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6 tips for planning your next team’s offsite

Company or team in-person offsites (also known as company retreats) play an important role in reconnecting distributed teams. They make it easy for remote or hybrid teams to build and maintain human connection among their members.

Chase Warrington, the Head of Remote at Doist, discussed during the 2022 Cosmic Conference, the impact of in-person off-sites on the employee experience in distributed organizations.

Below is a list of 6 tips he shared to plan your next epic team offsite.

1. Have a clear “why” for your offsite

When the reason you’re planning the offsite is clear, you can design an experience fit for purpose. That’s why Chase encourages you to ask yourself: What is the objective of your off-site? How do you want attendees to feel at the end of it? What is the reason you are together? Answering these questions is essential to create alignment in your team.

2. Follow the 20/30/50 rule

Chase recommends you structure your off-site using the 20/30/50 rule. This means allocating:

20% of the time to work

30% of the time dedicated to off-site activities

50% free time

It may seem like a lot of free time, but Chase explains that spontaneous activities spark collaboration and improve creativity, innovation, and performance of teams.

3. The offsite and all the activities in it are optional by default

Remote or hybrid work is flexible by nature and so, you don’t want retreats to become a source of rigidity. Chase encourages you to give people the freedom to choose the activities they want to attend and offer them choice. It’s also important to take into account for different employee groups. If you’re planning a 5-day offsite, you might want to account for caregivers by condensing the most important activities to 1 or 2 days so they can attend those and return home afterwards.

4. Develop a pre-offsite communications plan

It’s critical to ensure that all employees are clear on the objective and plan for the off-site well in advance. Chase suggests you develop a plan to communicate with attendees, sharing all necessary information related to logistics and desired outcomes. He also recommends diversifying the content formats to accommodate different employees’ preferences (e.g. Try a loom video, or share a packing checklist).

5. Ensure there is a communication plan to share information during the offsite

Depending on the structure and type of off-site you are hosting, you will need to have a communication plan in place to share information with attendees during the off-site. You will want to share reminders, and updates on any changes, or even answer questions and concerns. Chase encourages you to use a tool/platform that is unrelated to work because you want the team to disconnect and enjoy their time.

6. Collect attendees’ feedback post-offsite

Collecting feedback provides valuable insight into what attendees enjoyed about the offsite and what you can improve for years to come. Chase recommends you share an internal anonymous survey with your team to collect the relevant data that will help you plan better offsites in the future.

As Chase said, “Remote first doesn’t mean remote only”. So, take the time to build meaningful in-person experiences for your team using the above tips.

If you want more details from Chase’s session you can check it, here.


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