"When did you start college?"
Translation:¿Cuándo empezaste la universidad?
Is there a problem with the translation: Cuándo comenzó usted a el colegio
"Colegio" means grade school, not college. "College," (at least in the American sense) translates as "universidad." You do not use the preposition "a" after comenzar, unless you are adding another verb: "¿Cuándo comenzó usted a ir a la universidad?" or "¿Cuándo comenzó usted la universidad?" Use of "usted" is correct, but if you are talking to a college student, you are far more likely to use "tú."