The Worst Leaders Of All Time

We all know that We “learning from others” is one of the most effective ways that leaders develop. Whenever I ask leaders to think back and reflect on how they developed their leadership capabilities, they inevitably will mention two categories of managers they’ve learned from. 

First, there’s the role model, inspiration leaders that they observed and got advice from. Then there are the “boss from hell” examples – the ones we look at and say “that’s how not to be a leader – and I vow never, never to act like that!”

There’s already a lot of information on this blog about great leaders… but what about the worst leaders? Can’t we learn from them as well?

So here it is… my list of the 10 worst leaders of all time! Please comment to add your own favorite worst.

10. Michael Scott from “The Office”. With unshaken enthusiasm, Michael believes he is the office funnyman, a fountain of business wisdom and his employees’ cool friend. He has no clue that his employees tolerate his inappropriate behavior only because he signs their paychecks. Painstakingly trying to be liked and look cool, Michael comes off alternately absurd and pathetic. His prize possession is his “World’s Greatest Boss” mug — which he had to buy for himself. 

9. Vlad the Impaler (15th century): Author Bram Stoker based his signature character Dracula on him. However, “The Impaler” did not kill to feed but for the pleasure of watching others suffer. It has been said he caused more “rivers of blood” than any other tyrant in history. Dracula is a teddy bear compared to this guy.

8. Dagwood’s J.C. (Julius Caesar) , the tyrannical boss, who frequently threatens to fire Dagwood from his workplace when (as frequently happens) Dagwood either botches or does not finish his work, sleeps on the job, comes into work late, or pesters Dithers for a raise or promotion.

7. Charles Dicken’s Scrooge. Scrooge has only disgust for the poor, thinking many would be better off dead, “decreasing the surplus population”. He has a particular distaste for the merriment of Christmas, his single act of kindness being that he gives his clerk, Bob Cratchit, the day off with pay, more as a result of social mores than any true kindness on his part. He sees the practice as akin to having his pocket picked on an annual basis.

6. Perry White, Clark Kent’s boss. Perry is famous for being boisterous and loud, as well as being a fairly strict editor. He is known for shouting, “Great Ceaser’s ghost!” when angry, exasperated or surprised. Perry also dislikes being called “chief” and typically responds by shouting, “Don’t call me chief!”–often in response to remarks made by Jimmy Olsen.

5. Gorden Gecko, from the 1987 file “Wall Street. Some classic Gecko quotes:
– “Greed, for lack of a better word, is good. Greed is right. Greed works. Greed clarifies, cuts through, and captures the essence of the evolutionary spirit. Greed, in all of its forms, greed for life, for money, for love, knowledge has marked the upward surge of mankind.”
“And if you need a friend, get a dog.”
“Lunch is for wimps.”

4. Pol Pot (Cambodia; 1975-1979): He was influenced by Mao’s cultural revolution, and 25 percent of Cambodia’s population died from starvation, overwork and executions in Pol Pot’s attempt to form a Communist peasant farming society. He conducted deadly purges to rid the area of the “old society,” and anyone suspected of being disloyal was shot or bludgeoned with an ax.

3. Charles Montgomery Burns, normally referred to as Mr. Burns or “Monty” of the Springfield Nuclear Power Plant and Homer Simpson’s boss. Mr. Burns also embodies the stereotype of a manager: he forgets his employees’ names (especially Homer, despite the fact that they seem to interact on a daily basis) and is unconcerned for their safety and well-being. His aspirations to apply obsolete technology to everyday life or references to Victorian era people or places provide a common source of humor on the show. Kent Brockman also credits Mr. Burns with having stolen Christmas from 1981 to 1985. Recently he has become less evil and more eccentric. His trademark expression is the word “Excellent”, muttered slowly in a low, sinister voice while tenting his fingertips.

2. Tie: Hitler and Stalin. Nuff said.

1. And the all time, all around worst leader….. The pointy haired boss from Dilbert (otherwise known as PHB)! A company that has too many PHBs is often called a PHC, or pointy haired company. He’s every employee’s worst nightmare. He wasn’t born mean and unscrupulous, he worked hard at it. And succeeded. As for stupidity, well, some things are inborn. His top priorities are the bottom line and looking good in front of his subordinates and superiors (not necessarily in that order). Of absolutely no concern to him is the professional or personal well-being of his employees. The Boss is technologically challenged but he stays current on all the latest business trends, even though he rarely understands them.