Planning Your Best Company Offsite Yet! [Tips + Examples]

In the age of remote work, company offsites are especially important for cross-team bonding, strengthening company culture, and improving the overall position of any great company. In the absence of office settings and regular company meetings, offsites are necessary to provide the in-person face time that promotes employee bonding and boosts team morale.

It’s estimated that by 2024, 35% of in-person meetings will be replaced by virtual meetings. At the same time, 78% of people are looking for a more supportive work culture. The numbers say it all–remote work culture is here to stay, but so is the importance of human connection.

If you're looking for a way to bring your in-person or remote team together and increase productivity, a company offsite may be just what you need. Successful offsites take careful planning and execution, and while it’s unlikely that your event planning skills are as fine-tuned as your people management skills, that’s okay!

This guide will provide useful tips to help you plan a memorable, budget-friendly company offsite along with real examples of a successful offsite from Cooleaf partner, Stability Healthcare.

Ready to plan your next offsite? Let’s jump into our best strategic planning tips!

1. Define your goals and objectives.

Before you start planning your company offsite, it's important to define your goals and objectives. Have a brainstorming session with your team to decide what you hope to achieve with this event. How will this event align with your core values? Are you looking to improve team-wide engagement, encourage a more successful team, or boost morale?

Setting an agenda early on will help you plan a team offsite that’s streamlined, effective, and most of all–fun! Even if you’re short on time to plan, starting with your mission in mind is critical. Don’t jump into the details before you’ve established what you want to accomplish!

Cooleaf partner Stability Healthcare kicked off planning for their offsite, Summit 2023, with a clear set of goals in mind. With only 2 months to plan, these goals proved critical for driving each element of planning including everything from budgeting, to picking a location, to event execution.

Sarah Griffiths-Briggs is the Director of People Operations at Stability Healthcare. Their vision, says Sarah, was to cultivate “full team engagement.” This meant that Summit was planned for every member of Stability Healthcare’s team, not just the people who were the highest achievers or earners.

To start planning, Sarah and her team established these goals:

1. Team building. Since Stability Healthcare’s team grew quickly post-COVID, a disconnect set in because of how fragmented everything had become during the pandemic. This offsite was an opportunity to come together in the spirit of team bonding.
2. Aligning everyone, across all teams. Stability Healthcare’s culture had become fragmented by each  department. This offsite would offer some much-needed time to dive into core values and get all teams on the same page.
3. Bring the C-suite in front of team members. Remote work has shifted how leaders interact with their teams. Executive-level team members are more distanced from their teams due to different responsibilities and schedules. This offsite would draw back the curtain, providing the chance for Stability Healthcare’s leadership to connect with their employees on a deeper level.

Planning an offsite for your team? Download Cooleaf's Manager's Handbook for leadership best practices!

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Setting goals for any event is the key to success, even more so when you’re planning to engage an entire team or any large group!

Once you have a clear understanding of your goals, you can tailor your offsite activities and agenda to meet those objectives. Communicate your goals to your team so everyone is on the same page about ground rules and working toward the same outcomes.

2. Choose the right location and venue.

The location and venue of your company offsite can make or break the success of the event. Consider factors such as accessibility, amenities, and atmosphere when choosing your offsite location. You want to make sure that the venue can accommodate your group size and has the necessary equipment and technology for any presentations or activities.

Additionally, the atmosphere should be conducive to the goals of your offsite. For example, if you're looking to boost creativity and innovation, consider a location with inspiring views or unique architecture.

For Stability Healthcare, their company offsite was the first time their entire team would come together to meet in person–so they knew it had to be an unforgettable time! With an incredible experience in mind, they decided to send their 210-person team to Paradise Point Resort and Spa in San Diego!

3. Plan engaging exercises and team-building activities.

One of the key components of a successful company offsite is making sure there’s no shortage of team-building for your people to collaborate and engage one another. These activities can help break down barriers between team members, boost morale, and encourage collaboration. Consider activities such as group game night, problem-solving challenges, outdoor team-building exercises, or even a friendly competition.

Using an engagement platform like Cooleaf to host these activities is an excellent way to keep everything streamlined and accessible for every member of your team! Stability Healthcare used Cooleaf as their “corporate communication tool” for all things related to Summit.

Stability Healthcare’s People team used Cooleaf to post schedules and add new updates leading up to Summit. “Communications stuck because they were in one place,” says Sarah. They also hosted a Summit challenge that coincided with the conference!

The challenge encouraged team members to share photos of their travels to and from San Diego. Some team members had never met before and were traveling together and interacting for the first time. People who had never been called out were tagging each other and engaging with their teams. Everyone was interacting through their personal photos and celebratory posts. Sarah was in awe of the feeling it created; “There was just this huge sense of interdepartmental continuity.”

