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To better understand President Trump’s strategic leadership, it is useful to reflect on some of the historical writings and ideas of Carl von Clausewitz and Niccolò Machiavelli, two great thinkers on political philosophy and strategy, as well as the leadership qualities of some of the greatest American presidents. In more recent times, we will also explore the insights of the founding leader of Singapore, the late Prime Minister Lee Kuan Yew, who was well known and respected for his strategic leadership. In a brief span of fifty years, he transformed Singapore from a small trading port to one of the most advanced countries in the world. As we will soon discover, good strategic leaders also have visionary strategic plans.  

Leadership Research

A large part of my career involved researching on the nebulous subject of leadership. It started with looking at the styles of leaders in history, reviewing leadership theories and analysing the leadership models of the Singapore Armed Forces, the U.S. Army, and Canada. The research then delved deep into the categorization of leadership by types, styles and levels and involved a leadership evaluation system, like the 360-degree method pioneered by John C. Maxwell.

Despite the in-depth research, it was almost impossible to identify any one theory that could consistently define and explain a concept or trait of leadership that could be applied to most situations. There were as many theories as there were leadership styles. Each environment had its own ‘favorite’ qualities or values. In addition to the countless theories, the lack of a consistent and overarching leadership theory could also be attributed to the fact that great leaders thrived with their characteristics and actions during a phenomenon happening at that particular, unique moment in time. Certain leaders, with certain qualities, were just at the right place and at the right time to address those specific concerns or needs of their followers.

The 1930s saw the introduction of  ‘great man’ theories that suggested that good leaders are essentially born to lead. The theory presented that leaders are born with certain qualities like charisma, confidence, intelligence and social skills that naturally make them good leaders, implying that leadership could not be learned. Then came the trait theories, that suggested that people could inherit certain traits like self-confidence and courage, which are shared by many great leaders.

On the other hand, the contingency theories suggested that the environment determines the style of leadership best suited for a particular situation. Good leaders are expected to strike the right balance between the needs of the specific situation and to apply the appropriate leadership style accordingly. Situational theories suggest that a specific situation dictates whether an autocratic, democratic or collaborative leadership style should be adopted. Behavioral theories argue that it is the actions of the leaders rather than any innate qualities that determine the success of their leadership and therefore people can, in fact, learn to become good leaders. Transaction theories suggest that an ideal leader is one who takes into account the inputs of others. Some examples of transactional theories include participative leadership and management theories.

Transformational leadership theories focus on the connection between the leaders and followers, where leaders motivate and inspire people by setting clear goals and expectations for achieving higher performance and providing support and recognition to bring out their full potential.

Based on most of these theories, the Singapore and U.S Armed Forces leadership models strive to develop core leadership traits, styles and skills to churn out effective leaders. The U.S. Army’s model in particular places emphasis on certain character values and attributes, as well as the development of critical skills and behaviors.

Similarly, the Singapore Armed Forces leadership framework[1] also places emphasis on values, competencies, styles and self-awareness and 14 skills including critical thinking, ethical reasoning, planning, decision-making, communications, teambuilding, and personal mastery.

There are also many leadership assessment tools that inevitably advocate for or codify certain leadership qualities or styles that could help identify good leaders. Some of the more popular assessment tools include DiSC (Dominance, Influence, Steadiness, Compliance), Myer Briggs, and 360.

Having explored all the various theories, models and assessment tools, it became apparent to me that having a long list of qualities or styles to develop successful leaders would be of little use to organizations. In larger institutions, it was thought that the fundamental concept of leadership could ultimately be narrowed down to the level of trust followers place on their leaders. The challenge for junior leaders was how to earn the trust of their workers or followers. Unfortunately, the seemingly simple concept of trust proved inadequate, leading to further wide-ranging and diverse views on why people trust their leaders.

My analysis ultimately led me to identify a small number of higher-order qualities consistently found in most successful leaders and that could encompass most of the critical abilities needed for success. From my research, I found, rather unsurprisingly, that the leadership qualities identified by Carl von Clausewitz continue to ring true and feature significantly in most situational models and research studies. These qualities are essentially the following: courage, determination, self-control, coup de’oeil and a mind that is inquisitive, comprehensive and calm.  

