Is this new umpire eventually going to be doing games as a single umpire or do you usually have a two person crew?
If he is going to be doing games as a single umpire, then start out the pre-game by letting everyone know you are there to observe and only to correct any obvious rules misinterpretations (not judgement calls). This way you can focus more on his mechanics, positioning, and calls; and not the game itself.
If you are usually doing a two person crew, then you are stuck having to really pay attention to the game and not your partner. You don't want to be mentoring him in the wrong way to do things. I guess the best you can do is watch him when your attention doesn't need to be focused elsewhere. The only alernative there is to see if you can find a fellow umpire to actually watch your partner from outside the field. Maybe you know one who is playing on one of the teams you are umpiring and can give an honest evaluation or can come watch when they don't have a game.
This is often a short coming of SP is that no one mentors new umpires on mechanics and positioning. They are just basically given assignments in lower leagues and told to go call the game. No amount of rule reading and clinics can truly prepare you for the actual game. I think it is great that you and/or your association provides this for new umpires. When I first started there were a few umpires who either played on teams I umpired or would come over from their field between games and offer helpful hints. Our association didn't have a mentoring program, but all our umpires were willing to take time to help. Since most of them played also, they probably figured it was in their best interest to have competent umpires doing their games.
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