A step-by-step playbook for organizing a successful company retreat for your remote team

by Amara Pope

Are you considering doing a company retreat for your remote team?

Perhaps you feel it will help you bond as a team, but you might be worried about the work required and costs involved.

Below we’ll dive into how you can organize a successful company retreat. We’ll go through the various considerations of holding a company retreat, the benefits it’ll bring your team, and how to find the perfect location.

Worried about the logistics? You’ll find tools and ideas to make planning and organizing much easier. Touching on experiences written up by remote teams worldwide, we’ll look at the costs you can expect to incur, and how you can reduce these costs. You’ll see the exact amount companies around the world spend per person.

But first: how can you expect to benefit from a company retreat?

The benefits of company retreats for remote teams

There are numerous benefits for running a remote team: flexible schedules, no commute, and the ability to hire the best – no matter where they live. You can also lose out on some of the intangible benefits of being co-located: Impromptu brainstorming sessions in the kitchen over coffee or building strong personal relationships during after-hours socializing.

One way remote companies can mitigate these downsides is by having a company retreat for your remote team. Ranging from a couple days to a week or two weeks long, these events gather all the company together in one location.

One of the benefits is you’ll be able to get to know your colleagues in person. Josh Pigford comments that many people in his six-person team hadn’t “done more than video chats with each other”, so he felt having a company retreat helped “give a great sense of everyone’s personalities”.

Having everyone co-located for a short period of time can unleash creative energy. Joel Gascoigne at Buffer argues his team gets an insane amount done on their retreats, pointing to new products such as Buffer for Business or an updated iOS app being released.

Personally, I’ve found when I was working together with teammates on a company retreat, new ideas flourished thanks to the change in environment. Even simple things such as getting lunch together often result in interesting conversations that give you ideas for new directions.

A retreat also makes it easier to brainstorm and plan for longer-term projects, by having the team physically together and in direct communication. The fact that your time is limited to the duration of the retreat also adds an impetus to agree on a plan, rather than postpone a decision until the next meeting.

And there’s one final benefit: company retreats can be just plain fun! You get to hang out in awesome locations, have fun, and build an even better future for your company.

Finding the perfect retreat location

relaxing retreat location

Going on a company retreat takes time away from home, so it’s important the retreat is something your colleagues can look forward to. This is especially important if they have to cover commitments back home.

Therefore, it makes sense to choose a location that people can get excited about. Going to a local hotel conference room to spend the week inside listening talks is hardly the type of retreat that will inspire people.

The weather will be a big factor, so many retreats try to go somewhere the weather will be warm – this includes places like Mexico, Florida, or even Thailand for the more adventurous teams. Just don’t try to snag a bargain by booking in the off-season: Wildbit tells the story that they made a big effort to find the perfect house with a pool, but when they arrived they found that it was too cold to swim in the off-season.

The size of your team will impact where you can go. A friend of mine works at a company that brings together several hundred people once a year, so they need to find an entire hotel that they can book out for the retreat. A smaller team of 10 people can find a larger house to rent on Airbnb. When you need space to hunker down and get work done, your best bet would be using a network like LiquidSpace. LiquidSpace features workspace listings in thousands of locations from the biggest and best workspace providers, landlord partners, and private businesses. There you can find training space, conference rooms, event space, and more, on flexible terms from an hour or longer. Ideally, the location should have fun activities such as a pool, hot tubs or a BBQ.

Company retreats can also be an opportunity to meet some customers in person. Small Improvements has offices in Berlin and also have team members working remotely. They held their company retreat in San Francisco, where they met their local customers in person and saw how their products were used.

As we’ll see later on, the costs of a retreat can add up considerably, so choosing a low-cost location in and flights can be one way to reduce the expense.

Logistics: Scheduling, getting there and on-site organization

Once you’ve decided on a location, it’s time to get down to the nitty-gritty of organizing the retreat. The earlier you start planning the better.

The first logistical task is to find a date for the retreat. I’ve found scheduling tools such as Doodle invaluable because people can mark their availability. Then you can choose the dates on which the most people are available. From experience, you’ll struggle to find dates that work for absolutely everyone, particularly for larger teams, but that shouldn’t stop you from going ahead with the dates that work.

