Step-by-step guide to launching a memorable retreat

Earlier this month, we had our second company retreat — an entire week to disconnect from our day-to-day life and better reconnect all together. We had the chance to live in one of a kind, fully equipped house with every amenities you could think of, allowing us to create unforgettable memories together.

Although this type of event is fantastic to experience, its preparation is far from easy.

Here is a quick step-by-step guide that may help you define and plan your next team retreat.

In a rush? Here is a Notion template you can use with this guide to ease your prep.

1. Define the exact purpose of your gathering

There are countless reasons why you'd wish to take a break from your day-to-day work schedule and experience unconventional time with your fellow teammates.

❓ Ask yourself:

• Why do we need a retreat?

• What are the key elements we wish to take away from this event?

• How could this event improve our team culture?

• How could this event improve our (collaboration, communication, etc.)?

In our case, as a fully remote company, being physically together at the same place and time was the ultimate purpose. Knowing this, we prioritized the accommodation and picked a memorable house that promoted intimacy, quality time, and creativity.

If you better understand why you need a retreat, you'll make it that much more impactful. On top of that, it will make the overall planning decision much more straightforward.

2. Define your resources

Your most important assets are your estimated budget and time. Once you've figured out these two, you have a great framework to start working.

❓ Ask yourself:

• How often do we wish to do this? Once, twice a year? More?

• How many days can we dedicate to a retreat without impacting too much the workload (1, 2, 3, or more days?)

• What's the annual budget dedicated to each retreat?

For example, our assigned resources were:

• Two retreats per year

• A full work week each time (5 days)

• €30K ($30K) per year (approx. €15K per retreat, or €1K per team member)

Alexis (People Ops Manager) and Valentin (CEO) unveiling to the whole team the t-shirts specifically made for the offsite.

3. Set up an ideal planning

When scheduling the week for a whole group, you neither want to be too precise nor too vague, as it could get unpredictable. Find the sweet spot in dividing your schedule into a big chunk of time.

Such as:

• Travel time

• Workshops

• Team-Activity

• Free-time

• Restaurant

  
  

Our team final retreat schedule

4. Organize impactful workshop(s)

Being collectively gathered in a different environment is a fantastic opportunity to work differently, experiment with new topics, and gain some perspective from the day-to-day schedule through so-called workshop.

❓ Ask yourself:

• What are the key elements we wish to take away from these workshops?

• What are the out-roadmap topics we could work on?

You can literally come out with any ideas for these workshops as long as they answer your specific goals.

Example: 1-Day Hackathon

As an example, our first workshop was a 1-day hackathon.

The goal was to work as a team on any company project that could be solved/delivered in one working day.

The day went as follows:

1. The day before, we asked the entire team to come up with as many ideas as possible about projects or features that could benefit Specify in any shape or form.

2. People shared their ideas in a dedicated Canny board, and we spent the evening upvoting the projects that inspired us the most.

3. The next day in the early morning, we created four squads to work on the most upvoted projects.

4. Each squad had the entire day to come up with a delivery of their projects.

5. At 6 PM, every squad showcased their work to the team with a Pitch presentation and, when possible, a live demo.

💡 Fun fact:

One of the squads worked on a long-waited Raycast extension with Specify. Learn more about the release.

Because of the time limit, that day was intense and challenging, and we also had a lot of fun. This day turned out to be very productive. We'll do it again. 🙌

5. Organize, plan and book your retreat with Notion

So you figured out the why, your resources, and the planning. It's now time to dig into the actual organization and prep of the retreat.

This moment can get quite long and frustrating since there's much to choose, book, and think of.

To make it easier, here is a Notion page to organize the preparation process you can duplicate as a first base for your next team retreat.

• Organizational Dashboard (todo, budget, invoices)

• Agenda

• Trains

• Car & Drivers

• Food (Grocery & Restaurant)

• In Your Suitcase

• Rooms distributions

Overall, I recommend you make this document collaborative. So everyone can help and contribute to the event.

6. Our retreat experience

We picked the Moulin d'Hortoy, France, for its outstanding amenities and remote location. We wanted to isolate ourselves in nature to reconnect better together.

As a result, we experienced an increased team connection and collaboration thanks to our different activities, workshops, and free time together. We had a blast!

Almost the whole Specify team (we missed you Yann 😷)

That's it, folks! I hope this little guide will help you in the decision and organization process of your next company retreat. Enjoy ✌️