Lessons in Strategy from
Four Great Military Leaders of History

June 23, 2016 © Copyright Glomacs

Lessons in StrategyMany of us have heard of Sun Tzu, Hannibal and Khalid ibn al-Walid but few of us have heard of the ancient Greek, Pagondas. How exactly can an ancient Greek, a Chinaman, a North African and an Arab help us in the 21st Century? Well, all of these famous military leaders have something valuable to teach us regarding business strategy today. 

Whilst most business is a civilised activity that creates value, it does have at least two things in common with its military counterpart: it is intensely competitive and demands the design and implementation of highly effective strategies. Whether you operate in the private or the public sector there is always a competitor or possible alternative to your product or service offering. 


Strategy on the battlefield (from ancient Greek word Strategia meaning army generalship), as we now understand the term, did not appear until the 5th Century BCE. Up until then armies would simply meet face to face and attack each other with swords, spears and other weapons until exhaustion forced one side to retreat or be killed. Numerical superiority was invariably the deciding factor. 

However, in 424BCE at the Battle of Delium, 25 miles north of the modern day city of Athens in Greece, a general named Pagondas had his army adopt a radically new form of combat as they fought against an army from Athens. 

15,000 Athenian troops marched out to the valley near Delium but they turned back after their supporting troops from other city states failed to appear. Rather than allow the Athenians to flee, Pagondas urged his Boeotian forces to pursue and attack them because he knew they would soon return to kill, capture and enslave them. This was the first use of the principles of ‘forward defence’ (or ‘preclusive defence’) and ‘pre-emptive attack’, i.e. neutralising an external threat before it can do any harm or striking an enemy that poses a long-term threat rather than an immediate threat. 

In addition, and at a crucial moment when his infantry on the left flank tired, Pagondas ordered fresh companies of his Theban cavalry that had been held in reserve to attack the Athenians. This was the first recorded use of dedicated reserves joining an attack. As a result, the Athenians panicked and fled to a fort in nearby Delium. After a siege that lasted two weeks the Athenians forced them out by using history’s first recorded instance of a flame thrower. The Athenian’s never attempted to capture this part of Greece again. 

For the first time in army generalship, Pagondas chose to monitor the battle from a distance and direct his troops, rather than taking part in the fighting at the front of the army. 

As a result, the Battle of Delium holds a key role in the development of early Western military strategy and also proved that surprise innovations can often turn the tide of an evenly matched struggle.

Strategic lessons: 

  •  Have a clear outcome, display strategic intent and think in terms of consequences 
  •  Be proactive; even to the point of being pre-emptive 
  •  Monitor the implementation of your strategy carefully and change tactics when necessary 
  •  Display innovation and creativity 

Ask yourself: 

  •  Is your organisation stuck fighting a situation with traditional tactics? 
  •  What ‘forward defence’

Sun Tzu 

At about the same time as Pagondas, the Chinese general Sun Tzu was putting into writing his principles of warfare in what is now known as ‘The Art of War’. This work was probably expanded by others in subsequent centuries and it greatly influenced military thinking in Asia and later the West. 

One of Sun Tzu’s major insights was the recognition of the dynamic and fluid nature of events on the field of battle and the tendency of leaders to become confused in what has subsequently come to be known as ‘the fog of war’. Consequently, leaders and strategists must operate from the most robust information and constantly adapt to the rapidly changing reality. His maxim was that “All plans are temporary”. This has been perpetuated in the military expression that “No plan survives contact with the enemy”. Sun Tzu knew from bitter experience that a plan can become obsolete as soon as it’s designed; tactical and operational flexibility is the key. 

He also stated that deployment of forces depends on objective conditions in the physical environment and the subjective beliefs of the opposition forces in that environment. 

His principles, like Pagondas’, can be applied to warfare, management and diplomacy. Evidence that his principles continue to resonate are the regular adaptations of his ‘The Art of War’ and the fact that Napoleon Bonaparte always travelled with a copy of it. 

Strategic lessons: 

  •  Develop scenarios of alternative situations and have contingent plans for these futures 
  •  Regard strategies as being emergent and adapt your tactics accordingly 
  •  Use the environment to your advantage 
  •  Exploit the psychology of your adversary 

Ask yourself: 

  •  Are you basing your decisions upon a ‘fog’ of outdated plans, assumptions and marketing/customer intelligence?
  •  What aspects of the marketplace or socio-economic environment could you exploit to your advantage?


Hannibal was a North African general from the mighty city of Carthage who harried the Roman Republic from the 3rd to the 2nd Century BCE. He is most famous for taking his fight to the Romans by crossing the two mountain ranges of the Pyrenees and the Alps and the mighty River Rhone with 50,000 infantry, 9,000 cavalry and a number of elephants. His troop numbers reached these levels because of his ability to attract people to his cause on the journey. 

It seems that the Romans were completely unaware of Hannibal’s movements. Furthermore, they never considered he would ‘bypass’ their preferred defences by moving his army over the mountains to attack them in their own homeland. Though numerically outnumbered in the enemy’s homeland, he was victorious against the Romans at the Battle of Cannae in 216BCE thanks to the revolutionary manipulation of his forces. 

