I have a student who is serious about getting into advertising – he has a degree but would go back to school to study if need be. What kind of trainings should he look for, or in what area of advertising is it easiest to break into?
If your student wants to break into the creative side of advertising, tell him that he should go to a "portfolio school." He'll be able to refine his creative skills and leave with a "book" that will be his resume to get a creative job at an advertising agency or at an in-house advertising department.
If he wants to break into account management or media, then I would suggest he start in advertising sales. Tell him to start at a newspaper or radio station, or anywhere selling advertisements. Eventually he is going to make contacts that will get him into an advertising agency if he wants to, or maybe he'd like staying in sales.
Wish him good luck for me!