At the Krusty Krab, Mr. Krabs is holding a meeting, saying that Pearl is going to be working at the Krusty Krab during her Summer vacation and that she has lots of new ideas to help improve profits for the restaurant. Pearl immediately arrives, and Mr. Krabs comes out of the office to greet her. Squidward does not like the idea of being told what to do by a teenager, and he and SpongeBob agree to stand up to her to protect their jobs, but SpongeBob quickly falls through on this, and loves the flamboyant new uniform that Pearl gives them. After exchanging many ideas, Pearl and SpongeBob agree to turn the Krusty Krab into the "Kuddly Krab", and from a restaurant into a teen hangout cafe.
The Kuddly Krab quickly becomes a hit, but when SpongeBob is told to make a salad, which he has never heard of, he makes a Krabby Patty and shows it to Pearl. She tells him to take off the buns and the patty, leaving only tomatoes and lettuce. Upon returning to the kitchen, SpongeBob is horrified to see that his stove is gone. Pearl explains to him that Krabby Patties are no longer "hip", and that they now serve only tea and salad. She then gives Squidward the new job of wearing the mascot costume outside, which he rips his costumes off leaving him naked, while two spouses on a car surprised and a police officer making a note and putting it on Squidward as a loincloth.
SpongeBob goes into Mr. Krabs' office to complain, and Mr. Krabs admits that they are indeed causing the restaurant to lose money. He says that Pearl has to be fired, but cannot bring himself to fire his own daughter, and asks SpongeBob to fire her. ("It's okay if she hates you!") When SpongeBob calls Pearl into the kitchen to fire her, Pearl begins to weep, and explains to him that she was only pretending to like her job and has been trying to get fired from the beginning. However, she cannot let her father know this, and she and SpongeBob stage her being fired. Mr. Krabs hears this from his office & keeps having a fight with himself on whether to go with it or stop SpongeBob, and has a heart attack upon hearing Pearl being fired after shouting at SpongeBob to get on with it because of his empty safe. Pearl then kisses SpongeBob, after Pearl drives off with her friends to the mall, SpongeBob enters his office to report his success, and sees Mr. Krabs in a coma on the floor. He revives him with a twenty dollar bill, and convinces him that his daughter is happy with her life outside of the family business. However, Mr. Krabs does not know how to get his money back for the Kuddly Krab's decorations, and SpongeBob buys it all for one year's salary.
This episode was originally called "Working Pearl," but was later changed to "Bossy Boots." Comcast still lists it as "Working Pearl" to this day, and DirecTV originally used this title, too, but it was soon changed to its current title. During Nickelodeon's Best Day Ever marathon, it was referred to as "Working Pearl" by Patchy the Pirate.
This is the second episode with the word "Boots" in the title. The first is "Squeaky Boots."
Because of this, many fans would actually get the plot of these episodes mixed up thinking one is the other.
Quite coincidentally, both of these episodes feature Mr. Krabs, SpongeBob, and Pearl as the main characters.
The ideas Pearl and SpongeBob come up for the new Krusty Krab are:
The Kutie Krab
The Kooky Krab
The Khaotic Krab
The Kissy Krab
The King Krab
The Kandy Krab
The Kool Krab
The Kowboy Krab
The Kurly Krab
The Kreepy Krab
The Killer Krab (Pearl got scared by this one)
The Kuddly Krab (they used this one)
In this episode, all-caps closed-captioning ceased until "Best Day Ever" when they went back to all-caps closed-captioning. However, every episode from "Help Wanted" to this one had text in explanation brackets in non-caps to make it stand out, and then, as of "Best Day Ever", the text in explanation brackets are in all-caps. These days, when it comes to closed-captioning on "SpongeBob," the closed-captions don't put text in explanation brackets in all-caps to make it stand out.
This is the first time SpongeBob's grill is removed. The second time is in "Krusty Dogs." Pearl did it this time, Mr. Krabs did it in "Krusty Dogs."
The first and last times SpongeBob says "salad", he says it correctly, but then the rest of the times he says it incorrectly.
In Polish version, this episode called Nowa szefowa which means A New Manageress.
When SpongeBob and Squidward are in Mr. Krabs' office his door has a porthole window, but when Mr. Krabs leaves and Squidward and SpongeBob are shaking hands, the porthole is gone and there's a life ring instead.
When Squidward is outside after SpongeBob and Pearl go inside, a car seen beside Krusty Krab. But when Squidward shakes The Kuddly Krab sign, the car disappears.
When SpongeBob walks into the kitchen to fire Pearl, on a close-up on his face, he's missing his K's on his uniform.
In the closed captioning, "Krabby Patty " is written "Crabby Patty."
When SpongeBob bumps into Pearl, her eyes are black instead of blue.
SpongeBob's sleeves are gone during one shot of the new menu.
The K's on Mr. Krabs new uniform were rounded, but when it zooms in to the scene of Mr. Krabs lying on the floor, the K's are completely straight.
Fred's voice sounds a lot older than other episodes.
In one of the final shots, SpongeBob's house is shown, but Squidward's house is nowhere to be seen.
When Pearl says "SpongeBob, order up!", captions simply say "Order up!."
When SpongeBob is in Mr. Krabs' office SpongeBob says, "Sure Mr. Krabs, but I've got some bad news," but the closed captions simply say, "I've got some bad news."