How to Become a Malevolent Leader: A Field Guide for Aspiring Fraudsters and Tyrants

“A crook is a crook, and there's something healthy about his frankness in the matter. But the guy who pretends he's enforcing the law and steals on his authority is a swell snake”

Alphonse Gabriel “Al” Capone aka “Scarface,” American gangster

The king of gangsters Al Capone, Photograph, March 5th 1932 (Photo by Imagno/Getty Images)

The king of gangsters Al Capone, Photograph, March 5th 1932 (Photo by Imagno/Getty Images)

Do you want to be a terrible leader?

Not terrible as in not good. But in the classical sense: venal, amoral, remorseless. Feared and admired. Destructive and self-serving.

Then this is the how-to guide you’ve been waiting for.

The list of dishonest brokers who betray public trust, trample duties and laws, ruin people’s lives, cheat, steal, and lie as easily as breathing is astronomically long. Think of Martin Shkreli, Elizabeth Holmes, Adam Neuman, Travis Kalanik, Bernie Madoff, Jeffrey Epstein. Consider all the politicians and elected officials, sports and entertainment moguls, religious leaders, news and media influencers, corporate titans. Not to mention countless others out of the limelight running shadow operations in offshore locales around the world.

Have you watched people like these ascend to stratospheric levels of power, influence and wealth, and wondered how they do it? Do you want to understand, were they born malevolent? Are avarice and duplicity learnable skills? What’s the formula for balancing charisma and malice? How can they have families? What’s the secret to evading accountability in broad daylight?

Becoming a toxic, self-serving leader is, in truth, not easy. It’s actually challenging. To enter the pantheon of elites, be prepared to be misunderstood, underestimated and underappreciated. Treated unfairly. Constantly attacked.

Al Capone once complained about the bad reputation of his criminal enterprise: “Some call it bootlegging. Some call it racketeering. I call it a business,” he said.

That’s exactly right. It’s a business. Big business.

But where do you learn how to command a successful organization by bullying, demeaning, and breaking your team’s spirit? Is there a B-school program to train in being shamelessly exploitative and abusive? To perfect the art of the grift, practice the subtleties of the scam and innovate impressive new cons? Sharpen your skills in manipulating with impunity? Deceive and defraud without batting an eye?

There’s no shortage of resources dedicated to legitimate CEO improvement: consulting firms, management gurus, books and magazines, websites, universities. If you want to up your leadership game, develop great leadership skills and habits, be an awesome, socially responsible executive, you barely even have to get out of bed. Just go online and take your pick.

Bartolucci traditional toy shop with wooden Pinocchio dolls on Via dei Pastini, Rome, Lazio, Italy. (Photo by: Education Images/Universal Images Group via Getty Images)

Bartolucci traditional toy shop with wooden Pinocchio dolls on Via dei Pastini, Rome, Lazio, Italy. (Photo by: Education Images/Universal Images Group via Getty Images)

But where do you find the consultants who coach mendacity and duplicitousness? Or tap headhunters whose Rolodexes are stuffed with brilliant but amoral toadies? Is there a clearing-house for unscrupulous lawyers specializing in shady dealings and book-cooking accountants with stints at Enron or AIG on their résumés?

Most aspiring strongmen, kingpins, kleptocrats, fraudsters and even dime-a-dozen grifters and corporate tyrants aren’t born with a silver spoon or can wait for daddy to be indicted to take over the family syndicate. It takes cold-blooded focus and dedication. Grit. Drive.

That being said, being streetwise and cutthroat is old school. Raw talent in gas-lighting, cruelty and coercion aren’t enough. Success is a complex combination of character and competencies. Pretty much the same as for any leader. But there are important differences, too. Ruthlessness is not for the faint of heart. Predation and hucksterism, to pluck just two from the catalog of core traits and abilities, are chockfull of sophisticated psycho-social intricacies and technical maneuvers. And poise is a crucial but under-rated characteristic. Some can be learned and developed; others, you either have or you don’t.

Heading a criminal enterprise isn’t 9-to-5. You have to be prepared for personal sacrifice. Recall Prince Humperdinck’s poignant monologue in “The Princess Bride” when he declines Count Rugen’s invitation to watch a torture session: “Tyrone, you know how much I love watching you work, but I’ve got my country’s 500th anniversary to plan, my wedding to arrange, my wife to murder and Guilder to frame for it; I’m swamped.” If you’re looking for work-life balance, this isn’t the work for you.

A prime requisite of leadership is followership. Understanding how to bully, demean, and break your team’s spirit is an important KPI of every malevolent boss. There are so many ways for people in positions of authority and influence to have a powerful impact. One is knowing how to incentivize, coerce and manipulate your workforce. Like it or not, all those enablers, collaborators, and facilitators are mission-critical to abetting and supporting your malicious work.