Instead of deploying his soldiers in a phalanx to engage the enemy in a frontal assault, Hannibal rapidly reconfigured his forces by causing the centre of his line to withdraw suddenly and, when the Romans surged forward, Hannibal directed his left and right flanks to encircle and destroy the enemy. The Romans were also taken unprepared by Hannibal’s new cavalry tactics. Once Hannibal’s cavalry had repelled the Roman cavalry, his horsemen did not pursue them very far but attacked the rear ranks of the Roman infantry instead, forcing them towards his men. The envelopment of the Romans was complete, and their destruction total. Indeed, more than two millennia later, the German General Von Schlieffen modelled his First World War ‘Schlieffen Plan‘ on Hannibal’s strategy at Cannae as did the German High Command in Second World War for their 1940 ‘Invasion of France’ via the dense and seemingly impenetrable forest of the Ardennes. 

Strategic lessons: 

  •  Show courage and dare to do the unthinkable 
  •  Exploit deception by focusing the opposition’s attention elsewhere 
  •  Live your mission, vision and values and communicate your plan in a compelling manner 
  •  Make use of your distinguishing competencies and inimitable resources 

Ask yourself: 

  •  How could you use your knowledge of your competitor’s habits and weaknesses to outsmart them? 
  •  How could you challenge regular thinking and outmanoeuvre your competitors whilst they are enjoying an inappropriate feeling of confidence and complacency? 

Khalid ibn al-Walid 

Khalid ibn al-Walid, who lived in the 7th Century CE, was a companion to the Prophet Muhammad, Peace Be Upon Him, and the greatest of Islam’s military leaders. He is known for the incredible range and variety of the military strategies he designed and their determined implementation. It was under his leadership that the Arabian peninsula, for the first time in history, was united under a single political entity, the Caliphate. Indeed, these early Arab conquests are astonishing and without precedent. Never before had nomadic peoples waged such a successful wave of conquests over such a vast territory. Tradition records that he was victorious in over a hundred battles against the numerically superior armies of Rome, Byzantium and the Persians. 

One of the characteristics of Khalid ibn al-Walid was the speed of his military operations. He would move his entire army at the speed of a single rider. He was a great exponent of rapid and disruptive guerrilla tactics that demoralised the enemy. This ‘bias to action’, together with very well disciplined troops, invariably stood him in good stead. 

Modern military theorists now consider Khalid ibn al-Walid to be a chief proponent of military ‘Operational Art’, i.e. the superlative design, planning and conduct of military operations. It was, in particular, his ability to command, motivate and lead from the front that endeared him to his men and produced fear in his enemies. 

Strategic lessons: 

  •  Be proactive, display a ‘bias to action’ and take advantage of the ‘first mover advantage’ 
  •  Use your own and your customer’s faith, beliefs and convictions to supercharge your efforts 
  •  Display situational awareness and respond with tactical flexibility 
  •  Protect and develop your organisation’s reputation, good name and honour 

Ask yourself: 

  •  What allies could you collaborate with? 
  •  Are you spending too much time planning and not enough taking action?

The Five Main Strategies that Emerged 

The above and other great military campaigns of history suggest that there are five main classes of strategy that can be used against an enemy: direct, indirect, envelopment, bypass and guerrilla. All can be greatly enhanced by the application of ‘Force Multipliers’, i.e. unique capabilities your side possesses that supercharge or multiply your effectiveness. 


Direct attacks, as illustrated by the Athenians at the Battle of Delium, rarely work as the initial advantage is always with the well-entrenched defender. The attacker will always sustain enormous losses. Even if successful, the means and will to follow through must be factored in and assured. 5 


Indirect attacks, as illustrated by Pagondas, exploit a weakness in the defender’s position whilst usually using a secondary attack to distract them. It applies the principle of ‘concentration of force’ to overwhelm part of the defender’s position. 


Envelopment attacks, as illustrated by Hannibal, start with a primary attack that distracts the enemy. This is quickly followed up by the enveloping or pincer manoeuvre that contains, directs and destroys the enemy. 


Bypass attacks, as illustrated by Hannibal, allows the attacker to avoid the strength and preparedness of the enemy by adopting a completely unexpected approach. It also frequently allows new territory and resources to be gained on the journey. 


Guerrilla tactics, as illustrated Khalid ibn al-Walid, used as part of an overall strategy have the effect of demoralising, disorienting, disrupting (especially supplies), distracting and ultimately creating enemy attrition. 


The ability to think strategically and design and implement highly effective strategic plans is an essential requirement for leaders. By learning about the campaigns of the great leaders of the past and by mastering new and proven contemporary planning models and techniques you will ensure that your department or company remains relevant, highly competitive and world class. 

By further developing your strategic planning skills you will see how these ancient strategies ultimately gave rise to the cost leadership, differentiation and focus strategies employed by great leaders today. These powerful approaches will help you to deliberately and confidently either expand, stabilise or retrench your activities in today’s increasingly unpredictable and volatile world.

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