How To Plan a Company Retreat: Your Complete Step-by-Step Guide

Planning a company getaway? Here’s your complete step-by-step guide on how to plan an awesome corporate retreat in 2022.

A company retreat is a great way to break up the usual routine and get colleagues together in a fresh environment. It’s the ideal setting for team bonding, thinking outside the box, and tackling challenges with creativity. 

Sounds great, right? But how do you make sure your retreat is actually enjoyable and not just another corporate event your employees or clients have to attend?

We’ll show you how. In this guide, you’ll learn:

  • What exactly is a company retreat, and what are the benefits of having one?
  • How to plan an awesome company retreat (9 steps & best practices)

We’ve also included a 10th bonus tip at the end, so keep an eye out for that. 

Ready to plan a company retreat to remember? Let’s go.

A team of colleagues posing for a photo during a company retreat
The Workshopper Team during a company retreat in Italy

What is a company retreat and why should you run one?

A company or corporate retreat (sometimes referred to as an “offsite”) is an event which takes employees out of the usual working environment. It can last a day, a few days, or even five—it all depends on the nature of the retreat and where it’s held. 

Whether you hold your company retreat in the same country, somewhere abroad, or online, it’s essential that it takes place away from the office or wherever your employees typically work. It’s a retreat, after all—not a meeting. 

There are many different reasons you might plan a company retreat. Perhaps you want to facilitate team bonding and collaboration, or maybe you want to provide some kind of training. Perhaps you want to get colleagues together to solve a particular problem. A corporate retreat can serve many purposes; it’s up to you to define the goal and plan the agenda accordingly. 

What are the benefits of a company retreat?

The major benefit of a company retreat is that it takes place in a fresh, new environment. This allows people to step away from day-to-day operations and routines, encouraging them to embrace new perspectives and think outside the box.

At the same time, being away from the usual business setting can help colleagues get to know each other better, build empathy, and generally create a stronger bond. This has benefits for teamwork, communication, and team morale. 

If planned and executed well, a company retreat is a great opportunity to problem-solve, innovate, learn, strengthen relationships, and boost productivity beyond the event itself. All good things, right? 

Onsite vs. virtual retreats: Which should you go for?

Remote work has become the norm across many sectors, so you might be wondering what this means for your company retreat. Should you opt for an in-person getaway or keep it virtual? 

Aside from considerations like budget and any Covid-19 restrictions in your area (or your desired destination), factor in the needs and preferences of your employees/colleagues/client, as well as the goals of the company retreat. 

Are people keen on the idea of traveling and meeting in person, or would they feel more comfortable with a virtual retreat? What do you hope to achieve from the retreat, and how might a virtual retreat vs. an in-person gathering impact that outcome? 

The Workshopper Team during the company retreat

Ultimately, you want people to feel comfortable while still benefiting from the change of scenery that a company retreat typically provides. It may be harder to achieve this “away from the norm” vibe with a virtual retreat—there’s a risk that it’ll end up feeling like any other remote meeting or workshop. But, with careful planning, it’s certainly possible. 

If you do opt for a virtual retreat, take extra care to differentiate it from everyday meetings—for example, by using different software, setting up breakout rooms, and putting on some out-of-the-ordinary activities. 

Whether you’re running an in-person retreat or a virtual event, it requires meticulous planning. You want it to be memorable for all the right reasons! So, without further ado, let’s take a look at how you can plan an awesome, unforgettable company retreat. 

Note: We’ve written our guide with in-person retreats in mind, but all of the steps and best practices provided can easily be applied to virtual retreats, too. 

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How To Plan an Awesome Company Retreat: 9 Steps & Best Practices

1. Plan the company retreat with a clear goal in mind

The very first step is to define a clear goal for your company retreat. What do you want to have achieved by the end of the retreat? What should people (and the company) get out of it? 

If you already have a clear goal in mind, you’re off to a strong start. This will be your northern star as you design and plan the retreat. 

If you don’t yet have a specific purpose for your retreat, no worries! Now’s the time to figure it out. Consider the following:

  • Is there a problem you want to get together and solve? For example, defining company values, coming up with the direction for a new product, feature, or campaign, or setting goals for the upcoming quarter.
  • Is there an aspect of company culture that needs improving or nurturing? This could be anything from fostering better communication to creating a more inclusive, psychologically safe workplace.
  • Do you want to use the retreat as an opportunity to offer training in a certain area? For example, perhaps you have lots of recently-promoted managers and team leads who could benefit from management training (or something similar).
  • Do you want to focus the company retreat on celebrating achievements and boosting morale?

As you can see, corporate retreats can be tied to all kinds of goals. Just make sure you know what your goal is before you start planning—and don’t hesitate to get input from others, too. 

2. Find the perfect location for your company retreat

Ok, perfect is maybe too strong a word, but you want to get as close as possible when choosing the location for your company retreat. 

The surroundings will really set the tone for the retreat, so it’s important to find a setting that not only allows for the kinds of activities you want to run, but also gives a bit of a “Wow” factor. Think nature, waterside, luxury, historical, or unique—or all of those things combined! 

A view of the Workation Village located in the North of Italy
The Workaction Village in Italy

The best retreat locations encourage people to relax and explore during their free time, and offer ample opportunity for socializing and spending time alone. When considering a venue or location, think about where people will sleep, what facilities are available for work and recreation, and what food options are available. 

You’ll also want to make sure the location isn’t too difficult to get to (especially if you’re expecting people to find their own way there). The perfect location might not be so great if you have to travel 10 hours by bus to get there. 

