Organise a company retreat

An Ultimate Guide

Why did we write this guide?

Surf Office is an organiser of productive, authentic and effortless company retreats. We have been doing it for a while and develop plenty of processes and technology to make a company retreat easy to plan and facilitate. We call it “Retreat as a Service”.

We’ve gain a lot of insights working with our clients, seeing what works, what doesn’t work.

The goal of this comprehensive guide is to show that anyone can and should organise a company retreat but also explaining obstacles and challenges you can find on the way.

Why should we organise a company retreat?

It’s usually a combination of various different reasons why companies organise retreats. These are the most common ones:

1. You are a distributed team or your company has multiple offices

There is a growing number of (usually tech) companies which don’t have any office and a whole communication is by Slack, Skype, Zoom and similar tools. To meet from time to time in person is a need and that’s why companies like Automattic, Invision, Buffer or Zapier organise retreats regurarely. 

2. Strengthening bonds between the team

If you are a startup that’s growing really fast, 

3. Hiring the best talent

A retreat is a great opportunity to build company culture and also to attract new talent—who wouldn’t like to work for a company that organizes a trip like this once a year?

Annika Helendi while describing Teamweek retreat in this Medium article mentioned “We are getting 500+ applicants for each job opening”. 

Some companies like Doist (maker of famous Todolist) include company retreat into employee benefits.

4. Putting a successful strategy in place
Designing a roadmap for the next months
Developing a new go-to-market strategy


5. Innovating with new ideas
how the get outside of normal framework to think differently
Brainstorming a new product
Creating a first product prototype
Building a new internal tool

Example Buffer – paid plans story

6. Building a local community

Local meetup – clients, potential employees, developers if you have a community

meetup barcelona peakon – tweet 

7. Benefit for your employees

Just swipe your office for a week to sunnier location. This is less common (there is usually a goal).

Melewi’s Chief Operating Officer, Peach Nacion, explains why. “It’s the perfect way for the team to spend some relaxing, all-play-no-work, quality time together. It’s also a way of rewarding and giving ourselves something to look forward to after all the hard work we’ve put into our projects.”

When to organise retreat?

You want to organise the team offsite in the dates when everyone from the team would be available to join. That’s why summer months are not the best option as your employees might want to travel with the family or friends. And as everyone is travelling during the summer, everything is obviously more expensive.

Spring and autumn months (we are talking about Europe and US) are definitely the most popular, especially because of the January and February are the best months for an agency and or an e-commerce company to calm down after “Christmas months” and think about the strategy for the next year.

When to start planning?

It’s always better to start planning sooner or later. Sooner you start, more options you have. In Surf Office we simplify this process and we ofter book smaller retreat even last minute (depends on season and the location) but if you are organising a retreat by yourself, you need to do a lot of research with accommodation, work/event space, activities and restaurants. Larger is the group, the complexity grows exponentially.

Booking a restaurant for 10 people might be one call but reservation for 50 could be a small “project”.

This might give you a general idea about when is a good time to start planning:

👥 Smaller teams up to 10 people: 3 months

👥👥 Medium teams 10+ people: 6 months

👥👥👥 Large company retreat with 100+ people: 12 months

It of course depends on how you like stress, want to improvise and how much you are willing to pay for a whole thing (last minute is usually organisation in this case is more expensive).

How to choose the right date?

For smaller teams is probably the easiest option to open this topic in Slack or similar chat and discuss the date option. I wouldn’t recommend it for a large group where this chat can evolve into never-ending stories and reason about the “the best friend weddings” and “long-time ago booked trips” your employees have already committed.

My tip is to do some research before choosing the dates to avoid:

  • Bank holidays
  • School holidays

Then choose choose one date ahead of time and wait for complains. You will anyway struggle to find the dates that work for absolutely everyone, particularly for larger teams, but that shouldn’t stop you from going ahead with the dates that work. If there are not many people with serious reason who consider these dates unacceptable, stick to it. Otherwise you will end you in the never-ending spiral of choosing the dates.

How does it work?

1. Schedule a call with our company retreat expert

We would like to hear more about your plans and how we can make your next company summit a success.

Do you have an office in one location or is your team distributed? Can employees bring their partners? Is the retreat going to be more about work or fun?

2. Planning with your dedicated project manager

Even finding and booking one single restaurant for the dinner can be a painful project. Is the food going to be good? Is the price fair? How many of our team members have diet restrictions?

Each retreat is a combination of multiple smaller projects and with a large group the complexity might be scary.

But no worries, we mastered this process and made it fun and easy.

Our experienced project manager dedicated to you will help you with a whole organisation from searching for flights to crafting unique surprise activities for your team.

3. Detailed plan and schedule of your company retreat

At the end of the planning process you will end up with the bullet-proof schedule. There is no room for improvisation with a large group.

Everything must work perfectly, all the activities and transfers must be just-on-time.

Sounds like a dream end, right? That’s how we work.

You are ready for your epic company retreat.

Organize your next company retreat with Surf Office

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“I just wanted to say a thousand thanks to you for all of your hardwork and help in the organising of our team summit. It was a huge success and we couldn’t have done it without you!”

Emma Louise Bowen, People & Operations Manager in Peakon