Remote Company Retreats: Strategy, Ideas, and Activities From Experts

Speaking with many remote leaders, I know you're always looking for ways to improve your remote management experience, create stronger connections, and foster thriving team dynamics.

Remote work offers incredible flexibility and freedom, and with the right approach, you can enhance collaboration and camaraderie despite the physical distance.

In this article, I'll explore how remote company retreats are likely a good solution and how you can prepare yours, with inputs from two key experts.
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How often do remote teams meet? And how often should they meet?

According to the latest research from Stanford's Work From Home project, 45% of workers who were fully remote during the previous week meet their coworkers in person at least monthly.

And when we meet our coworkers, we most likely do so for a few hours. Whole days or more is very limited.

So how often SHOULD we meet?

The same research shows that remote workers who meet their coworkers more often have higher average earnings. So, it literally pays to hang out with your colleagues!

For fully remote companies, as remote thought leader Darcy Marie Mayfield recommends, companies should aim for 2 – 4 off-sites per year.

Organizing retreats for remote and hybrid teams can be challenging, requiring significant coordination and effort from the entire team. 

However, the benefits of these retreats can be immense, providing a valuable opportunity for team members to connect, collaborate, and grow together. 

With careful planning and a commitment to teamwork, these retreats can be a powerful tool for building a solid and successful team.

This article will examine why companies invest in remote team retreats, how to organize them, and which ideas and activities to put on the retreat schedule.
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Company Retreats: The Secret to Remote Team Building

Offering team retreats has become a must-have for remote companies. Dropbox, for example, countered record-high turnover with retreats and saw retention soar. 

Doist is another remote-first company with teammates in 35 countries. They bring the whole company together once per year and organize mini-retreats as focused team meetings. For example, the marketing department going to Mexico City and the back-end team gathering in Paris.

(Read our interview with Chase Warrington, Doist's Head of Remote, here.)
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Stephanie Lee, Director of People Experience at Nansen, took 120 people from across the world to Bali earlier this year.

As she shared in our interview, she profoundly believes in the power of these retreats. Stephanie says that people who attended the retreat are much more likely to approach each other and connect for projects and collaboration. 

"If you can really set aside a big part of your employee experience budget to run a company retreat, the payoff is incredible." – Stephanie Lee, Director of People Experience at Nansen

Help Scout’s CEO and co-founder, Nick Francis, recently reflected on their 14th retreat, mentioning that every time the company does a retreat, it reminds him of what they lost during the pandemic and why retreats are so important. 

“Without a doubt, retreat week is the most important week of the year for this company,” he said. “Since we work remotely, retreats are really the only time we have to break bread with our colleagues, build relationships, and talk about the future of our business, all in one place." Nick Francis, CEO and co-founder, Help Scout.

If you're in search of a vendor for employee engagement that can assist you in planning a comprehensive team retreat like those, Midstay is worth considering.

The importance of strategy for your retreat

According to Stephanie, strategy is critical for company retreats. You may think about a week of fun in the sun, but the best retreats are organized with incredible intentionality.

A good retreat requires thinking about the company's needs at that point in time. The demands of the experience differ depending on the company's composition, and structuring team sessions around those needs is essential.

Stephanie also recommends setting the right expectations at the beginning: be present, contribute, and rest when needed. We're here to connect, but it is a work event. Doing this will increase the chances of a successful retreat that genuinely moves the needle. 

Help Scout reminds us that no matter what, personal connections should remain at the heart of retreats. "While we’re still working on finding just the right balance in retreat planning — time spent informally and in structured activities, the best groupings for meals, and the right mix of team-building activities — we know that continuing to prioritize connection will shape the experience of future retreats, too."
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The Challenges Of Planning Retreats

In his Forbes article, Chase Warrington, the Head of Remote at Doist, noted some of the challenges you may experience when planning retreats or offsites:

• When planning offsite events, teams may lose focus on their regular work. 
• Leaders may get caught up in coordinating details, which could be more effective in using their skills and attention. 
• Poorly synced calendars can disrupt company-wide workflows, resulting in various teams being out of the virtual office in consecutive periods.

Doist solved this by building an offsite program with clear ownership that would allow us to maintain a sharp focus on our day-to-day work while still enjoying all the benefits of bringing our teams together.

In an interview I had with Chase in November 2023, he added that they do more than just retreats. The annual retreats are actually a part of a broader strategy that also includes mentorship trips, where a new hire gets sent to work with their mentor face-to-face for a week, and a bi-annual mini-retreat where direct teams spend a week together somewhere.
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Ideas and Activities for your remote team retreat

As Stephanie highlighted, start by looking at your company's biggest challenge and design your retreat program around it. Your latest employee engagement survey is a great place to start.

With this challenge in mind, put together your itinerary. Some ideas to consider:

1. Team-building activities: Bring your team together on the plan activities that promote collaboration and teamwork, such as a company retreat, group problem-solving challenges, team-building games, or simple icebreaker questions.
2. Professional development workshops: Consider inviting speakers or hosting workshops to help team members develop new skills and gain knowledge in their field.
3. Outdoor adventures: Plan outdoor activities such as hiking, kayaking, or camping that encourage team members to bond and connect in a relaxed setting.
4. Cultural excursions: Organize trips to nearby cultural sites or events that enable team members to immerse themselves in the region's history, customs, and traditions.
5. Unstructured time: Leave plenty of unstructured time in the itinerary for team members to connect and socialize with each other. This can be as simple as scheduling meals together or providing downtime for team members to explore the local area independently.

Remote work expert Darcy Boles emphasizes this last point in a recent post for WorkTripp:

"The biggest myth is the offsites should be filled with content. People will begin to realize how intentional we should now be spending any synchronous time together to support autonomy outside of onsites and connection within them." – Darcy Boles

Tips for planning your next team retreat

1. Tap into experts. Help Scout recommends getting support for the details of planning a retreat so that you can focus on the big picture. Travel and logistics can get incredibly complex, and a (local) partner can be helpful in doing the work.
2. Set clear ownership. Doist highlights the need to set clear ownership for organizing the retreat, and "giving them full responsibility for executing the strategy."
3. Build the hype. The offsite doesn't start on the first day of the retreat. Darcy recommends to tap into "invites, drip campaigns, travel tips, expectations, pre-sway" for a successful retreat, as they "help shape the feeling of the event and calm any nerves of those who don't travel often."
4. Leave space for connection. Help Scout suggests not overlooking the time people need to connect casually, for example by adding blocks of open time, and offer seated dinner times.
5. Build shared experiences. According to Help Scout, doing work together helps create more understanding across the company. "This shared experience of connecting around our product and supporting our customers team so they can also enjoy the retreat connects us all to the company and to one another."
6. Automation, Systems, Processes. Doist also recommends using an app to create "a series of automated tasks, which can be replicated and adjusted for all company retreats with the click of a mouse.

Using a retreat planner

You may not want to do all the work yourself. If you're looking for some support, check out these great companies:

• Midstay saves you time on research, planning and organizing your company retreat. Packages are customized to your needs.
• WorkTripp focuses on retreats and team offsites in nature that build connection, culture and creativity.
• The Offsite Co creates seamless, streamlined and epic internal events and retreats for remote companies.
  

If you organize a team retreat for your remote company, hopefully, the above will be helpful. If you're looking for a step-by-step planning help, then this worksheet from WorkTripp will come in very handy – and it's free!