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5 Signs Your Boss Might be a Psychopath (Your Emails Might Hold the Biggest Clues) How do you know if you work with a psychopath? Asking for a friend.

By Linda Lacina

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They're charismatic, unpredictable and make you do things you never imagined.

These traits could describe the most inspirational bosses you ever had. But as we learned at a SXSW panel this week, they could also describe psychopaths when combined with other key traits such as ego, self-deception and callousness.

In fact, the panel's experts say there's almost one psychopath for every 100 people, with rates shooting up in the workplace, especially in leadership, thanks to psychopaths' ease with manipulation. Research finds that nearly 4 percent of corporate CEOs are psychopaths, and this rate is nearly doubled among middle managers. (Shockingly, the share of psychopaths among middle managers is nearly as high as the share of psychopaths in medium security prisons.)

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In the world of startups, psychopaths could be particularly hard to spot. Psychopaths might be irrational and driven by ego, but so are successful entrepreneurs, points out Brian Stolle, a venture capitalist who says he's worked with founders who fit a psychopathic profile.

Entrepreneurship, by nature, forces you to do unnatural things such as putting aside friends and family for the good of a company. And since no startup is successful without a team, Stolle says, charismatic startup founders must convince others to commit the same seemingly unnatural acts, making it all the more difficult to separate old fashioned hustle from a psychopath's expert manipulation.

"They convince you that something can be done that no one else thinks can be done," Stolle says.

They can be hurtful and cold, with bullying driving costly turnover and destroying a staff's quality of life. Thankfully, true psychopaths do share certain traits -- ones you might recognize from chats, texts and emails. These distinct language and behavior patterns can help anyone cope and possibly even make the most of a psychopath's contributions to a team.

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What's psychopathic and what's not
There's a difference between psychopaths and just people we'd consider difficult or even erratic or violent, says Michael Woodward, a registered psychologist who has studied psychopathic murderers. A psychopath stands out, Woodward says, thanks to a "blend of interpersonal, lifestyle and behavioral deficits" that they can mask, at least for a period of time. Woodward explains, "They come across as very charming and very gregarious. But beneath that veneer lies a lack of remorse, an amorality and a real callousness."

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What to look for: In language
1. Hostility: Psychopaths have an emotional deficit and don't discuss others much or express anxiety. However, psychopaths do use a a lot of negative, hostile language, regardless of who they're talking to, since they aren't able to modulate their speech for different audiences. They'll talk the same way to a friend, to a work colleague or on a post on on social media. This behavior can be jarring -- shocking even.

2. Profanity: Psychopaths also like to swear. So much so, that Stolle uses profanity as a test when evaluating which startups to work with. He asks founders to drop the F-bomb in conversation to see how they'll react.

3. Complex language: An emotional deficit can also make psychopaths hard to understand. There's a connection between emotional understanding and its impact on reading and writing, says Jeff Hancock, a professor at Stanford University known for his research on how people use technology to deceive. This disconnect means a psychopath uses more complicated language and odd phrasing especially in written communication.

Tenses psychopaths use can be another important tell. Though they usually talk in first person, when describing a negative event, they'll switch to third person. They'll also couch that event further in the past then it might have occurred. Both of these strategies help them distance themselves from a problem to which they might have contributed.

What to look for: Actions
4. Lies: All of us lie -- often a few times a day -- but psychopaths don't lie for a specific purpose, Hancock says. While most members of the general population might fib to save someone's feelings or hide a mistake, psychopaths lie sheerly to manipulate. They receive pleasure from the mere act of deceiving people -- something he calls a "duping delight."

What to look for: Motivation
5. Selfishness: Psychopaths are driven by their own needs, and talk of sex, food and money will consume their conversations. In describing this phenomenon, Woodward described something he calls "the chicken wing effect," a term sparked by his own research with convicted murderers.

When discussing a killing, Woodward was shocked at how little one prisoner talked about his actual crime and how much detail he'd used to describe the 15-cent chicken wing deal he'd snagged at a strip club the day of the murder. Non-psychopaths would never think to bring up these details and would, in fact, discuss a crime in moral terms. Psychopaths, on the other hand, are stuck in survival mode, Hancock adds, and can't move up from the lowest rungs of Maslow's hierarchy of needs.

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What to do:
Tread carefully. Psychopaths can be erratic bullies, but they recruit protectors. These might be appointed lackeys who act as close confidents or even investors that they know will wait out a dicey situation for a strong exit. Unfortunately, members of human resources are often among their protectors, since psychopaths are often in leadership positions. As a result, the people in the best position to stop a situation from worsening choose not to, reinforcing bad behaviors over time.

These protectors aren't even truly safe from a psychopath's erratic behavior. Psychopaths care about people who serve a need for them. Once someone stops serving that need, they're discarded. Psychopaths can turn on these allies on a dime and even push them out of an organization, Woodward says.

Help them succeed. Because psychopaths are bold thinkers, Woodward says, they can do great things for organizations initially. Feeding their hero mentality can fuel good constructive acts for a company -- at least in the short term.

Show your interest. Psychopaths are interested in themselves, but also interested in you being interested in them. "They genuinely believe in their expertise and their abilities," Woodward says. Keeping this in mind can likely make your interactions with a psychopath more successful.

Negotiate through writing. Psychopaths are most successful face to face, Hancock says. They play off non-verbal reactions using mimicry and by simulating others' emotions. They're engaged, seeing the effect of their manipulations first-hand and in real time. Written communication, on the other hand, removes people from their charms. And as chats, emails and texts become less interesting to psychopaths, they can become more practical, effective and powerful overall. "Text-based communication is a shield," Hancock says.

Set ground rules. When working with a psychopath, a few simple guidelines can be essential, Stolle advises. If you choose to do something, ask if it's something you want to do and aligns with your values, he suggests. Checking against these principles can keep you focused on the task's needs, not the psychopath's needs, and protect your own peace of mind.

Linda Lacina

Entrepreneur Staff

Linda Lacina is a special projects director at Her work has appeared in the Wall Street Journal, Smart Money, Dow Jones MarketWatch and Family Circle. Email her at

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