In the words of Clausewitz:

“War is the realm of danger; therefore courage is the soldier’s first requirement”

“Two qualities are indispensable: first, an intellect that, even in the darkest hour, retains some glimmerings of the inner light which leads to truth; and second, the courage to follow this faint light wherever it may lead.”

“We repeat again: strength of character does not consist solely in having powerful feelings, but in maintaining one’s balance in spite of them. Even with the violence of emotion, judgment and principle must still function like a ship’s compass, which records the slightest variations however rough the sea.”

 “If the leader is filled with high ambition and if he pursues his aims with audacity and strength of will, he will reach them in spite of all obstacles.”

“…as man under pressure tends to give in to physical and intellectual weakness, only great strength of will can lead to the objective.”

‘If we then ask what sort of mind is likeliest to display the qualities of military genius, experience and observation will both tell us that it is the inquiring rather than the creative mind, the comprehensive rather than the specialized approach, the calm rather than the excitable head to which in war we would choose to entrust the fate of our brothers and our children, and the safety and honor of our country.’

Coup de oeil is the ” quick recognition of a truth that the mind would ordinarily miss or would perceive only after long study and reflection”

A significant takeaway is that unlike many leadership theories suggesting that leaders are born with the primary qualities, Clausewitz believed that leaders, and military genius in particular, could be developed through realistic training and experience.

Carl von Clausewitz

strategic leadership

Carl von Clausewitz was a Prussian military theorist in the late 1700s who studied and wrote on war and strategy. He envisioned a strong strategic leader as one who was bold, courageous and determined, who possessed coup d’œil or the ability to understand a situation with a quick glance, and who has a calm and comprehensive disposition to make the right strategic decisions at an opportune time.

Clausewitz advocated a swift and decisive strategy of attacking an opponent’s strength or their center of gravity, with maximum force. “Center of gravity” here refers to attributes of the opponents which, when defeated, would seriously jeopardize their chances of winning. His ideas were used with great success by the Germans through their blitzkrieg tactics during the Second World War. This ideology continues to guides certain aspects of the strategic and operational planning of the U.S. Army and Air Force today.

Niccolò Machiavelli


Niccolò Machiavelli, a 15th-century Italian philosopher often referred to as the father of modern political science, advocated for a certain degree of political ruthlessness to govern conquered states or control human nature. The realities of political affairs and public life require that rulers be strong and willing to use coercive force to ensure compliance. According to him, one needs to have a flexible disposition in politics regarding good and evil approaches to resolving an issue based on the circumstances. He argued for politics to have its own set of rules. Machiavelli’s ideas have helped shape the development of some modern political theories and the American Constitution as well.

Machiavelli had a deep understanding of human nature. He viewed humans as trustworthy during prosperous times but understood that they could quickly become selfish and deceitful during difficult times. Humans may be loyal when they receive favors, but such goodwill is never absolute. They respond more consistently to fear than to love.

“Love endures by a bond which men, being scoundrels, may break whenever it serves their advantage to do so; but fear is supported by the dread of pain, which is ever-present.”

Machiavelli argued that for princes or political leaders to remain in power, they need to be ruthless enough to be feared and kind enough to not be hated. Both ruthlessness and kindness should be viewed as a means to an end and not in terms of their intrinsic moral values. The application must always be based on benefitting the state and staying in power. He advocated for political leaders to maintain the goodwill of the people and avoid being hated, to undertake great projects that will enhance their reputation, and to choose wise advisors while avoiding flatterers.

The American Republic

It is not surprising that the founders of the American republic were familiar with the Machiavellian school of thought. In the development of the American Constitution, Machiavelli’s writings were included as references. The founding fathers designed the republic to carefully balance powers given to the executive, judicial, legislative branches, as well as to the people, taking into account the nature of self-interest in human beings and the possibility that the government could also abuse its powers or become corrupt.

“Upon this, a question arises: whether it be better to be loved than feared or feared than loved? It may be answered that one should wish to be both, but, because it is difficult to unite them in one person, is much safer to be feared than loved, when, of the two, either must be dispensed with.”

