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How to Plan a Company Offsite: Tips and Best Practices

Blog / May 19, 2023 / with Christoph Drebes
Two colleagues doing high-five. Another smiling colleaue in the background.


Let’s start with the basics – what is a corporate offsite? Is it the same as a corporate retreat? What’s a workation? What’s the difference? 

Workations are a way to connect employees effectively in the long term. The language used varies, but they all refer to a company event that takes place outside the office. However, the name chosen does often reveal something about the intention of the event. 

  • Corporate offsites vary from company to company. They may be organized team by team or be an all-hands event. They could be presentation-based or workshop-based. They could last for one day or several days. “Off-site” or “offsite” is essentially the most flexible term. 
  • Corporate retreats are often taken over several days with a smaller group of people, usually at the management level. These events generally have clearly defined business objectives. Retreats also include an element of team building and socializing. 
  • Workations are generally a blended program of workshops, private work, and team-building-oriented leisure activities.  

The term “workation” is also sometimes used to describe a temporary digital nomad – an individual who travels to a holiday destination while working remotely. However, many European organizations commonly use “workation” instead of “offsite.” 

Why should you invest in an off-site event? 

Here are our top three reasons: 

1. Stimulating focus and creativity

Even when a workforce is used to working hybrid and remote, there’s no substitution for time spent face-to-face. Being in a different location can bring out creativity, with 34% of workers saying that they have their best business ideas while traveling. Offsites can also allow people to voice concerns and questions and can provide a space to focus on topics outside of the day-to-day operations of the company. This is ideal if you need to develop a new strategy or evaluate past performance in depth. 

2. Investing in company culture

Company culture can’t be built exclusively online. Many companies do a great job of building a supportive remote-first culture, empowering people to get to know each other whether digitally or physically. However, there are limits when everyone is trapped on the other side of a screen. Many remote-only companies rely on off-sites and workations to help their employees to get to know each other personally. These relationships then lead to better collaboration after the event ends.  

3. Rewards and retention

Corporate off-sites can meet two needs at once – the need to achieve business goals and the need to retain employees. By arranging off-site events at unique travel destinations and building in fun activities, the trip is as much a benefit or a reward for employees as it is a business trip. If you want to ramp up the reward element of an off-site, then the organization should pay for these activities or leave one day of the trip open for personal exploration of the destination.  

 Mystery Minds Team at Offsite

How to plan a company off-site 

First and foremost, it’s not always clear whose job it is to plan an off-site. 

Does the responsibility sit with People & Culture? If you have an Events team, does it sit with them? How about Internal Communications? Will you hire an external agency to help you take care of logistics? If you don’t have a dedicated team for corporate events, that might be the best option. 

Often, the decision to invest in a corporate off-site comes from the C-Suite. At other times, it might come from a department head whose team is struggling. 

One thing to clarify is that organizing an off-site is rarely a one-person job. There are a lot of moving parts, a lot of decisions to be made, and a lot of research to be done. 

This article will take you through some of the basic steps, but you can also download our checklist to make sure you haven’t missed anything. 

Planning a corporate retreat: the most important steps 

Collecting expectations 

The first step is understanding the expectations of the organizers. Are there particular goals they want to achieve? How many days do they think they’ll need?  

Is this off-site happening in a moment of crisis where you need to rethink strategy entirely? Will there be a lot of sensitive topics to discuss? 

Or is this off-site happening after a great quarterly or annual performance? In that case, it could function as a chance to understand what brought the success and how to replicate it.
Additionally, you might want to increase the amount of non-work activities so that the trip functions as a celebration as well.

Once you know what your C-Suite and Team Leads expect to get out of the trip, gather some insights from the whole team. If you’ve previously held an off-site, consider the feedback that you were given after that event.
If this is your first off-site, then a quick survey might be very helpful in your decision-making. 