Once a date is set, it’s time to organize flights and find accommodation, and start thinking of planning transportation. For smaller teams, ask the team members to purchase their own tickets and then reimburse them afterward. This lets people decide to extend their trip – if they want to do some sightseeing outside of the company activities. At the same time, you are asking employees to front the costs before being reimbursed, which isn’t always ideal.

Asking your employees to figure out the best flights will take valuable time away from their work. You could consider engaging the services of a travel consultant to plan the best value flights. Some services such as Flightfox or the Flight Doc provide travel advice on finding the best deals.

A consideration to think about is catering on-site. For larger retreats in hotels, you can sometimes use onsite services. Smaller retreats in a large house, however, will require some planning. A week-long retreat will involve 21 meals over 7 days, so it’s not an inconsiderable task. Options include having a schedule for team members to team up to cook on different days as Baremetrics did. Zapier mentions paired cooking as being one of the most fun events of the retreat.

Another option for larger teams is to hire a private chef, particularly if you want to focus on working together, rather than cooking together. Food restrictions are also something you can add to a pre-retreat survey, so you can be sure to plan for everyone’s needs.

Who should plan the company retreat?

As we’ve already seen, organizing a company retreat is no small matter. Even a very small team will require someone to spend a considerable amount of time planning the details. When you get to larger team sizes, the logistics start to get quite complicated.

Buffer sent a scouting team to visit their retreat location in Barcelona, Spain, ahead of time, so they could look at different locations to find the perfect one. Another option is to have volunteers work on a planning committee responsible for organizing the event.

A quick Google search for “company retreats” shows plenty of commercial providers offering package deals to reduce the organizational work involved.

How long should the retreat last?

Retreats generally range between 2 to 10 days. However, the sweet spot appears to be about 5 days bookended with 2 days for travel, as vacation homes often rent for 7 days at a time. Longer than a week starts to get too long for people who have commitments.

Flight durations are also a consideration: If some team members have to fly halfway around the world, they’ll struggle with time zone differences, so having a slightly longer stay for them will help them get over their jet lag and enjoy the retreat.

The retreat goal: Focused on work or recreation?

people having a meeting

I’ve noticed several different approaches to company retreats. Some companies use it as a team-building vacation with plenty of extracurricular activities planned during the day. Others focus on long-term planning and brainstorming, whereas others focus on getting day-to-day work done but in a co-located setting.

At Buffer, they comment that, while they work 9-5 during their retreats, they focus more on conversations, sessions, and ad-hoc syncs, rather than their normal day-to-day work. They can take advantage of being around their colleagues.

In his book “The Year Without Pants” Scott Berkun talks about his experience at the retreat for Automattic, the company behind Wordpress.com. Automattic opted for a self-organized retreat: each team is instructed to pick a project they’ll ship in the week-long retreat.

Scott comments that many retreats fail because the time is spent on discussions about future work or “meta-work”, rather than shipping something tangible. The result, he argues, is people are bored to tears from the endless team exercises and strategy updates, rather than tackling a problem they can solve together and ship out to customers, there and then.

Zapier splits their 4 work days into themes such as support, marketing, product, and team. Each morning, a few team members give short talks outlining the challenges in this area, and then the teams split into cross-functional groups to build something small such as a prototype or a feature that helps that day’s theme. At 5 pm they demo what they achieved.

“All hands” company retreats will present some challenges from an operations standpoint. Your customers will still want their emails answered and their servers online, regardless of whether you’re all at home working or off enjoying yourself on a fancy retreat. Therefore, consider setting up a roster to handle operational issues, so everyone gets some time to enjoy the activities, while customers still enjoy the service they deserve. Zapier staggers arrivals by having the founding team and international travelers fly in a day early and leave a day late, so customer support is still available when everyone else is traveling.

Organizing recreational activities

There’s little point in flying thousands of miles to an exotic retreat destination if you’re going to be locked up in an air-conditioned meeting room for the entire week.

Optional evening or afternoon activities can help people blow off some steam and unwind. Some remote companies attract a lot of introverts, who enjoy having time to unwind alone. It’s important to schedule downtime so people can recover, as they may well be meeting countless colleagues for the first time in person.

The activities will depend on where you’re traveling to. When I spent some time in Koh Lanta in Thailand, I saw that many teams tried early-morning, Muay Thai, introductory classes. Some groups even attended yoga sessions on the beach together. Day trips to nearby islands on long-tail boats were also a favorite activity. You can also check out city guides such as GetYourGuide to find nearby guided activities.