If you’re planning a virtual retreat, think about location in terms of what software and tools people will use to congregate, as well as how you can set it up to feel different from a standard meeting. 

3. Don’t overpack the agenda—leave room for work and play

Just as you’d write an agenda for a workshop or meeting, it’s important to have an itinerary for your company retreat. However, the sole focus shouldn’t be on maximizing productivity or cramming in as many activities as possible. 

Workshops and group sessions are great, and you’ll need them to move towards your goals. However, they can be exhausting. If you schedule too many organized sessions, all people will want to do at the end of the day is lay down alone in a dark room. 

So: Plan your itinerary carefully. Include essential workshops and group sessions, and leave plenty of space for organic team building and downtime, too. Aim for a balance and ensure people have enough time, energy, and flexibility to grab a coffee with a colleague, go for a nice walk, or have a swim at their own leisure. 

4. Build fun into the agenda

The best company retreats are those where people feel comfortable and relaxed. Hopefully, your chosen location will go some way to putting people at ease and getting them in holiday mode. 

A long table setup for wine tasting during a company retreat
Wine tasting at the Workaction Village in Italy

Beyond that, put on some activities that are purely for fun—and, in doing this, remember that “fun” means different things to different people. Steer away from the clichéd raft building and “trust fall” exercises, and instead consider what people might actually enjoy doing. 

What you go for will depend on your location, but some of our favorite activities include:

  • Group bike rides or walks
  • A guided tour around the local city or town
  • A quiz or game night
  • A wine tasting

Plan a variety of activities that will appeal to as many people as possible, and make sure there are options that are accessible for everyone. In fact, that brings us to our next point…

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5. Plan a corporate retreat that caters to everyone

Some people will be thrilled at the thought of attending a company retreat. Others will feel a little nervous about being out of their usual surroundings. Some people will want to socialize the entire time, while others will need plenty of space to recharge their batteries. 

Not everyone will eat the same foods or follow a similar diet, and not everyone will drink alcohol. Not everyone will want or be able to take part in physical activities. 

Everyone will have different needs, and everyone should be given equal opportunity to take part in, and enjoy, your company retreat. Plan your retreat with inclusivity and accessibility at the forefront. Ensure everyone has sufficient food options, and that your planned activities don’t risk excluding certain people or making them uncomfortable. 

6. Communicate the plan (and expectations) ahead of time

If there’s one thing a company retreat does well, it’s taking people out of their comfort zone. This can work wonders for creativity, innovation, problem-solving, and team bonding. In the lead-up, it may also create some anxiety. 

You can alleviate any pre-retreat anxiety by communicating early and clearly. This requires you to plan well ahead of time and keep people in the loop as to what they can expect from the retreat. 

People will want to know:

  • The exact dates and location of the retreat
  • What kind of accommodation will be provided
  • How to get to the retreat (is transportation provided?)
  • The purpose of the retreat and what the expected outcomes will be 
  • If there’s anything they need to prepare in advance
  • The agenda/itinerary 
  • Whether they will be expected to answer work emails and perform day-to-day operational tasks during the retreat

The more you can communicate ahead of time, the more at ease people will feel. This sets a great tone for a relaxed, productive, and enjoyable company retreat. 

A group of colleagues exploring the company retreat location
The Workshopper Team exploring the Workation Village in Italy

7. Work with an expert facilitator

If you want to ensure a successful team retreat, it’s worth hiring a professional facilitator. Facilitators are trained to lead productive workshops and meetings. They’re experts at handling conflict, teasing out the pain-points, and guiding people towards a solution. 

There are many benefits of working with an external facilitator. For one, they’re not involved in team dynamics or office politics, so they can address problems and challenges from a different perspective—and help others to do so, too. At the same time, people often find it easier to be open with a stranger; if it’s a manager or leader running the session, they may be more wary of what they do and say. 

An expert facilitator will enable effective, solution-focused discussions, and equip your team with new ways of working that they can take with them beyond the retreat. You can learn more about facilitation and why it’s such a valuable skill here.

8. Establish action points at the end of the retreat

You started your company retreat with a specific goal in mind. You wanted to solve a particular problem, come up with new ideas, or improve company culture (to name a few possibilities). As your retreat winds down, it’s important to consider how you’ll take what you’ve learned and carry it over to the “usual” workplace setting. 

Towards the end of the retreat, carve out some time for everybody to get together and turn the retreat learnings into concrete actions. Ultimately, what needs to be done to ensure that you all continue working towards your goal? And who is responsible for implementing those actions and changes? 

Committing to clear, concrete actions will ensure the impact of your company retreat lasts beyond the event itself. This is important for achieving your original goal, and for making sure everybody knows that their time and input is valued. 

A group of colleagues gathered around a campfire during a company retreat
Team campfire at the Workation Village in Italy

9. Get feedback 

Planning and running an awesome company retreat is no small task. There’ll be things that go well, and things that can be improved for next time. After the retreat, send out a short survey to gather feedback—and make it anonymous so you get to hear people’s honest thoughts. 

When it comes to planning your next company retreat, refer straight back to your survey data so you can address any pain-points and ensure an even better experience the second time around.

Bonus tip: Treat your guests to a VIP goodie bag

A company retreat should be something special. If you have the budget, end your retreat on a high with a VIP goodie bag for your guests. Make it luxurious, unique, and as personal as possible—it’s a great way to say “thank you” and close the retreat on a positive note. 

So there you have it: Everything you need to plan and deliver an awesome company retreat. For more tips, check out this guide on how to design and run a successful workshop

Emily Stevens