What Shakespeare, Ecclesiastes, Machiavelli, Darwin, and Hammurabi have to say about business leadership

When studying leadership we imply its existence and general success, whether by continuity or by repetition in history. These coordinates do not include short-term success. The leadership lessons that can be drawn from a single victory or a profitable quarter are hollow.

Therefore, continuity and repetition in history, over decades and generations.

However, inquires into leadership often do not concern such a foundation, or Darwinian approach, and rather speak of what is leadership as an advertisement for the author’s own palate, often while ignoring a subconscious inclusion of their personal concept of good.

There is no obligation to address the ought while assessing the is.

This inquiry is not an attempt to define good or bad leadership, moral or immoral leadership, or any other conscious or subconscious qualifiers.

My taxonomy on leadership based upon what some of the ancients have to say on the topic.

Darwin, Machiavelli, and Ecclesiastes 3

The first principle is the principle of constant evolution. This is the rule that serves as an exception to my forthcoming taxonomy – my taxonomy is not fixed. It comes with many flavors and varieties, though they all collapse into the same philosophical categories. 

Machiavelli describes the three forms of Government (Monarchy, Aristocracy, and Democracy) as all being individually good, yet all containing the seeds for their own undoing. 

“For a Monarchy readily becomes a Tyranny, an Aristocracy an Oligarchy, while a Democracy tends to degenerate into Anarchy. So that if the founder of a State should establish any one of these three forms of Government, he establishes it for a short time only, since no precaution he may take can prevent it from sliding into its contrary, by reason of the close resemblance which, in this case, the virtue bears to the vice.”

Niccolo Machiavelli. Discourses on the First Decade of Titus Livius. Ch II.

This idea is not exclusive to States, or leadership, or the early Renaissance, but comes from a much older tradition – The Bible. Written by thousands of years of oral tradition and witness to the rise and fall of nations and leaders.

“To every thing there is a season, and a time to every purpose under the heaven: a time to be born, and a time to die; a time to plant, and a time to pluck up that which is planted… a time of war, and a time of peace.”

Ecclesiastes 3:1-8. King James Bible.

Alongside my taxonomy, which, like all categories, has a character of rigidity and determinism, lies this principle of evolution and cyclic change.

Although, within all such independent of forms of Government (or styles of leadership), there exist categories and foundational concepts (my taxonomy) that are so tightly correlated with notions of leadership, that without them, all our moralism’s pass as mere well-wishing, and all our vision statements pass as mere poetry.

The seven factors of leadership


Leadership is power. This is its foundation, from which all strategies, good or bad, flow. Without power, you cannot lead. This is so because power gives you the capacity to act.

Ought implies can, as “the action to which the “ought” applies must indeed be possible under natural conditions.”

For any ascribed ought of leadership (like Plato’s love of Justice), there requires the capacity to perform it, maintain it, create it, and enforce it. 

Yet power is transitive. It is not a thing in and of itself. But a meta-element, and thus must be understood, in the context of leadership, by the elements that form it and are wielded by it. These are:

  • Legitimacy and Good Counsel
  • Being Above the People and Of the People
  • and War and Peace.

Legitimacy and Good Counsel

In Machiavelli’s cyclic history in forms of Government (Monarchy, Aristocracy, and Democracy), we see different styles of leadership, yet all are different claims to legitimacy.

The King is anointed by God, and therefore legitimate; sometimes the King is legitimate through name, heritage, and title. This claim to leadership – and challenge – was a central point in Shakespeare’s histories. Henry Bolingbroke usurped the crown from Richard II. Though Richard II was deficient in good counsel, was hardly a man of the people, and led his kingdom into costly and non-power-enhancing war, he had a strong case for his legitimacy. Henry did not. This plagued Henry’s reign. While Richard would score quite poorly in my leadership taxonomy, Henry IV was not without his deficiencies. This would not be corrected until Henry V, who, having the opportunity to advance his legitimacy, pushed for and distinguished himself in foreign wars.

This can be applied to business in situations where a poor leader (yet, especially one who has legitimacy) is fired, and replaced by someone who corrects for their faults but lacks legitimacy.

