A BBT practical advice classic.
Here’s an excerpt:
Right Level of Learning
It is important to choose a school which is a close fit to your son’s level of learning. Boys’ yeshiva high schools, with the exception of a community school, tend to be narrowly tailored to a specific level of learning. It is important to consider schools where your son will be challenged, but not so much that he will feel frustrated or be on the bottom of the class and struggling to keep up, nor too little that he will feel bored too soon or where it would be difficult for him to find a chavrusa of similar skill. Larger yeshiva high schools might have more than one class/shiur, with the different classes tracked. It is important to determine if there are different kinds of boys in one track vs. the other and which group your son is most likely to be part of.
How to determine what learning level a school is on can sometimes be a challenge. Yeshivas, like other schools, like to strengthen their reputation to prospective families, and sometimes schools will declare, at an open house or elsewhere, that they serve “the best boys” or have a “top program.” It is important not to be naïve and take everything a yeshiva says about itself at face value. That is, it is important to go beyond these statements and find out what the learning level of the boys who are currently there really is to determine if it is a good match. [Similarly, if a school brags about its graduates who go on to the Ivy League, try to find out if they are bragging about one or two unusual boys, or whether it is typical for its graduates to go on to the Ivy League.]
I would hesitate to send a boy to a “top” school if his grades in learning don’t match up or if he is unmotivated. Some rabbanim recommend that a boy go to a “better” school rather than one with a lesser reputation if a boy is borderline in his learning abilities, because, if things don’t work out initially, it is easier to transfer from a better school to a lesser school than visa versa. I would say this should only be followed where the boy is very motivated and is the type to put in the extra effort he will need to maintain a fair position in the class, and if you as parents are willing and able to pay for tutoring if he needs it. It does him no favors to languish at the very bottom of the class at a “better” school rather than thrive at a more modest school (unless there are other factors present that would counterbalance this possible sense of failure and lack of accomplishment).
Read the whole thing.