Team Retreat Planning: The 7 Most Overlooked Elements
Planning a retreat or offsite?
Use these seven guiding principles to design an impactful experience.
“This offsite meeting needs help!”
That was the message I got from a friend asking me to design and facilitate their upcoming retreat. On paper, they looked like a successful team. But like most, they operated in silos and had communication breakdowns. Each leader was focused on their respective part of the business. They were a group of leaders on the same team, but they weren’t teaming.
I met with the CEO, Jaime, to discuss the offsite and he handed me an agenda. “I’ve planned out our time together and what we need to focus on.” It was two days packed with operational updates, reviewing financials, and workstream summaries. It was no different than their biweekly meetings. There was no space for discussion of new ideas or debate to work through problems. The whole meeting was a list of agenda items that could be given as a preread.
I started asking Jaime questions about the team and its dynamic. He shared the tensions across different workstreams because the leaders weren’t communicating or collaborating. We listed out the challenges the team was facing and defined the ideal outcome of the time together. As we worked through the list, it became clear: they needed empathy and understanding of one another, not updates on financials and operations.
I find most teams are like Jaime’s…in need of a different type of offsite discussion. These meetings are a big investment of time and energy. They shouldn’t be treated like every other meeting. Leaders often make the mistake of packing agendas with financial reviews and workstream updates in a series of droning updates. These are important but can be done in advance.
Here are seven guiding principles to use when planning your next retreat:
Use the time for things you can only do in person
Updates and summaries should be sent in advance as a preread to save time for discussions and working sessions. The time should be spent differently than your standing meetings, otherwise, why are you coming together in person? Choose topics that allow people to work on the biggest challenge the team faces or where it is headed.
Leave more space for conversation than you think
Don’t try to pack the agenda with too many items. Leave space for reflection, discussion, and even constructive challenge and disagreement. Provide some questions to prompt reflection. Seek divergent thinking before convergent. The tendency is to push through disagreements and work toward agreement or consensus. That promotes groupthink and excludes different perspectives. Structure discussions so each person can share their perspective before discussions and debates ensue.
Lean into storytelling
Don’t expect people to jump right into the hardest conversations. Use thoughtful icebreakers that include storytelling to learn more about one another, gain empathy, and form a comfort level and trust. The benefit of being in person gives the team the chance to get to know each other differently. As they share professional and personal experiences, oxytocin is released, and they feel more trust, understanding, and compassion toward one another. Give the team different prompts to learn about each other’s professional and personal experiences and what they’ve learned from them.
Plan many breaks
The rich dialogue will come in the moments before and after sessions or on breaks. Discussions over coffee or on walks, and over meals will help team members learn more about each other. These moments create the foundation for building empathy and trust with one another.
Focus on Meaning
Research on introverts indicates that they experience an energy drain when a conversation or activity isn’t meaningful. Many would rather forgo small talk because it feels meaningless and insincere. Their brains prefer to dive deep. Agenda items should be meaningful and productive.
Paired Conversations
Identify people that have tension to work through or need to work together better and pair them up for a conversation. Dedicate a good thirty minutes for people to pair off and reflect on what is going well and what they could do differently. This often works best as the last item before dinner. Every time I plan these conversations, there is always a breakthrough in understanding and working together.
Closeout Hearing From Everyone
Peak-end rule refers to how we reflect on an experience based on the way it ends. The way the meeting ends impacts the way participants view the experience. To help everyone close out on a positive and satisfied note, leave time to hear from each person. I love using the prompt from Stanford: “I like, I wish, I wonder.” Each person takes a turn sharing “What I like about this team…,” What I wish for this team…,” and “What I wonder if this team will do…” It’s a chance for everyone to firm up commitments with each other and end in a meaningful way.
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