You’re having a retreat, how many people will come?

So you’re having a company retreat. But before you get to planning, before we talk about the venue, budget, or team-bonding activities. There’s one crucial question to answer, how many people are coming?

We’ve all had that experience, in true Cady Heron fashion, we grab “enough cheese and crackers for eight people” only to find out the party is closer to 80 people.

Don’t worry though, we’re going to help you. Not only will you have an accurate portion for snacks, but with our help, your retreat will be legendary- I’m talking status equivalent to “the plastics”. You know without the toxicity.

Anyways, I digress. So, how many people are coming to your retreat?

First things first, there are a few things to consider. If you were one of those kids who also skipped to the last chapter of the book or read the riddle answer before solving it, we’ll give you the opportunity to skip to the answer.

Consider Timing

There’s not going to be a time that works for the entire team. Regardless, it’s important to consider which time of the year makes the most sense. It might seem obvious but considering quarter goals and project deadlines is crucial; this way you’re not scheduling a retreat in the middle of trying to finish an all-hands-on-deck project.

For team members who are key stakeholders for the retreat, check their availability before picking a date.

Another thing to consider is the venue, if you have a destination you really want to take your team to, consider when the season is. If it’s during the slow season, you might be able to get more bang for your buck.

-> Speaking of Times, The New York Times recently did a feature on us! (Yeah, we’re kind of famous)

Plan early

Not only will getting a head start on planning help you budget, but it also gives the team enough time to schedule it on their calendar.

When we say plan early we mean early. For teams with over 100 people, we recommend you start planning a year out. For teams of around 50, 6 months is fine and if your team is small, we’re talking 10 people, 3 months will do.

Be Flexible

So, if you’re planning a year in advance there’s a high chance that your headcount may change. You may have new hires, people may retire or go on maternity leave, whatever the case the number will change. You can try to predict a future headcount, but the main thing is just understanding that the key to a good retreat, is flexibility. 

So having considered all those factors, it’s time for the big question: how many people are coming?

Drumroll, please!




  1. Discuss Your Vision & Goals

  2. Pick 2-3 Possible Dates

  3. Set a Budget

  4. Find the Perfect Venue

  5. Schedule a Rough Itinerary

  6. Order Food & Drink

  7. Find a Workplace and Set Workplace Content

  8. Plan Team Building

  9. Schedule Special Events

  10. Confirm Transportation and Swag

  11. Review your Retreat

  12. Set Up a Retreat Communication Channel

  13. Enjoy the Retreat

Feel like too many steps? Have an expert help you. Schedule a free consultation call today!

Taylor Moreno