After 500 Years, Why Does Machiavelli Still Hold Such Sway? Relative morality is usually considered a bad thing-except if it gets results

Posted: January 27, 2014

James O’Toole is a senior fellow in business ethics at Santa Clara University’s Markkula Center for Applied Ethics and the author of 17 books, including The Executive’s Compass and Leading Change.

After 500 Years, Why Does Machiavelli Still Hold Such Sway?

The past few months have seen a flurry of celebrations for the 500th anniversary of Niccolò Machiavelli’s classic leadership “how to” text, The Prince. It may be five centuries old, but The Prince remains one of the most quoted leadership tomes of all times. The reason for its persistent popularity is clear: “Big Mac” was an unabashed realist. His leadership theory is based on the premise that most people are bad. Thus, his advice to leaders seeking to gain and maintain power: “Learn how not to be good, and to use this knowledge and not use it, according to the necessity of the case.”
The secret, then, is for leaders to manipulate followers, telling them what they want to hear by playing on their vanity, cupidity, and other weaknesses. In particular, Machiavelli counsels leaders to be hypocrites with “nothing coming out of their mouths” but pities about “mercy, faith, integrity, humanity, and religion” while at the same time being prepared to betray those who buy the act. To buttress the argument, he cites examples of successful leaders “who have had little regard for good faith, and have been able by astuteness to confuse men’s brains, and who have ultimately overcome [other leaders] who have made loyalty their foundation.”
Note that Machiavelli doesn’t say leaders should always lie or be bad. Instead, he asserts that successful leaders need the ability to read people, size up changing situations, and adjust their actions accordingly—in effect, doing whatever it takes to realize their ends. And, if being virtuous works under some conditions, then what the hell, leaders should do that, too!
In the realm of statecraft, Machiavelli’s theory goes under the name of “realism” and been practiced successfully over the centuries by such masters as Prussian Chancellor Otto von Bismarck and former Secretary of State Henry Kissinger(whose 1994 book, Diplomacy, stands as the authoritative word on realism). In the management arena, Machiavellianism is the basis of “situational” or “contingency” leadership, the dominant theory taught in business schools today.
That theory is widely embraced, because researchers have failed—despite years of effort—to identify the one or two things that all successful leaders always do. In the absence of such universal principles, scholars conclude that successful leaders must, as Machiavelli counseled do “whatever it takes to achieve their ends, given the conditions they face.” That line of reasoning may be a bit circuitous (and fatuous), but it’s devilishly hard to refute!
Yet, Machiavellianism has drawbacks. As such early critics as Shakespeare identified, situational leadership is amoral and, hence, its practitioners untrustworthy. Even the most ardent realists find the amoral, expedient aspects of situational leadership to be off-putting; yet, when push comes to shove, they fall back on the conclusion that Big Mac was right: It all depends.
Because self-awareness is useful in the business world, over the decades I have administered a little test to help managers clarify their own personal values with regard to situational leadership. I’ve asked more than 1,000 executives and MBA students to review two factual business cases. The first deals with a successful CEO who was always virtuous, even when it wasn’t in his self-interest. He believed that all his followers were always entitled to respect, honesty, and the right to be heard, even when his company was losing money. The second case describes the behavior of a famous CEO who admitted abusing, humiliating, and publicly mocking direct reports who dared to disagree with him. Then, when the situation changed, he consciously altered his behavior to come across as a sensitive mentor and coach. He also said he would not hesitate to change back to being abusive, “if that’s what the situation required.”
In the 60 seminars where I assigned those cases, only about a third of the participants said they would be willing to model their own leadership after the behavior of the first CEO. Despite the fact that he was successful, and no matter how much they claimed to admire him, they argued the only way to succeed in the “real” organizational world was to accept that, now and then, a little Machiavellianism was necessary to succeed as a leader.
Do you agree? Here’s a short version of my Original Big Mac Test to help you decide where you come out. How many of the following statements do you agree with?
• It’s naive or idealistic to believe that leaders can always behave virtuously.
• Leaders have to compromise principles here and there if they are to succeed.
• There are no moral imperatives in the real world of organizations. (All business ethics are situational.)
• Any leader who completely trusts others is asking for trouble.
• It’s unwise to tell followers the real reason you did something, unless it’s useful to you to do so.
• It’s necessary for leaders to occasionally treat people as means to the higher end of achieving their own goals.
• Leaders don’t owe followers trust because followers will turn on them if it’s in their self-interest.
If you agreed with all, or most, of these statements, count yourself a member of the Machiavellian majority. But I wouldn’t be too proud of it.


About bambooinnovator
Kee Koon Boon (“KB”) is the co-founder and director of HERO Investment Management which provides specialized fund management and investment advisory services to the ARCHEA Asia HERO Innovators Fund (, the only Asian SMID-cap tech-focused fund in the industry. KB is an internationally featured investor rooted in the principles of value investing for over a decade as a fund manager and analyst in the Asian capital markets who started his career at a boutique hedge fund in Singapore where he was with the firm since 2002 and was also part of the core investment committee in significantly outperforming the index in the 10-year-plus-old flagship Asian fund. He was also the portfolio manager for Asia-Pacific equities at Korea’s largest mutual fund company. Prior to setting up the H.E.R.O. Innovators Fund, KB was the Chief Investment Officer & CEO of a Singapore Registered Fund Management Company (RFMC) where he is responsible for listed Asian equity investments. KB had taught accounting at the Singapore Management University (SMU) as a faculty member and also pioneered the 15-week course on Accounting Fraud in Asia as an official module at SMU. KB remains grateful and honored to be invited by Singapore’s financial regulator Monetary Authority of Singapore (MAS) to present to their top management team about implementing a world’s first fact-based forward-looking fraud detection framework to bring about benefits for the capital markets in Singapore and for the public and investment community. KB also served the community in sharing his insights in writing articles about value investing and corporate governance in the media that include Business Times, Straits Times, Jakarta Post, Manual of Ideas, Investopedia, TedXWallStreet. He had also presented in top investment, banking and finance conferences in America, Italy, Sydney, Cape Town, HK, China. He has trained CEOs, entrepreneurs, CFOs, management executives in business strategy & business model innovation in Singapore, HK and China.

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