What We’ve Learned From Planning 300+ Offsites in 25+ Countries
The biggest mistakes companies make when planning offsites, how to save 20%+ on your budget, and how to maximize the ROI of your team retreats in 2025 (and beyond)
Earlier this week, I had the privilege of presenting to the TroopHR community about (some of) what we’ve learned from planning over 300 offsites in 25+ countries.
Companies have trusted Offsite to help them plan hundreds of retreats globally, and in the process, we’ve saved our clients over $5,000,000 as well as thousands of hours that would otherwise be spent planning team retreats—all while increasing the ROI of these offsites.
Whether you're planning an All-Hands Meeting, executive team retreat, department-level offsite, President’s Club event, customer conference, or any other type of “offsite”, getting it right requires careful planning, negotiation, and execution.
Here’s how you can apply what we’ve learned through planning hundreds of successful retreats to save time, reduce costs, and maximize impact.
The Biggest Mistakes Companies Make When Planning Offsites
Over the years, we’ve seen countless companies fall into the same traps when planning their offsites.
Here are the most common (and costly) mistakes to avoid:
🚨 Waiting Too Long to Plan – By the time many companies start planning, they’re left scrambling with limited venue options, higher costs, and logistical nightmares. Start planning ideally 6 months in advance—longer for larger retreats.
🚨 Not Having a Clear Goal – Every offsite should have a defined purpose. Whether it's team-building, strategic planning, or innovation workshops, clarity around objectives ensures the event is structured for impact.
🚨 Choosing the Wrong Venue – A bad venue choice can lead to logistical headaches, accessibility issues, or a lackluster experience. The right venue should align with the goals of your retreat—whether that means a focused conference setting, an inspiring natural environment, or a high-energy resort.
🚨 Overloading the Agenda – A packed schedule may seem productive, but it leads to exhaustion and disengagement. Balance deep work with breaks, team-building, and social time to ensure attendees stay energized and engaged.
🚨 Ignoring the Little Details – Poor WiFi, bad food, or inefficient transportation can overshadow even the most well-planned agenda. Sweat the small stuff—it makes a big difference.
How to Save 20%+ on Your Offsite Budget
The cost of team retreats can add up quickly, but with the right strategy, you can save 20% or more without cutting corners. Here’s how:
✅ Plan Ahead – Start planning at least 3-6 months in advance for groups under 100 and 6+ months for larger events. The more lead time, the better deals you’ll secure on room blocks, airfare, and vendor pricing. With the curated Offsite marketplace, you can save up to 50% on room blocks, meeting space, and more at thousands or premier offsite venues globally.
✅ Leverage “Total Spend” with Hotels – Commit more of your budget to a single venue (e.g., lodging, meeting space, food & beverage, AV, and activities) to unlock discounted rates and added concessions. This can result in waived meeting space fees, reduced food and beverage minimums, and even better room rates.
✅ Mitigate Risk in Your Contracts – Venue contracts are full of fine print that could cost you thousands if you’re not careful.
Negotiate better attrition rates (so you don’t pay for unused rooms)
Secure friendly cancellation clauses (to avoid massive fees if plans change)
Lower F&B minimums (so you don’t overspend on catering)
✅ Break Down Every Line Item In Your Budget – Many companies try to budget retreats at $1,000 per person—including flights, accommodations, food, and activities—which is often unrealistic. Once they start to plan every line item in their budget, often they find the budget balloons and finance isn’t very happy.
The better way forward is to plan all costs upfront, getting into the weeds on potential expenditures, and then finding creative ways to optimize costs while maintaining a high-quality experience for attendees.
✅ Use the Right Tools for Cost Optimization – Platforms like Offsite.com help compare pricing across locations and vendors, while tools like AllFly can estimate flight costs based on where your team is located.
How to Save 50-100+ Hours of Your Time
Offsite planning is a full-time job, and too often, the burden falls on an already overworked Chief of Staff, EA, or People Ops leader.
