How to set up a company retreat for your remote team [Step by step guide]

by Kevin Payne
Company Retreat

In a world where remote teams are quickly becoming the favored norm among many working professionals, it may or may not have crossed your mind to set up a company retreat.

After all, when you introduce company retreats into your remote work culture, it can only help strengthen ties between team members and make employees feel like they’re valued where they are.

If you’re wondering whether or not a company retreat for your remote team is the next best step, read on. We’ll show some of the most compelling benefits, some potential challenges, as well as the actual steps you can take to set up your first successful remote team retreat this year.

Table of Contents

Benefits of running remote company retreats

There are several reasons you might want to host your very first remote team retreat.

Your team can unlock powerful new strategies together

There’s no denying the power of being able to sit in the same room as your teammates and brainstorm new strategies to grow your company.

And while we readily have video conferencing tools that come complete with add-ons like whiteboards, screen sharing, and smaller team huddles, being able to plan and brainstorm in person is just not a luxury that most remote and virtual teams regularly have.

Because of this, a company retreat makes for a perfect way to do company-wide planning and brainstorming, then proceed to execute and do follow-ups virtually.

Strengthens camaraderie and morale

One thing that most remote companies struggle with is keeping employee engagement high. After all, it’s often hard for most remote employees to bond with their coworkers — can you imagine talking about, say, your kids with a coworker over Zoom?

Because people will be meeting up in person, it’s a great way to keep your employees engaged, strengthen their interpersonal relationships at work, and keep morale high throughout the year.

Lowers employee turnover

One advantage of setting up a company retreat for your remote team is that it can help you lower employee turnover.

Many startups and companies struggle with keeping top talent, and one reason many employees leave even a remote job that offers them flexibility is a lack of strong company culture.

A company retreat is a great way to build and strengthen your culture so that even remote employees don’t feel so quick to jump ship at the next opportunity.

It’s great for attracting talent

Finally, one compelling reason a company retreat for your remote team should be high up on your list is that it can attract the best and the brightest talent from all over the world.

One of the skills that many HR managers need to master is making their company seem more attractive to their potential hires. And with many companies now going virtual — many of whom are part of the top 500 companies in the world, such as Airbnb or Microsoft — it becomes harder to set your company apart.

A company retreat is a way to do just that. If you play it smart and create content, like LinkedIn articles or blog posts about your retreat like this one, that can go a long way to show potential candidates what makes your company one of the best in your industry.

Challenges of setting up remote company retreats

However, as great as company retreats are, there may be some challenges you might face even from the planning stages. Read on to discover what these are, so you know what to prepare for as you set up your first remote company retreat.

Travel itineraries per member

If your team is spread out across multiple countries and continents, getting everyone to convene in one place can mean some challenges in creating travel itineraries per team member.

Your HR or People team will have to look into flights and other modes of transportation that will get everybody to your retreat destination safely. Depending on your chosen location, this could mean planning flights for everyone, together with any travel plans to and from the airport.


Another challenge that might arise when you plan a company retreat for a remote team is potential visa issues.

Depending on where your team members live and their nationalities, they might require travel visas to join your company retreat.

Every country can have a different set of requirements and rules for applying for a visa, and you might run into problems during the application process itself, such as visa rejections or delays.

Because of this, plan way ahead of time to make sure that everyone is able to secure travel documents like visas well before the trip.

Encouraging everyone to join

One challenge you might also face when setting up a remote company retreat is surprisingly getting everyone on board. For one reason or another, some team members might be hesitant about joining the trip.

Be it because they have family commitments like small children or sick partners or parents or other circumstances that make it hard to travel (such as the recent pandemic that caused multiple outbreaks and lowered people’s willingness to travel, even if for a week), you need to be sensitive about these concerns and plan accordingly.

Steps to set up a successful remote team retreat

Convinced that you need to plan a remote team retreat? Before you book flights for everyone, here are some of the steps you should know to make sure your gathering is a fruitful one.

1. Set your company retreat’s objectives

First of all, you have to be clear about the objectives of your company retreat. A retreat is not a vacation, and you should have some goals to achieve with your team.

Here are some ideas for objectives you might want to set during your remote team’s company retreat:

  • Strategy and planning for the next quarters
  • In-person feedback rounds and sessions
  • Hackathons and activities to encourage creativity
  • Hosting workshops for career development
  • …and of course, organizing fun team building activities, like sight-seeing, games, and free time for team members to use as they wish

2. Plan out the schedule

After you’ve narrowed down your clear objectives for the trip, it’s time to plan out the exact activities that you can do on the schedule.

