6 Rules for Planning a Company-Wide Corporate Retreat That Doesn’t Waste Everyone’s Time
Do you plan company-wide team retreats at least once per year? If so, this is for you...
How do you get the most out of that once-a-year, "we're all in this together" moment that costs six figures (or more for larger companies) and steals a week from your team's calendar.
Is it a big investment? Yes.
And it’s also a massive risk, if you don’t plan it well.
But to me…
A company-wide offsite is a massive opportunity.
You’re bringing together 100, 500, maybe 1,000+ people from multiple departments, time zones, and cultural contexts.
You’ve got a CEO who wants to "set the tone” for the upcoming 12-24 months.
You’ve got Finance sweating over the budget.
And you’ve got everyone else wondering: Is this going to be worth it?
At Offsite, we’ve helped teams like Perplexity, Remote, HubSpot, 15Five, Guild, Webflow, ElevenLabs, and countless others plan hundreds of team retreats around the world, for groups of 10 to 1000.
So here it is: a blueprint to help you not blow your next All Hands.
Let’s get into it…
Rule #1: Don’t Treat It Like a Conference. It’s a Culture Moment
This isn’t Dreamforce.
You’re not trying to impress investors or appease sponsors.
The goals of an All Hands Meeting are typically:
building trust and intimacy
increasing cross-department collaboration
celebration a successful year of growth
rallying the troops after a difficult moment
personal and professional development
strategic planning for the upcoming quarter or year
…or a mix of various items above and more!
The best offsites are built around a single story or theme.
You may need to guide your CEO, C-suite, and other company leadership through brainstorms and clarifying conversations to make sure you’re aligned on objectives for the All-Hands Meeting before you begin booking venues, structuring an agenda, etc.
Your meeting's objectives should be in alignment with your organization's broader mission and strategic objectives.
They should also be specific and measurable.
Instead of something vague like "Improve team morale," aim for something like "Increase our employer net promoter score by 20%."
This clarity makes it easier to gauge your meeting's success (and get Finance to approve next year’s All-Hands Meeting faster than this year!).
Rule #2: Create An Engaging Agenda
With your objectives in mind, you’ll want to think through how to create the most engaging and highest ROI experience possible for you and your company.
Because your All-Hands Meeting is a work trip, I’d recommend scheduling your strategic planning sessions, brainstorms, problem-solving time, trainings, and other “sessions” before deciding on meals, fun activities, and other logistics.
Below, I’ve linked to our All-Hands Agenda Template for a 100-ish person offsite, but I’d recommend checking it out for any team size up to 500 employees.
Three types of sessions I’d recommend for almost any All-Hands Meeting would be a “State of the Union”, customer chats, and hot seats.
State of the Union - a 30-60 minute overview from the CEO of the upcoming quarter/year’s company-wide objectives.
Customer Panels - If possible, inviting key customers, investors, or partners to your offsites can be a great way for them to meet members of your team, while bringing your team closer to the people and organizations they are positively impacting on a daily basis.
Hot Seats - breakout groups lasting 45 minutes each to work through a pressing problem you, your team, or your company is facing. Brainstorm creative ways to capitalize on an exciting opportunity.
As you might expect, the team at Offsite has planned hundreds of various agendas for different types of offsites, companies, and business objectives, so based on the objectives your company’s All-Hands Meeting, we can provide more custom recommendations.
Other random “pro-tips” for agenda creation, which you’ll find in the template above, include:
Travel In and Travel Out Time - We recommend most companies budget for “Travel In” and “Travel Out” days because travel may be unpredictable (ie flight delays) and/or anxiety-inducing for those who do not travel often.
Optional group workouts - Group workouts can be led by employees to save money, or local vendors can be hired to lead classes. They are a great way to start each day energized.
Activities don’t have to break the bank - Volunteering is an activity type we recommend to many Offsite clients as it is both cost-effective and great for building camaraderie. We can tie volunteer outings back to company values and/or connect the benefitting cause to the offsite destination (such as a beach clean-up in Miami, FL). We also love Company-Wide Talent Shows because they not only keeps costs down when planning a team retreat, but allows your colleagues to showcase their unique skills and passions if they choose to do so.
Schedule “flex time” - adequate breaks of various lengths can serve as additional time for work sessions if you are running over from a previous activity, or it can be used for co-working, rest, calling family, and more.
Use table questions at meals - conversation starters can prompt your team to develop deeper, more meaningful connections with their colleagues. Some example questions include:
What are you proud of but never have an excuse to talk about?
What is the best purchase you’ve made for less than $20?
What is one thing you think is holding you back at work?
Serve healthy food - keep your team’s energy high throughout a gauntlet of sessions, activities, social interactions, and more. Not only will your team be at your All-Hands Meeting, but many will continue answering client emails, taking sales calls, and handling other matters, so serving healthier food options is critical.
End each day on a high note - Everyone should leave your All-Hands Meetings more connected to colleagues, more engaged with their work, and more aligned on company strategy. I’m all for healthy conflict, debate, and high candor interactions, but an agenda should allow for those moments to occur in the middle of the day followed by a party, exciting activity, or moment of celebration to encourage a positive environment.
