Business Retreat Ideas for Your Remote Team - How to Avoid Overwhelm When Choosing the Perfect Destination, Venue, Activities, and Facilitators

 Business Retreat Ideas for your remote team or fully distributed company

When it comes to leading a remote team or fully distributed company, business retreats are no longer a luxury - they are a necessity and when used properly become a strategic tool.

We have all participated in our fair share of stale and lifeless networking events, drab conferences, bland training weekends, and mediocre company trips.

Before you say, "That's not for me," consider that there is a better way to connect that is fun, impactful, and human!

Why host a business retreat for your remote team?

Remote workers spend an exorbitant amount of time communicating through computers with team members they've never met in person.

Business retreats offer team members an opportunity to deepen their connections which promotes trust, communication, and enhances high-performance.

Additionally, your team needs a way to rebel against their norm of social isolation.


Business retreats feed the undeniable desire to reconnect with ourselves, others, and this amazing world without sacrificing schedule flexibility and location independence.

Whether you have just begun to consider the use of business retreats or are a long time retreat user, the planning process can be overwhelming.

Apply these business retreat planning best practices!


 A curated invitation-only event for the leaders of remote teams and fully distributed companies -  Unplug from Technology Plug-into Life!

A curated invitation-only event for the leaders of remote teams and fully distributed companies - Unplug from Technology Plug-into Life!

Retreat Destination

Often the first things that comes to mind when you hear the word retreat is “destination.”

Unless your company has a policy requiring team members to operate out of a home-office, your remote team is likely made up of both home-based workers and digital nomads.

For remote workers who tend to work from home - travel can be equal parts exciting and exhausting. Home-based workers are also more likely to have domestic partners and children making it hard for them to get away for extended periods of time. Knowing this you might be inclined to choose a business retreat destination that is easily accessible.

To the contrary, for digital nomads travel is a way of life. They are less likely to have partners and children. This might seems ideal when planning a business retreat, but since they are never in one place for very long it can be harder to pick a central location.

While choosing a destination is vital to planning a successful business retreat - you can’t exactly host the retreat nowhere - don’t fixate on this element at first.

The more you consider the who, what, where, when and most importantly the why of the retreat  the perfect business retreat destination (the where) will start to become apparent.

If you can’t resist check out some of our destination reviews to spark your creativity!


Retreat Venue

Another aspect of the “where” is the retreat venue. Be it a hotel, Airbnb, or a co-living space, decisions about the where are best made after consulting with you team.

Again consider the demographics of your team - home-based vs nomad, as well as male/female, night-owl/morning person, introvert/extrovert, etc.

Does every person require a private room?

Are some people willing to share?

Are people willing to share bathrooms?

Does it serve the group to have the intimacy of a large house or the formality of a hotel?

Keep in mind that the venue sets the tone - and the boundaries.

When honored boundaries strengthen relationships and build trust, when violated even slightly and by accident boundaries will erode the bedrock of you team.

An article published on PsychCentral explains that one way boundaries are violated by mistake is “Jumping to Closeness.” The corresponding sense of social overwhelm can cause team members to withdraw or over share and live to regret it.

In other words don’t force intimacy - it makes people feel vulnerable and can backfire.

On the other end of the spectrum - don’t avoid vulnerability by choosing a space that offer zero opportunities for intimacy. Dr. Brene Brown explains,


“...we associate vulnerability with emotions we want to avoid such as fear, shame, and uncertainty. Yet we too often lose sight of the fact that vulnerability is also the birthplace of joy, belonging, creativity, authenticity, and love.”

If you - as a leader - aren’t comfortable with some degree of vulnerability, don’t waste your time or money hosting a retreat.

Ultimately the impulsive or even habitual selection of a retreat venue - without considering personal preferences and balancing boundaries, vulnerability, and intimacy - will be your retreat’s downfall.

Where as the intentional selection of a retreat venue will provide the perfect balance of privacy and connection and help your team cultivate trust.

We recommend Airbnb for retreats of the more communal end of the spectrum and for more formal retreats.

 Airbnb is the best way to rent unique, local accommodations on any travel budget. Get $40 off your first trip of $75 or more!

Airbnb is the best way to rent unique, local accommodations on any travel budget. Get $40 off your first trip of $75 or more!


