7+ Tips for Planning a Staff Retreat


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. It’s a time to rejuvenate the team, get everyone excited around a united mission, set goals for the upcoming year, and build bonds between team members. 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.

Below are staff retreat ideas for a productive and fun (yeah, we said it) offsite with your team. 

1.  Create a survey to get staff retreat ideas and feedback

Before every staff retreat, we at Whole Whale distribute a survey to get a sense of what the team would find the most valuable. What topics are high priority for us to cover at this point in time? What sessions have they found the most or least engaging in the past? Then, you can assign team members to lead the sessions they are interested in (more on this below). If it doesn’t make sense for them to lead that session, or for it to be brought up at retreat, it’s still a good chance to discover what challenges the team is facing for you to address at an appropriate time. We also use this pre-retreat survey to find out what snacks people will want, which can make or break a retreat (only half joking).

We also share a quick survey after the retreat to get feedback on what they did or did not find helpful, as well as staff retreat ideas for next year. It’s best to get responses no more than a week after, when it’s still fresh.

2. Everyone can lead a session

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. Obviously, this is more difficult if you have a larger team, so we don’t require everyone to lead a full session. Consider grouping a few people up or putting people in pairs and have them 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 new and doesn’t know a ton about the organization yet, we have them plan a game night or group dinner.

3.  Active participation is key

The session leader shouldn’t spend the whole time talking at everyone as they sit around and listen. Get the whole group involved: Turn the session into a brainstorm, game, or workshop. 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, I lead a session on client management. I 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. I gave everyone a stack of sticky notes and 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 in each section. After those 10 minutes, we 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.  Plan an AMA (Ask me Anything) with your CEO or Executive Director

Not every CEO or Executive Director may be willing to do this, but it speaks volumes if they are game. In an AMA (Ask me Anything), employees put anonymous questions in a bowl throughout the day, then at the end of the day everyone grabs their drink of choice as our CEO pulls the questions out of the bowl and answers them. We’ve had questions range from salaries to starting a family to favorite color. The CEO always has the option to “pass” on a question that he doesn’t feel comfortable answering, but that has rarely been done (re: maybe once in the last three years). This type of transparency builds trust in the leadership.

5.  Have a staff retreat theme 

What are you trying to accomplish during your staff retreat? Having a staff retreat theme reminds everyone of the goal of your time together. It will also help employees plan their sessions around this theme. At Whole Whale, we like to have an overall theme, and then break each day into a sub-theme. In 2016 we riffed off of Hillary Clinton’s campaign slogan “Stronger Together.” The overall 2016 theme: We know who we are, we know how we are going to grow, but how do we be the best? Daily themes included:

  • “Working Together: How do we as individuals contribute to the mission of WW?”
  • “United Together: What does our future hold?”
  • “Stronger Together: How do we be the best?”

Other themes have included:

  • “Where do we want to be next year?”
  • “Building a team of teams: Strengthening departments and reducing silos”

6.  Schedule in free time

You’re going to be spending a lot of time together talking about work. Make sure to schedule in breaks and some free time so staff members can reboot however they need. Plus, 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 will cost more money than staying at the office, being in a new place will help individuals be open to new ideas. You want everyone to be fully present, and when you take people out of their normal setting, it will be less tempting to check their phone or answer emails. The fewer distractions the better. Plus, it’s a good chance to get some team pictures for your website or social media

8.  Use your time responsibly  

There will be a lot to go over in a limited amount of time — use that time wisely. Have someone take notes on each session and don’t be afraid to bookmark a discussion if you are running out of time. The session leader is responsible for following up on and scheduling further discussions after retreat as necessary. Make sure that all the time you spend on coming up with new ideas isn’t wasted. There should be someone in charge of implementing the changes after staff retreat is over, whether it’s the session leader or another appointed employee.

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. In order for that to happen, we have two rules for our time together:

  • Minimal phone use — we ask people to be present
  • Use “yes and” instead of “no/you’re wrong/but/can’t”  — this keeps things positive so everyone feels open and comfortable enough to share

If you follow those two rules and try some of the staff retreat ideas above, we guarantee you’re going to have an amazing (and productive!) time. Then, 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.