Again, I’m missing a lot of “pro-tips”, but you can always email me at jared@offsite.com for more 😎.
Rule #3: Create An Inclusive and Valuable Experience (or Risk Damaging Your “Employer Brand”)
Your reputation as an employer and company culture are on the line when you plan an All-Hands Meeting.
Especially if you’re a remote-first, hybrid, or distributed company…
There are two ways this can go.
Plan and execute a successful All-Hands, and you’ll increase employee engagement, retention, and alignment.
Miss the mark, and you may fracture relationships across departments, risk losing top-performers, or cause pain to valued team members if you don’t create an inclusive environment.
How can you engage your team months before an offsite and ensure their experience both during and after the offsite will be valuable?
Use pre-offsite feedback forms to take care of logistics like dietary preferences, travel sensitivities, and even swag sizes.
Examples of logistics-based questions include:
Do you have any dietary sensitivities?
Do you require any accessibility or special needs? (consider Mothers' Rooms, ADA needs, ASL interpreters, service animals, etc)
Are there any blackout dates for which you can't travel to our offsite?
Those things are important, but as a CEO...I personally find value in some of the employee engagement metrics we're able to track through pre and post-offsite feedback forms as well.
Here are a few examples of pre and post-offsite feedback form prompts to consider when planning your next team retreat:
"connected to colleagues" questions
On a scale of 1-10, how connected do you feel to your direct team members?
On a scale of 1-10, how connected do you feel to your direct supervisor?
On a scale of 1-10, how connected do you feel to your executive team?
"company outlook" questions
On a scale of 1-10, how excited are you by your company’s future?
On a scale of 1-10, how likely are you to recommend your company as a great place to work to others?
On a scale of 1-10 how do you feel about your company's commitment to its core values?
"career development" questions
On a scale of 1-10 how do you feel about your future at your company?
On a scale of 1-10 how dedicated to you feel your company is to your development?
On a scale of 1-10, do you feel you have opportunities for advancement at your company?
You might also prompt your team (pre-offsite) on sessions they'd like to cover during the offsite, such as:
pressing problems in the company,
learning and development (and/or professional skill development) items there'd be interest in, and of course...
what kinds of fun activities they may want to plan ("do you prefer more active and outdoorsy experiences or relaxing activities?").
In your post-offsite feedback forms, you can ask for reviews (1-10 or open-ended prompts) on the sessions you organized and apply that feedback to future retreats.
If you use tools like 15Five, Lattice, or Culture Amp, you can even incorporate these prompts into your normal reporting motion.
Rule #4: Clarify Roles Before You Get Onsite
Retreat chaos usually stems from one thing: ambiguity.
Who's running the mic?
Who owns breakout room setup?
Who’s watching the clock to ensure we stay on-track time-wise?
If you don’t have a run-of-show, you’re setting yourself up for stress.
What we recommend:
Create a real run-of-show, by the hour, with names next to every line showing who owns what.
Brief every exec or session leader on goals, audience, and timing.
Assign someone to manage vendors, answer questions from attendees, and handle curveballs.
Of course, Offsite can do all this for you (and more) if you’re interested!
Rule #5: Capture Photos and Videos
Great offsites become a cultural reference point you’ll want to look back on fondly for months and years to come.
But too many teams forget to document the experience.
At minimum, capture:
Photos and videos (hire a real photographer!)
Session notes, decisions, and action items (and assign next-steps)
A post-retreat recap shared in writing, via an internal blog, slide deck, or Loom
Optional but awesome:
A recap video (great for social media and your Careers page)
A team-built Spotify playlist from the week to listen back to in slower months
A Slack thread of favorite moments or quotes
Enjoy the magic of your offsite forever when you capture the magic as it is happening.
Rule #6: End With Clarity, Not Just Confetti
You did it. The team is sun-kissed, emotionally bonded, and more connected than ever before.
But before you send them home…
Make. The. Takeaways. Obvious.
The final session should not be a low-energy brunch. It should be a strategic reset.
Have the CEO (or cofounders) reinforce:
What we learned
What we’re prioritizing
What we’re doing differently starting the next day
Then follow up in writing.
All you have to remember is:
Who does what by when?
Closing Thoughts
Company-wide team retreats can be great culture-builders for almost any company.
If you you nail it (WHEN you nail it!), you’ll accelerate trust, unblock misalignment, and make your team feel more like… a team.
Follow these 6 rules and your All Hands won’t feel like an obligation.
It’ll feel like the cultural heartbeat of your company.
At Offsite, we’ve helped over 350 companies plan high ROI and transformative team retreats, all within budget. We’ve saved our clients over $6,000,000 (and counting) as well as thousands of hours they’d otherwise spent to plan team retreats.
If you’re ready to plan an offsite and want help creating a high ROI, cost-effective All Hands Meeting, reply to get in touch or email me at jared@offsite.com.
Thanks
Jared
PS - 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.