Got questions about life? Love? Parenting? Work? Today we introduce Whit’s End, a new advice column by local husband, father, teacher, coach, former executive and former Marine Corps officer Al Whitaker.  Each week Al will address readers’ questions about anything ranging from school issues, coaching problems, relationship quandaries and more!  His experience is vast, and he holds a degree in psychology, too. To submit a question, email [email protected]. – The Eds.

My son will be entering the 9^th grade at an excellent independent school. He is a good student, but does not always assert himself.  For example, he will not tell his teacher if the homework took him two hours when he was told that it should take an hour.  If he is having a difficult time with an assignment, he won’t ask for help or tell the teacher that he needed extra time.

Since I know what he is like, how much should I help him?  If I monitor whether he is working or on-line, he tells me to stop treating him like a criminal.  If I know that he is weak in certain areas or doesn’t check his work carefully, shouldn’t I offer to look it over first? Isn’t my job to see that he gets the most out of his school experience and does as well as possible?

Also, how often should I communicate with his teachers? Would asking for a weekly report from his teachers be reasonable? I’d like to make sure sooner rather than later that he doesn’t get behind or unnecessarily struggle at a school that has a reputation for being rigorous academically.

I just feel if I don’t get involved, something will go wrong, and he will miss a valuable opportunity.

Concerned Mom in Baltimore

Dear Concerned Mom:

Knowing how much to help is a tricky balancing-act for both of you.  You don’t want him to slip, especially without a safety net. But the only way for him to gain confidence is to believe that he doesn’t need the net, even though you know that people are there to “spot” or catch him if he does fall. However, you should not be one of those catchers.