Selling Sunset Season 6: A Case Study On How Not to Host a Retreat

A show about how great venues can't compensate for poor retreat design.

Last week I co-facilitated an organizational retreat with Aslam from

Shura

- a project that left us tired and happy, glad to have blended our skills together in such a positive way. The next day, despite our plan to rest and recover through good walks and nature activities, we found ourselves spent emotionally and physically - needing time to do absolutely nothing. For me, part of that “nothing” looked like binging the latest season of the Netflix reality show Selling Sunset. Between the ridiculous clothes, over the top real estate and repetitive plot points, I reset and then spent the rest of the weekend reading outdoors and in beautiful coffee shops before we returned home.

Part of the show’s “storyline” this season revolves around a staff retreat that takes place in Palm Springs. Despite the exorbitant cost of the accommodation ($25,000-30,000 USD per night) and the time investment required to participate, little thought is given to actual design of the retreat. Afterwards those who attend seem scarred by how bad the team conflict was during their time together.

In many ways, the show is a case study of how not to hold an strategic planning or organizational retreat. And so, using examples from Selling Sunset, here are some tips to help make your next gathering a success.

1. Hire a facilitator (or two!)

   In the television show, there is a budget for accommodation, food, and leisure activities, but despite the group’s discomfort with conflict and reluctance in having team conversations, there is no external facilitator. Without a facilitator, the significant conflict between teammates quickly descends into a reality tv showrunner’s dream come true - chaos.

   For your own gathering, consider what skill sets are important for the group you have and the particular issue/purposes you have for your time together. Choose someone who can help hold and support these goals for your gathering. Through my somatic courses and the deep democracy courses offered through Waterline, recently I’ve been learning more about the importance of having a facilitator who is not neutral necessarily, but rather, is not “hooked” or deeply immeshed in the dynamic that a group may find itself shaped by. Having an external facilitator can help surface patterns and rhythms that emerge and help your group work with what is in the room.

   There is no single overarching equity lens that any one person holds. Having multiple facilitators, especially in an overnight retreat creates a more supportive and resourced environment.

2. Be clear on your purpose

   Have a purpose for your gathering and ensure that that purpose is jointly understood by your team. Where do you specifically want to be at the end of your time together? Do you want to for example, set goals, strengthen your team, plan strategy, reach decisions, or share organizational learnings? All of these are different purposes, and require a different kind of design. In the Selling Sunset retreat for example, beyond “having a girls trip” the purpose of the retreat is unclear. There is no (visible) preparatory work or clear intentions/outcomes set at the outset, and the gathering suffers as a result.

3. Have an agenda in service of that purpose

   A new environment and beautiful surroundings can help you and your team to access a different way of being, but it cannot do everything. A well-crafted agenda with a good opening and closing that considers trust and risk required to participate and has sessions that build upon one another is needed to realize your goals. Do you have low trust in your group? You’ll want to spend time crafting team agreements that make it safer to share and surface fears within your team. Do you need time to better understand one another’s point of view, or create a deeper sense of teamwork? Unstructured and structured time for participants to have focused and open conversations can help them connect in new ways.

4. Create containers for the conversations you need to have

   

   In Selling Sunset, there is team conflict, poor/nonexistent HR policies, and frustration between staff and leadership. To counteract that, the only work-related activity on the retreat is a suggestion box mentioned a couple of times before being placed in a corner of a room. During one group meal, without framing the activity or giving instructions about how feedback will be addressed, suggestions are read out. Without adequate framing, participants are defensive and the evening quickly disintegrates. To have difficult conversations, a retreat or meeting must have a process to move through the emotions and defensiveness that hearing challenging feedback can elicit.

5. Be flexible and open to emergent re-design

When things aren’t working, be open to moving away from the agenda and trying something new to get to the desired outcomes. This may mean redesigning your agenda in the moment, and prioritizing emergent conversations that are related to the broader goals. If there is resistance in the group to the intended activities, pause, and ask where that resistance is originates, and the wisdom it might hold.

6. Incorporate somatic practices

Our bodies and minds are connected, they are one. Within a retreat, plan for activities that allow participants to practice new ways of being rather than simply talking about new ways of being. These activities might include (though are not limited to) any practice that allows one to expand their capacity to live their values. Practices such as grounding, centering, regulating, reflecting and meditating can all be useful to incorporate within your workshop and retreat design.

What are your recommendations for designing a team retreat? I’d love to hear from you.

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