Who’s invited: Just team members or families welcome?

One consideration is whether to invite inviting family members to join. This probably only makes sense if you plan for the retreat to be more of a vacation than a week focused on shipping ideas and making plans.

The reason why to consider including family members is that taking a week to fly around the world is a big ask for many employees, especially if they have family commitments. Allowing people to bring their family makes it easier for everyone. There’s the additional benefit that it allows you to get a fuller picture of your teammates and socialize without feeling guilty about leaving family behind.

At the same time, consider whether you can afford the considerable financial costs. Buffer writes that they cover 50% of the travel and accommodation costs of dependents, as a compromise.

Visas, Wi-Fi, and expired passports: The little things that can mess up your retreat

You don’t want the best-planned retreat to be let down at the last minute by issues such as spotty Wi-Fi or out-of-date passports.

You might think the Wi-Fi at the house you’ve rented will be fine, but a lot of people start using it the basic Wi-Fi many holiday locations provide will struggle.

Having a backup plan will help reduce the risk of slow Wi-Fi. You could consider bringing a mobile broadband router with an unlimited data plan or buying some local sim cards if you’re abroad to provide a backup plan.

If some of your team members are traveling internationally, they’ll need to have a valid passport and check any visa requirements. Sending out a checklist a few months before will give people the time they need to get all their paperwork in order.

Co-living: An alternative for longer retreats?


As digital nomadism – living and working without any fixed abode – becomes a cultural phenomenon, several options have started to become available that combine co-working with accommodation and catering.

Personally, I spent a month at KoHub, a co-working space located on the Thai island of Koh Lanta, that offers packages with co-working working facilities, accommodation, and two meals a day. When I was there I met quite a few start-ups that brought their entire team to work together for a month.

Pieter Levels breaks down the economics of such remote work retreats. His take is pre-packaged remote work retreats only work from an economic perspective at the premium, “white glove” end of the scale. What he feels works better is a self-organizing approach where teams create their own temporary co-living arrangement together with other teams, which he has created an online community around.

Costs: benchmark for costs involved from around the web

So far, we’ve been talking about the fun side of retreats.

But what about the financial cost?

Well, from a survey of publicly available data, retreats are not cheap. Based on public information shared by Buffer, Baremetrics, Wildbit, and Small Improvements, the average cost per person for a retreat was $3,672.94 with costs ranging from $1748/person on the low end to $5429/person on the high end.

The big costs are flights to the destination and accommodation on-site. For example, Wildbit says these two items eat up about 50% of their budget. Finding destinations with good connections will make it easier to find cheaper flights in, whereas locations outside of major cities will make it easier to find affordable, high-quality accommodation.

Naturally, the flights will also be a higher proportion of the costs if your team is spread globally, rather than just from, say, USA.

So, is the cost worth it?

As we can see above, the cost is certainly considerable.

At the same time, remote companies avoid renting a prestigious real estate in prime locations. According to research done by SquareFoot, the average annual cost of renting office space per employee ranges from an eye-watering $14,800 in New York City or $13,032 in San Francisco to a still sizeable $4,194 in Atlanta.

Based on the figures above, a remote company will have plenty of change left over if they opt to forgo a prestigious office in a major city. One company did just that: Automattic, famous for its remote working culture, recently shut down its 14,250-square-foot office, as Matt Mullenweg, the company CEO, felt there were better ways to use the money rather than renting mostly unused expensive office space.

In conclusion, the message from remote companies on the topic of retreats is universally positive.

Wildbit says that retreats are “a time where we put names to faces, get to know each other’s personalities in real life, and of course plan for the growth of the product”.

Buffer CEO makes the point that for him company retreats are about choosing not to live a deferred life, but instead choosing to have amazing experiences and travel the world now, rather than some unspecified point in the future.

As the CEO of Small Improvements put it, he sees company retreats as “as an investment, not as a cost”.

Thomas Carney

About the Author:

Thomas Carney writes about SaaS marketing and growth over at ThomasCarney.org. His latest side project is building a community around minimalist travel and digital nomadism at MerinoWoolRocks.com.

View a free demo of Time Doctor

help managers focus on what matters most

time doctor ratings

Related Posts