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How To Design A Retreat Your Team Will Love

This article was based on episode 149 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify, iHeart Radio, Amazon, and Stitcher. Get the guide to planning a team retreat when you become a member at Purchase any full episode guide at

Now that COVID vaccinations are widely available across America and we are entering warmer months with greater possibility for outdoor activities, it’s a good time to consider bringing your team together to reconnect on both personal and work fronts. Team retreats vary widely in activity, length, and location. I’ve participated in team retreats that have totally blown me away and ones that felt like a complete energy drain.

I checked in with Seth Linden, founder and principal of Gather Consulting, to learn how he thinks about designing a successful retreat. An advisor for philanthropists, foundations, and nonprofits at the intersections of education, leadership, and community, Seth understands the importance of creating retreats that are mutually beneficial and allow everyone’s voice to be heard. Here, he shares the process of what to do before, during, and after a retreat to create an experience your team will cherish.


Decide on the Purpose

Citing Priya Parker’s book The Art Of Gathering (which I was so honored to be quoted in!), Seth insists that the most important thing to designing your retreat is to clarify its purpose. This way, you can ensure that everything you plan aligns with that purpose.

Co-Create the Agenda

The agenda should not be created only by those running it. Engage your team members in a collaborative process so they take ownership over the retreat as well. Brainstorm with your team prior to setting the agenda to better understand what they want to learn and what they want out of the retreat.

Think About the Environment

Subtle changes in the environment can have such a dramatic effect on how comfortable people feel letting their guard down. Think about specifying a “dress-down” dress code as people tend to feel and share differently in t-shirts than suits. Outdoor environments can create a lightness in mood and help people think more expansively. A lounge can foster a relaxed atmosphere ideal for creative thinking and relationship building while a boardroom may signal a seriousness to the conversation or work to be done.

Build in Body Time

Whether you are gathering in person or virtually, we need to move our bodies and take care of our physical needs. Include multiple breaks, stretches, and even walking conversations in the agenda design to help keep people’s attention focused and energy high throughout the retreat.

Plan for Goodies

Although I tend to decline gift bags of any sort, most people enjoy receiving these small gifts. The items you choose should relate to the retreat in some way or be (almost) universally loved, like chocolate, notebooks or tea. Consider also including something fun or playful that will enhance the retreat experience. For virtual retreats, this may be a “thumbs up” paddle to raise when you agree with a speaker.


Create Safe Spaces

Once the retreat has begun, the most important thing is to set the tone and intentions right from the beginning. Make sure to explicitly state that the retreat as a safe space where everyone can share authentically. As the leader, you can encourage vulnerability by role modeling. Act bravely by saying when you aren’t sure of an answer and acknowledging when you’re uncomfortable but staying in the conversation regardless.

Make Room for Everyone

Make sure there’s an equity of voice by setting that value from the onset. Acknowledge the desire to address the inequity that often impacts the opportunities for marginalized voices like women and people of color. This can gently remind those who tend to talk a lot to consciously hold back in order to give quieter people a chance to speak up.

Connect Through Ice Breakers and Ropes Courses

There are many ways to help people connect and build deeper relationships. In addition to more traditional ice breaker questions, you can ask more explorative questions like “What does humility mean to you?” or “Tell us about a time when you did something new that was meaningful or impactful to you.”

There’s no formula for whether or not to include activities like ropes courses or karaoke in a retreat. Go back to your purpose, talk with your team, and take the pulse of the group. Be sensitive to the capabilities, desires, and appropriateness of these types of activities for your particular set of people. Talking with your team will help you decide on the right type of “fun.”


Bring the Work Forward

In order to bring the lessons, decisions, and next steps from the retreat back into normal life, clarify what each person wants to carry forward. Set up accountability partners so that your participants can check in with each other and continue the conversation in a more formal way.


After a long year of being isolated from our colleagues, many of us are itching for opportunities to reconnect in person. Although it may still be a while until we are able to fully engage without any restrictions, now is an ideal time to begin planning a team retreat.

Whether you are able to gather in person or online (due to COVID or a geographically dispersed team), you can design a meaningful retreat that inspires and connects your team members. And we could all use a little bit of inspiration and connection.


Get my guide to planning a team retreat when you become a member of the Modern Manager community at Or, purchase an individual episode guide at to help you implement the learnings and continue to enhance your rockstar manager skills.

This article was based on episode 149 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify, iHeart Radio, Amazon, and Stitcher. Never miss a worksheet, episode or article: subscribe to Mamie’s newsletter.




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