You can reduce planning time by:
Using a Clear Process – Every offsite should follow a structured planning process:
Define objectives
Set budget parameters
Gather pre-offsite feedback
Plan travel & logistics
Lock in agenda & activities
Manage vendors & contracts
Handle team communications
Planning in a different order (such as searching for venues, only to realize certain venues don’t fit within your budget) is a recipe for disaster.
Gather Feedback Before You Begin To Plan – Instead of back-and-forth Slack messages about travel preferences, or doing work without the buy-in and alignment of leadership, use pre-offsite feedback forms to collect data upfront and centralize responses. This will also help with logistics once you manage caterers, restaurants, shuttles to and from the airport, rooming lists, ordering swag, and so forth.
Managing Leadership Expectations – Executives need to communicate what they want to accomplish at the retreat early on. Otherwise, you (as an EA, Chief of Staff, People Leader, and/or internal event planner) will waste time chasing decisions and revising plans. I know this drives you CRAZY, so hopefully some of the ideas in this article can reduce some of the stress that comes with offsite planning.
Learning from Each Offsite – After every retreat, conduct a post-event survey to measure what worked and what didn’t. Over time, you’ll build a playbook that reduces planning hours while improving results.
How to Increase the ROI of Your Offsites
An offsite should be more than just a company-sponsored vacation or “boondoggle” —it’s a high-leverage investment in your team’s alignment, engagement, and productivity. Here’s how to get the most out of your next retreat:
✅ Define Clear Objectives – Every offsite should have a primary focus. Some examples include:
Strategic planning (big-picture vision setting)
Team-building (creating trust and stronger relationships)
Brainstorming & innovation (generating new ideas)
Decision-making (aligning leadership on key priorities)
✅ Sequence Each Day for Maximum Impact – The flow of your offsite matters.
Start by building trust and intimacy with informal gatherings and icebreakers.
Reserve strategy-heavy discussions for the middle when focus is highest.
Include flex time so employees can recharge, handle work, or call home.
End each day on a high note—whether it’s a group dinner, an engaging speaker, or an exciting team activity.
✅ Measure Success – The best companies track the ROI of offsites by monitoring:
Employee engagement scores (pre- and post-retreat)
Retention & team satisfaction
Alignment on company goals and key decisions made
New ideas that arise from brainstorming during your offsite
Increased trust, intimacy, and connectedness among colleagues
✅ Create a Cadence of Offsites – One-off events won’t create lasting impact. The most effective companies plan a rhythm of offsites throughout the year. Consider a wide variety of opportunities as part of how you operate a remote, hybrid, or distributed team where you would benefit from being together IRL:
Quarterly executive retreats or senior leadership offsites to plan OKRs and prepare for board meetings
Annual Sales Kickoffs (and/or kickoffs for Product, Marketing, and other teams)
Department-level offsites (to get your specific team aligned and engaged)
One company-wide All-Hands Meeting
Customer Conferences
And so forth. There’s never a bad reason to have an offsite (of course, I’m pretty biased in saying that, but hey! I’m passionate about what we do….)
Make Your Next Offsite Count
Planning an offsite is one of the highest-leverage projects you can make as a People Leader But if not done correctly, it can also be a massive time drain and financial burden, not to mention a drag on company culture.
By planning ahead, negotiating effectively, and structuring your agenda intentionally, you can save money, reduce stress, and create offsites that drive real business impact.
At Offsite, we’ve helped companies like yours save millions while making their retreats easier to execute.
If you’re planning an offsite and want expert guidance, let’s chat.
BTW - want the slides from the actual presentation I gave TroopHR this week? Email me at jared@offsite.com to ask for the slides, and I’ll send ‘em your way!
Thanks for reading.
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 Buffer, Webflow, 15Five, Linear, Metabase, Hampton, and others trust Offsite for their team retreats.
Really helpful tips. Loved the part about balancing work and social time,too many meetings can drain energy. What’s the best team activity you've seen that helps people bond without feeling awkward?