Summit challenge results:

1. Post-Summit, it's not just the same people recognizing one another. After the offsite and the challenges on Cooleaf, team recognitions are more significant, more diverse, and more varied.‍
2. The team loved the challenge; more than just a single core group was excited to post selfies and share their experiences with one another.‍
3. Excitement kept flowing weeks after the offsite ended. Team pictures, memories, and recognitions kept coming even after Summit ended.

It's important to choose activities that align with the goals of your offsite and that everyone can participate in. Sarah said it best, “Don’t plan the event you want, plan the event your team needs.”

While planning, keep in mind that burnout is real! Don't forget to also schedule downtime for relaxation and socializing. Sarah and her team’s number one recommendation for offsite planning? Plan breaks so that people can still maintain the “remote work” habits they’ve become accustomed to!

With all the excitement of being together, your team members will need time to refresh and rest up in between non-stop activities. Sarah says it’s all about planning for rest, “Anticipate anxiety. People have developed so much social anxiety working from home so keep the first day very lowkey.”

Make sure you’re planning a variety of activities and free time. Allow people to settle in, consistently recoup, and then re-engage.

4. Provide delicious food and beverages.

No successful company offsite is complete without great food and beverages. Providing tasty meals and snacks throughout the day can help keep energy levels up and prevent attendees from getting hangry (we all know what it feels like to skip lunch in the middle of a busy, meeting-packed day...). Consider catering options that accommodate dietary restrictions and preferences, such as vegetarian, vegan, gluten-free, and dairy-free options. You can also add a fun touch by incorporating themed snacks or drinks that tie into the goals or activities of the offsite.

Making sure that alcohol doesn’t become the central focus of any company event is vital.

Provide plenty of activities that don’t center on drinking so that team members who don’t drink don’t have to drink. Offer plenty of water and other non-alcoholic beverages to keep everyone hydrated, comfortable, and safe. “You never know how remote work has affected people and what they’re willing to take part in,” says Sarah.

5. Follow up with action items and next steps.

After the offsite is over, it’s important to follow up with action items and next steps to ensure that the ideas and discussions that took place during the event are put into action. Assign specific tasks to individuals or teams, set deadlines, and establish a system for tracking progress. It’s also a good idea to schedule a follow-up meeting or check-in to discuss progress and address any challenges that may arise.

Expect feedback, and be open to collecting it! The goal after your offsite is to keep the feeling of connection going and refine any future events. Cooleaf’s survey tools are an excellent way to collect employee sentiment after your gathering. You can also use tools like Google Forms or build your own survey to get the team pulse once your company retreat ends.

By taking these steps, you’ll ensure that your company offsite is not just a fun event, but a productive and safe one as well.

The Do’s and Don’ts of Planning a Company Offsite

DO: Over-communicate critical aspects

‍Make sure that you’re giving your team as much information as possible up front! Things like what to pack, where they’ll be staying, any sort of dress code, and transportation details. You’d rather they over plan than under plan for travel arrangements, setting up childcare if needed, and making sure that any necessary work is done in advance.‍

DON’T: Give away every little detail

Leave some room for excitement! We see how this could sound contradictory...but we mean it! Keep little things that could leave an excitement gap open. Things like big-ticket activities (just let them know what kind of attire to bring) and what kind of food will be available can be general (let them know you’ll have vegetarian options without saying what’s on the menu).‍

DO: Utilize a tool like Cooleaf for regular communications

‍Don’t leave it up to emails and Slack messages. You’re going to want team members to know they can rely on a single information hub for all the information related to your event. Utilizing a communication tool like Cooleaf is a great way to post all relevant information and updates, host challenges, and collect team feedback!‍

‍DON’T: Wait till after to reflect on how it went.

Start to think critically about your planning in the moment. Take every opportunity to step back and evaluate how things are going! This way you can take notes as you go, rather than trying to remember every detail once the event has ended. We promise this will make it easier to reflect and plan (and more importantly, decompress) once the event ends.‍

DO: Create a calendar to give out to team members at the start of the event.‍

Wait until your event begins to provide an up-to-the-minute agenda for each day. If your event will only be one day, feel free to do this well in advance! If your event will take place over several days, however, make sure not to overwhelm everyone with the finite details too early on.

Whether you’re planning your corporate event for large or small teams, these steps are key for a successful offsite. Keeping these best practices in mind will not only make it easier to plan your upcoming event but will make you even more of an event-planning pro for your next team offsite.

^{If you’re looking for even more ways to make your offsite agenda shine, talk to our team!} ‍