Why Retreats Are a Must-Have in Your People Strategy—And How to Get CFO Buy-In

In 2020, we all became experts at working from anywhere.
In 2021, we figured out Zoom fatigue was real.
In 2022, we learned you can’t Slack your way into a high-trust team.

Now, in 2025, most People leaders know that culture can’t survive in isolation. It needs places to breathe, align, and connect. That’s what offsites are for.

But here’s the catch: retreats still get treated like line items to cut—not strategic investments to protect.

At Offsite, we’ve helped hundreds of companies like Remote, Buffer, Reforge, 15Five, and HiBob plan everything from executive retreats to sales kickoffs and all-hands gatherings. These aren’t just fun trips—they’re strategic tools HR leaders use to drive trust, clarity, and alignment across the business.

If you’ve ever had to justify a retreat to your CFO, this post will help you make the case—and make it count.

‍

1. What We Used to Call “Vibes” is Now Operational Risk

A decade ago, company culture happened by default. You sat next to your team, went to lunch, ran into each other between meetings. That casual proximity created alignment.

In a distributed or hybrid world, all of that has to be intentional. Without retreats, teams drift—slowly, then all at once.

So when someone asks:

“Why do we need a retreat?”

You can answer:

“Because our team hasn’t been in the same room in 18 months and we’re still expected to trust each other, deliver under pressure, and move fast. That doesn’t just happen on its own.”

‍

2. Speak CFO, Not HR

It’s not enough to say:

“We want people to feel more connected.”

You have to translate it into a language your finance team respects:

• Retention: Losing a mid-level employee costs $20k–50k.
  
  
• Speed: Misalignment delays execution, especially across departments.
  
  
• Morale: Burnout and disengagement show up in your engagement survey… and eventually, your Glassdoor reviews.
  
  

Frame it like any other business initiative:
What’s the cost of doing nothing?

‍

3. The Agenda Is the Strategy

A lot of companies think booking a venue = job done.
But the location matters way less than what happens while you’re there.

An effective offsite agenda has a few key ingredients:

• Space to Align: Strategy doesn’t live in slide decks—it lives in shared context.
  
  
• Space to Connect: You don’t need trust falls. You need time for people to actually talk like humans.
  
  
• Space to Breathe: Every great idea needs a little white space.
  
  

This isn’t about over-scheduling every minute. It’s about creating moments that don’t happen on Zoom.

‍

4. Cadence is the New Culture Stack

Most teams don’t need one perfect retreat.
They need a rhythm of connection.

A few real-world examples:

• Quarterly exec offsites to recalibrate goals.
• Annual all-hands to set the tone for the year.
• Team-specific retreats for onboarding or project kickoffs.
  
  

Think of retreats the way you think about planning cycles, sales kickoffs, or board meetings. They’re how alignment happens. They’re how culture is built.

‍

5. Don’t Make Your People Team Own Logistics

If you’re a Head of People, you’re probably already managing:

• Compensation reviews
• Engagement surveys
• DEI programs
• Employee relations
• Onboarding
• Recruiting alignment
  
  

Now add:
→ “Find a venue, source vendors, negotiate contracts, manage RSVPs, coordinate meals and A/V, build the agenda, and keep everyone happy.”

Not sustainable. Not strategic.

If your People team is in charge of both making the case and making the event happen, something will break. Usually them.

This is where the right partner matters. Whether you use Offsite or another platform, outsourcing logistics isn’t a luxury—it’s a way to protect your team’s focus.

‍

Here’s the Bottom Line

Remote work is here to stay.
But so is the very human need to connect in person.

Retreats aren’t a break from work. They are the work—when done right.
They’re where trust is built, decisions are made, and clarity replaces confusion.

So the next time someone says,

“Do we really need to do a retreat this year?”

Try responding with:

“Do we really think our team can thrive without ever seeing each other in real life?”

‍

Conclusion

Retreats are no longer optional for teams who want to move fast, stay aligned, and build lasting culture—especially in a world where in-person time is scarce and sacred. The most effective People leaders are no longer asking if they should plan an offsite. They’re asking how to make the investment count—and how to get buy-in from the budget holders.

When you shift the narrative from "perk" to "strategic lever," the conversation with your CFO changes. You’re no longer asking for permission to plan a retreat. You’re presenting a plan to build culture, reduce churn, and improve execution. And that’s something no smart finance team can ignore.

‍

Want to See What a Retreat Could Look Like for Your Team?

Offsite.com makes retreat planning effortless—from venue selection to vendor coordination to agenda support. Whether you're hosting an all-hands, an exec offsite, or a department-level gathering, we help you create retreats that deliver real business impact.