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7 Min Read

How Transformational Retreats Can Transform Your Business

Shane Metcalf, CPO of 15Five

In May of 2022, we held our eighth annual all company retreat in Venice, Italy. These retreats are purpose driven events designed to bring every employee together, re-align them around our company mission and OKRs, and to allow for vulnerable connections in a beautiful setting away from office walls. This was without a doubt the best retreat that we have ever created. 

Our previous in-person retreat was held in January of 2020 and we had to pause these experiences for two and a half years due to the pandemic. Maintaining a healthy culture at a high growth organization is challenging without in-person connection at least once per year. This helps to set a foundation of trust, connection and empathy

The retreats beautifully pair individual transformational experiences with business-focused sessions. People begin to know and trust themselves and one another in new ways, so that we can collectively execute on the lofty outcomes we establish during the business focused sessions. 

The way we think about these retreats is that it’s an opportunity to create an emotional renewal for everybody, and peak experiences. Psychologist Abraham Maslow talked a lot about the necessity of peak experiences to achieve a level of self-actualization and self-realization. That’s really how we think about these retreats. It’s almost a happy excuse to create peak experiences for people in the company that reconnect us to our deeper passions.

We see retreats as a way to strengthen a company’s culture and values. Success here involves many factors, such as choosing an inspiring location, creating effective content, facilitating deeper connections on the team, and delivering peak experiences along with time afterwards for integration.

Company retreats as transformational containers

The first thing to think about is, how do you create the transformational container for people? How do you do something really different that will allow people to share vulnerably and push themselves out of their comfort zones? 

It really is all about structure. You have to create safe environments and can’t leave it to chance because we can gravitate to fear-based thinking and default towards more superficial types of interactions. 

Here’s how to create the right structure that allows people to share deeply personal and moving experiences even if that’s not their MO. 

Table questions

Every night at dinner we organized the tables to each contain between eight to ten people and provided three questions for everyone to answer. Examples included, What are you learning or being taught about life/yourself right now? or Who is a 15Fiver that you’ve met this week that made a strong impression on you and why?

Looking around at every table, I noticed that everyone was so focused on each other as they shared. There was no rush, and even after dinner was over folks grabbed another glass of wine and kept going deeper and deeper into conversations about their lives. There was a quality of listening that happened where people made the space for vulnerability, sharing, and trust to emerge.

Reciprocity ring

One of the most deeply moving parts of the retreat was the reciprocity ring. Everybody gets in the same room where large pieces of paper are stuck to the walls. Each person gets their own sheet and they write their name and then something that they want or are struggling with. Every participant then walks around the room and reads other people’s sheets. If they can contribute or have something to offer, they write their name and what they want to contribute, or they offer a private conversation to follow up later.

We had 150 people participate. One that stuck out was a request for an employee’s cousin who was recently paralyzed in an accident, and needs to buy a van that could accommodate their disability . Not only were coworkers contributing cash right there on the sheet, but somebody had a friend who was selling a van for a great price. When the employee walked over and saw the level of support they just received, they were deeply moved. This brings out the better aspects of our nature. (The theme for the event by the way, that adorned our new T Shirts was, “Let’s Be Better Humans.”)

Breathwork sessions for emotional release

Through breathwork, people have this psychedelic type of experience that essentially guides one to open up to their own emotional body in ways that they have never had access to. One employee had been hit by a drunk driver seven years ago and had multiple knee surgeries, leaving them unable to sit cross-legged ever since, even after many types of physical therapy. They did a single breathwork session and were able to sit cross-legged for the first time since breaking their leg. It was powerful to create this opportunity for nearly a hundred people to heal in ways that they would have never expected to, especially at a company retreat of all places.

Elevating business focus

For our business-focused outcomes for these retreats, whether it’s a company-wide retreat or a leadership retreat, we are setting goals, we are talking strategy, we are doing business-oriented things— but taking them to the next level. My belief is that when we get out of the rhythm of our day-to-day experiences, it snaps us into a more heightened state of awareness. We’re more strategic and innovative, and future ways of thinking are possible.

  • Every morning we held business focused sessions. We kicked off the first day with a State of the Union presentation by 15Five CEO, David Hassell, where he shared his vision for the future of the company. This was followed by a presentation by Vincent Huang, our Chief Product Officer, who detailed our product strategy for the near future.
  • We also had collaboration opportunities, such as group exercises where cross-functional teams workshopped one of our main business challenges.
  • We held a fireside chat/ audience Q&A with one of our beloved customers to understand their world more deeply, unpack how strategic HR leaders relate to performance management, and discover how we can continue to provide software and services that make an impact. 

Bringing it all together

We create experiences that break down barriers and create authentic connections, so that we can deeply see the humans that make up the company, and then all align around the mission and company objectives. 

But it is also crucial to present the retreat to your employees so that they understand its real purpose – to accelerate business growth. But it’s also a time to truly reflect on and celebrate all the accomplishments that your business and employees have made.

Now, emotional releases brought on by breathwork and vulnerable sharing among the team may sound odd or even scary to some, but these are the experiences that allow people to have breakthroughs in their lives and as teams. Pairing these transformational experiences with clarity around business goals, and a sense of shared purpose as a company, makes employees fired up about achieving goals that they may have thought impossible just days prior. They return to work a week later, to problems and struggles that may have been causing frustration and shutdown, and are suddenly revitalized and able to redefine what is possible for themselves, for the team, and for our customers.