How to Run a Leadership Team Retreat

How to Run a Leadership Team Retreat


Team Building gets a bad rap.

I have never been a fan of “fun” team building activities. Cooking a meal together or playing whirlyball are enjoyable activities, but I rarely leave feeling that I know the values or principles or characters of my teammates any better. We have fun but we don’t bond at any kind of deeper level. It feels superficial. I seldom feel we function better as a team as a result of the time we took together.

It doesn’t have to be this way.

Team building comes from gaining a deeper understanding and appreciation for each other. Team building comes from a stronger connection and commitment to a shared purpose. Team building comes from developing and practicing better ways of working together.

This can include having fun, and playing together. But it shouldn’t be limited to games.

I was recently asked to design and facilitate a leadership retreat for the top ten executives of a 3,000 person organization. Here is how we used the time:


Preparing the venue:

  • Be thoughtful about the location. My preference is for natural light, quiet, surrounded by trees and water, spacious and uncluttered
  • Have materials on hand – agendas, paper, pens, markers, handouts
  • Have snacks and drinks available

Send out information about the retreat a couple of weeks in advance, so that people know what to expect.

  • Objectives: in our case, it was to deepen relationships, purpose and teamwork. The agenda was easy to develop once this was clear
  • Pre-read: we chose Bob Quinn’s fantastic Harvard Business Review article, “Creating a Purpose-Driven Organization”
  • Reflection Questions: we shared the “3-5 life experiences” question below, so that people could make themselves vulnerable on their own terms
  • Logistics: where to be and when. What to bring. All in one place.

Sample Agenda

  1. Opening. Comments by the leader: he shared his appreciation for the work everyone is doing; shared his hopes for the day
  2. Introductions if needed. In my case, the leader introduced me. I shared the agenda; shared important logistics – breaks, food, bathrooms etc
  3. Celebrations. I invited everyone to share one thing that is going well, personally or professionally. This primed the session to begin with positive emotions and gratitude.
  4. Jeffersonian-style Discussion. We chose this prompt:”What are the 3-5 experiences that most shaped who you are today?” Each person is given up to 10 uninterrupted minutes to share their story. After each person goes, the group can respond to affirm the person by questions or comments. Nobody is allowed to co-opt the other person’s story for him or herself though! When was the last time you spoke to a small group, uninterrupted, for ten minutes? Yet you could have heard a pin drop the entire time. Previously-untold stories set the tone for the day.
  5. Lunch. Get outside and go for a walk! Fresh airand sunshine keeps the energy going.
  6. Connect to Purpose. I facilitated a discussion on this topic: “How are peoples’ lives different because we exist?”
  7. Action Planning. “In pursuing our purpose, what decisions would be most effectively taken as a team? And what would be done more effectively as individual units? What implications does this have for how we spend our time together as a leadership team?”
  8. Closing. The leader shared reflections and appreciations with the group for contributions made. He invited others to share appreciations and reflections as they saw fit. Everyone spoke, with the same reverence for each other and depth that we began the day.

The conversation over dinner was so much deeper and richer as a result of the conversations that day. People saw the humanity in each other, and held a deeper appreciation for what each person was bringing to the table. I know that the team members will never be able to see each other the same way again.

To some people, this might sound boring. To others it might sound scary; making ourselves vulnerable to each other feels risky! After all, we have to see these people in the office tomorrow! That is okay. Deeper team building is not everyone’s cup of tea. But taking the risk to go beyond games is worth the journey.



1 thought on “How to Run a Leadership Team Retreat”

  1. Wow, thanks for sharing a sample agenda–it’s clear how the positivity within a group would grow with each activity! I love #3 and #4 in particular and will have to try them. I also agree with choosing a setting with plenty of natural lighting; I find that it helps the group to stay engaged and open to new ideas.

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