"The Breakdown" gets a new boss, Diana St. Tropez, a tough business lady with big plans to bring their outdated news program into the 21st century. Katie is thrilled since this is exactly the kind of strong, professional female role model she hoped for, but Carol is immediately wary of this new influence in Katie's life. Meanwhile, Chuck has trouble adapting to Diana's idea for a new panel segment of screaming pundits.

Diana sets Katie off on a mission to take the job at the station that she wants, but when Katie tries to be executive producer for the day, she soon realizes that Greg has it much harder than she realized. Meanwhile, Carol uses Greg and Katie's workplace competition as an opportunity to push the two of them together. After Diana insults Portia on a women-in-business panel, Portia declares a "squad feud" that forces their two very different worlds together.

Diana has been promoted again, this time to the head of the corporation that owns MMN, but before she leaves she finds herself embroiled in a sexual harassment scandal. This leaves Katie unsure who to believe - her mentor or her friends in the office. Carol becomes head intern and struggles to prove to the other interns, and herself, that she deserves the job.

When "The Breakdown" staff finds themselves embroiled in a lawsuit with eccentric billionaire Fenton Pelt, Chuck is convinced he can solve the problem. But when Chuck's attempts to save the show backfire, he enlists the gang's help to pull off an elaborate heist. Meanwhile, after realizing that she has feelings for Greg, Katie is determined not to make a move on her unavailable boss. Her intentions are put to the test, however, when Diana St. Tropez demands that the two spend the night together fact-checking a story.

Diana St. Tropez returns with good news for "The Breakdown" staff: Fenton Pelt has agreed to drop his lawsuit on the condition that Chuck Pierce deliver a humiliating on-air apology and resign from news forever. Chuck, defeated, agrees, until Portia reminds him why he got into journalism in the first place. With Chuck's final broadcast approaching, Katie convinces Carol to reunite for one last job, and they race against the clock to find the one person in New Jersey who could disprove Fenton Pelt's claims and save the show.