Bad Boss Leadership Horror Stories (Updated)

Do you have a terrible boss? Which leadership horror most story aligns to your bad boss experience? Halloween is time for Horror Story Bosses

Do you have a terrible boss? Welcome to the horror show. Which leadership horror most closely aligns to your bad boss experience? As another Halloween approaches, it is time to revisit and update our list of Horror Story Bosses.

The Headless Horseman with a Bloody Neck Stump, Rides on Top of a Black HorseHeadless Horseman

First on our list is the Headless Horseman. In The Legend of Sleepy Hollow, the headless horseman is the ghost of a decapitated soldier who seeks his head and is willing to take yours, as a substitute. The bad boss horror story is much the same. A leader who lacks ideas and thoughts of his own, may turn to taking the heads of others instead. Headless Horseman Leaders seek to defame, destroy and tear down others as a means of making themselves look better.

A Zombie Limps Toward the Reader, Dressed in Rags, With Skin Visibly DamagedZombie

Next on our list of bad boss horror stories is the Zombie leader. Zombies are the classic walking dead. In fiction, these undead are animated for the sole purpose of feeding on human flesh. Zombie Leaders are trapped between an inability to move on to the next life (a promotion) and an unwillingness to do the work of the previous life (direct reports). As a result, Zombie Leaders are also walking dead – useless to the organization while seeking to feed on the production of others.

A Banshee Woman with a Ghstly Look, including a visible Skull, Screams with her Mouth Wide Open Banshee

Next up is the Banshee. In fictional horror, the Banshee is typically a female ghost who’s whaling shrieks frighten, harm or even kill their victims. Often mistaken for a seagull manager, the Shrieking Banshee Leader believes yelling and screaming will change the outcome. These individuals often lose control of their tempers and emotions as they spew angry remarks and attacks on victims.

A person with a wolf head and human hands grabs at the viewerWerewolf

Another regular occurrence in the world of bad bosses is the Werewolf leader. The Werewolf in literature is a man or woman that changes into a wolf during a full moon. They prowl the night seeking human victims for dinner. The Werewolf Leader becomes a monster every time a particular issue comes up. For fear of becoming their next victim, team members cower until that issue has passed. The Werewolf Leader can not be confronted on this issue, so it goes unresolved.

A Female Vampire Hisses as She Grabs at the Viewer.Vampire

Our next bad boss horror story is the Vampire. Vampires are night crawling, blood-suckers afraid of daylight. Often defending themselves in a sexual harassment lawsuit, the Vampire Leader is not unlike the Werewolf, in that certain conditions change their nature. However, unlike the Werewolf Leader, who becomes a raging monster, the Vampire Leader hides from their issues. When a tough decision must be made, the Vampire Leader is often nowhere to be found.

A very freaky looking clown, with scars on his forehead and blood on his hands gestures for you to approach himClown

Our first new addition to this year’s bad boss horror stories is the Evil Clown Leader. The most famous evil clown lives in the sewers and hunts small children by luring them in with their humorous look. The Evil Clown Boss operates in a similar manner. They put on a nice façade often pretending to be your best friend. However, once you let down your guard, the Evil Clown often attacks your reputation and quality of work. These bad bosses are the ultimate in two-faced coworkers.

A humanoid alien, with no hair or eyes and giant teeth with large gums and no lips growls at the viewerAlien

Our last in this year’s list of bad boss horror stories is the Alien Leader. In horror movies, the alien is a freakish beast from a foreign environment. These monsters look completely inhuman and we often have no idea where they came from. The Alien Boss often creates a similar response in their victims, by stirring questions like, “Where did that come from?” and “is that even possible?”. An Alien boss if often completely disconnected from reality with their team.

So, which is it? What leadership horror story – or stories – have you survived? Let us know in the comments.

And if you could use a little help in preventing bad boss horror stories at your workplace, contact us at, or do some more reading on our content site at

Thank you, and remember – keep serving!


Picture of Ben Lichtenwalner

Ben Lichtenwalner

Ben Lichtenwalner is the founder and principal of Modern Servant Leader and Radiant Forest, LLC. He has studied and promoted servant leadership awareness and adoption for over 20 years. He is the author of 2 leadership books and has 2 decades of corporate management and leadership experience. His corporate experience spans CIO, VP, Director, and many management roles at Fortune 500, INC 500, and Nonprofits. Ben’s education includes a B.S. in Management Science & Information Systems from Penn State University and an MBA from Lehigh University. Ben's Full Profile Here: About Ben Lichtenwalner

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