Planning a Company Retreat for Your Remote Team - What Every Leader Needs to Consider at the Starting Gate

 Planning a company retreat for your remote team is a huge job. These pro tips will increase your success.

“The need for connection and community is primal,
as fundamental as the need for air, water, and food.”

~ Dean Ornish

Retreats are an extremely valuable resource for remote leaders and their teams. Perhaps the most obvious benefits of team retreats are in-person trainings and co-working time. However, this is just the beginning of how retreats can elevate your team’s performance!

Remote workers spend most of their time alone - working from home or on the road.

“We have all known the long loneliness,
and we have found that the answer is community.”

~ Dorothy Day

The real-time shared experiences that retreats promote community formation and accelerate team bonding.

The result…

...increased trust amongst team members, better communication, increased collaboration, and enhanced performance.

Perhaps even more importantly, retreats bring company culture to life in fun and novel ways. Retreats provide leaders with an opportunity to celebrate company values right along-side company members. Additionally, retreats help team members connect with company culture in a new way.

The results...

...higher retention rates!

In order to host a successful retreat, you need to answer these 6 questions:

1. Why Host a Retreat?

Planning and hosting retreats takes ALOT of work, so the most important question to ask yourself when planning a retreat is why. You have to have a clear sense of direction!

I have already outlined some of the basic benefits of a retreat, but don’t just host one because I said you should or because other remote teams are doing it!

Instead, give some thought to the results you want the retreat to produce.

For some teams in-person training is the most important reason to host a retreat. If this is true for your team, what types of training will have the biggest impact?

Do these trainings needs to address hard skills, soft skills, or a combination of both?

For other teams, real-time in-person collaboration on specific projects is the primary motivation for a team retreat. If this is true for your team, what are these projects?

For others still, motivations might be much simpler and more pedestrian... just the mere act of being human together, unplugging, and finding ways to unwind and celebrate life!

To answer these questions you need to understand the needs of your company as a whole (now and in the future) and the needs of each individual team member.

Need some help getting your creative juices flowing?

Find out why other leaders are hosting retreats by joining our FREE Facebook group Remote Work Think Tank. Once your request is approved we'll send you a free copy of Remote Leadership - 10 Crucial Skills for Leading from a Distance.



2. Who Will Attend the Retreat?

Once you are clear on the why of your retreat, you want to look at the who.

It may not be necessary or appropriate to host a retreat for all team members at once. For example, perhaps it’s the best use of your company resources to host a retreat specifically for team leaders.

Another possibility is to host small regional events in areas where a significant amount of your team members live.

If your team can gather around a major city we recommend checking out Airbnb excursions!

 Host a day retreat for your remote team is the nearest big city using Airbnb excursions

If you're new to Airbnb you can sign up with our referral link and you'll save $40 on your first booking.

An entirely different option might be to host a full company retreat and invite not only team members, but their families too!

Additionally, you need to consider whether this event is mandatory or voluntary. This is not a simple question to answer, because it depends on a few variables.

If your team is made up of employees you can make the event mandatory, but only if you count the time spent at the event as “on the clock” time and pay team members accordingly.

If you don’t want to pay team members to attend the event you have to make it voluntary.

Additionally, if your team is comprised of independent contractors your looking at a whole different conversation.

Finally, will you pay for the cost of travel and lodging for all or some team members?

If the answer is yes, we recommend!


3. Where Will the Retreat Be?

Once you know the why and the who you can start to dig into the where.

There are many things to consider when choosing a retreat location, perhaps the least important of which is venue.

The time of year you want to host the retreat will help you figure out the best destination.

For example, if you want to plan a spring retreat you’ll need to consider weather patterns in certain regions of the world, so you can avoid being rained out.

The types of amenities and activities that you hope to have access to while on retreat will also influence the ideal location.

If you want to have a night out on the town then you will likely want to choose a destination with a safe and active nightlife.

To the contrary, if the primary motivation for the retreat is to reconnect with nature and unplug from technology, you will want to choose a rural or remote (😉) setting.

Where ever your end up Airbnb and both have a variety of options for all budgets!

4. What Will You Do On Retreat?

When considering what to do you always want to ensure that each activity has a clear connection to the why.

This is not to say that a retreat with a training focus need every single activity to be a training session. In fact, we advise against that.

In this case you would want to consider what types of activities complement and enhance learning.

For example, a good night sleep, healthy food, and frequent breaks will ensure your team members are set up for success during training time!

Also consider different learning styles. How can you think outside of the box to present trainings in fun, interactive, and immersive ways?

If you are hosting your retreat for different reasons you will want to explore similar questions.

Basically, when planning the what be mindful not to become too rigid and forget about the importance of pacing and contrast.

5. When Will the Retreat Happen?

Previously I mentioned the time of year as an important variable to consider when choosing where to host your retreat.

This is one type of when to consider.

You will also want to keep in mind the monthly, quarterly, and yearly internal demands of your team a whole, as well as, seasonal external demands of your individual team members.

For example, if you run an accounting firm, obviously hosting a retreat during tax season would be a mistake.

Similarly, if a majority of your team members are parents, hosting a retreat around a holiday or during school breaks (unless families are invited) is likely in poor taste.

6. How Will You Bring the Retreat to Life?

Once you are clear on the why, who, where, what, and when you can begin to tackle the how.

Planning a retreat and bringing it to life is a huge job. As the leader you will need to decide how to approach project management.

Will you manage the project yourself?

Will you recruit team members who are willing to volunteer their time to the project?

Will you hire an event planner?

That is just the first step of how...

The how is all about the details and the integration of the why, who, where, what, and when. It’s the glue that brings your retreat to life.


Retreat planning is a skill that must be developed over time. Our team has put together a free resource to help you speed up your learning process and get results faster. Download your free copy of Top 15 Things Your Need to Consider When Planning a Company Retreat.

Or if you are the type leader who prefers to work specifically in your area of genius and allow your team members to do the same, consider hiring experts, such as the Rebel + Connect Team, to help you ensure that each and every retreat you plan is a huge success! Claim your free consultation today.


We hope you enjoyed the article. If you have planned a successful company retreat for your remote team please leave a comment in below and share your wisdom with our audience!


Rebel + Connect creates custom retreats for remote teams. A Colorado based company owned and operated by Charlie BirchRachel McGehee, and Summer Weirich, we operate remotely and service clients from all over the globe. Join us as we create cultures of meaning and celebrate human connections in a digital world!

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