Thank you all for your replies. I'm writing notes to bring to my boss, our "head instructor," to help the boy.
As for riding alone, it's difficult. Our arena stays open (we keep the doors open so the horses can come in out of the weather; we lease the property and the owner has no lean-to or other structure in the pasture) and the dirt "humps" up over where the track should be (but is nowhere to be found). During the weekdays after cleaning we're exhausted and no one feels like riding because we just spent over an hour digging and chiseling away the dirt, ice, and frozen poo.
Our normal regime is to let the young kids rider first (and the older riders help them prepare their horse and mount up), then they ride for an hour or so. Then reverse process for the older riders. The reason for this being that we feel most of our younger students shouldn't be cantering, and one girl is afraid to, and we don't want to stifle our older rider's "day." On this specific day my boss decided that riders of all ages were going to ride together.
She is the kind of person who wants to see the good in everybody, we all know the type, and took the boy's word for it that he's a "great rider" because he rides our smoothest horse (a painted TWH, you can literally hardly feel the difference between his walk and canter/gallop) like a champ. She never got to see him "in action" over the summer because she was running the business on her own while her partner was out of town and ran around like a chicken with her head cut off. One of our "expert" riders turned out to have had no previous instruction and recently was thrown from her horse when he simply spooked and side-stepped. Then there's the boy, who my boss was thoroughly disappointed with.
Regardless, my boss gave him lessons over the very subject over the summer in the round pen, bareback, on Ben (our lesson horse who, outside of being stubborn and not wanting to keep his trot, does perfect). My boss made him ride bareback on Ben that day so he wouldn't have the chance to death-grip that blasted saddle horn. He rode decently for about a week after that and then, plop, right back into old habits.
The horse that he's on in the picture, Lightning, is another lesson horse. He's extremely easy to get "going" (a light tap = trot, a kick = GOGOGO!), and equally as easy to stop -- if one doesn't jerk the reins (if they do he throws his head up as high as he can).
This past riding session I rode a mare, Sugar, and showed him my posture (I did the poles so I would have less chance to think about my posture and "fake it"). He said, "So what am I doing wrong?" and I showed him at a stand-still (he wanted me to display the same posture while I was trotting/cantering, and I refused him, explaining once more how dangerous it was). He later rode the same horse and made the same mistakes as before, the same mistakes as he did over the summer.
I'm going to try (if I'm not riding as well) to take more video footage of him riding, and then take him into the "warming room" (which is the viewing room, attached to the arena) and show him the videos on my laptop and explain to him what he's doing. Would this be an effective way to do this? That way we're not embarrassing him again when it comes to someone else riding his horse, and definitely more-so than shouting out?
In addition, this boy is one of our volunteers and rides "drag," a position in the back of the trail ride where they watch the back of the guide in case something happens they don't happen to see. Thus making his position as a rider even more important because there will be times that we trot (and some horses, as we all know, trot fast or others can canter in a line full of trotting horses), and the last thing we need is someone falling off on the trail, where they are more difficult to reach.
Another oddity: He does perfectly fine on Ben. I'm thinking now that maybe he just can't match up to Lightning's rhythm to find his balance??
"Adapt or perish, now as ever, is nature's inexorable imperative." (H.G. Wells)
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