Company Retreat Benefits #OpenLetter (Part 3 of 3)

This article is part of a LinkedIn series “An Open Letter To…” written by professionals from around the globe addressing issues they feel are worth championing. Click here to submit your own open letter.


Dear Leaders,

As Sheryl Sandberg, COO of Facebook, says, “Leadership is about making others better as a result of your presence, making sure that impact lasts in your absence.

As a leader of a remote team, the above sentiment is extremely important since you aren’t usually in close physical proximity to your team members. How can you create a lasting impression on everyone?

One way to ensure your presence has a lasting impact is to share real-life real-time experiences. This is commonly known as a company retreat.

I have spent eleven years working in the events industry. As a result, I’ve attended and planned my fair share of events. This is why I currently serve as the Director of Events at Rebel + Connect.

Bad Events

Let me tell you, there’s nothing worse than getting ramped up for an event, traveling to the event, and finding yourself in a drab environment with stiff chairs and PowerPoint slides. Even worse, after the event is over you learned nothing, made no meaningful connections, and essentially just wasted your time and money.

Example 1

Before starting Rebel + Connect, Charlie and I both worked for the same remote company. When it came time for our annual company retreat, we were both extremely excited to attend and profoundly disappointed by the experience.

The destination and the venue of the aforementioned retreat were amazing, but unfortunately they were underutilized. Instead of making use of the Stanley Hotel and its history, and the gorgeous surrounding natural beauty of Estes Park, CO, we spent our time indoors seated in chairs at tables in a conference room amid lectures. When it was time for lunch, I wished that I had brought my own, because the food was mediocre at best and we were seated inside. It would have been much more rejuvenating to eat and enjoy the natural beauty outside!

When all was said and done, I felt equally connected to the people that I was already close with, but I did not feel like new connections had been inspired by the retreat as I had hoped. Don’t even get me started on the lack of community in this group.

Example 2

A few months ago Charlie and I arrived early enough to have a drink and a snack before the event began. We paid our tab and proceeded to the event space early so that we could get good seats.

Unfortunately, we walked all around the hotel and could not find the event’s specific location. While on the hunt, we encountered numerous people who were also having difficulty finding the event’s location. The hotel staff had no answers and the idea that there was an event happening at the hotel seemed like news to them. We were all baffled.

Eventually, we found the room. It was across the parking lot in a completely different building! We were greeted by stiff chairs in rows, a powerpoint session, and worst of all...the featured speaker was not in attendance!

The only thing that we learned at this event was how to give them our money and what not to do when planning our own events.

At Rebel + Connect we focus on the combination of amazing content, adventurous experiences, and amazing destinations. Additionally, we assure that you will be clear about all of the details during your retreat from reality.

So what really went wrong?

These events were planned by a leader who was not taking the needs of the participants into account.

Let’s assume you have recruited your ideal team, meaning you now have team-members that fit your company culture like Cinderella’s glass slipper - everybody hired works well together, and they really shine in their roles. As the wise and strategic leader you are, you may be hesitant to rock the boat by overwhelming your team members with additional projects that don’t play off of their strengths.

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Why Hire Us?

A professional event planner knows the importance of keeping the intended audience in mind. At Rebel + Connect the first thing we want to know about our clients is why they want to host a retreat.

If you aren’t entirely sure, we will help you gain clarity. The retreat planning we do is not about what we want a retreat to be, rather it is about what you need the retreat to be.

In addition to clarifying the why of your retreat, a skilled event planner will help you clarify the who, what, where, when, and how. This includes, but is not limited to identifying the facilitators you need to connect with and the activities that will best allow your team members to go beyond their comfort zones, while still maintaining a foundation of safety and inclusion.

Not only will a seasoned event planner take pressure off of you and your team members during the planning process, their presence during the retreat will ensure everything runs smoothly.

Even the best laid event plans are just that, plans. For example, unexpected variables like weather can threaten to derail your event. A veteran event planner is thinking three steps ahead and has a backup plan ready to go before you even realize there is a problem.

As editer Julius Solaris says, “Event professionals eat pressure for breakfast, tension for lunch and skip dinner, while keeping themselves composed.

If you are the leader of a remote team, retreats provide you with an opportunity to break away and rebel against the day-to-day.

Research Says…

Retreats create intimacy and vulnerability, and as Brené Brown shares, “vulnerability is the birthplace of innovation, creativity, and change” which means that with the right facilitation, your team will grow in dynamic ways.

In her TED Talk from March of 2012 Brown also states that she defines “vulnerability as emotional risk, exposure, uncertainty.” She explains that, “It fuels our daily lives….Vulnerability is our most accurate measure of courage.”

