Several years ago I did an outdoor leadership course with the Appalachian Mountain Club. This is a great program with ongoing instruction and practice periodically over several years. The main skill to be learned is that of promoting an environment where individuals in a group activity develop a commitment to the success of the group. This is easier said than done but the skills can be learned with guidance from an experienced group leader. I found it interesting to observe so called leaders I would encounter in everyday life, particularly political or business leaders. Your outing with friends and family will likely be a memorable experience and you are thinking ahead to options. In mountain travel, a leader would have a bailout option in the event of an emergency or adverse weather overtaking the party. Post pics of happy and smiling cyclists.