W.O.W., if you never expected him to be responsible before then you can’t start with teaching him responsibility towards the entire family and household before you teach him responsibility for his own daled amos first. So it brings us back to the same original theory. He is now sixteen years old, the oldest child in the family and it is time that he learned to be responsible for himself. So start with his own room, his own clothes, etc. Have him help in regard to taking care of himself first. Then you should try and ask him to clean up after himself in the kitchen. You can only expect of him what he is capable of doing. Expecting more is a futile effort. So choose something you know he can do and then show appreciation and encouragement. Don’t be snide like “you see you could do it if you only try”. Try to be more encouraging like “I appreciate your cooperation”.
In coaching we prefer to drop the word “proud” because pride is a need that we need fulfilled and it is not necessarily a feeling that reflects the needs of the subject of the actions. So we try to use more positive words such as “respect, appreciate and admire”. Those words are received much more warmly and openly. Kids want to be respected, appreciated and admired. When they are in this matzav they don’t necessarily care if you are proud of them.