Papa Johns is a great example. In 2018, John Schnatter very quickly gained a reputation as a racist due to recorded and unambiguous statements. He lost power – he was neither above the people, nor of the people; he obviously avoided good counsel; he removed the possibility of peace and started a pointless and unwinnable war.

But what of his replacements? His Monarchy passed to an Aristocracy – the board of directors. This aristocracy uplifted a diversity council, as well as NBA Hall of Famer, Shaquille O’Neal. These choices made up for many of Mr. Schnatter’s failings, but they lacked the legitimacy that he had. Schnatter started a pizza company from zero and led it to a multi-million dollar enterprise. While a diversity council and Shaq have nothing to do with pizza restaurants whatsoever. 

But legitimacy comes by more ways than God and title, but through meritocracy. We move from Monarchy to Aristocracy on Machiavelli’s cycle.

We are very much in this period today (in the US and Europe, in general).

The claim for aristocratic legitimacy is on the basis of talent – they know what is best for the people, or at least can do better than the current monarch.

This was Plato’s claim for the Philosopher King, and the guardians. This is also the claim made by many American institutions, President Xi of China, and the European Central bank, to name a few. Think of think tanks, the media, the Department(s) of _________, epidemiologists, economists, people with fancy degrees, etc.

Aristocracies begin by creating systems and establishing norms that make the people better off (like social security, peacekeeping, and international trade), and evolve into an oligarchy that uses their position for their own benefit (see “it’s a big club and you ain’t in it” bit by George Carlin).

Plato concludes as such in The Republic, and it could well be argued that many politicians today have gone down the same route, given the amount of wealth they acquire while serving in public office.

We finally pass to legitimacy through democracy – a mandate from the people. Legitimacy is not determined by God, or title, or name, or ability, but by a majority preference.

The importance of legitimacy is as important today as in history. Take the 2016 US election as an example – the central charge is against the legitimacy of the President. “Not my President” is a charge against legitimacy.

The source cited is our electoral system and the secondary role of the popular vote. While populism offers a clear answer for what it calls legitimate, it offers little philosophy for what it calls good, and therefore runs its course quickly: “For, suddenly, liberty passed into license, wherein neither private worth nor public authority was respected, but, everyone living as he liked, a thousand wrongs were done daily.” (Machiavelli)

Good Counsel provides an opportunity for leaders of different flavors to balance their weaknesses and check their extremities.

Although, good counsel is not an absolute good, and can undermine the legitimacy of leaders.

They can undermine it in two ways. The first is through bad counsel – especially flattery. The greatest enemy to a leader, through their advisors, is flattery. 

By God, I cannot flatter: I do defy

The tongues of soothers; but a braver place

In my heart’s love, hath no man than yourself;

Nay, task me to my word; approve me, lord.

William Shakespeare, Henry IV, Part I

What drink’st thou oft, instead of homage sweet,

But poison’d flattery? 

William Shakespeare, Henry V

They do abuse the king that flatter him:

For flattery is the bellows blows up sin.

William Shakespeare, Pericles, Prince of Tyre 

The second way is through too good of counsel, from noble, talented, ambitious, and perhaps even legitimate, advisors.

If your advisors (or staff) are better than you, why are you in charge? If you are a Monarch, and anointed by God or through birth, perhaps these advisors will pose no challenge. But if you are an aristocrat or populist, your power will be undermined through better-skilled advisors, as aristocracies form through talent, and populists place little premium on loyalty.

An owner-founder is like a Monarch. They can handle talented, ambitious staff. This serves them, as no Monarch, no matter how talented, can ever be more than one person… So long as they reward these staff members according to their ability.

In other leadership situations, it’s not so stable. A CEO is appointed by a board. This is an aristocracy. Managers are appointed by CEOs/Directors. And so on.

Everyone has been in a situation where they feel that “they know more than their supervisor.”

What do you do? You go for their job, every day. All your actions are a threat to this supervisor.

