Company offsites get hyped as the fix for everything. Culture booster? Of course. Strategy breakthrough? You bet. Burnout cure? Where do I sign? And hey, sometimes they are. But here’s the truth: a truly game changing offsite doesn’t start when you roll into your Airbnb or crack open that first Pellegrino in the welcome circle.

It starts way earlier. Like, weeks before anyone boards a plane.

Let’s talk about the often skipped but totally essential part of any offsite: pre trip planning. And no, we’re not talking about logistics. We’re talking about mindset, alignment, and momentum.

1. Get Clear on the Why

Before you pick a destination, you need to answer one question: What’s the point of this trip?

Is it about connection? Strategy? Celebration? Deep work? Too many teams skip this step and end up with a trip that’s fine, but not focused and definitely not worth the time and money.

2. Involve the Team Early

If you want people to be excited and engaged, make them part of the process.

Ask questions like:

• What would make this trip feel worthwhile to you?
• What do you need (logistically or emotionally) to show up fully?
• What’s one thing you’d love to do or learn as a team?

Even better, get them to vote on a few destinations, themes, or activities. Shared ownership = higher buy-in = better vibes.

3. Define Success 

We measure product launches. We measure OKRs. But… retreats?

Before the trip, decide what success looks like. That could mean:

• Our product team aligns on the next 2 quarters of work
• People from different functions leave with stronger bonds
• Everyone gets 3 hours of uninterrupted deep work each day

This gives your trip structure. And helps you make better choices (like skipping that fifth happy hour in favor of a group hike and reflection).

4. Build Pre-Trip Momentum 

Now, here’s the fun part: get people excited.

Try this:

• A shared playlist for the flight
• A Slack thread to share “fun facts” or packing tips
• A pre-trip Zoom with mini intros, agenda walk-through, and Q&A
• “Trip bingo” with fun goals like “try a new dish” or “talk to someone new”

It builds anticipation and lowers anxiety. Especially for new hires or introverts, knowing what to expect makes a huge difference.

So, What’s the TL;DR?

Team retreats don’t start with check-in. They start with clarity, collaboration, and a sense of shared purpose all well before you ever leave home.

If you want your next offsite to actually move the needle (instead of just producing pretty photos), start earlier. Ask better questions. Involve your people. Set the tone.

Let’s stop treating offsites like vacation + meetings, and start treating them like strategic tools for culture and connection.

And if you need help figuring all this out?

Vamos is building the platform that helps you plan less and align more.

Join the waitlist here: Govamos.io