We have a weekly ride, and we try to find out ahead of time if someone is new and doesn't know the route. In that case, we make sure someone's looking out for them. We typically split into two groups, but again, make sure someone's in the back group who knows the route. Lately, we've had a few folks coming back from injuries, so they've volunteered to lead the 'Z' group, so anyone who wants to come and try the ride to see if they can keep up will know there's a slower group coming up behind. When some women wanted to move up from the Z group to the main group, we made sure we had a sweep willing to ride with them. Our biggest problem was finding someone willing to ride sweep.
For 3 days, I get to part of a thousand other journeys.