You can ask:  

  • Would you be able to travel overseas? Some employees might not be able to join overseas trips due to visa restrictions and entry requirements, caring obligations at home, or concerns about accessibility. 
  • What would you want to get out of an off-site event? Employees will have their own desires. These might include meeting colleagues face-to-face, understanding the company’s trajectory and strategy, taking part in fun activities, or seeing a new city or country. 
  • What kind of activities would you be interested in? If you already have a list of potential activities suggested by the leadership team, then you can ask employees to rank their interests. That way you’ll know which ideas have the most support. 

Remember, you’ll never be able to please everyone. At the end of the day, you must plan to deliver the business goals first. However, knowing what would please the most people will help you to deliver a schedule that meets different needs. 

 Mystery Minds Team Workshop

Location, location, location 

One choice that you must make early in the process is where to hold your corporate off-site. 

LinkedIn is full of stunning photos of corporate retreats by the beach. This has contributed to the idea that off-sites are commonly held overseas in expensive, flashy locations.  

That’s not true. The majority of off-sites are still held relatively locally, often in hotels that offer specific support for organizations running workshops.
The photos are less idyllic, but the organization is still able to meet its business goals.

Naturally, there are pros and cons for each option. 

Pros of having an overseas off-site: 

  • Your employees are away from their routines and fully immersed in the trip. This can contribute to greater creativity. 
  • If staying in a rural location, natural beauty can provide inspiration and relaxation after the day’s workshops.
  • Many employees see overseas travel as a corporate benefit – it isn’t something that every organization offers, so can set you apart as an employer.
  • Your team is more likely to have new experiences together, helping to form closer bonds and supporting team-building initiatives. 

Cons of overseas corporate retreats: 

  • Travel expenses are usually higher and can include additional fees like visas and luggage costs. 
  • You may have to allocate more time to travel, reducing the amount of time spent at the location.
  • Depending on the country chosen, you may face language or cultural barriers.
  • You may face legal questions about whether your team can work while abroad, particularly if you enter the country on a tourist visa.
  • You may need additional insurance.
  • If you need to travel by air, your trip will likely struggle to be eco-friendly.  

Remember that if an overseas trip is too expensive and logistically complicated, you can get many of the same benefits of an overseas trip by heading to an area of natural beauty in your own country.  

 Colleagues Working Together Outside in Front of a Lake

Picking the ideal hotel 

Once you’ve considered the above factors, taken into account the preferences of senior managers and employees, and chosen your location, it’s time to select a venue. 

There are several essential things you’ll need:  

  • Enough capacity for your whole party
    Avoid splitting your teams across multiple venues. While it isn’t illegal to ask employees to share rooms, it should be avoided if possible so that everyone has a private space.
  • Plenty of space for collaboration
    You should have at least one seminar or meeting room available that fits your entire party. You may also need smaller rooms for group work. Venues that are used to catering for workshops will also be able to provide materials such as flipcharts, marker pens, and notepads.
  • Reliable WiFi connection
    A reliable internet connection is essential. This will be less concerning in some regions than others, but if you’re heading to a rural location, then you should check the connectivity and consider bringing your own portable router.
  • Ability to provide meals
    There are several ways that you can arrange the catering during an off-site. However, your team will need a minimum of breakfast, lunch, dinner, and coffee (with snacks), with flexibility if you’re going to dine at local restaurants on some evenings. Make sure to establish which meals you need each day and at what time and that the venue is able to handle any dietary requirements.
  • Setting
    You may want to find a balance between being completely rural and completely urban. If you plan to eat dinner outside the hotel, then it’s ideal if you can walk to several restaurants. Similarly, your venue shouldn’t be too far away from any activities. 

You will probably need to reach out to several venues before finding one that meets your criteria. Make sure to get full, itemized quotes in writing and to get written confirmation as soon as you’ve reached a decision. 

 Mystery Minds Team Having Lunch

Creating a corporate off-site schedule 

The creation of a schedule is something that you’ll need to work on with the different department heads and senior managers attending. They may have particular things they want to achieve within their team, but there will only be so many hours in a day. 