 – The Prince by Machiavelli

Machiavelli’s Discourses on Livy, written in the early 15th century, was used to advise the need for civic virtue in a republic to ensure that the public space of all citizens was preserved even at the cost of personal interest.

“The Citizens in a Republic who attempt an enterprise either in favor of Liberty or in favor of Tyranny, ought to consider the condition of things, and judge the difficulty of the enterprise; for it is as difficult and dangerous to want to make a people free who want to live in servitude, as to want to make a people slave who want to live free.”

– Discourses on Livy by Machiavelli

Abraham Lincoln

Abraham Lincoln is often considered one of the greatest presidents of the United States. Not only did he persevere through a violent and costly Civil War, but he also enacted the Emancipation Proclamation to abolish slavery, gave the Black population the right to serve in the Army and Navy of the Union, and successfully reunited the Union after the war. His approach towards reunification did not involve imposing the Emancipation Proclamation conditions or other retributions against the defeated Confederate States. Instead, he focused on prioritizing the reunification process. His now-famous Gettysburg Address accurately captured the spirit of the times where he dedicated the sacrifices during the war to the founding principles of liberty, equality for all and a “government of the people, by the people and for the people”.

It is difficult to appreciate the heavy burden that weighed on Lincoln when he took the decision to push ahead with a war against his fellow Americans in the South and which would eventually result in a total death toll of 620,000.  The reasons often cited for the American Civil War are dissent over ]]states versus federal rights, economic disparities, the abolition of slavery, the election of Abraham Lincoln as president and The Battle of Sumter. In a way, they are all linked. The differences in the economies of the Northern and Southern States were impacted differently by the abolition of slavery, federal versus states’ rights and the election of Lincoln. It resulted in the secession of South Carolina and several other states, and consequently the Battle of Sumter.

Lincoln today is most remembered for his honesty, humility, courage, justice, and grace. At the core of his belief was that all people deserved equal treatment and to stand firm for what is right.

Franklin D. Roosevelt

Franklin Delano Roosevelt is yet another U.S. president who will always be remembered as one of the greatest U.S. presidents in modern times. As the longest-serving president from 1933 to 1945, he not only led the country out of the Great Depression but also successfully defeated the Axis powers during the Second World War. His other achievements include setting up the Federal Deposit Insurance Corporation and the U.S. Social Security System, both of which still exist today.

The Second World War saw unprecedented levels of death and destruction. President Roosevelt faced the daunting task of motivating the American people to sacrifice their livelihoods to support the war effort while also shouldering the responsibility of mobilizing 11 million American soldiers for the cause. A total of 405,000 American soldiers lost their lives.

Roosevelt is most remembered for his innate sense of confidence, willingness to explore every possible solution during the Great Depression, his persistence and perseverance, and a firm belief that everything would eventually work itself out.

Ronald Reagan

President Ronald Reagan, a former Hollywood actor, is largely considered as the most influential president in United States’ history. He is credited for his strong stance against the Soviet Union, ending the Cold War, introducing the Strategic Defense Initiative missile system, heading the largest peacetime economic boom and enforcing strict legislation against drug offenses. In 1984, Reagan won in 49 of the 50 states, a record 525 electoral college votes and 59% of the popular vote.

Ronald Reagan is known for his boldness and courage to go against conventional wisdom or the mood of his times. His presidency helped to revive the indomitable spirit of Americans through sheer toughness and determination. Even during his most trying times, he was able to bounce back with renewed optimism and could also be ‘warmly ruthless’ with anyone who got in his way.

Lee Kuan Yew

In modern times, political leaders and heads of states have sometimes needed to defend their reputation and policies ruthlessly. Singapore’s founding Prime Minister, the late Lee Kuan Yew, often vigorously defended the government’s reputation against false accusations by his political opponents or the media. His political opponents often lost against him and were made to pay substantial amounts in damages, which he then eventually donated to charity.

