Psychopathic Bosses & Enablers: Characteristics and Tips To Cope

Key Takeaways:

  • CEOs represent the career choice with the highest percentage of psychopathic traits.
  • If you believe your boss is a psychopath, you can determine if you are enabling their
  • psychopathic behavior in some way.
  • There are helpful tips to cope with a psychopathic boss at work.

People with psychopathic traits can thrive in leadership positions. So it’s easy to see why people often ask, “How can I tell if my boss is a psychopath?” Since there are bosses with psychopathic traits in the workplace, employees need to take precautions to protect themselves while not enabling their bosses behavior. Fortunately, there are tried and true tips to cope with psychopathic bosses.

Note that throughout this article, I’m referring to leaders with some psychopathic traits, not psychopaths per se. While there is a lot of literature on psychopathy and the criminal justice system, there is less on corporate psychopathy. It is difficult to determine whether leaders with psychopathic tendencies are effective leaders or not. One study shows a weak correlation for psychopathic tendencies and transformational leadership and concludes that psychopathic tendencies in organizational leaders may be overblown.

Psychological and organizational psychologists Paul Babiak and Robert Hare, authors of Snakes in Suits: Understanding and Surviving the Psychopaths in Your Office conducted a study with corporate professionals in management development programs. Their study showed corporate professionals had more psychopathic traits than others in the community.
Furthermore, while psychopathy was positively associated with charisma/presentation style, it was negatively associated with ratings of responsibility/performance like being a team player, management skills, and overall accomplishments.

To help better understand bosses that are psychopaths, I interviewed Jack McCullough, author of The Psychopathic CEO: An Executive Survival Guide.

What is a Psychopath?

In short, psychopathy is a personality disorder defined by egotistical tendencies and a lack of empathy, remorse, or moral code. Although psychopath doesn’t appear in the most recent fifth edition of the Diagnostic and Statistical Manual of Mental Disorders (DSM-5) as an official diagnosis, it was included in the first two editions. It was replaced in the third edition by antisocial personality disorder (ASPD), which focuses mainly on the behavioral aspects of psychotherapy.

ASPD is a mental disorder in which a person has no regard or real feelings for another. Those with this condition may be deceitful, manipulative, and display a lack of restraint. ASPD is often used interchangeably with psychopathy, but psychopathy is actually one of three afflictions associated with ASPD. We can think of it this way—all psychopaths have ASPD but not all
people with ASPD are psychopaths. About ⅓ of people with ASPD are estimated to be psychopaths. Youth with psychopathic traits are often diagnosed with Conduct Disorder.

Characteristics of a Psychopath

The following characteristics are from the Psychopathy Checklist-Revised, a tool Jack refers to in his book, The Psychopathic CEO: An Executive Survival Guide:


  • Glibness/superficial charm
  • Grandiose sense of worth
  • Pathological Lying
  • Conning/Manipulative


  • Lack of remorse or guilt
  • Emotionally shallow
  • Callous, lack of empathy
  • Failure to accept responsibility for one’s own actions


  • Need for stimulation/proneness to boredom
  • Parasitic lifestyle
  • Lack of realists, long-term goals
  • Impulsivity
  • Irresponsibility
  • Promiscious sexual behavior and multiple marriages


  • Poor behavior control
  • Early behavioral problems
  • Revocation of conditional release
  • Criminal versatility
  • Juvenile delinquency

Because of these common characteristics, they naturally are attracted to specific careers.

Top 10 Careers with the Most Psychopaths

According to Oxford University research, CEOs represent the career choice with the highest percentage of psychopaths.

  1. CEO
  2. Lawyer
  3. Media
  4. Sales
  5. Surgeon
  6. Journalist
  7. Police Officer
  8. Clergy
  9. Chef
  10. Civil Servant

You’ll notice at the top of the list are CEOs. Research suggests that one in every five CEOs is a psychopath. Are you surprised by that?

Famous CEOs with Psychopathic Traits

Together with corporate psychologist, Dr. Dave Popple, Jack identified a list of famous CEOs who seem to “check the boxes” for Antisocial Personality Disorder (ASPD). Of course, there is no formal clinical diagnosis for anybody on the list. These are simply professional opinions based on assumptions of public knowledge.

