a Q&A session before the retreat to make sure the whole team has the details they need. Around the same time, we create a retreat-specific Slack channel where people can communicate before and during the retreat, and send out calendar invites to each event during the retreat.

Provide A Variety of Choice to Make the Trip Inclusive

Options make it easier to be inclusive for the whole team. When planning retreat activities, make sure to keep your whole team in mind and think about what they want to do.

Our survey helped us with this as well, since we saw what kind of interests our team had and which activities were most popular. We planned multiple activities at the same time, so people could choose between things like mountain biking and yoga, or just spending some casual downtime at the hotel.

Inclusive Remote Work Retreat

This way, everyone felt included and no one felt pressured to participate in activities they weren’t comfortable with.

Create a Mindful Agenda, But Have a Contingency Plan

As an entirely remote company, our team only sees each other for these five days of the retreat once a year. Because of that, we spend a lot of time planning, reviewing, and adjusting the agenda to make sure that we’re using our time in the best way possible.

That said, it’s normal for even the most carefully planned retreats to hit a snag. So before your team retreat, think about what is most likely to be disrupted, and have a contingency plan for those moments.

Consider Working With an Event Planner

Retreat planning is a lot of work. If you don’t feel like your team has the bandwidth to cover all these details, you may consider working with a professional event planner.

Companies like Moniker are dedicated to planning company retreats, and will help you choose a destination and retreat venue, plan your itinerary and activities, and take care of logistical details.

Share Retreat Swag

Swag is a great way to remember your retreat. We love sharing our retreat swag with the team. You can choose something more evergreen with your company logo or create a retreat specific logo like we did for Park City.

Share Team Retreat Swag

Include Team Members Who Can’t Attend In-Person

For remote companies, it can be difficult to get 100% attendance at your retreat. That said, you can make sure your team members who aren’t attending in-person can still be part of the retreat.

If possible, try to include these team members in important meetings and presentations via videoconferencing. Record sessions and share that day.

Plan an activity that teammates can participate in virtually, such as a scavenger hunt. Send them a gift card to enjoy a meal or activity with their friends and family during the retreat.

These details will help your whole team feel more connected, even if they can’t attend in-person.

Record Everything

It’s always a good idea to revisit a retreat in the months that follow. That week can be intense, so it’s difficult to absorb every single item that was discussed. That’s why we try to record everything—team meetings, customer interviews, brainstorming and planning sessions. We keep everything—all the photos, videos, presentations, and documents—in a shared Dropbox folder so we can access them whenever we want.

These also serve as excellent onboarding material for new team members that join in between retreats.

Fun and Inclusive Remote Work Retreat

Send Out a Post-Retreat Survey

The best way to build a fantastic team retreat is to keep improving every time. That’s why it’s essential to gather feedback from your team. Make the survey anonymous and encourage everyone to share their honest opinion of the location, venue, activities, and agenda of the retreat. As you gather feedback, continue to iterate and design an even better retreat next time.

Start Preparing for Your Next Company Retreat

Ready to start preparing for your next company retreat?

You can take the four steps that we discussed above as a starting point, and use the templates we’ve shared to help you get started.

If you want to chat about planning a retreat, I love talking about this process. Feel free to reach out with any questions at mary@close.com.