As soon as I started driving the longer Green Tortoise trips I found that they company had it's own version of the icebreaker that was very effective and fit in perfectly with the trip as a whole. It was summed up in what the owner of the company used to reverentially call "Rule #1 of Green Tortoise Trip Leadership":
Get people naked together in water
As I drove a few trips I noticed that those that started with a skinny dip always seemed to go better. Getting onto the bus after the swim stop you could feel that the energy of the group had changed and it was clear that this experience had a unique way of overcoming the initial shyness about meeting the other folks on the bus. There was a sense that the group had bonded through doing something together. From then on there was a feeling that this was a group, which made all aspects of living on the bus, traveling to new places, cooking food together, etc. much easier and more fun for everyone.
In retrospect, I realized that there were two key factors to this activity: trust and shared experience.
Entering a new group setting there is a natural human fear of rejection that comes up. As a group, human beings want to be accepted by groups of other human beings. When you are suddenly thrown in with a group of strangers there is a natural reaction to close yourself off to some extent until you build some trust with these new people and bond with the group.
Getting people naked in water accelerates that process. There are many levels of human experience, the physical being the most tangible. A group skinny dip removes the physical barriers and defenses that we all have and allows others to see us as we really are and we see the others as they really are. Once that's out of the way, exposing your thoughts or baring your soul suddenly seems much easier (after all, this group of people has already seen you naked).
Creating a Shared Experience
All people are 99.9% the same, but we expend a tremendous amount of energy categorizing the .1% in which we're different. If a new group can have a shared experience right off the bat, then they can start seeing the commonalities between each other more quickly. The fact that skinny dipping is a little outside the norm for most folks only makes the experience that much stronger and sets the tone for the rest of the trip being something out of the ordinary.
Trusting Your Leaders
I always had at least one passenger come up to me after skinny dipping and say, "I've never done that before". Through creating an environment where people can step outside their normal comfort zone and experience something new, the leader also earns the trust of the people he or she is leading. If successive experience continues to reinforce the leader's trustworthiness, then the job of getting the group to do things gets much easier and the group is able to work together more effectively.
Trust is the foundation to any high-functioning team.
Skinny Dipping in the Corporate Pool?
It should go without saying that skinny dipping is an activity that I would NOT try to transplant into a corporate environment, but I see the same dynamic at work in any good 'ice breaker' exercise. While going around a conference table and telling one funny fact about yourself is not going to have the same impact as a night swim, it is working on the same principle that a group activity that builds trust and acceptance will help a group of people who don't know each other become a more well-integrated team. One of the best activities for a group to build shared experience is going someplace outside of work together. It doesn't take a lot of time or money, but if it gives the members of the team a touch point of experience to refer back to they now have a much stronger foundation of experience to build upon in their work relationships (without running afoul of HR).