Retreat Activities

“We are on retreat, now what?” is not a question you want your team members to be asking (themselves or each other).


You need to plan activities, but not just random activities - purpose driven activities.

At Rebel + Connect we recommend a balance of cultural immersion, time spent in nature, community service, and rest and relaxation.

Why cultural immersion?


John Coleman and Bill George of Harvard Business Review explain

“As the world becomes increasingly global, the need for true global citizens to lead organizations in business, nonprofits, and government is far greater than in decades past. Global citizens who understand the importance of cultural nuances are able to bring people together across organizational boundaries and are more effective working and collaborating anywhere in the world."

Culturally immersive travel is a wonderful teacher. It promotes cultural competence, sparks curiosity, encourages self reflection, and facilitates changes in perspective. All these skills are vital to the success of remote teams.

Why time spent in nature?


Your team members spend hours upon hours interacting with the world through their computer screens. Digital detox is vital to your team’s sustainability.

Prolonged screen time can cause:

  • anxiety

  • depression

  • sleep disorders

  • neck and back pain

  • poor eye site

  • headaches

All of these symptoms have a reduce productivity or stifle performance!

On the other hand time spent in nature:

  • reduces stress

  • improves mood

  • increases focus

  • increases energy level

  • accelerates recovery from illness

  • boosts immune system

  • lowers blood pressure

  • improves sleep

All of these benefits enhance productivity and promote peak performance!


Plus, both cultural immersion and time spent in nature will call out a sense of adventure!


Why community service?

No reason to reinvent the wheel, check out the below infographic!


Why would you pay for team members to rest and relax or god forbid sleep?

The reasons mirror the benefits of spending time in nature! Rest and sleep improve memory, creativity, productivity, learning, and attention.

In the context of a business retreat the idea of intentional downtime is to give people some space to self organize. Not so much of course that they ask the dreaded question “now what?” but enough downtime that they can just be human together!

Additionally, scheduling enough sleep time into your retreat will ensure your people don’t return home run down, but recharged and ready to resume their regular work routine.

Best Selling Books on Sleep...

Again - never assume - ask your team for input regarding all the above mentioned types of activities!


Retreat Training

While we are major advocates for the implicit learning that happens during activities mentioned above, it’s also a good idea to have explicit hard and soft skills training components on your business retreat.

A well trained team will out perform a poorly trained team at every turn - there is just no way around, it you have to invest in people development. While you can and should offer virtual training to your team, in-person training remains superior.

The training should be informed by both the immediate needs of the team members and the long-term goals you have for the company!

Identifying team members and organizational weaknesses is hard enough, but finding the right facilitators can feel like a full time job.

They need to have a depth of knowledge about their topic and also the skill of speaking to who is in the room!

Finding speakers, trainers, and facilitators who understand the realities of working remotely - are not always easy to find.

Once you find them, they can be risky to hire! It can be nice to experience their style and content first hand before investing in their services.

That’s why we host Think Tank Live. A free video training series - hosted inside our facebook group Remote Leadership Think Tank - this series airs weekly and sometimes bi-weekly and features experienced remote leaders, professional coaches/trainers/facilitators.


When you join the group you have a chance to clue us in our your biggest leadership challenge, we make note of that challenge and intentionally book speakers who can address the most pressing concerns of our members.

That way when it’s time to host a retreat you either know of the perfect people to hire or at least have a good sense of where to turn for recommendations.


Business Retreat Ideas - Conclusion

When done properly, hosting a retreat will give you amazing ROI!

However, planning a retreat is a huge job that requires high levels of expertise.

You wouldn’t hire a social media strategist to handle your payroll or ask your CPA to head up a re-brand. Retreat planning is no different!

You and your team members all have your own areas of expertise and your time is priceless and limited.

However, so often we hear from remote teams that retreats are planned by a group of internal volunteers - then we hear about poor ROI on retreats.

Don’t sell yourself short. Avoid overwhelm by working in your area of genius vs spreading your team too thin and missing out of the long-term gains of a professionally planned retreat.


Have you planned a business retreat yourself and in retrospect with you had hired a pro to get the job done?

Share your business retreat planning horror stories in the comments section below!


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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