Why Your Boss Doesn’t Realize They’re an Asshole

Karla Starr
7 min readOct 27, 2021

Here’s part of the chapter “Our Greatest Strengths Are Our Greatest Weaknesses” by Gordon Livingston in the criminally under-read Too Late Smart, Too Soon Old:

There are certain personality characteristics that are highly correlated with academic and professional success: dedication to work, attention to detail, ability to manage time, conscientiousness. People who have this constellation of traits are generally excellent students and productive workers. They can also be difficult to live with. Think about it; those who demand much of themselves frequently have high standards of performance for those around them. In a work situation, this is usually an adaptive approach…

It is often puzzling to such people that approaches that make them successful in their work are so poorly received by those they live with. Practically any human characteristic — competitiveness, orderliness, even kindness — when indulged to an extreme can produce undesirable results. Perhaps this is just another argument for moderation in all things. But we need to acknowledge that those qualities of which we are most proud can prove our undoing.”

Fact: the most outwardly successful people I’ve known are also the least well-liked — even unlikeable — people I’ve ever known. It’s actually pretty easy to have a fancy-sounding title while remaining completely ignorant of being a widely disliked person. Let’s call them USP: Unliked Successful People.

Here’s a brief overview, according to social psychology, of How Managers Become Assholes Without Realizing It:

Narcissists are initially quite charming at first. Perhaps they get away with the occasional lapse into dick-ish behavior because they’re shielded and/or emboldened by a form of pre-existing status. Using appearance, money, intelligence, or connections as a passive aggressive weapon can start young.

“For young people who are lucky enough to have wealthy parents or good looks, the schoolyard is an easy place to get by: Not only do peers want to befriend them and ascribe them significant social power, but they also are willing to overlook and even reward their sometimes nasty behavior. For children who do not have such luck, the road is much more difficult.”¹

Of course, we’re not all capable of perfect empathy with everyone all the time. But there’s usually a tiny difference that sets the USP apart in the beginning: prioritizing…

Karla Starr

Speaker & author x2, inc. Making Numbers Count (w/ Chip Heath). Behavioral science, cultural history, numbers.

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