Retreats can rally a team, solidify a new direction, move an idea forward. When well-designed, they can be fun, productive, and knock out multiple goals at once. Yet with all of this potential, bad retreats, where people leave feeling confused, deflated, or like they wasted their time, still happen to good organizations. Don’t let a retreat fail happen to you.
With the time invested in planning and attending a retreat, plus expenses like space rental, food, supplies, activities, and hiring facilitators, your hard costs can be quite expensive (not to mention the opportunity cost of lost trust, team alignment, and potential progress). Unfortunately, there are a lot of potential mishaps – poor planning, lack of communication, dialing it in and just doing what’s always been done, setting unrealistic goals, providing an uninspiring environment, failing to plan for energy, lack of facilitation skills…
What does your retreat need to accomplish?
Before you do anything else, get crystal clear about the purpose of the retreat. Why are you planning it in the first place? What do you hope to accomplish? Think it through before you start any other scheduling and planning. This will help you understand the resources, time, and people needed to be successful. Some different types of retreats to consider:
Types of Team Retreats
Explorative retreats help you further your understanding of an issue or opportunity. The types of activities are geared toward research, and might include group discussions, presentations, independent study, interviewing people, or taking field trips. While the methods are varied, the outcome is further understanding of new ideas, industry changes, or the needs of your communities and the people you serve. For this type of retreat, you may not have decided to make any changes just yet – you are seeking information that will inform a decision or make a case for future action. This kind of focus is especially valuable if your team is not on the same page about whether change is needed, or there is a lot of risk involved with action or inaction.
Generative retreats are about coming up with ideas. Ideally, you have already made a decision to try something new, but haven’t chosen the solution. The openness to a variety of possibilities gives your team space for creativity, which can be incredibly energizing. This type of team retreat might include independent brainstorming, group discussions, or use of methods that output a physical artifact, like creating concept sketches, models or other types of prototypes. One best practice is to mix up the format between individual, small group, and full group activities. Sometimes called “converging and diverging,” the concept of working together, then apart, then back together generates a wider range of ideas, helps avoid group think, and keeps people from getting burnt out by catering to different styles. Some people may contribute more readily in a solo writing exercise, while others relish the chance to talk things out. This kind of retreat is perfect when you are feeling stuck or unsure how to best solve a complex challenge.
Strategic retreats are about coming together to make, finalize or share choices. This might include people presenting their perspective and making a case for a direction. In some cases you may be bringing your whole team into the decision-making process, and choose one course from multiple potential paths by taking a vote. When the retreat is focused on sharing a strategic direction that has already been finalized, the retreat may be more about explaining how and why decisions were made, discussing changes brought on by the new direction, or deciding who owns what going forward and assigning tasks. Activities can include vision writing, goal setting, or creating a work plan.
Sprint retreats are about getting things done. You typically go into these with some decisions made. You may already have clarity about your path forward, have drafted a project or product plan, and even assigned ownership of tasks. People may work solo or in project teams to push something forward quickly. Your whole team may be working on one shared project, or you may knock out multiple smaller projects all at once. For sprints, it is important to be realistic about how far you can get in your allotted time. If you devote a day, perhaps you won’t finish the entire project, but you can get to the first major milestone. These retreats are a great option when you have an important idea or project that has languished on the back burner, or something urgent comes up that needs to get done immediately. They can also be very effective when your team needs a quick win or jolt of energy, like after a long budget freeze or delayed strategic decision.
Professional development retreats are geared toward building individual or group skills. Examples of activities include independent study, internal knowledge sharing, hiring an expert trainer or speaker, taking immersive field trips, or tackling skills-based volunteer projects. The topics can be gaining industry know-how, mastering work-specific tasks, or honing softer skills, like giving and receiving feedback. This type of retreat is perfect when you have identified an underrepresented skill, or added a new service or offering that requires new expertise. Any time you offer professional development opportunities, it signals that investing in people is important – even more so if people get to choose where they focus their learning.
Team-building retreats are for fun, getting to know one another, celebrating or letting off steam after a challenging period or big project. These might include sharing food together, taking nature excursions, fun games, or competitions. Organizations often choose to offer team-building retreats on a regular basis, whether monthly, quarterly, or once per year, both to build trust, relationships, and a sense of camaraderie. The regular cadence is like having an organizational holiday, creating your own cultural calendar for your team. This type of retreat can be incredibly valuable if you’ve hired a lot of new people at once, and want to offer a unique onboarding experience.
Sometimes retreats may include more than one of these, all in one retreat. It would be nice if we all had just one clear cut problem, but often this is not the case. Do you have one singular, or many outcomes in mind? While it’s crucial to be mindful of what is realistic to accomplish, including more than one focus can be very successful, as long as there is shared understanding about the progress you expect to make with each focus.
Important Considerations for Retreat Planning
Once you’ve determined your goals, you can move on to other important aspects of planning your retreat:
- Get creative with the agenda. Match activities to the outcomes you hope to achieve. Look into new methods from a design thinking toolkit, or something else you may not have tried before. Don’t just show up and plan to talk through stuff. Those sorts of days can feel amorphous and draining. It takes a really skilled facilitator to keep an entire group engaged for long stretched of just talking without structure.
- Communicate the purpose and agenda for the retreat ahead of time. People like to have some context about why a retreat is needed, what you hope to accomplish, and any expectations you may have. If your team goes into a Friday retreat expecting to take action on Monday morning, and then leave your retreat without a decision, they will be disappointed. Be specific about where you will end the day and what steps will happen post-retreat. People get really really bummed out if they spend a day, a week, however long your retreat, only to walk away not knowing how it will move forward.
- Plan for energy. Think about things like room set-up, lighting, food, coffee, background music, warm-up activities (like this one), active breaks, reflection periods, facilitating a mix of individual and group activities. For longer retreats or very heavy subject matter, this stuff gets even more important.
- Assign roles. Know who is leading what. Have different team members facilitate different activities, or bring in an outside facilitator. Make sure someone is capturing notes, recordings, or photos as needed. Other roles might include putting people in charge of time keeping, food, or energizers during breaks. Set the expectation that role of all others is to be present and participate in conversations and activities.
If you go through these steps, all of your thoughtfulness and intention will make a big difference toward making your retreat a success.