Here are some things to consider:  

  • Start each day with an all-hands kick-off meeting
    In this daily meeting, you can run through the day’s schedule and clarify any logistical questions. It’s also the ideal time to share updates and last-minute changes to the schedule.
  • Begin the trip with an overview session
    Ask the leadership team to present the current status of the organization and the goals for the trip. This should be another all-hands session.
  • Ensure all workshops are owned and properly prepared
    Each workshop should have clear goals and prepared materials. It is likely that the organizing team will have to remind Team Leads to prepare their workshops a few times in the run-up to the event.
  • Add in fun and team-building
    The percentage of time spent on team-building activities will vary depending on your leadership team’s goals. However, evenings are usually ideal times to schedule fun activities. Examples include murder mystery dinners, karaoke nights, cooking classes, or wine tastings. You can also schedule a full day in the diary for a fun activity to make the most of the daylight and enjoy your surroundings.
  • Make sure to plan time for delays and unexpected events
    It’s the rare event that runs perfectly to plan. However, by planning extra time for people to eat meals, change for outdoor activities, or just move from one location to another, you can create a buffer and relieve some stress for organizers. 

 Three Colleagues Working at a Whitebord


One of the most important parts of planning a successful off-site is communicating the details often and early. That’s the way to get the highest participation rate and the way to prevent things from going awry while on the trip. 

Here are some useful tips for communicating your plans for a corporate retreat: 

  • Send out invites as soon as possible
    Make sure that people block their diaries as soon as possible. It’s also cheaper to book travel and accommodation well ahead of time. 
  • Keep all information in one place
    We recommend creating a single page that contains all the need-to-know information about the off-site. Initially, that will include dates, venues, travel information, and the costs the organization will cover. Later, it can also include a complete schedule.
  • Keep talking about the event
    Build the hype with regular reminders in team meetings. If you aren’t present in most meetings, encourage department heads to regularly remind their teams to sign up.
  • Present a teaser
    If you’ve noticed sign-ups drying up, then share tidbits of information to get people excited. If you’ve already shown everyone the venue, then consider presenting one of the planned activities or something cool about the location.
  • Encourage people to network in advance
    While building the hype for your big, in-person event, you might want to encourage employees to get ready for socializing by using your internal networking tools. If you don’t have hybrid or remote-friendly networking options yet, Mystery Coffee is a great way to get started.
  • Keep some things secret
    You don’t have to share everything ahead of time! It might be a good idea to keep some things between you and the leadership team – whether that’s a special activity you have planned or some company freebies you plan to give out once you arrive. 

 Two Colleagues Doing High Five

What happens after a company off-site? 

You’ve planned an off-site, it’s gone off without a hitch, and hopefully, everyone is telling you how much they enjoyed it. 

So what next? 

Here are some ideas for following up on corporate offsite outcomes: 

  • Collect feedback
    Gather the initial thoughts and opinions of attendees. What did they think worked particularly well? What would they want to do differently next time?
  • Evaluate the long-term success of the event
    Check-in with leadership teams 3-6 months after the event. Do they feel that the offsite had a long-term impact on their team’s collaboration? Are they still using the documents and strategies that came out of their workshops?
  • Give feedback to vendors and partners
    If you’d consider returning to any of the locations, venues, or activities, make sure to stay in touch with them and build good relationships.
  • Encourage attendees to stay in touch with each other
    Don’t let the boost to company culture end once everyone is back at home. Make it easy for employees to network with each other and encourage interdepartmental socializing with programs like Mystery Lunch.
  • Start planning your next event
    Don’t leave it too long before starting to plan the next off-site – remember that it can take up to 9 months to prepare for a big event! 

Remember that you can always use our free checklist to plan your offsite event.
Good luck, and let us know how it goes!

Download the free checklist!

About the author:

Christoph Drebes

Christoph is an entrepreneur from Munich and co-founded Mystery Minds in 2016. Mystery Minds' mission is to make the world of work more human by creating meaningful, personal connections between colleagues. The remote-only team already works with over 250 international companies, helping them to strengthen internal networks and overcome silo mentalities.

Originally published on May 19, 2023 at 8:00 AM, amended on March 18, 2024 at 4:32 PM


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