There are Super Bad Guys out there who have lost their moral compass, break the law, lie and charm easily, steal and cheat, and take advantage of others. They want to get ahead at all costs. They’re in a separate class from Bad Guys because their unethical behavior crosses over into many parts of their lives, and in some cases, their behavior is criminal. Under desperate circumstances, some people will push themselves to commit acts they would normally not commit. Other people have a long history of unethical behavior that permeates their entire life. Regardless of the reason for their problems, you can’t hang out with Super Bad Guys. They are extremely dangerous, and they could take you down with them. They can ruin your career and certainly hurt your self-esteem. Some should even go to jail.

They’re Out There

Sadly, these guys exist in corporate America. They’re extraordinarily talented and ruthless, and you may not realize they are, oh, so much better than you at watching and observing and manipulating. They don’t care about you; they only see you as a potential conquest, either financially or sexually, or as someone they can use. This type of guy doesn’t have a grasp on reality. He doesn’t acknowledge who he is; he doesn’t question his own behavior. He acts out of habits that have been reinforced by a lifetime of deceit and narcissism. He lives in a different world, one created by delusions. Alcoholism, womanizing, gambling, and a street-fighting approach to business often seem to be part of the package.

What’s a girl to do? First, be smart. Super Bad Guys usually have a reputation and a history. Because these habits are not new, if you ask around, you’ll discover the guy is associated with accusations of cheating, harassing, and even fraud. Back away from him—don’t try to fix him. His problems are far too severe for your kind and well-meaning heart. You can’t stop him either; you’re not the police. You can warn people about him, but I wouldn’t try to put an end to his deceitful career. You have to assume he will eventually get his comeuppance, and in the meantime, you have better things to do. Stay away from Super Bad Guys.

Identifying Marks

If you suspect you’re dealing with a Super Bad Guy, watch for these signs. Does he brag about tricking people, especially financially? Does he seem to have an unusually high level of debt or seem desperate to make it big? Is he overly preoccupied with wealth and rich people? Does he propose complicated financial arrangements and appear unimpressed when he’s told they’re illegal? Does he snicker about people who lie to the government? Does he openly admit he cheats on his taxes? Does he have a history of having been investigated? Does he heavy-handedly try to force self-serving conclusions even when the facts don’t support them? Does he have a history of working for disreputable companies or with disreputable people? Is he constantly jockeying for a more favorable position in business transactions? Does he have slime-ball friends?

Be cautious when you are dealing with businessmen from other cultures. American ideas of fair business practices are not global, and some cultures are more tolerant of bribery, fraud, and corruption. Men from other countries sometimes don’t have the same dim view of under-handed business dealings that I do. These guys don’t get why America has laws forbidding foreign corrupt practices and aren’t particularly inclined to obey them. Watch out for guys who seem cavalier about American securities laws or about rules in general. They may be willing to take more risks than you would, but they’re still gambling with your career.

If you run across one of these guys, I hope it’s during the job interview process and before you’ve gone to work with him. Some Super Bad Guys have risen to pretty high levels in an organization, so don’t assume that just because he’s at a senior level, he must be okay. Listen hard for these red flags when you’re contemplating changing jobs, and don’t ignore them if you hear them. Ask around about him outside of the company. Make contact with people who used to work with him but who have moved on. Try to talk to the person who held the job before you. Listen for code words when people describe him—“a real dynamo,” “He could sell snow to the Eskimos,” or “I actually felt sorry for the guys on the other side.” These are not necessarily positive reports, and you may be being warned.

Extraordinary Skills—Used for Evil

People who are very good at negotiating and reading people can also be those who don’t have a clear understanding of right and wrong. It’s not surprising, but it is scary, because it means your enemy is formidable and ruthless. This guy, when he’s told no, will try to move the goalposts so maybe “no” doesn’t really mean “no.”

Do you know somebody who just won’t take no for an answer? How about someone who restates something he’s been told in order to gain an edge or put a different spin on the message? Do you know a strong negotiator who somehow seems to be able to get the other party to put something back on the table when you thought it was completely off? Now, you can see how these extraordinary negotiating skills could be used against you.

Super Bad Guys don’t change their spots; that’s why a sexual predator often has a terrible reputation as a womanizer and exploiter. Don’t assume you’ll get through to the good side of him; don’t fool yourself into thinking you understand him in ways other women don’t. If he has taken advantage of other women (including his wife), he’ll take advantage of you. Don’t be fooled by a charming and warm exterior—he didn’t become a master manipulator by being transparently evil! If you’re paying attention and not trying to fool yourself, it’s not that hard to unmask him. You’ll see it’s easy to catch him in a lie or that he has left a whole series of women behind who are ashamed of their association with him and acknowledge they were vulnerable and exploited.

I went to work for a company that employed a known predator, and I asked about him during the interview process.
“Oh no, he’s changed,” one of his colleagues told me. “He’s had health issues, so he’s changed his ways.”
Ha. I’d only been there a few weeks when I discovered that not only had he not changed his ways, but he was harassing one of my employees. I was furious and confronted the head of human resources. To her credit, she and the board took action immediately to get rid of him*, but it didn’t take him long to land at a new company, despite his reputation and dismissal.

Super Bad Guys are often tolerated in corporate America, and boards and management teams look the other way when they’re otherwise pleased with an executive’s performance. You wouldn’t think this would be true in this age of litigation, but it’s surprisingly persistent. So, don’t be too trusting, look for identifying marks, and know your enemy.

*Because the idea of complicity among men is being talked about these days, I’ll mention that he would have been much harder to bring down if two brave young men had not come forward to report his bad behavior.

Excerpted from The Discreet Guide for Executive Women: How to Work Well with Men (and Other Difficulties)

© 2012 Jennifer K. Crittenden