When should you start planning your next retreat?

When organizing a retreat, one of the most common questions we get is – when should we start planning?

Sooner is always better than later, and the earlier you start, the better – in general. At Surf Office, some smaller team retreats can be booked even at the last minute, depending on the location and the season when it’s taking place.

However, if you’re organizing the retreat by yourself, you need ample time to do everything properly.

This means researching things such as accommodation, the space for working and other events, as well as venues for various activities and meals.

If you can’t manage this all on your own, it’s best to hire someone.

If you hire Surf Office, we’ll take care of the dirty work, while you enjoy the nicer part – working and team building during your retreat.

More people – more problems

Have you ever tried booking a restaurant for 10 people? If not, we’ll give you a hint – it’s not always simple.

Now imagine booking a restaurant for 50 people. All of a sudden, something as simple as having a meal together becomes an ordeal.

The biggest factor in how soon you should start planning for your retreat is the number of attendees.

So, here’s a quick rundown:

👥 Smaller teams up to 10 people: 3 months in advance

👥👥 Medium teams of 10-50 people: 5 months in advance

👥👥👥 Large company retreat with 50+ people: 8 months in advance

Some other factors at play:

How much you like stress (tighter deadlines mean more pressure)
How much you want to improvise (don’t be surprised if the only last-minute accommodation is sleeping in a trailer)
How much you want to pay (last-minute usually means more expensive)

Choosing the right date

One of the hardest parts of organizing your ideal retreat is finding the date for it. Unfortunately, you’ll be hard pressed to find a date that works for everyone in your team. Some more bad news – the bigger your team is, the bigger the headache around finding a date that works for all team members.

For smaller teams, this is not such an issue, as you can open a Slack channel (or whichever communication tool you use) and discuss a date that everyone can attend trouble-free.

For bigger teams, it’s best to avoid using group chats to arrange a date for the retreat. Before you know it, it turns into a discussion on whose birthday is happening that weekend and who booked a romantic getaway with their partner months ago.

For a more general tip, do some research in advance and avoid bank holidays and school holidays. This is good practice to keep everyone in mind.

Once you’ve done this, choose a date, sit back and wait as complaints start rolling in. Don’t worry, there will be complaints. Try not to take this too seriously, as you’ll never find a date that works for every single person.

If there aren’t too many people with serious reasons for not being able to attend, stick to this date and start arranging your retreat. Otherwise, if you’re trying to please everyone, you will inevitably fail.

To handle the more practical side of choosing a date, teams such as TimeDoctor use Doodle. This tool allows your team members to mark when they’re available.

Organize your dream retreat today

Do you want a retreat that’s more about enjoying the good things in life than worrying whether Janet from accounting gets a single-bed room as she requested?

At Surf Office, we make organizing retreats a breeze. We do the heavy lifting, while you do the things you love. We can’t promise to pick an ideal date for you, but we can promise you’ll have a great time.