Secretary of Evil

On the other hand, the dental benefits are great.

"I'll just go ahead and pencil you in for a 10 o'clock brainwashing."

— Nastasia, Super Paper Mario

Big Bads are great at concocting elaborate, evil schemes, but their grand ideas don't often address the finer details, like how the Mooks are actually going to get to the MacGuffin and do so without starving. Enter the Secretary of Evil. She (and very likely a she due to expectations of women as supporters and not leaders) is the one that ensures there are No Delays for the Wicked, solves any logistics problems, and maybe even sorts the Sorting Algorithm of Evil.

The Secretary of Evil tends to be portrayed as The Spock, serving the will of their employer absolutely, focused entirely on the job at hand, and without any regard for the atrocities being committed. This is especially likely if the boss is stupidly evil, in order to explain how anything gets done.

Expect to see one of these in a proper Evil, Inc., unless it is headed by a Diabolical Mastermind, who does their own planning. Often The Dragon or equivalent to one within the organization; however, they tend to remain in the background and not be confronted directly, sometimes falling into The Unfought. On the other hand, an inattentive boss that leaves all the real work to the Secretary puts them in a prime position to pull all the strings and become the real villain. She may also be an Ignored Enamored Underling.

The Good Counterpart to this trope is Girl Friday. However, despite intelligence superiority being a crucial part of real-life warfare, it's rare for both heroes and villains in a fictional setting to have this type of character.

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Examples:

Anime & Manga

• Juliet Douglas in Fullmetal Alchemist (2003) is the Homunculus Sloth, who disguises herself as the secretary of Fuhrer King Bradley's, who is also secretly a Homunculus.
• The Criasu Corporation in HuGtto! Pretty Cure being a case of Evil, Inc., has Listol as the secretary to Kurai.
• Matori in Pokémon: The Series takes care of Team Rocket's background works and monitors if the bumbling Trio is doing anything productive, and was only known as "Giovanni's secretary" in the English dub for 347 episodes, long after her name in Japan was revealed. Though from Sun and Moon forward she also doubles as Mook Lieutenant.
• Precarious Woman Executive Miss Black General: Secretary is pretty much the only competent member of Group RX, as their nominal leader has a severe case of Chuunibyou (even though he actually does have Psychic Powers). She also has a crush on her boss and can cause explosions, and getting her to slip up and reveal her crush leads to said explosions.
• Satans Secretary (Maō no Hisho) is about exaggerating this trope. The demon king kidnaps a human as a secretary... and she proves so efficient (and inhuman) that it scares him.
• Princess Sya in Sleepy Princess in the Demon Castle is such an example, even if the Demon King would prefer her to stay in her cell instead. Despite being a captive, if there's any paperwork in her proximity, she'll complete it faster and more efficiently than if all Ten Elders worked together.

Comic Books

• In The DCU, the Calculator usually serves as the logistics guy for the Society of Villains.

Films — Live-Action

• Downfall (2004): The story is largely told from the perspective of Traudl Junge, secretary to Hitler.
• Licence to Kill: One of the major evil characters is Truman-Lodge, the Sanchez Cartel accountant, who provides exposition in how the cartel does its schemes but also constantly badgers his boss Franz Sanchez about any waste of money. His personal Villainous Breakdown at the film's climax is set off by Bond's Roaring Rampage of Revenge causing the cartel's hundred-million-dollar facilities (and lots more in drugs) literally going up in smoke and, after snarking off one time too many to Sanchez about the waste, gets blown away with an Uzi in response.

Literature

• A Song of Ice and Fire: Lothar Frey works as the steward for his father, the Lord of House Frey (known for being a vindictive, untrustworthy Family That Slays), and manages the family castles. When Lord Frey decided to betray the Starks, Lothar infamously handled the planning of the massacre.

Live-Action TV

• Orphan Black: Astrid works as a secretary within the Dyad Institute, responsible for the unethical cloning experiments, helping Olivier keep track of the various clones he's assigned to monitor.

Podcasts

• Rosie in The Magnus Archives works as the main secretary for the Magnus Institute and reports directly to the head of the institute Elias Bouchard. She's aware that something sinister is going on with the place she works, but is so desperate to keep her job that she keeps her mouth shut when she sees her boss do something suspicious. In season 5, she's still working for Elias/Jonah even during an apocalypse that's left most of the world stuck in personalized hell dimensions.

Tabletop Games

• In a strange moment from the Dungeons & Dragons adventure Queen of the Demonweb Pits, while exploring the home plane of Lolth, the titular demon spider goddess, the party will in fact encounter her secretary who (despite being a marilith, a six-armed snake demoness) is content to take their information and show them in to her boss for a boss fight.

