A Perfect Retreat Schedule for a Large Distributed Company

If you lead a remote or distributed company, you’ve probably thought about running a retreat. With 10 or so people on your team, that probably sounds very doable.

But what about organizing a retreat with as much as 100, 200 or even 500 people? It may sound scary, but it’s not impossible.

At Surf Office, we’ve hosted retreats for as little as a dozen to as many as a few hundred people. Here is what we’ve learned from our experience hosting retreats for large companies and how you can do it without making logistics a living mess, all while creating a schedule your team will enjoy.

The ideal length of the retreat

If your team is distributed all over the world, you need a longer retreat, as a day or two won’t cut it. We’ve seen larger teams organize offsites that are 3-5 days long, which is the ideal length if you want a good mix of work and rest.

Monday: Arrival and start of the retreat

Most retreats start on a Monday, which means that everyone should arrive and settle in their accommodation by then. For people that have to travel long distances, make sure to buy the tickets for Sunday, so they’re fresh and rested on Monday morning. For those with shorter travel times, Monday flights are fine.

On that note, don’t really count on doing anything productive on Monday. People arrive at different times, they are tired and excited to meet each other, so you really should have Monday as the day to settle in.

They can use this day to explore the city, work from the hotel, set up smaller meetings or whatever they please. Just make sure that no work is mandatory on Monday. Also, don’t go to the other extreme and throw a party on the day everyone arrives. After all, you want everyone to be fresh for the big meeting the following day.

Tuesday: The official start

With a large group on a retreat, it’s usually the practice for the CEO of the company to open up the retreat with a speech on the second day of the arrival.

When EVBox went on their 200-person retreat in Madrid late last year, they officially kicked it off on the second day with a presentation about the company’s vision for 2019.

You can also extend the speech into a longer presentation on how the company is doing. Maybe throw in some numbers and stats, to keep everyone in the company up to date.

You may think it’s too much, but for someone flying in from the other end of the world, they will appreciate being informed about the company progress.

Then end the day with a company-wine dinner event somewhere nice.

Wednesday & Thursday: Work, play, repeat

On Wednesday, you should dedicate the day for productive work. Consider organizing a hackathon or innovation day to brainstorm new product ideas or to work on solutions together. (Keep scrolling to read our tips on hackathons!)

On Thursday morning, split up into smaller teams and have them work on their pre-determined projects. Then use the afternoon for a team bonding activity. Don’t underestimate the power of team bonding! By allowing some time for bonding between teammates, you give them the opportunity to let their guards down and truly connect with each other, which is a sure way to increase employee happiness and consequently, employee retention.

Some of our clients’ favorite activities are sailing on the river in Lisbon, treasure hunting in Barcelona, or learning to surf in the small village of Ericeira.

Before setting off for team activities, though, it’s a good idea to have another speech or an announcement to let everyone know about what was accomplished during the retreat.

Thursday is also a great day for an evening party if you’re leaving on Friday.

Friday: Hasta luego!

On Friday, give your team the choice to either work on loose ends or time off from work and other activities as this is the departure day. They will appreciate it, especially those who have a long flight ahead of them. After all, you want your team rested, energized and inspired once they get back to their homes.

Hackathons and innovation days: Working on a single goal

Large companies that go on retreats often organize hackathons to come up with new ideas, build new product features and have everyone in the company working together on a single goal. For these meetings, we recommend having one large room for everyone participating.

Depending on the size of the group, you should also have at least two smaller meeting rooms for breakouts so teams can rest and get some time for themselves.

Recently, the team at Mattermost did a design hackathon when they went on a company retreat in Lisbon. The goal was to give everyone a chance to zero in on products and projects that they were passionate about.

“It was fun to come together and see people excited to work on something that’s really close to their heart! It was an amazing experience.”

– Corey Hulen, CTO and Co-founder at Mattermost

Another useful tip for hackathons and innovation days is to organize catering instead of going out to eat. It will save considerable time and simplify your logistics greatly.

Something else that may seem obvious but it’s worth mentioning: check with the hotel to make sure the internet actually works. You probably take it for granted, but many hotel managers don’t. At the same time, ensure there are enough projectors in meeting rooms and that they all work. You can visit the hotel in advance to check if everything works according to plan.

Stick to the schedule but be flexible

When organizing a retreat, it’s important to have a schedule and stick to it. From our own experience, having a loose schedule with too much flexibility can turn into a proper mess, with everyone going around as they wish and you won’t get any work done or spend time together.

However, don’t go too crazy – leave some free time for the participants to do whatever they please. You can use the evenings to organize dinners or other activities, but it’s completely optional. Your team will find a way to organize themselves, and not everyone wants to socialize in the evenings anyways – some folks just want to take a nap or call their family.

Let Surf Office handle the logistics

While organizing a retreat can be an extremely rewarding experience for large teams, it can also be quite demanding, time-consuming and expensive when you’re not connected with the right providers. If you feel like you’d benefit from outsourcing the logistics of a retreat while you enjoy spending time with your team in a gorgeous location, contact the Surf Office team – we’ll make sure you’re in good hands.