The charge we are making in this case is a charge against legitimacy. If we are better (more knowledgable, skilled, productive), than our supervisor in an aristocratic system; or better (more popular, likable), in a democratic system, then we do not believe our leaders are legitimate.

Most companies run several systems at once. CEOs are Monarchs, Directors/Managers are Aristocrats, and teams form democratically.

Above the People and Of the People

If a leader is not above the people, then on what basis are they in-charge?

If a leader is not of the people, then how can they be understood by the people? Or how can they understand the people?

It seems the multitude strongly prefer (1) a type of hero, and (2) a member of their tribe, to lead them. This isn’t a contradiction, it’s a balance that must be struck in order for leaders to advance and maintain their power.

Shakespeare’s play Julius Caesar offers strong insight into this duality. After Caesar’s assassination, and Brutus’ speech to the people declaring Caesar ambitious and therefore a threat to the prosperity and liberty of Rome, Marc Antony delivers an oration, that, in a few sentences, outlines this core leadership factor.

“He hath brought many captives home to Rome

Whose ransoms did the general coffers fill:

Did this in Caesar seem ambitious?

When that the poor have cried, Caesar hath wept:

Ambition should be made of sterner stuff.”

William Shakespeare. Julius Caesar. Act III Scene II.

Caesar was above the people, by bringing unparalleled wealth and prosperity to Rome, and its people. He was also of the people, in that he was attuned to their needs, and the needs of the lowest among them, and was responsive to them.

This duality is represented in mythology as well. Mesopotamian and Egyptian myths synthesize the leadership structure (or “the Great Father”) in a single element: attention. Leaders must pay attention, in order to understand their people and to be capable of solving their problems (as well as fend off enemies), and leaders lose their power when they fail to pay attention or become willfully blind. The greatest of these stories is the Enûma Eliš, the Babylonian creation myth, which centers around the supremacy of the God Marduk.

This ancient creation myth has more to do with the philosophy of leadership, and my taxonomy, than perhaps anything. The Enûma Eliš was a manuscript for Sumerian leaders for thousands of years. The story was embedded into the culture, so much so that leaders were bid to perform a yearly ceremony in the style of Marduk, and to tell their people all the ways in which they failed to live up to Marduk’s example. These traditions and this mythology significantly influenced Egyptian and Greek mythologies, and by extension, philosophies and forms of government. Marduk is mentioned at the beginning of Hammurabi’s Code and, transversely, the Enûma Eliš was the most significant philosophical text in the time of Hammurabi’s rule and law-giving. 

“When Marduk sent me to rule over men, to give the protection of right to the land, I did right and righteousness in . . . , and brought about the well-being of the oppressed.”

The Code of Hammurabi

The final text that best highlights the above the people and of the people dichotomy is the aforementioned Code of Hammurabi. You must be above the people to establish and enforce a unified law; you must, within that law, make the risk that the people hold equal, between rich and poor, ruler and ruled.

The Code, by its establishment and legacy, is evidence of its power and validates Hammurabi’s above the people credentials. But the law itself provides evidence that makes his rule of the people as well. There are four laws in particular that testify to this.

  • Code #6: If any one steal the property of a temple or of the court, he shall be put to death, and also the one who receives the stolen thing from him shall be put to death.
  • Code #48: If any one owe a debt for a loan, and a storm prostrates the grain, or the harvest fail, or the grain does not grow for lack of water; in that year he need not give his creditor any grain, he washes his debt-tablet in water and pays no rent for this year.
  • Code #53: If any one be too lazy to keep his dam in proper condition, and does not so keep it; if then the dam break and all the fields be flooded, then shall he in whose dam the break occurred be sold for money, and the money shall replace the corn which he has caused to be ruined.
  • Code #229: If a builder build a house for some one, and does not construct it properly, and the house which he built fall in and kill its owner, then that builder shall be put to death.

Code 6 recognizes that dishonesty in society is not only through the actions of one bad person, but through the people that allow it.

Code 48 protects people who take short-term risks in the face of out of control circumstances. Imagine this code applied COVID-19. More commonly, this is the contract clause protecting us from liability in the case of “acts of God.”