Realizing the political and economic uncertainties of Singapore’s early years, Prime Minister Lee Kuan Yew often pursued his strategic policies vigorously, without fear or favor. He spoke plainly and truthfully about the hard choices the country faced and often pushed through many of the politically sensitive policies such as the Sedition Act, Group Parliamentary Constituencies, Religious Harmony Act, abolishment of the Privy Council Appeal System, and the controversial public housing quota system. He was a strong advocate of the rule of law to protect the common public space of the citizens. He established the Corrupt Practices Investigation Bureau that had wide-ranging powers to prosecute at all levels of public and private service.

His strong leadership, strategic vision, and determination paid off handsomely; today, Singapore is widely acknowledged as one of the most successful nations in the world. Singapore boasts the best primary and secondary education in the world; according to the 2020 QS World Universities ranking, two of its universities share the spot as top 11th schools globally. The nation also enjoys strategic national reserves of more than $300 billion and, in 2017, had the third-highest GDP per capita in the world. It has one of the most advanced armed forces in the region and is also ranked as the second least corrupt nation in the world.

Lee Kuan Yew was not only a visionary, but also a very determined and demanding leader who was relentless in his pursuit of excellence. Following Singapore’s separation from Malaysia, the country did not have many resources to work with. Lee pushed his team of ministers to continuously seek improvements, expecting a high quality of performance from each of them. He encouraged the adoption of some of the ideas and best practices used around the world to further advance the country. Those working under him inevitably felt a great degree of pressure, as he did not hesitate to remove anyone not meeting his high standards. Lee Kuan Yew had the rare ability to pick good leaders who were able to translate his strategic vision into operational plans. He played the more crucial role of bringing all the individual components together. Scholars from Singapore were sent to the top universities around the world and relayed their knowledge on operational efficiencies back to Singapore through direct communications with Prime Minister Lee. In this way, some of the best practices overseas were quickly injected into the establishment of Singapore’s public service, resulting in an incredibly successful and high-functioning city-state.

Political & Strategic leadership

Having explored forward-looking thinkers and strategists, what are the exact qualities that make for great strategic leaders? Gleaning from their varied experiences and leadership styles, one can argue that a leader should be honest, trustworthy, bold and courageous, determined, decisive, have a visionary and comprehensive mind that is not easily perturbed or defeated, have coup d’oeil and a winning mindset.

While political leaders should possess all the qualities expected of great strategic leaders, they also require a few additional qualities. To be able to win elections, they need to be excellent communicators and campaigners. They must be able to tap into the sentiments of the voters and carefully articulate their vision and policies to win over the trust and confidence of the people. They must not only be able to defeat their political opponents but also protect their own reputation and policies ruthlessly against unscrupulous attacks or smear campaigns. They must possess boundless energy, have the ability to respond to unexpected crises as well as the flexibility to negotiate with their opponents to either build consensus or achieve a compromise.

Strategic Planning

Good strategic leaders develop and implement good strategic plans. A review of the strategic planning literature at most business schools and the Kennedy School of Government, as well as the way in which it is taught, suggests that most public administrations and academic institutions lag behind many multinational corporations and the military in terms of rigor and sophistication in strategic planning.

World-renowned Harvard professor Michael Porter’s generic theory on cost or differentiation business strategies are scope limiting, while McGill professor Henry Mintzberg’s emergent strategy is a caveat for lack of foresight or a more detailed analysis. While game theory is useful in selecting amongst various choices, it is not helpful in developing strategic options. Novel strategic plans often emerge after repeated iterations of the options from the generic to specific and then back to the generic.

There are some institutions within the U.S. military that are well endowed in the mechanics of strategic planning. It is critical that the strategic elements of all the U.S. government agencies become informed by these military institutions so they may better develop and manage their own detailed and comprehensive strategic drawer plans. Appendix 2 shows some possible steps that could be used to implement better strategic planning in the U.S. government as a whole.


Good strategic leaders are trustworthy, courageous, determined, intuitive, comprehensive and decisive. In order to successfully govern, they need, at times, to be ruthless in defending their reputation and policies, and must be prepared to use coercive force when necessary.

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[1] https://www.researchgate.net/publication/266535593_SAF_LEADERSHIP_24-7_A_Framework_for_Leadership_Development_in_the_Emerging_Environment