Hot Take: You Don't Need A 4 or 5-Star Hotel To Plan A Transformative Team Retreat
You need to create deep, meaningful connections between attendees so they can leverage the offsite for strategic planning, problem solving, brainstorming, cross-department collaboration, and more.
Jared here.
Let me say something that might ruffle a few feathers among our competitors who’ve filled their websites with pretty pictures, email you constantly with sexy travel destinations for your team, and think offsite planning is one big company-sponsored vacation…
The best offsites don’t need infinity pools, beaches, or Michelin-star dining (although those things are really fun!).
The best offsites require intention.
Why are you gathering?
What do you want to teach, accomplish, decide, debate, or incept during the offsite?
What lasting transformation do you want to see from attendees in the weeks/months/years to follow?
Answering these questions is far more important than picking a fancy venue (although, we can help you with that too!).
At Offsite, we’ve helped plan over 300 retreats for companies like Remote, 15Five, Guild, Buffer, and Perplexity.
We’ve seen clients scrape by and plan on the cheap, and we’ve helped executive teams spend $7k+/person on Napa Valley wine tastings or ski trips packed with once-in-a-lifetime experiences.
Here’s the truth: teams don’t bond over high thread counts.
They bond over unique shared experience.
And the best way to ensure your intentions for the offsite are executed properly is to plan an engaging, impactful, and results-oriented agenda.
The Real Job of Your Retreat Agenda
Think of your offsite like a product launch.
You’ve invested in flying people in, pulling them out of day-to-day work, and capturing their full attention for 48–72 hours. That’s rare air.
So what’s your job as an offsite planner?
It’s not just to fill time.
It’s to orchestrate transformation.
Specifically, a “5-star” agenda should deliver:
Clarity on priorities, goals, and the big picture (ie why are we here?”)
Connection between teammates and across functions, geographies, and seniority
Momentum that carries into the next quarter or year (ie where’s the ROI?”)
Belonging—the sense that “these are my people” and “this is my place”
Most agendas fall short because they confuse “activity” with “impact.”
Or, they pack the agenda with sessions that could have been a Zoom meeting, an email, or a memo.
Not you, though! Not today…
Here are some “pro-tips” as you develop agendas for your upcoming team retreats.
The Energy Curve: Map the Arc of Your Retreat
Every offsite follows a natural emotional arc. If you want yours to land, you need to match your sessions to the energy curve.
Here’s the typical 3-day retreat flow we recommend (and use ourselves):
Day 1: Arrive + Connect
Afternoon arrival, casual welcome
Low-pressure group dinner
Optional fireside or low-key evening activity
Goal: Ease people in. Make them feel safe, seen, and social. No heavy content yet. In fact, many times I’ll challenge my team NOT to talk about work until Day 2.
Day 2: Align + Build
Morning: Strategy session, vision from the CEO, big-picture goal(s) for the offsite (they’ll be different if you’re at an All-Hands, versus a Sales Kickoff, versus an Executive Team Retreat)
Late morning: Breakout groups or facilitated working sessions
Afternoon: Collaborative problem-solving and brainstorming sessions
Evening: Group activity (cooking class, bowling, karaoke)
Goal: Maximize engagement during peak mental hours, then blow off steam while creating unique shared experiences for your attendees.
This is the “fun stuff” but it is planned with intention.
Bonus: If you haven’t seen these before, here are some agenda templates our clients love. We hope to publish more of these, soon…let me know if you find them helpful and what sort of agendas you want to see next.
Day 3: Reflect + Launch
Morning: Personal/Professional Development
Mid-morning: Operational planning or OKRs
Lunch: Closing remarks and next steps
Afternoon: Departures
Goal: Turn insight into action, and end on an emotional high note.
The best retreats feel like a journey.
Not a meeting marathon. Not a party weekend. Rather, a meaningful arc that makes people want to show up differently when they get home.
What to Include in a 5-Star Agenda
Here’s a framework we use at Offsite when helping clients plan their run-of-show:
1. Strategic Alignment Time
This is your moment to reset or reenergize the company narrative. Think:
“State of the Union” from C-suite
Fireside chats with customers
OKR planning
Whiteboarding!
2. Team Connection Time
People remember moments, not slides. So give them:
Offbeat games or improv
Small group dinners (with rotating seats)
Outdoor adventures (like a challenging hike they’ll feel proud of, or ice plunges, or time at the pool if you’re looking to relax).
3. Unstructured Time
Counterintuitive, but critical. Let people:
Call home
Bond naturally
Recharge their social batteries
We often build in “flex time” after lunch or before dinner. We also protect mornings for optional activities—yoga, journaling, coffee walks.
4. Reflection + Integration Time
Otherwise, the offsite is a memory, not a catalyst. Build in:
Gratitude exercises
Shoutouts and public appreciation
Planning “action items” post-retreat
Photos and videos to remember the special time together IRL
What to Avoid: The 3 Agenda Killers
Before you repeat last year’s schedule, make sure you’re not falling into these traps:
1. Overstuffing the Agenda
If people feel like they’re sprinting from 8am to 10pm every day, you’ve overcooked it.
Leave whitespace.
2. Skipping Emotional Moments
Don’t be afraid to go deep.
Some of the best retreats we’ve seen include vulnerability exercises, shared life stories, or “letter to your future self” prompts.
These are the sticky memories that glue teams together.
Pro-Tip: Be sure to lead by example if you’re going to program these into your agenda and/or be sure your principal is on-board and have them lead by example.
3. Defaulting to Presentations
You already have Zoom for that.
Use in-person time for interaction.
Workshop > presentation.
Think “campfire,” not “conference.”
What It Looks Like in Action
Quick story: One of our clients recently created a vlog in their viewpoint to discuss the importance of team retreats.
He also showed the whole journey, from traveling to the offsite to being “on the ground”, to thinking back on the value of the entire experience.
We not only took care of all the logistics for them, but we also helped them create an agenda where:
The cofounders were able to give a “state of the union” on company finances.
Traditional presentations were swapped out for more engaging sessions where everyone got a chance to voice their opinions and align on strategy moving forward.
Traditional “fun time” was also turned into valuable content creation time to benefit Stan’s marketing team.
Result? Their team left fired up, crying happy tears, and crystal clear on how they’d support one another.
That’s the power of an intentional agenda.
Want Help Planning Your Next Offsite?
You don’t need to break the bank to create a meaningful offsite.
But you do need to get the agenda right (and it helps to nail the logistics, too!).
That’s where we come in.
At Offsite, we take care of all the logistics/details of team retreat planning, and then…
We offer “Chief of Staff” level partnership on thinking through your business and “people” objectives for the offsite, to help you generate the highest ROI possible while creating transformative experiences for you and your team.
Ready to make your retreat unforgettable?
Make a free account at offsite.com and start planning today.
Thanks for reading!
—Jared
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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.