Code 53 protects us from the ineptitude of others; while also highly incentivizing non-lazy behavior in matters that could be consequential for others.

Code 229 (my personal favorite), holds people responsible for the material impact of their work. Imagine this level of responsibility in the 2008 housing crisis. Moreover, it establishes a sense of equality of risk under the law.

Risk cannot be avoided under this framework. The common people hold risk – if they are lazy, criminal, or simply produce poor work, they lose, but if the builders and makers (the merchant class), and the wealthy and elite of society, if they do not accept the same risk, then this is an unjust system and your leadership does not correspond to being of the people.

As a type of modern example, if someone gets voted out of office or loses an election due to poor performance, but then gets hired by a lobbying firm or media outlet and becomes even wealthier than before, the people know that they did not accept any risk. 

The Code of Hammurabi was written to protect the people from predation, and only a ruler that understands their people could devise a law broad enough to speak to their actual concerns and lived experience.

War and Peace

War is not simply characterized by conflict, but by development, change, and opportunity.

Peace is not simply characterized by a lack of conflict, but by stability, continuity, and conservation.

As it was in Ecclesiastes, it has always been: there is a time for war, and a time for peace. Over the lifetime of a leader, too much of one will undermine their power. But during the reign of one leader, from time to time, the levers of war and peace must be manipulated. 

This is so because conflict is (at times) a response to something that is wrong. If something isn’t right, then peace is not the answer. Apply this thinking to sexual harassment allegations. Is “peace” the answer in response to woman after woman coming forward with similar testimony?

“It ought to be remembered that there is nothing more difficult to take in hand, more perilous to conduct, or more uncertain in its success, than to take the lead in the introduction of a new order of things. Because the innovator has for enemies all those who have done well under the old conditions, and lukewarm defenders in those who may do well under the new.”

Niccolo Machiavelli. The Prince. 1513. (W.K. Merriott translation. 2006)

The levers of war are to be used when development, change, and opportunity are needed. If society isn’t growing, if the culture is too stagnant, or if a company becomes set in its ways, a bit of war is the answer.

War, in this sense and by my meaning, does not mean an armed invasion, but a true toppling of the apple cart.

Suppose your team is too comfortable in their job and their tasks – the leader must insert the spirit of competition, and the recognition that jobs are secure by their efforts, not by rights.

In the inverse, and still using our example of “your team,” those overly concerned about change or transition, or too exposed to new developments happening around them, need assurance and a bit of protection. They need to be offered a sense of stability, or shown the continuity that will remain despite all the change.

War and peace also have their own extremities, or seeds of their own demise. Too much war (or rather, too much change, development, and opportunity seeking), undermines its own goals. Nothing can grow in a space of constant change.

Likewise, no foundation can be set beneath something that develops too quickly. And eventually, if you keep seeking opportunities, you will never be able to spend the time assessing and making good on those opportunities.

These are the limitations of war for our taxonomy of leadership.

In peace it is the same. Too much stability leads to decay. Too much continuity and conservation leads to a lack of change or new ideas in such a continuous, closed system. 

It is for this reason that we praise war heroes and peacemakers – and chastise warmongers and cowards.

No leader receives praise for avoiding a war that is on their doorstep, just as no leader continues their reign if they push for a war that is unwinnable, or one that pushes the will, resources, or manpower of their people beyond their capacity.


Leadership without power is nothing, and power is created and maintained by an effective balance of the six other factors:

  • Legitimacy and Good Counsel
  • Being Above the People and Of the People
  • War and Peace.

Leaders must maintain these to a high degree and in relative balance.

While all the virtues and vices of the world could be then listed as contributing or harmful factors in the character of the leader, or their system of rule and leadership, they are circumstantial.

Throughout history, we see a narrative of leadership that continually implies statements of power, and then assessments of a leader’s legitimacy, and the quality of their closest advisors; or a leader’s relationship to their people, mixed with their abilities beyond their people; or a leader’s ability to balance the forces of change with the forces of stability. 

This is my taxonomy of leadership.

All else is a conversation about preferences or circumstances.