In his interview with, Coby Chapple of GitHub stresses the importance of connections made in-person at their annual retreat for the productivity of their predominantly (65%) remote company. A disconnect between team members \ can dissolve magically after a successful company retreat. Colby says, “even when you’re remote, you no longer just see someone as an avatar—you’ve build [sic] up some background context and empathy for that person and that means you’ll be much better at working together and helping each other out. If you can effectively do that on a company-wide scale, then working remotely becomes far less isolating.”

From my own personal experience working at a remotely distributed company, I enjoy these continuously strengthening connections every single day. I had the opportunity to meet with most of the other fifteen regional managers at an in-person retreat about eight months ago and the connections that I made are ongoing. Instead of hearing just a voice on our conference calls, I hear advice from a real person now - a person that I care about even more because I know and trust them.

This continued connection is just one example of the ROI you can expect from Rebel + Connect’s Concierge level of retreat planning.

Here are some examples of how remote teams are using retreats to enhance worker experience and company culture:


One of the core beliefs of Buffer is living in a place that makes you happy and thus they have a fully distributed team.

Buffer knows the importance of having regular retreats for the members of their team. At their fifth retreat (at the beginning of 2015), the company spent more than $111,874 on the retreat. This amount covered lodging a catamaran cruise, a trip to the zoo, surfing lessons, and much more!

Employees were also encouraged to expense “a breakfast, a taxi ride, a SIM card, a dinner—whatever they feel is appropriate—throughout the week.” The company tries to “make retreats as ‘no cost’ as possible for team members, since [they] all still pay rent/mortgages back home while [they’re] on them, and little things can quickly add up.”


Ryan Baker, CEO & Founder of Timely, suggests “to keep the work content to a minimum” while on company retreat. “A brief session on how the company is going with discussion is enough. The rest of the time just enjoy each other’s company.

We will help you to figure out if your company would benefit from a work-free retreat, or if your company could use some in-person group working time like Buffer incorporates into their retreats.

Authentic Form & Function

Chris Arnold, partner of Authentic Form & Function shares that they have two retreats each year, one is “a full-week ‘working retreat’ where the entire team gathers in the same space to work a typical business week” while incorporating enjoyable exploration time sprinkled in the mix along with team dinners.

Their second annual retreat is used “to unplug from work and take time with the team in a more casual setting.” There are certainly benefits to both types of retreats; rather than stressing about the planning, leave it to us to bring your company’s needs and desires to life!

Kin HR

Fareed Raja, marketing strategist at Kin HR, suggests that “retreats should be easily accessible.” With Rebel + Connect’s Concierge Package you don’t have to worry about Travel as our Director of Travel, Rachel, will handle everything for you from booking plane tickets, to arranging travel from the airport, to arranging rides for group activities, and so on and so forth!

As your Director of Events I will help you determine if you should have “the whole team living under one roof” for the retreat as Raja suggests, or if you should consider separate living spaces so that introverts have the opportunity to recharge in between activities. Raja’s other tip, to “be proactive and find your team’s preferred locations/activities through surveys.” is addressed with the survey that we provide for your team after the Discovery Session.

Station Avenue Productions

CJ, Owner and CEO of Station Avenue Productions, advocated the practice of outsourcing company event planning. You want to ensure that your event is organized well and runs smoothly. “Events can define businesses and are a direct reflection on business leadership. A professional event coordinator can structure your ideal event — working autonomously in most respects based on your direction, vision, goals and budget.”

An internal event (your retreat) is just as important if not more important than an external event. The perfect retreat will connect your team on a deeper level - a level that can not be reached in the day to day operations of the remote work environment.

Choose Rebel + Connect

Our expert team provides several options:

The Discovery Package guides you through all of the necessary steps to determine what your vision actually looks like and how it complements your team.

The Atlas Package provides you with your own personalized catalogue that offers vetted providers for your choosing.

The Concierge Package handles everything from beginning to end - we are devoted 110% to creating and managing your event. That is what we are here for! You don’t have to worry about anything in the planning process. We book flights, secure facilitators, schedule team excursions, arrange transportation, order food, book rooms/housing, provide on-site event managers, and much more.

A Rebel + Connect retreat will “ignite the light” inside of your employees as Katy Perry sings, and they will “show [you] what [they’re] worth” to a level that far supersedes the excellent work they have produced previously!

The shared experiences on your retreat will help your team to reach their goals, fulfil their destiny, and become the best versions of themselves - versions that will benefit your company for years to come!

Baby you're a firework Come on let your colors burst ... Even brighter than the moon, moon, moon And it's always been inside of you you you And now it's time to let it through

Here’s to your next (or first) team retreat!


P.S. If you found this article thought provoking, interesting, helpful, etc. please leave a comment below!

This letter is the third in a series, read the others here: “Open Letter…” from Charlie Birch, Co-Founder and Director of Program Development “Open Letter…” from Rachel McGehee, Co-Founder and Director of Travel


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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