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Your Guide to Planning a Work Retreat

Company retreats are an excellent way to connect with your colleagues outside of your day-to-day work. For remote teams, most workers crave the in-person time - just to connect and get the connection that’s lacking over Slack or GChat messages.

Whether your team sees each other every day or is scattered around the country working remotely, you need to take the time to plan your next professional gathering with purpose. That’s why we created your go-to guide for planning your next work retreat.


Ask yourself - why are we planning this retreat? What purpose does this gathering serve? These are incredibly important questions that will guide your planning process - and it’s crucial that you start with them, even before logistics. Priya Parker’s book, The Art of Gathering is a very helpful tool. She recommends this chart as a starting point to move your gatherings about nothing to gatherings about something. Apply this to your next work retreat:

Table from The Art of Gathering by Priya Parker, p. 25

When planning logistics - location, budget, activities - go back to the purpose of your retreat. Let it guide you.


Is this a remote retreat? Hybrid? Will your team be traveling to the retreat destination? It’s best to get the overall budget then break it down per person so you know what you’re working with. Again, think back to the retreat’s purpose to help you decide what’s necessary and what’s not. No matter the size of your budget, you can get creative to make sure you still plan a retreat that’s meaningful for all attendees.


Decide how you’d like to gather. Many organizations are embracing the hybrid work environment, and you have to decide where you’d like to gather. Is this in-person? Remote? Is it hybrid? Do employees have the option to be there in-person or over a video call platform?

Oftentimes the culture of the organization helps predict this, but it’s still good to offer options for folks that may have different needs. Some ideas for unique places to host your retreat include: a boutique hotel, a public library, a team member’s vacation home, a luxurious cabin or eco-lodge, a coworking space or business incubator, a retreat space or a really cool Airbnb.

The courtyard at La Suprema Works & Events

You’ll want to know how many employees are attending in-person and take a look at company rules. It’s possible you’ll need to book with a corporate hotel, and thus your team can stay there - but that doesn’t mean you have to use the hotel’s meeting rooms. Get creative and mix-it-up! It’s important that the gathering space feels inspiring.


The beauty is in the details, right? Here are a few logistical questions to consider while planning your next work retreat:


How many employees need a place to stay? Everyone or just a few? Will employees share rooms or will they all be separate? Make sure you look into company policies and ask for folks' preferences before booking.


Will employees be expected to arrange for transportation to and from the retreat location? Will they receive a travel stipend? Who is responsible for booking flights and rental cars? Does the retreat location have parking? If you’re heading to an international destination, are there visas required? It’s best to have a document with all of the travel details for employees, because this is an area where people tend to stress easily. Save yourself the time and create a living document to share with your guests when they have questions.


What dietary preferences or food allergies do your team have? This is super important and will likely impact how you plan meals during the retreat.

We recommend planning some meals as a group that are already included and some meals on their own to have some flexibility. It also allows time for folks to explore the new place they are in. Another idea is having teams taking turns cooking or choosing restaurants. This gives everyone the opportunity to take some ownership of the food.


This one is IMPORTANT! When you’re creating the schedule, go back to the purpose. Are we sounding like a broken record by now? We hope so, because the purpose should determine your schedule more than anything else.

Who is running sessions? Are they prepared? How will you know they are prepared? What materials do you need?

Activities - Leave the to do list behind for a moment!

Leave room for fun! National park or hiking trails, live music scene, arts and culture - are there any shows coming through the area? Bowling, hiking, an escape room - these are all activities that are available in most locations throughout the year and are a great way to connect with colleagues outside of Slack or Asana.

Part of the retreat’s purpose is likely to support team members in connecting with their colleagues. Leaving room for some activities unrelated to their day jobs can be incredibly rewarding and memorable.

At La Suprema, we’re happy to host Tucson-based companies, and companies traveling from out of town to plan their next work-retreat.

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