Get Out! Best Practices for Planning an Offsite
Quick, what’s the first thing you think of when you hear “offsite”? As an attendee, is it great content? Deeper connections? Fewer distractions? Or is it feeling overwhelmed by the idea of travel, what to wear, and social anxiety? As a leader, is it the hope that the team can rally around a vision, collaborate, and return invigorated and inspired? Or is it fear about potential for wasted time and lack of engagement?
At Collabry, many of us have vast experience planning strategic offsites (and we have the lanyards to prove it!). Over the course of our careers, we’ve also been the unfortunate attendees of an offsite that was lacking. So when we were asked to pull together some best practices, we were happy to oblige.
Offsites make sense, especially post-COVID when many became permanently remote. In a 2024 report by Flowtrace, they found that 76% of employees expressed a strong preference for attending in-person offsites, with many citing the importance of face-to-face interaction for team cohesion. And in a 2022 Buffer survey, 74% of remote workers said their companies organized at least one offsite event per year, with 31% indicating they had two or more offsites annually.
Even if people are back to the office, a focused offsite can turbocharge alignment and collaboration, build relationships, and increase accountability. Ideally, these qualities lead to more successful, enjoyable work environments with a greater sense of belonging and improved results on goals. According to a 2023 report by HubSpot, companies that regularly host offsites report a 15% increase in employee engagement and a 10% improvement in team productivity within three months after the event.
On the flip side, offsites can also be costly and time-consuming — a collection of details that can create the conditions for magic or the potential for disappointment.
An A+ offsite is possible! We’ve created a checklist to help you make the most of this important team-building, business-driving tool:
Before
Define the goals and desired outcomes. This isn’t just for offsites, but it’s especially for offsites. What does success look like after the offsite? Many times, this step is skipped — and it is perhaps the most important! Include potential attendees and planners in the discussion.
Define roles and responsibilities. Ensuring that everyone is clear on their role, including who needs to approve plans, content, etc., is essential. Even when there are not enough cooks, there are too many in a disorganized kitchen.
Decide on the format, e.g. in-person, virtual, hybrid. So much depends on the format, but ensuring that the space (literal or virtual) is up to the task can save a lot of drama later.
Box in the budget. The great forcing mechanism!
Define your audience. Who needs to be there? Will each attendee benefit from the offsite? The better you know your audience, the more relevant the event.
Consider environmental impacts, such as locations accessible with direct flights versus multi-stops, carbon offsets, and impact on the location itself.
Logistics
Send “save the date” calendar invitations — early! For folks with caregiving responsibilities in addition to their work, aim to provide several weeks’ notice to allow for personal schedule planning. And be prepared for discussions with invitees who may not be able to attend in person.
Reserve the venue, including meeting rooms, breakout rooms, and private spaces — your dates may be driven by what is available. Again, consider venues that are accessible for all people, eco-friendly, and even minority-owned.
Reserve hotel room blocks.
Determine security badge needs if you’re hosting on a company-owned property and if you have remote workers coming in.
Make meal reservations and order food (remember to consider special dietary needs).
Order snacks. There is nothing worse than a snack desert. People will remember little else. And don’t forget hydration!
Ensure technology needs (WebEx, Teams, Zoom, monitors, cameras, power strips) are covered. Charging stations are like snacks for phones.
Create building or venue maps that include main locations, bathrooms, quiet rooms, etc. Even if this is all on an app, it is beneficial to have physical signs.
Leverage technology like AI to automate notetaking, action items, icebreaker ideation, brainstorming prompts, etc. The output is only as good as the input, so knowing the goals and audience ensures best results.
Send a “Know Before You Go” communication that includes helpful information such as transportation, weather, dress code, contact info, local insights, etc.
Content
If appropriate, choose a working theme for the offsite (ex. Olympics!).
Broadcast clear deadlines for content submissions with frequent reminders.
Prepare content, allowing time for editing and review. Ensure that approval requirements are clear. Do you need additional writers? Graphic design support? Proofreading?
Create a central repository for the content and naming conventions to ensure access and version control.
Facilitation
Prepare and distribute agendas before the offsite.
Plan icebreakers and team-building activities. If you have opted for a theme, consider ways these exercises can deepen the impact.
Be relevant; lean into current events, case studies, user input.
Make the day interactive (not just a series of speakers talking at people).
Bring in some inspiration, whether that is a keynote speaker on an adjacent topic or something unrelated — like learning to make a sushi roll!
Remember that your attendees have bodies! Incorporate inclusive movement activities (chair yoga, anyone?), restroom breaks, and hydration!
Honor the introverts. Having a few quiet places for more intimate discussions or even alone time will help everyone to show up at their best.
Manage the archetypes:
For the Talkative Tornado, be sure to communicate a time limit. Consider using a bell or music to gently prompt them to wrap it up.
For the Topic Derailer, review the agenda in advance. Use the Parking Lot concept and reference a time when the team can discuss further (“That’s a great question/point. Let’s add it to the agenda for xyz meeting.”)
For the Quiet One, look for ways to bring them in, especially if it looks like they are trying to break in but can’t get traction. Ask 1:1 if there are any thoughts they’d like to share.
After
Send a thank-you note with meeting notes and actions with specific owners and deadlines.
Schedule time in a new or existing meeting to follow up on action items and discussion points — sooner than later — so you don’t lose momentum.
Send a survey for feedback: What was good, what could be improved, and would they recommend the event to others?
These guidelines are a great gauge to determine if you have the strategy in place and the bandwidth to produce an offsite event. Of course, variables like size, audience, and duration need to be factored in, and no two offsites are the same.
Humans are wired to connect and relate to one another. We’re also overwhelmed by information and time demands. A well-executed offsite can provide the opportunity for deep connection, deep thinking, and flourishing.
Do you have any go-to tips for offsites? Are you needing to plan one or even a series of them? Let us know how we can be of service.