How to Design a Nourishing Corporate Retreat in Three Easy Steps

By: Naomi Matlow 

As a community driven travel company that lets you take your life and work on the road, Unsettled is part of an evolution in work culture today. On our retreats, we actively get to see the potential role remote working can play in our future and what it means for the other areas of our lives. In a recent interview for Story + Rain, Unsettled Co-founder Michael Youngblood shared just how close this future is:

“People will work outside of how we define office environments today. Upwork recently partnered with a survey outlet and they discovered that in 2027, there are going to be more people working in freelance work than actually working in conventional full-time single employment. In 2027, there’s going to be this tipping point where everything shifts. And I think what will happen with all of these people working remotely is that they’ll be looking even more for a community to work in.” 

This idea has been echoed by many who are looking into what our work environments of the future might look like. As Ethan Pollock, an associate director of research and policy for the Aspen Institute’s Future of Work Initiative, tells The Atlantic, “Humans are inherently social beings, so as work becomes more independent…it further emphasizes the need to create other ways that people can connect with each other.” 

Whether you’re a remote worker or not, most of us in the future will be actively seeking a sense of community. The more our society and our culture is obsessed with work and productivity, the less we are personally nourished and supported by the communities where we live, work, and contribute. If our workplaces (physically or remotely) do not nourish us, we will all quickly reach a state of burnout. 

So, what does it take to be connected to your workplace and the co-workers that come in and out of your life and your inboxes on a daily basis? A really good team retreat can help solve this lack of connection and community, and done well, it can help reep extra benefits from our work heavy lives. The key lies in authenticity and offering something of real value to those involved outside of traditional work goals.

So what do we mean by nourishing employees? Today, employers need to recognize that they have a greater responsibility than simply providing their employees with a place to work, a living wage, and employee benefits. As our world has evolved into a more fragmented and isolating place, it is essential that employees feel connected to their workplace, their coworkers, and the communal sense of purpose or goal. If we want employees to contribute successfully to how much is asked of them, a sense of community is warranted. 

Below we share some key aspects of how you can use an intentional framework to bring people together and help nourish a sense of community. Based off of our Unsettled retreat framework, utilize these 3 simple steps when you model your next team retreat and see what unexpected benefits show up. 

3 Steps to Creating a Team Retreat:

  1. The Framework: Define Your Why

Like all great adventures do – start with a question: Why are you having this corporate team retreat? 

Is it to further a sense of community, to deepen perspective, bond over a shared goal, or simply have fun? Push yourself to go deeper than only productivity related goals or instilling a high performing team. You want your team to connect with each other and get to know each other beyond their output. 

Put yourself into your team’s shoes. Why do they need a retreat? Think about trends bigger than your workplace today. Is interpersonal connection important? Unstructured time and space out of the office? Creative brainstorms? Meaningful dialogue? Building trust? Before you focus on the bottom line, or other obvious questions you think about everyday, ask yourself why going offsite to get that time and space is so needed within your community.

In this case, Simon Sinek was right, it starts with why. 

  1. Your Why is Only the Framework: Build it Out

Once you have outlined your team retreat’s objective framework, every meal, breakout session, activity, and one-on-one conversation should support the why. The answer to your why is found in the design framework and it should be activated at every opportunity. 

A framework is meant to be a supporting structure, not the end all be all. Once you have answered the why questions (and there are more than one you’ll need to ask), begin to fill in all of the time slots that you have across your retreat. Keep in mind the full spectrum of how you can support your why – for example, does down time let an idea sink in, could a silly moment help people connect? Use your time strategically and keep it human! 

  1. Measure the Why: Count What Counts

Begin to think about measuring success while you are still in the design process. If you have answered the why questions then you have defined your outcomes without even knowing it. Take your why and your framework and turn it into a survey or other feedback tool that can help you track how much you are moving the marker around the key areas you want to impact. This is part of the design process, so before you ever leave the office, you should be able to see exactly what you hope to achieve. 

Defining what this new version of success looks like for you around some of these soft skills is key. At the end of the retreat, while you’re on the ground, upon your team’s return, or perhaps 4 weeks later (or even better all of the above), it is important to collect feedback, share that survey, and measure the outcome. Was the team retreat successful in your framework’s objective? What could be improved upon? Did the markers move in the directions you hoped? Know what impact you were hoping to have, your why areas, and then you can see if your team has made improvements in these key areas. 

Come back to these three steps anytime you see there is a need or an opportunity to bring people together. Your “why” can change and evolve with your company, team, and goals – fitting into this flexible and fluid framework.

If you are looking at investing in your team, outside of just payday, a corporate retreat may be something worth exploring. Over the years, we have learned a thing or two about what it takes to curate exceptional shared experiences and build community in some of the world’s most incredible destinations. If you are interested in partnering with Unsettled to design an experience for your team, or have any questions, you can learn more about us here. Get in touch!


Unsettled is a global community for those who live and work differently. 

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