As things stand, your son has no reason to change his ways. The emotional burden of the problem is being borne by you. In effect, this is your problem, not his. For him to solve the problem, it has to belong to him. You, therefore, need to take the monkey off your back and put it on his. If the monkey causes him enough discomfort and distress, he will figure out a way to tame the monkey.
On Day 1, send him to school with a folder full of daily report cards — half-sheets of paper on which you’ve printed “Bobby turned in all of his homework today, finished all of his classwork on time, and all of his work was B or better.” Underneath this goal statement are printed Yes and No and the teacher’s name beside a place for her teacher’s signature. At the end of every school day, Bobby takes the DRC to his teacher, upon which she circles either Yes or No (Make sure you emphasize to her that it’s all or nothing) and signs her name. Bobby brings the card home.
On a daily basis, at-home privileges — television, video game, outside play, having friends over and regular bedtime — require a Yes. If he loses privileges more than once through the week, they are lost on the weekend, as well. That means that on any given day, Bobby will be working for both a short-term and relatively long-term goal. Obviously, you should arrange all of this with his teacher in advance.
This is an example of what I call the Agony Principle: Adults should not agonize over anything a child does or fails to do if the child is perfectly capable of agonizing over it himself. In other words, the person who experiences the emotional consequences of a problem will be motivated to solve the problem.
If my experience in such matters holds true, Bobby will tame his monkey in a few weeks. At that point, however, for the improvement to “stick,” you and the teacher must continue to enforce the new system for at least three more months.
Family psychologist John Rosemond answers parents’ questions on his website at rosemond.com.