T rail Boss:
Before the ride the trail boss should set out what will be accepted throughout the ride, what passing habits they want used and where it may not be advisable, if there are areas that require single line riding, where they may want you to let a rider clear a traverse before you proceed etc.
The reason for the trail boss is obvious but we will explain it anyway. This is the person who is in charge. They are responsible for the path/route that is ridden, for the speed of the ride, as well as the safety and welfare of the horses and riders. On designated routes he/she should be the one that knows the route well (others should as well but that isn’t always the case.). On free form rides (choosing the route as you ride) they should at least know the area well. They are also the one that should make the inspection of the horses and tack, for one, to make sure both are adequate and another, to allow him/her to judge the capabilities of horse and rider...Likewise they can at this time, check for any possible special concerns such as studs, mares in season, etc.
The trail boss should also determine if any equipment is needed by each rider as well as by the group, and who should carry it. At the start of the ride the trail boss should notify riders of the plan of the ride such as length of time needed (which is approximated and judged by the abilities of the group), the expected distance the group will travel, and the skill required for the ride. Each of these factors may be altered. For instance, if time is the main factor then distance may change. If the distance is the criteria (such as an established route), then time estimates may change. If the skill level is higher or lower than they planned on then the route itself may change. This can also happen on route as the trail boss reevaluates the group. It is also his/her responsibility to see that everyone is kept safe (as within his/her means and allowing for circumstances.) As such if there is an unfortunate incident it is up to the trail boss to make the call on how to proceed.
In the event of someone wanting to or having to leave the group and “short cut” back to the staging area, it is their call on whether a designated rider(s) accompany them or whether the group cuts their ride. The trail boss should be able to adapt to changes in the trail as well as noticing changes in the terrain or surroundings that could affect the group. There should be a level of confidence and trust in the trail boss, as once you are on the trail you should depend on him/her in most cases. They should also have the willingness to listen to drag riders, outriders, and even free riders in aspects of safety or comfort issues. If any rider should feel comfortable approaching the trail boss with concerns or questions, it must be accepted that the trail boss has the final say while on the trail.
The trail boss should also realize that the trail ride will travel at the speed of the slowest rider and fit the abilities of the least able rider. He can, of course, offer alternative (escorted) detours such as a route around a hill that is too steep for some, or a crossing to deep etc. The better planned detours will lessen the time of separation as well as waiting time for one party to rejoin the other.
The trail boss may, of course, decide to make another group from the free riders that better suit their abilities, (such as have a group that is faster ride ahead.) At this time the trail boss should, from his ranks, designate a sub-trail boss and drag. If needing to draw on free riders for this purpose, the new designated positions should be chosen on ability and trust instead of familiarity or friendship. If larger separations occur (out of sight for extended periods) then an interim rider should be chosen as a go between groups if no other communication (radios etc.) is available. They may need to separate an unruly horse from the group of position (off to the side, or near the back etc.). They should be aware of where his riders are (both assigned and free riders) and their general condition.