Having a clear itinerary makes sure that your company retreat is neither over-scheduled nor under-scheduled. Too many activities can mean your team is scrambling to hop from one thing to the next, while too little might not make for the most engaging trip.

When in doubt, give allowance for every activity, even if it’s just half an hour. If you’re planning any trips outside your hotel or house rental, add some padding for travel time, traffic, and the like.

Pro-tip: even if it is your HR and management that plan the trip together, don’t hesitate to include your employees’ thoughts about activities you can all do together during the retreat. This makes them feel more involved and that their ideas are valued at your company, especially if they’re implemented during the trip.

3. Balance work and fun time

As we mentioned before, a retreat isn’t a vacation — but it’s not purely a working trip either. There should be a balance between work-related activities, like meetings, hackathons, workshops, and presentations, as well as fun activities like games, team-building exercises, and any tourist activities you can all do together.

You might also want to leave time in a day for people to get work done. After all, even if you are on a retreat, there is still work to be done. Let your team catch up on work in their own time, and be sure that this free time is scheduled into your itinerary.

4. Get everyone to buy-in

One important step to make sure you’re planning a successful company retreat for your remote team is to encourage everyone on the team to attend.

We mentioned in the previous section that some people may hesitate to join a company retreat for one reason or the other, but that doesn’t mean you can’t do your part to encourage people to attend anyway.

One great way to make your point come across and encourage every team member to come to the retreat is to announce and pitch the retreat with a video presentation

Inside this video, you can make the announcement that you’re planning a company trip in the coming months, the goals and objectives your management team has set out, and how their participation will impact the company retreat in a positive way.

If there are team members who have concerns, be sure to hear them out and address them. You might be able to arrange for something that will make sure these concerns are addressed and increase the chances that everyone buys in and wants to attend to make it a fruitful retreat.

5. Deal with the team retreat logistics

Once you know how many people will be attending the retreat, you can move on to planning specific things for your logistics needs, such as the place to stay, the number of rooms (or houses) to book, and other things for the trip.

Here are some things you’ll want to think about as early as now:

  • Will you be renting cars for the trip? How easy is it to rent cars? Are there enough team members who can drive comfortably in rental cars? (Note that different countries will have different drivers’ sides, license requirements, and the like.)
  • If you won’t rent cars, how will the team go around? Public transportation, or hire a rental bus with a driver?
  • How will you secure travel insurance for your team? Or are team members meant to secure their own, to be reimbursed later?
  • What will the meal situation of your company retreat be like? Will you cover all meals by giving a stipend per individual, or will you plan for the team to make meals together? How and when will you secure any food items you might need for the duration of the retreat?
  • How close or far is your hotel, or rental place, from the tourist spots or outside areas you plan to visit? How long will it take to travel to and from these locations? 
  • What is the rooming situation? How will roommates be decided on, or will each person have their own room during the retreat?
  • Do you need to rent conference rooms for the trip? Will you need things like projectors, whiteboards, and the like for any activities?
  • What materials do you need for activities like workshops, games, and the like? Who is responsible for bringing them along?

6. Smoothen potential roadblocks

Earlier in this article, we shared some of the potential challenges you might face when you’re setting up your company retreat. Arm yourself with the knowledge of these potential challenges so you can plan accordingly.

Don’t forget to involve your team as well, as they might have questions and concerns that could become potential roadblocks you address.

It’s important to anticipate roadblocks that might come, and then make any measures necessary to smoothen them out or prevent them from happening during the retreat.

7. Make sure you got the right tools in place

Finally, one thing you need to make sure you have during the retreat is the right tools. Some of these will be in-person tools for the retreat but don’t forget about the teammates you might have that aren’t able to join the retreat at all.

Prepare for anything, and be sure to still involve people that are unable to make it. You might want to stream events, presentations, and workshops via Zoom, or have people take part in town hall meetings and discussions virtually as well.

And if you do have team members that aren’t able to attend, you can make sure they keep productivity up from where they are with employee monitoring software like TimeDoctor, so they can log their work activities when company events and talks aren’t happening.

Key takeaways/Conclusion

If you’re ready to plan your company retreat for your remote team, look no further than all the tips we’ve shared in this blog post. Commit to making sure every member of the company gets to be involved and valued during this retreat, and watch as the retreat translates into company ROI down the road.

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