How to Plan a Company Offsite with Gable

In distributed companies, People leaders use company offsites as their go-to tools for maintaining company culture. Company-wide and team offsites help bridge the geography gap in distributed teams and help employees meet, connect, and work better together.

But for all their benefits, company retreats require strategic planning and can quickly become overwhelming for People managers, especially if different teams hold various events during the year. The best solution we’ve seen works for distributed teams: create a playbook (or a few) you can reference whenever you want to get your remote team together in real time.

Here’s what your company's offsite playbook should cover:

The basics of a company offsite

Offsites are a proven tool that helps distributed teams form stronger bonds and be more engaged with their work and colleagues, so making them happen shouldn’t be a hassle. The idea of an offsite guide or playbook is to make it easier for both People teams and employees to organize in-person events that have a consistent experience and don’t carry the burden of too many extra work hours.

The basic building blocks of a successful team offsite are locations, workspaces, and accommodation. With this approach, you should list several go-to places, so your teams never lose time choosing from scratch. When you decide on cities, your next steps should be hubs, workspaces, and hotels.

How to choose cities for your offsite meetings

When selecting the go-to cities for your offsite playbook, start by determining how many people you are planning a trip for. Organizing a team get-together for 5-6 people is quite different from a company-wide offsite of 30, 50, or more employees.

Then, analyze where your team is located. Offsite locations should be as easily reachable as possible for as many employees as possible. If your team is geographically spread across time zones or continents, compare different cities for prices, locations, and workspace availability.

If you’re choosing large metro cities like New York or London, make sure to cluster employees and activities around a specific hub in the city. Hubs are usually neighborhoods, and this approach avoids the time-consuming commutes for employees if their accommodation is too far from the designated workspace.

When considering your go-to offsite cities, account for the budget. If budget constraints are tighter, as they usually are for smaller events, pick more cost-effective cities.

Finally, consider the weather and atmosphere you want the offsite to have. Organizing a New York City get-together is a different vibe from a getaway in Denver, so think about what you want to achieve with an offsite and consult your employees for feedback and suggestions.

Creating a consistent offsite structure and timeline

When all your travel, workspace, and accommodation details are hashed out, dive into the structure, schedule, and timeline of the offsite. Decide on what type of activities employees will have during the trip and ways to balance the work hours carefully with time to rest and create connections between employees.

How will you structure the time if your offsite event happens from Monday to Friday? Will you have working mornings, optional downtime in the afternoons, and team activities in the evenings? What effect will this have on employee engagement?

If the event is company-wide, create the agenda around your team, not the other way around. For example, think about how you can best support your customer-facing teams to get the same amount of rest, recharge, and connection as everyone else.

As you’re planning offsite activities, keep in mind that multi-day team meetings can quickly become exhausting after two years of remote work and fewer in-person meetings. Designing the event with optional downtime can help here – but don’t forget to account for rest for everyone. The FOMO around being together is real, and your employees can easily succumb to exhaustion for the simple reason of not wanting to miss out on connecting with coworkers.

Selecting workspaces and hotels

When choosing a workspace, start with the number of people you have on the offsite, and add any requirements you may have for the space, like phone booths for urgent calls, parking spaces, and other amenities.

As workspaces are often harder to find and lock down in advance, we recommend starting with them before you reserve the accommodation for your team. With Gable, you can access 700+ workspaces across the US and abroad – or request a new space for your offsite.

Once you’ve picked the work venue for the offsite, you can move on to hotels. If your event is happening in a big metropolitan area, having the hotel within walking distance of the workspace or at least a short subway ride away would be ideal. In smaller cities, the commute is more tolerable, but reducing it as much as possible would still be prudent.

Activities and team bonding

Finally, once everything else is done, you can plan city-specific activities you want the team to participate. This is the part where your creativity can shine, and you can make the best out of the city you chose. For example, if you’re meeting in NYC, bar-hopping could be combined with museum visits, bike rides, and sometimes close to the waterfront.

Example of how to plan a team offsite

To illustrate what planning an offsite with our guide would look like in real life, let’s start planning the next offsite for the Gable team using the tips we listed above.

Choosing the city

Let’s say we’re hosting an offsite for 30 people. Our budget won’t allow for a big city like New York, but we’d still like to be in a city center somewhere. For this trip, we choose Denver, as it’s easy to reach for everyone and offers plenty of activities for our team to enjoy.

Creating an offsite agenda

Our offsite event in Denver will last three days. We want one day dedicated to socializing and the other two to have five work hours. To make things easier for our customer-facing teams, we will work in the mornings and leave afternoons and evenings for activities and rest. We plan to have the second evening entirely off, with no activities, so everyone can get downtime.

So our schedule is as follows:

  • Day 1: Work time in the morning, team activities in the afternoon, social time in the evening
  • Day 2: Work time in the morning, social time in the afternoon, downtime in the evening
  • Day 3: All day dedicated to team activities

Booking workspaces for team offsite

Considering that we have 30 employees coming to this offsite, we need a workspace that can comfortably accommodate this number of people and provide everyone with enough space to focus and collaborate. After some deliberation, we settled for the Training Room at Candy Factory Coworking in Denver.

We decided on this space because it’s conveniently located, can fit our entire team, and has enough room for small groups to cluster together and take a break or focus when needed. Additionally, we can always book extra conference rooms if we need them. After we book Candy Factory and ensure the workspace is locked in, we can move on to hotels – and there are plenty in the area. We can choose from Hyatt, Warwick, Holiday Inn, and Hilton, depending on their room availability. It should be easy for team members to check in, get settled in their room, and reach the workspace easily when they arrive.

Brainstorming team-building activities

Let’s go back to our schedule and research enjoyable activities in Denver for our team members.

For Day 1, we have a team activity planned for the afternoon and socializing in the evening. We did a quick quiz with our team with suggested activities, and unsurprisingly, most votes went to an escape room.

Luckily, there’s no shortage of escape rooms in downtown Denver, so we settled for Mansion Murder at Escapology and booked a slot, followed by a celebratory drink in their on-site bar. After the escape room, we will head to dinner at Linger, where we booked a private room for the team.

For day 2, we planned for after-work social time for everyone, and again, our polls came in handy, as visiting a local brewery is high on the team’s wishlist. After consulting with some of our Colorado natives, we decided Jagged Mountain is the best choice for beers and dinner.

On day 3, we don’t have work on the schedule, so we need to plan an all-day activity for 30 people, and it’s precisely where our choice of the city shines. Denver is a hustle and bustle city, but there are endless possibilities for exploring the outdoors nearby. We decided on hiking, but we didn’t want to overwhelm those among us who are less experienced, so we chose a longer but easier route – Waterton Canyon. It’s only 35 minutes from Denver, and it boasts excellent views of the river and lake and the chance to meet Bighorn sheep along the way.

There you go – a whole offsite planned for the Gable team, with minimal hassle and a focus on employee experience, connection, and camaraderie.

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Andrea Rajic