  1. Harvey Weinstein
  2. Elon Musk
  3. Donald Trump
  4. Steve Jobs
  5. Elizabeth Holmes (who was recently sentenced to 11 years in prison)
  6. Adam Neuman

Most recently, Elon Musk has been in the news for a Twitter shake-up characterized with a cavalier attitude and a lack of empathy while laying off employees. Jack believes Asperger’s syndrome may account for some of Musk’s behaviors. No matter who you work for, when your boss is a psychopath, it’s easy to become an enabler.

Types of Psychopath Enablers:

If you believe your boss may be a psychopath, you will want to assess whether you exhibit any of the qualities of the several types of enablers of psychopaths, who often end up victims.

  • Fearful enabler: An employee who fears they have limited job prospects and has to remain employed out of economic necessity is a classic fearful enabler.
  • Charmed enabler: One who may be vulnerable to flattery or deceit and only views the psychopath with admiration, fondness, and respect.
  • Indifferent enabler: Somebody who sees what the psychopath is doing to others, but doesn’t care as long as they aren’t affected.
  • Greedy enabler: One who profits by the psychopath’s actions. For example, their stock options and 401K are doing great, and they are making more money than ever, so why rock the boat?
  • Gullible enabler: Similar to the charmed enabler, they just can’t imagine that a person they like would “do something like that.”
  • Forgiving enabler: They easily dismiss a wrong and are willing to forgive because they believe the psychopath is really a good person, is misunderstood, or is getting help, etc.
  • Hopeless enabler: They already feel defeated, so believe there is no point in reporting wrongdoing or taking action because nobody will care what they report.
  • Embarrassed enabler: They are a victim of the psychopath who remains silent out of a sense of shame or embarrassment.
  • Transactional enabler: One who rationalizes that the psychopaths exploitation of others is fair (i.e. “its okay he’s having sex with her because he is making her a star”).

To handle the situation without enabling, consider effective ways of dealing with it.

Tips to Cope with Having a Psychopathic Boss

  • Learn more about psychopathic personalities. Take time to discover characteristics of a psychopath.
  • Document. Jack recommends thoroughly documenting everything about your boss. This includes reckless or inappropriate behavior, lying, or engaging in other detrimental behavior. Also, document everything about yourself too. If the CEO praises you, document that. It’s hard to fire someone who is doing great at their job.
  • Seek legal counsel. Along these lines, make sure you are saying no, setting limits, and not unwittingly signing documents or agreements that make you liable. Your career and reputation are on the line. Corporate lawyers work for and are loyal to the company. If you seek legal advice, choose a trusted professional whose loyalty is to you, not the company. The set-up to fail syndrome
  • Evaluate if the job is worth it. Be honest with yourself and ask if the emotional strain and the liability risks are worth being affiliated with your psychopathic boss.
  • Build a solid Plan B. Jack recommends preparing both a Plan A and Plan B. While Plan A is how you deal day-to-day if you decide to stick it out, Plan B is your exit strategy. As general career advice, it is best to leave on your own terms so start planting seeds for a new job search in case Plan A becomes unbearable.
  • Practice healthy detachment. In my book, The Financial Mindset Fix: A Mental Fitness Program for an Abundant Life, I share how to detach with love. Through healthy detachment, we shift our focus from the other person to ourselves. We engage in activities and self-care practices that strengthen our relationship with ourselves. When we do this, we become whole.
  • Identifying what is your responsibility and what is not. Consider the Serenity Prayer which reminds people in recovery of the need for acceptance, change, and wisdom. The following infographic outlines what you can and can’t control.

How to Recover from Having a Psychopathic Boss

  • Consult a therapist. You can use the Psychology Today’s Therapist Directory to locate a therapist near you. You may want to consider EMDR for trauma therapy.
  • Career counseling or coaching. The best time to start a job search is when you already have a job, not after you’ve left one. But, if you left your job because of a psychopathic boss or are fired, these services will be equally beneficial.
  • Practice self-care. Proper sleep, nutrition, exercise, and healthy limits with technology, work, and substance use can be a great start to a healthy self-care routine. You can measure how well you are doing by using my Self-Love Wheel Exercise.
  • Access support. Support matters when it comes to your mental health. I created a self-help Support Wheel Exercise as a self-evaluation tool. The exercise allows you to see where your strengths and weaknesses are when it comes to cultivating support.


Ultimately, you hold the power when it comes with staying with a psychopathic boss or leaving. Learning to recognize and thoroughly understand them can be incredibly helpful as you most likely will continue to encounter and manage psychopaths when you are in the corporate world.


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