Dan Foreman (DENNIS QUAID) is a content, 51-year-old head of sales for the weekly magazine, "Sports America" who runs a staff of equally content employees, including Morty Wexler (DAVID PAYMER). Things are about to change in various unexpected ways for Dan, however, in both his personal and professional lives. It seems that corporate giant Globecom -- run by the energetic if enigmatic Teddy K (MALCOLM McDOWELL) -- has just bought Sports America's parent company.
Accordingly, one of its executives has decided that the perfect person for Dan's job would be up and coming whiz kid Carter Duryea (TOPHER GRACE), not worrying that the 26-year-old has no prior experience in ad sales. Things would seem to be great for Carter, but his wife of less than a year, Kimberly (SELMA BLAIR), isn't happy and leaves him, and none of his new employees, including Dan, particularly like him.
The situation is worse for the veteran who's just been kicked out of his office. Not only has his oldest daughter, Alex (SCARLETT JOHANSSON), just moved out to go to an expensive college in the city, but also his wife, Ann (MARG HELGENBERGER), is unexpectedly pregnant. Thus, he has to swallow his pride and accept the change at work since he needs the money. As the two men try to work around their differences, their tenuous relationship is threatened when Carter starts secretly seeing Alex on the side, hoping that his much older subordinate doesn't discover he's dating his daughter.