Yess Boss is the story of Rahul (Shah Rukh Khan), a young man with ambitions to be rich and successful. Rahul works for an advertisement agency and does everything including covering up for his married, playboy Boss (Aditya Pancholi), so that one day his Boss will grant him his dream to run his own Ad agency. Rahul meets a young middle class girl Seema (Juhi Chawla) with aspiration to be a top model and like Rahul dreams to be rich and famous.

Trouble arises when the Boss after seeing Seema at a fashion show asks Rahul to set him up with Seema so that he can take advantage of her like many other models in the past. Rahul must choose between his love for Seema and dreams to be rich. Will he go along playing a stooge with his 'Yes Boss' salute and sacrifice his friendship, ideals, and true love?