How To Deal with Difficult CEOs and Serial Killers
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How To Deal with Difficult CEOs and Serial Killers

September 2nd, 2021

DISCLAIMER: I am not a psychologist or medical professional. These are my observations over the last 25 years.

The American fascination with serial killers has exploded in the last decade. Streaming services and the networks produce a documentary or TV show about a serial killer each month. But, the fascination with this phenomenon is less about the crime and the psychological make-up of the serial killer.

I’ve been in the sales and marketing industry for almost 30 years. I’ve seen my share of difficult managers, VP’s, and CEOs in that time. But over that time, I realized some of the worst bosses shared traits associated with famous serial killers. Of course, I am not saying the difficult executives I’ve encountered have been psychopaths; I am saying some had similar tendencies. According to Forbes, studies show that roughly 4% – 11% of CEOs display psychopathic behavior regularly.

Based on my fascination with serial killer behavior and decades in sales, here are my self-taught techniques for dealing with psychopathic behavior and the documentaries where I learned them:


Richard Kuklinski / The Iceman Interviews / HBO & Apple TV – Richard Kuklinski, also known as the Iceman, was convicted of four murders in 1988. Kuklinski, a mafia hitman, was suspected in more than 100 murders. In his first televised interview in 1988, a psychiatrist challenges Kuklinski about his rationale for killing one of his victims:

Kuklinski: “You almost made me mad.”

Psychiatrist: “I know. Can you figure out what that is?”

Kuklinski: “I don’t know.”

Psychiatrist: “Could it be I was challenging you, and it sounded judgemental?”

Kuklinski: “Could be. I don’t know.”

Psychiatrist: “How mad are you?

Kuklinski: “Pretty. I feel a little flushed. I’ve reached a point in my life where I feel annoyed.”

Psychiatrist: “What would you like to do to me?

Kuklinski: “Doesn’t matter. It hasn’t gotten to the point where I would do anything stupid.”

Scrutinizing Kuklinski was a trigger. After that, he couldn’t accept a deeper dive into his logic.

In my experience, some ‘higher-ups” fall into this category. For example, I’ve attended meetings where CEOs have discussed the company’s direction. When the Q&A session started afterward, they became defensive when anyone pointed out negative aspects or asked, “Why?” Often, defensive people see the world through a negative lens. Defensiveness is a coping mechanism. When dealing with defensive people:

  • Know their triggers
  • Keep calm. Defensive individuals don’t take well to emotions. A heated reaction will most likely make the situation worse.
  • Instead of saying, “I don’t understand,” say, “Tell me more, so I understand.” Rephrasing your question removes the burden from the defensive person and creates a dialogue with the load on the person asking the question.
  • Give solutions instead of questions. Questions can come across as a challenge. Start your sentence with, “What if we tried,” or “Have you already considered…”
  • Stay away from blame and make the conversation constructive.


Ted Bundy / Conversations with a Killer / Netflix – Almost everyone has heard of Ted Bundy. Bundy crisscrossed the U.S. in the 1970s, killing more than 30 women during that period. This former law student was articulate, intelligent, and charming. Famously, Bundy represented himself at his 1981 murder trial. As one of the attorneys who worked with Bundy stated, “He thought he could lie his way out of anything and charm the judge. He was wrong.

Bundy’s narcissism was part of his undoing. He believed he was more intelligent than everyone else. In the workplace, there will always be coworkers who think they’re more intelligent than you. But, those who take it to the next level are more troubling. People with a high sense of superiority may not necessarily feel superior. It is the opposite. The Superiority Complex stems from people who feel inferior:

  • Avoid Criticism – Their feelings of inadequacy may surface and lead to an explosive situation. If you question their logic, be sure to do it in private.
  • Create a Win-Win situation – Someone who feels superior will want to view a situation as win-lose. Reframe your conversation to create a mutually beneficial solution.
  • Compliment Them – This may sound disingenuous. But, the best way to work with a narcissist may be to tell them how important they are. Be aware that they may also take credit for your efforts.

Pathological Liars

Henry Lee Lucas / Confessions of a Serial Killer – Texas Investigators described Henry Lee Lucas as more of a pathological liar than a serial killer. Lucas first admitted to killing more than 100 people. The number quickly ballooned to 200 and eventually more than 600 during interviews with Texas authorities. Investigators interviewed him for involvement in more than 3,000 murders and missing persons cases. But, of course, he lied about his involvement.

Lucas was convicted of two murders and served a life sentence until he died in 2001. Years later, partially due to the research in the documentary as mentioned above, it was determined Lucas concocted the stories of his involvement in hundreds of killings. He was a psychopath. But he was a better liar.

Most people will deal with some form of dishonesty at work. Pathological liars are different. There is no apparent motive. They see it as more of a challenge and a chance to practice their skills. They have honed their craft at lying, and a pathological liar seldom gets caught. The keyword is seldom:

  • Determine Why They are Lying – Someone exaggerating accomplishments differs from someone taking credit for your work. People get facts wrong all the time. So don’t overreact. If you determine a more devious reason, the first step is to limit interaction and information with the person.
  • Don’t Get Sucked Into the Drama – If you corner a liar, they will raise the stakes to avoid the consequences. The drama may include yelling, personal attacks, or randomly changing the subject. Whatever the case, it won’t be a good look in the workplace.
  • Approach the Person Privately – People who feel comfortable lying suffer from insecurity. Meeting them head-on may exacerbate the problem. Instead, approach them with, “You said X happened, and it was more like Y.” So, instead of the liar being the problem, you make them part of an explanation.

The underlying thread of difficult people is insecurity. Dealing with difficult people in the workplace comes down to three elements:

  1. Stay Calm
  2. Do Not Confront Them in Front of Coworkers
  3. Understand They Feel Inadequate