Planning a company retreat by yourself: What could go wrong?

Are you organizing your first retreat? 

Or do you already have experience and feel confident doing it again because everything went smoothly the first time?

We’ve been organising company offsites for almost 10 years, and during this time we’ve met our fair share of DIY retreat planners.

Some have been lucky and had great success while others have made huge financial losses because of unforeseen circumstances.

To increase your chances of success, we’re listing the most common issues with planning a retreat yourself.

1. The venue cancels last minute

Just when you think you have everything planned, the venue cancels last minute. 

And you don't have any backup accommodation.

This sounds like a nightmare, but it happens more often than you’d expect. 

Hotels can cancel your booking because they have a more attractive group inquiry, and with Airbnb, this happens even more often. 

So, you have to start searching for a hotel again. 3 weeks before the retreat. And you are way more limited with the location because you already booked flights and all other services. 

As a result you are going to pay more than planned and have a compromised experience. 

Booking accommodation via a third-party planner prevents this potential failure. Hotels don't cancel reservations to long-term partners like Surf Office because they know we wouldn't bring them any other group again. 

2. Hidden costs

It’s common for hotels to add additional fees and taxes during the offsite planning process. And any changes to a booking are ridiculously expensive. 

It’s almost impossible to sign a contract with a hotel that is favorable to you if it’s your first (and probably last time) booking the venue.

Surf Office has longterm partnerships with hotels. We always show you the total price at the beginning, no surprises. Those who organise a retreat themselves will typically pay more than those who organise their retreat with Surf Office.

3. Unreliable activity providers

Understanding the quality of the service for corporate groups is extremely hard to evaluate from online reviews because these are usually written by individual customers. 

Imagine having a group of 50 people waiting for a tour. The guide doesn't show up and nobody is picking up the phone. Sounds like a nightmare, right?

This happens all the time.

Surf Office has built long-term relationships with proven and vetted activity vendors which minimizes issues like this. Plus, we always have a backup.

4. Choosing the wrong activities and restaurants

Booking a retreat has very different nuances than booking a vacation. 

There are very few restaurants that both accept group bookings AND offer good quality. Some activities look cool but don't make sense for a group, and so on. 

These bad experiences compound when you’re making plans for a large group.

We often hear things like: “But one of our colleagues knows the area very well.” 

To which we respond: ”How many times has your colleague booked a team-building activity for 50 people?”

With our local expertise, we make your retreat epic by recommending team-building activities that have already been tested by hundreds of customers.

5. Hundreds of hours wasted communicating with vendors

Never-ending email threads, or worse still, vendors who don't respond at all. 

Whatsapp messages at midnight. Fake invoices. No replies after the payment. Unanswered phone calls.. 

All vendors want a prepayment. But how can you hand over the money when you don’t trust them?

With Surf Office, there are no back-and-forth emails or calls with vendors. Invoicing is simplified and your dedicated retreat planner is the sole point of contact. Your booking is 100% guaranteed (whatever happens, we always have a backup) and you can dedicate your time to planning an internal program.

6. Unfavorable weather conditions

You’ve spent months planning your perfect retreat itinerary: a week at the beach where people can enjoy activities such as surfing, beach volley and outdoor cocktails. 

It feels like nothing could go wrong… until you notice that a tropical storm is forecasted for the full duration of your stay.

Our experienced retreat planners monitor for any possible unforeseen issues, such as weather conditions. If we see that a storm is coming and most of your activities are outside, we will quickly arrange alternative, indoor options for you to choose from and coordinate with the vendors to get refunds on the activities that will not take place. 

7. Messed up transfers

Transfers are one of the most challenging parts of retreat planning. Even for us, after organizing hundreds of retreats. Finding a reliable transfer company is one thing, but if you’re a remote team and your colleagues arrive at different times, scheduling all this is a different “beast”.

In each Surf Office location we have 3+ reliable transfer partners we work with longterm and they rely on the volume we send them every year. Retreats for remote companies are our bread and butter. Eliminating delays for scheduled transfers is our top priority.

8. Your In-house event manager becomes unavailable

Let’s say you have an in-house person capable of organizing a retreat. Maybe that’s you.

First of all, it's an immense pressure to put on that person. Because CEOs expect nothing less than a PERFECT retreat. 

But what if that person gets sick or leaves the company? 

In these situations, you need to have a backup. 

We have seen dozens of examples when a client’s point of contact became unable to continue midway through planning a retreat. Even though we handle all the logistics, it was always very hard for the company to find a backup and manage the rest.

Surf Office has a team of retreat planners that can easily replace each other in any case.

Surf Office helps you find the right venue and takes care of all the logistics. But our biggest value is to make sure that nothing goes wrong during your retreat. You could say you’re buying “insurance”.

About the author

Peter Fabor is the CEO and founder of Surf Office. He started this venture in the Canary Islands back in 2013, operating apartments with a coworking space. First guests were individual remote workers. Surf Office later started to focus only on retreats and expanded to more locations. Now we organize retreats for groups from 30 to more than 300 people.

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