6 Easy Steps for Planning a Team Offsite Meeting

A work environment that fosters creativity, supports innovation, and keeps teams engaged in their projects can be difficult when daily tasks and to-do lists pile up, meetings are scheduled on top of meetings, and email messages roll in nonstop.

To find focus and build both productivity and collaboration, step out of the daily grind and leave the office. While company retreats and team offsites have long been a popular strategy for team building, when organized properly, they can do much more. As shared in The Why, When, and How of Successful Retreats from Just Works Consulting and Jeremy Phillips Consulting:

“Retreats can build organizational muscle for strategic and creative thinking that can be carried back into daily work. A retreat can be an opportunity for taking stock, reflecting together, assessing and refining practice, and providing a turbo boost to specific aspects of work.”

In addition, many teams now work fully or partially remote, so they miss out on naturally occurring opportunities for interaction and relationship building that happen when everyone works in the same physical office. Josh Pigford of Baremetrics told us, “Sharing experiences with your team members is really important. If you’re dedicating years of your career to a company, you should enjoy and have strong relationships with the people you’re working with.”

He added, “Team offsites give you an opportunity to get to know each other and understand personality differences without the pressure of getting a specific job done and that change in context makes a big impact.”

Noel Tock from Human Made takes relationship building a step further at team offsites. Because the team is remote and many members are nomadic, several of them make travel plans together at retreats to co-work, and maybe even co-live, together in a different part of the world.

Leah Knobler from Help Scout said that their retreats increase team productivity and collaboration and she notices that when they return from a team offsite, there’s a noticeable increase in activity and collaboration on the team’s chat in Slack.

A successful team offsite is not as simple as just holding a meeting somewhere other than the office. To help you create an experience that builds team cohesion and focus, we took cues from companies who regularly use retreats as a tool to foster innovation and broke down offsite planning into six steps.

1. Define and communicate the goal of your team offsite

Since team offsites typically require company money and team time, it’s important to define and share the desired outcome for your outing with your entire team. Getting buy-in from leadership and team members requires communicating the impact the offsite activity will have on the business.

What that impact looks like is up to you, but it should align with your business goals, values, or ideally, both. Common goals include working on specific project like launching a new feature, completing a strategic plan, building alignment with new hires or after a team reorganization, bringing geographically dispersed teams together, celebrating a milestone, or simply giving your team a break from their daily grind.

You can use team offsites to focus on larger goals that may get lost in the shuffle of the day-to-day. In the lessons from their first retreat, Josh Pigford of Baremetrics said, “Being in one place gave us the opportunity to brainstorm and plan out the coming months as well as hash out some bigger design, development, and marketing problems.”

Once you know your goal, the next step is to create a rough structure for your retreat to ensure you achieve your goal.

2. Have a rough schedule for your activities

How much you structure your team offsite will depend on your goal, team size, and duration of the offsite. Have at least one task you want each department (or the team as a whole) to accomplish each day. Also schedule time for relevant one-on-ones, team reflections, and fun.

After their week-long retreat, Josh from Baremetrics said, “Have a rough idea ahead of time and giving some high-level structure goes a long way. I roughly planned out each day by ‘Morning,’ ‘Afternoon’ and ‘Evening,’ but didn’t get more granular than that, especially for the ‘Morning’ section since everyone has slightly different sleeping habits.”

Leah said Help Scout’s retreats are scheduled into four areas: visioning and goal-setting, working, team-building, and plenty of time and options for downtime and free time. They schedule structured team events such as karaoke, but also make sure the team has plenty of time to do their own thing and have time to themselves.

Human Made has a 'no client work' rule for the week they are together, and communicate that in advance with their clients. They’re also careful to ensure that their team knows about and prepares for activities planned ahead of time, such as identifying the projects they want to work on during a hack day. They also carve out a day for each team member to give a five-minute “flash talk” that touches on a personal passion or interest with the understanding that everyone is coming to the retreat prepared so that they can be fully present, not spending team offsite time preparing materials.

Although having a plan is key, keep some flexibility. You don’t know what ideas will arise, what opportunities will present themselves, or if someone will get sick. To ensure flexibility, have a contingency plan.

3. Plan your logistics out in advance

Human Made plan their retreat a year in advance. Because they often hold their retreats in far-off places, they send a small group of teammates to the retreat location location a few days in before everyone else arrives to get everything set up. Because they have over fifty people on their team, they hire two chefs to ensure meals are taken care of. In addition, they purchase all tickets for ground transportation and group activities beforehand so no one is stuck because they don’t have the right amount of coins for the local bus.

More importantly, they’re extra diligent in making sure that they have a strong Wi-Fi connection. Sometimes this means buying SIM cards for everyone so they can tether their phones. While your company offsite might not need quite as much advance planning, and also may not be held in a castle in Italy or a winter cabin in Norway, be sure to create a run of show for your event to ensure everything is accounted for in advance so everything can flow smoothly before, during, and after your retreat.

4. Consider bringing in a facilitator

A great facilitator can ensure you use the team’s time efficiently and effectively. More importantly, that person will make sure everyone’s voice is heard, not just the loudest person in the room and help create space for all team members to talk.

If you don’t have the capacity internally, look for an external facilitator. She suggests spending some time getting to know them (phone, video, in-person) before the offsite, to ensure their personality fits and that they’ll work well with your team. If you’re not the type of company who’s into trust falls, you don’t want someone telling you to do trust falls.

5. Make time for fun

To truly foster creativity, include time for non-work activities, as this is where great ideas happen or new connections are made. Courtney Seiter from Buffer said, “An important element of retreats is the time we spend not working, but instead getting to know one another.” Instead of formalized ice-breakers, the Buffer team will take part in a group activity that is special to the place they are visiting—like surfing lessons in Sydney or a volcano tour in Iceland.

She added, “In addition to pre-planned activities, there are plenty of self-organized activities—book clubs, board game nights, morning yoga, evening whiskey tasting—that anyone can spearhead or be part of, depending on their interest.” Even if you’re only taking a day, make sure there are ways for your team to take breaks and blow off steam.

While extracurricular activities are helpful, Leah from Help Scout suggests to not be too over-scheduled. She added, “downtime is where the special times happen. That’s where the jokes happen and memories are made.” 

6. Keep the momentum going

During your team offsite, and just after, set the stage for continued productivity. Throughout the event ensure you are documenting the ideas, brainstorms, and solutions that come up during each session. Make sure that everyone walks away with action items to work on after the offsite. Assign a specific person, or group of people, to take ownership and follow through with specific projects.

When your team offsite is over, invite everyone to share what they accomplished and collect their feedback. Feedback will enable you to improve future team offsites and understand what was especially effective. When your coworkers share their accomplishments, they also demonstrate the value that an offsite adds to your company culture and initiatives and showcases what you have accomplished together.

Overall, team offsites break down barriers that are created in companies, whether everyone works together in a single office or on a remote team. They allow space for coworkers to collaborate as their authentic selves and open up space for new ideas to emerge.

Reflecting on his first retreat with the company, Ross Parmly of Buffer said, “I began to realize that working with the greatest team in the world doesn’t feel complete without the chance to experience real hugs, across-the-table high-fives, and in-person moments of vulnerability.”

With clear goals, careful planning, and the right balance of fun and focused work time, we hope that you will take a chance and take your team, or your whole company, offsite to experience the benefits of productivity and creativity they bring.

Photography by Nick Dunlap