Video Games

• In Helltaker, Pandemonica serves as this for all of Hell. Appropriately enough, she's the first demon that the player meets and recruits into their harem.
• Kirby: Planet Robobot has Susie, the executive assistant to the Haltmann Works Company and the chief threat Kirby has to face on his path to stopping the evil corporation. Her true identity is the long-lost daughter of President Haltmann, who was thought dead after she was warped into Another Dimension. When it becomes clear that he's lost his mind, she attempts to "teach the old man a lesson" by stealing the device that allows him to control Star Dream, the reality-bending supercomputer that separated her from her father in the first place.
• Mega Man Star Force 3: Heartless is Mr. King's personal assistant, helping run both the King Foundation and the actual evil organization Dealer behind it. She is actually using this position to learn about King's plans so that she may leak them to WAXA and betray him at the right time. She is the only member of Dealer whose Wizard isn't even shown, let alone used to fight Mega Man.
• In Nefarious, Becky Rockler keeps the day-to-day of Crow's evil empire going as he's out capturing princesses to power his doomsday machine. In the good ending, she usurps control of his new kingdom to make herself a Princess and the game's true final boss.
• In Portal 2, Caroline is a downplayed version of this trope, largely because her boss Cave Johnson, and by extension Aperture Science, aren't exactly evil—it's more that Cave is a Cloud Cuckoolander obsessed with advancing scientific progress for progress's sake (case in point: tricking volunteers into sitting on folding chairs that inexplicably give them cancer just so they can try to cure it). Caroline serves as Cave's minder and Morality Pet, but at the very least, she shows the same lack of concern regarding Aperture's human test subjects that he does, suggesting that she too lacks compassion. That lack of compassion becomes more apparent after Cave forcibly uploads Caroline's consciousness into Aperture's computer systems, turning her into the insane A.I. known as GLaDOS.
• Super Paper Mario: Nastasia is Count Bleck's most-trusted member of his inner squad, and the only one in his entourage not to be fought. She speaks rather sardonically, usually ending in her signature, "'K?". Along with keeping his organization in line, she's also in charge of recruiting new talent. She's deeply loyal to Count Bleck, implied to be because he saved her life, resulting in her falling in love with him; she even takes Dimentio's spell meant to kill him, nearly dying herself.

Webcomics

• The Order of the Stick: Xykon's entire modus operandi is For the Evulz, leaving his right-hand-goblin Redcloak to deal with the logistics of their army and the places they've conquered. The consequences of this are explored when it's revealed that Redcloak has his own agenda for the Snarl they're attempting to unleash, using Xykon's resources for those ends right under his non-existent nose and setting him up for failure.

Western Animation

• In Codename: Kids Next Door, Anna Worthington is the secretary to Gallagher Elementary's fourth grade president James Nixon McGarfield. Though she worked for him even before he turned evil, after his Face–Heel Turn she continues to enthusiastically assist him with his schemes to make school miserable for their classmates. The reason for this devotion is because she is in love with him, but he has no idea.
• Sasha in Iron Man: Armored Adventures is this to Justin Hammer, snarkily reminding her Psychopathic Manchild boss that, while seeking revenge on Tony Stark is all well and good, the goal is meant to be making sure Hammer Industries outcompetes Stark International, and blowing things up with the Titanium Man is only tangentally related to that. At least, until she gets to use it.
• Miraculous Ladybug: Nathalie is a subversion. Normally, she is Gabriel Agreste's secretary for his self-titled fashion company and the manager of his son Adrien's schedule. When he becomes Hawk Moth, she covers for him and later transforms into Mayura to be his sidekick, but as Hawk Moth, Gabriel does not have an organization and Mayura does not do administrative work for him in that guise.
• On Robot Chicken this is parodied in the Star Wars sketches, where Palpatine and Vader often consult with Sheila, who seems to be their shared secretary. She's also apparently married to the bounty hunter Dengar.
• In Steven Universe the Diamonds' Pearls, if not used as "walking decorations", are kept in charge of communications and simple management.
• Leslie from WordGirl is this and much more to her boss Mr. Big. Besides being the secretary of the company he's the Corrupt Corporate Executive of, she's also his personal assistant and Hypercompetent Sidekick, doing everything up to and including menial labor and fighting for him. She's generally a Punch-Clock Villain who doesn't actually care whether or not her boss succeeds with his evil schemes, but in the episode "Leslie Makes It Big" she has a stint taking up active villainy on her own and has a good time doing so, and in "Yes Monkey" she's shown to be bored and despondent without him after temporarily resigning.

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