How to "De-Risk" Your Next Offsite (and Avoid the Mistakes That Kill Company Culture)
The next time you think about "planning an offsite internally", consider the risks associated with your reputation as an employer if things go wrong (as well as all the time and money you might waste)
At Offsite, we love a well-run retreat.
We’ve helped hundreds of companies plan team retreats in 25+ countries, from intimate exec offsites to 1000 person conferences, saving them over $6,000,000 collectively as well as thousands of hours (in time that’d otherwise be spent planning offsites internally) and generating huge business/people ROI.
While the upside of a great offsite (connection, alignment, employee engagement and retention) is HUGE, most people don’t talk about the potential risks.
When offsites go wrong, they don’t just feel like a wasted budget line. They can create serious employer risks.
Reputational risks. Safety risks. Legal risks. Team morale risks.
It’s the kind of stuff that keeps People teams, Chiefs of Staff, and CEOs up at night. As the founder/CEO of Offsite, I would know :).
And so…today, I want to pull back the curtain and talk about the hidden risks of offsites gone wrong, and how to plan smarter so your company (and your team) doesn’t get burned.
Why Am I Writing About This Today?
Unfortunately, we get 1 or 2 messages a week from companies who:
work with another vendor, who doesn’t take care of them…
or plans their offsite internally, only to realize how challenging it is to plan an exceptional team retreat
In both instances, we get last-minute SOS messages or we hear after the fact, post-offsite, about how much of a s**tshow the experience was and how they want to work with Offsite in the future to avoid the same issues.
Yes…we want to earn your business.
But we also care too much about you and your team to let you know spin your wheels with other vendors who have shown us time and time again that they cannot meet the increasing demands of Chiefs of Staff, Executive Assistants, and People Ops professionals like yourself who are trying to do right by your company in planning an exceptional team retreat.
Whether you use our Airbnb-style marketplace to save time/money on venues and vendors globally, and then plan the rest of the offsite yourself…
Or you’re looking for a partner to provide “done for you” offsite planning services…
Hopefully this article helps you de-risk your upcoming offsite.
Risk #1: Safety and Duty of Care
This is the most obvious risk, and the most serious.
You’re moving people, sometimes hundreds of them, to a new environment.
That opens up risks around:
Illness or injury
Travel mishaps
Unsafe activities
Alcohol-related incidents
If your offsite doesn’t have a clear safety plan, vendor vetting, and attendee guidance, you’re setting yourself up for liability and (even worse) putting your team at unnecessary risk.
How to Avoid It:
Choose vetted venues and vendors with strong safety records and insurance
Build clear Code of Conduct guidelines for the event, including expectations around alcohol, activities, and professional behavior
Ensure your event communications cover emergency procedures, local healthcare access, and travel policies
If you want a funny story, reply and ask me about the time Offsite had to hire security for a retail company we were working with that planned to unload~$200,000 of product to gift their employees at an offsite, and the hilarity that ensued within our internal Slack.
Risk #2: Inclusion Gaps That Hurt Culture (and Reputation)
Nothing will derail the ROI of your offsite faster than creating an experience where people feel excluded, unseen, or uncomfortable.
Offsites that aren’t designed with inclusivity in mind can quickly alienate teammates.
We’ve seen it happen:
Over-programmed days that don’t account for neurodiversity or introvert needs
Activities that make certain groups feel left out or unsafe
Poor accessibility for team members with disabilities
It’s not just a bad look. It’s a culture killer and can damage retention, morale, and your employer brand.
How to Avoid It:
Use pre-offsite surveys to understand team needs, sensitivities, and preferences
Offer optionality in activities and downtime
Ensure accessibility is baked into your venue, programming, and travel planning
Risk #3: “Offsite Hangover” and Broken Promises
An offsite with no follow-up is worse than no offsite at all. Why?
Because you’ve made implicit promises about alignment, transparency, connection that go unfulfilled when the momentum dies in Slack the next day.
This is where offsite planning bleeds into strategic operations and internal comms.
If your team leaves the offsite asking, “What was the point?” you’ve not only wasted money and time.
You’ve created cynicism, and a group of employees who are actively looking for their next jobs on your payroll.
How to Avoid It:
Set clear objectives and communicate them before, during, and after the retreat
Document decisions, insights, and next steps. Then, assign owners for each project.
Use post-offsite surveys and retros to close the loop and show the team you’re listening
Risk #4: Overloading Your Internal Teams
This one is subtle, but it’s real.
When offsite planning falls entirely on your People team, Chief of Staff, or EA, it can create hidden burnout.
Planning a multi-day retreat for 50–500+ people is a massive lift on top of a demanding “day job” which includes 17 other high-priority projects.
Worse, when internal teams are also responsible for running the event on-site, they don’t get to participate fully. That creates resentment and uneven experiences.
I’ve heard horror stories of execs/founders who, after all the extra work they placed on an EA or People Leader, didn’t even thank them at the offsite! Talk about lame….
How to Avoid It:
Use external support (like Offsite!) for logistics, production, and day-of coordination
Set realistic expectations around internal bandwidth
Protect your ops and People teams from death by 1,000 decisions by systematizing your retreat planning process
Offsites Should De-Risk Your Business, Not Create New Risks
At their best, offsites create focus, clarity, trust, and velocity.
They make your company more resilient. More agile. More connected.
At the close of your offsite, you should be proud to post about the experience online, and your team should be buzzing about how awesome it is to work at your company.
But when planned without intention, they can do the opposite: expose you to unnecessary risks, erode trust, and turn what should be a culture moment into a morale landmine.
The good news?
Every risk I outlined is avoidable with the right planning, the right partners, and the right process.
And if you want help?
You know where to go…
Learn more at Offsite.com and book a discovery call to start planning your next transformational offsite.
Thanks
Jared
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When you are ready to plan your next offsite, make a free account at offsite.com to search our curated marketplace with thousands of amazing offsite venues, up to 50% savings on room blocks, meeting space, and more.
Plus, we offer end-to-end offsite planning services if you want a “done for you” experience. See why companies like Remote, Buffer, 15Five, Linear, Hampton, and others trust Offsite for their team retreats.