Planning a Productive Staff Retreat: 9+ Ideas for an Engaging Team Offsite

Capacity

A staff retreat is a perfect opportunity to take a step back from the day-to-day work of your organization and spend some time thinking about the bigger picture. Especially for teams that are primarily remote, it’s a time to foster interpersonal connections and build trust among your team. It’s also a great opportunity to get everyone excited around a united mission, set goals for the upcoming year, and brainstorm approaches to the biggest challenges facing your organization.. All of this doesn’t just… happen. Staff retreats take thought, careful planning, and participation from the whole team in order for the time together to be a success. Everyone needs to buy in, and we have some tips to make your staff retreat really count.

Here are 9+ ideas to make our team’s next offsite fun and productive.

1.  Set (and communicate) a goal for your staff retreat

What are you trying to accomplish during your staff retreat? Having a staff retreat goal, or theme, reminds everyone of the purpose of your time together and can keep your team focused on the bigger picture throughout your time together. It can also help inform which sessions you prioritize and help you draw a connection between all of the activities throughout the week. 

2. Get the team involved in planning and leading

At Whole Whale, every person attending staff retreat can lead a session. This is an awesome opportunity for staff members to practice their presentation and leadership skills. It’s also an opportunity for the larger team to hear from people across departments and levels. For larger teams, consider grouping a few people up or putting people in pairs to lead a session together. Each person will feel invested in the staff retreat if they are responsible for planning a portion of the time together. Depending on the session, it can be helpful to group people who don’t work together all the time to build community across teams, and reduce silos. If someone is newer and doesn’t know a ton about the organization yet, we have them plan a game night or group dinner.

3.  Activities > Presentations

Given the effort and cost it can take to get everyone in the same space, we recommend prioritizing activities and sessions that everyone can actively participate in. No one wants to fly across the country to sit through a presentation they could have sat through on Zoom.

We prioritize sessions that are brainstorms, games, or workshops wherever possible. Amazing ideas can come from anyone on the team, and it can help to bring people with fresh eyes to help solve recurring challenges. Staff retreat should be a safe place where everyone feels comfortable contributing their ideas, even if they work in another department. For example, at a past staff retreat, we led a session on client management. We wanted to know what the team thought we were great at, what we were just ok at, and what we could really improve on when it came to managing our nonprofit clients. We put up three sections on the wall labeled “red”, “yellow”, and “green.” The whole team then had 10 minutes to place their thoughts on sticky notes, and organize them within each section. We then went through each section and had everyone talk through why they placed a certain aspect of client management under a certain color. It created an active discussion that provided ideas for improving the things we aren’t so great at yet. Even better — we got insights from staff members who weren’t client managers. They provided valuable perspectives that we wouldn’t have received if we only included the management team.

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4. Foster Meaningful Connections

As a remote-first team, recent Whole Whale retreats have focused on building relationships among our team. To do this, we incorporate sessions that allow each member of our team to share their unique perspective. Sessions that lead to conversations about personal workstyles, strengths, communication styles, or other personal outlooks can help your team get to know each other in a way that allows them to work better together. Past retreat sessions at Whole Whale have seen our team discussing results of the StrengthsFinder assessment, personal User Manuals, and even our personality types.

For sessions that require your team to break out into smaller groups, create those groups ahead of time so you can be strategic about who is working together. This gives you the opportunity to create groups of employees who may not typically get to work together, or groups of people who do work closely together and need that connection strengthened. This is also an opportunity to ensure that everyone is getting exposure to different colleagues over the course of the retreat.

5. Plan some just-for-fun activities

We know we know, there are mixed opinions on “forced fun”. Still, having a few sessions that are less work-focused gives your team the opportunity to interact in a different, lighter way. At our last retreat, the most-praised session was pub-style trivia about the members of our team. It was a fun opportunity for friendly competition and we all learned fun new things about our coworkers. 

For larger teams, consider running a few different activities at the same time and let people choose which one they’re most interested in. This gives your team the opportunity to have some control over how they spend a few hours, and gives teammates the opportunity to connect over a shared interest.

6.  Schedule in free time

This is our #1 recommendation. You’re going to be spending a lot of time together, and likely spending a lot of time talking about big ideas and challenges. Especially for remote-first teams, this is a big change from your staff’s daily activities. Make sure to schedule breaks and build in some free time so staff members can recharge however they need. This also gives your team the opportunity to connect more organically. Some of our best ideas (like starting Whole Whale University) came out of informal conversations when the team was just hanging out.

7.  Go off-site if possible

A staff retreat is a time to shake it up and get people thinking about problems or ideas in a unique way. Although it may cost more than sticking around the office, being in a new place can help individuals think differently and be more open to new ideas. It also often creates opportunities for new or different experiences and activities, which can enhance the experience your team has. 

8.  Limit technology use

Remote teams spend a lot of time on their computers and phones. To encourage active participation and reduce distractions, plan sessions that require as little technology use as possible. Print out needed resources or worksheets for sessions and distribute notebooks and pens to minimize the need for laptops or phones during sessions. We ask our team to minimize phone use throughout the retreat to take full advantage of the time we have together.

9. Communicate Next Steps and Follow Through on Them

It’s important that your team feel like their time and efforts were worthwhile, so make sure that all the time you spend coming up with new ideas and solutions isn’t wasted. Assign someone on your team to take notes and identify next steps or needed follow-ups from every session. Then, make sure someone is assigned to ensure that that work moves forward after the retreat is over. At the end of your staff retreat, there should be a buzz of excitement — a renewed sense of energy and commitment to the mission of the organization. Harness that energy to keep this work moving forward in the days and weeks following the retreat.

10. Collect feedback

After you return from your retreat, collect feedback from the team on how they think it went. We like to ask specifically about which sessions the team found the most productive, helpful, or engaging and use that to inform future programming. If your retreat had a specific goal, ask the team how effective they think the retreat was at accomplishing that goal. Don’t forget to share the positive feedback with your organizers and session leaders so they can celebrate their job well done.

When you get back from retreat and are thinking “what now?”, check out our list of  7 Things to Do After Staff Retreat.

 BONUS! Looking to build capacity on your team to improve your digital strategy? Check out our on-demand learning platform, Whole Whale University. When you subscribe, you get access to all our courses, webinar recordings, guides, and templates. We also offer team subscriptions if you want your whole organization to get on board.