The good news is that, according to research from Harvard Business School “… toxic workers are much more productive than the average worker.” Sure, legitimate institutions will occasionally get sandbagged by a rogue employee—Nick Leeson who single-handedly brought down the venerable Barings Bank or UBS’ Kweku Adoboli. But as the HBS article concludes, “there is a potential trade-off when employing an unethical person: they are corrupt, but they excel in work performance.”

But what academics and normal management consultants don’t recognize is that the honorable executive’s trade-off is the fraudster’s trade-up. No ethics? No problem. Ruthless effectiveness trumps moral bankruptcy.

And this, ultimately, is why the wind will always be at your back, even when the SEC is chasing you and you have more FCPA violations than Lava Jato. For leaders whose aim is unfettered power and control—social and institutional pillage by autocratic domination, not holacracy or conscious capitalism—it’s practically a frictionless world.

Without the stifling shackles of ethics, lawfulness or conscience, creativity and innovation are super-charged. Malice and greed can be fully unleashed without constantly kowtowing to compliance controls, legalities or the need to manufacture fiduciary legitimacy. Ask any leader who knows how to mock and dismiss the rule of law, social responsibility and regulatory oversight. They’ll tell you straight-up: the liberation isn’t just intoxicating, it’s rocket-fuel. Those snowflakes fussing over how absolute power corrupts absolutely? They’re frightened liars who say that just to keep everybody else in check.

Never mind TED talks and HBR articles, expensive consultants and the droning inanity of ethics and compliance seminars. Ignore the armies of experts touting cultures of integrity, whistleblowing and accountability. Forget all the best practices for creating human firewalls, fortifying perimeter defenses and mitigating insider threat risks. It’s all worthless, a huge waste of time and money.

Do you know why?

You have a superpower no other leader can ever acquire. And no institution can combat.

Indifference.

It’s as simple as that. You. Don’t. Care.

Former President Donald Trump speaks at a rally at the Charleston Civic Center on August 21, 2018 in Charleston, West Virginia. (Photo by Spencer Platt/Getty Images)

Former President Donald Trump speaks at a rally at the Charleston Civic Center on August 21, 2018 in Charleston, West Virginia. (Photo by Spencer Platt/Getty Images)

Integrity, morals, honesty. These are straightjackets. Cost centers. What you bring to your leadership is a truly unmatchable competitive advantage: shameless, utterly unrepentant sociopathy. You are unbothered by guilt, unperturbed by pro-social responsibility, unrestrained by care or respect for others or any harms that befall them.

All those law-abiding bosses are up at night worrying, replaying the tapes in their head about what’s ok; ruminating about their offenses and shortcomings; castigating themselves. For you, everything is simple: you see what you want and you take it.

So go. Be greedy. Be cruel. Lie, cheat, steal. Blame others. Mock your critics. Shame the naysayers and scam your shills. Gas-light and abuse people long and hard enough and eventually you’ll break them. They’ll beg to serve you and willingly sacrifice themselves to your needs.

Photo of sculpture of former US President Zachary Taylor in the United States Capitol Building splattered with human blood following the seditious insurrection by Trump supporters on Jan 6, 2021. Photo by Katherine Frey for The Washington Post

Photo of sculpture of former US President Zachary Taylor in the United States Capitol Building splattered with human blood following the seditious insurrection by Trump supporters on Jan 6, 2021. Photo by Katherine Frey for The Washington Post

It should be obvious this is satire. It’s not intended just to be clever or entertaining. There are several deliberate aims.

One is to critique the how-to-be-the-best-leader genre. Despite its popularity, it’s mostly unhelpful to leaders and organizations, and perpetuates false illusions about leadership and leadership development. It enables people in positions of responsibility and influence, as well as those who support them, to avoid addressing a host of challenging leadership issues. Chief among them is understanding leaders as complex individuals, not just as a role and function; and looking at leadership capacities, strengths and weaknesses as a non-linear developmental process shaped by life experience and context, not just a defined set of hard skills to be learned and practiced.

Another is to interrogate the close proximity and overlaps between wonderful and horrible leadership. Presenting a roster of disturbing ingredients, attributes and behaviors as positive and aspirational can illustrate in the opposite the primary characteristics, traits and skills actually needed to be a principled, ethical leader.

The United States, for generations a paragon of civil democracy, has just come through—is still not yet through—a period of brutality, abuses of power, the normalization of xenophobic dehumanization, near-genocidal inhumanity, and fraud, corruption and kleptocratic despotism on a mass scale. Millions of people are passionately enthralled in the cult of a malignant sociopath and have been subsumed into violent conspiratorial delusion. Large numbers of elected officials and lawmakers have rejected and continue to dismiss not only their sworn oaths of duty and office but soberly disavow science, shared understandings of objective truth, and the rule of law.

As a citizen, a father, and a professional whose work focuses on moral leadership and helping organizations better understand and mitigate malfeasance, it would be impossible for me not to address these issues.

This is an initial entry and will be elaborated further in future articles. Stay tuned.


This post was originally published on January 27, 2021 on the Forbes Leadership Strategy Channel


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