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Sun Tzu’s Seven Searching Questions- Revisited


Sun Tzu’s Seven Searching Questions- Revisited

A few months ago, I wrote about the early stages of the conflict in Ukraine through the lens of Sun Tzu’s The Art of War. While it appears likely that the war will carry on into the foreseeable future, enough time has passed for us to make an honest assessment of each side’s relative strengths and the state of the conflict today.

You may recall that in the very first chapter of the Art of War Sun Tzu presents the reader with Seven Searching Questions that should be asked in order to make predictions about which side will win out. This article will revisit each of Sun Tzu’s questions in order to evaluate the accuracy of the initial assessments and consider where we might look for key developments in the coming weeks and months.

The first question that Sun Tzu poses is “Which sovereign is imbued with the moral law?” In a more modern phrasing, Sun Tzu is asking us which side has the greater and more durable morale. 

There is no doubt that Ukrainian nationals, even in the aftermath of a brutal bombing campaign that targeted civilian centers, are far more commited to the conflict than their Russian counterparts. In truth, one of the conflict’s “silver linings” may be the emergence of a newfound Ukrainian nationhood which could be channeled toward combating the corruption that ensnared Ukraine in the past. While there have always been pockets of resistance to Putin’s autocratic governance within Russian society, the “mobilization efforts” that were initiated in September have caused that discontent to spread toward the broader Russian populace. Similarly, Russia’s international support has dwindled as was clearly displayed by the overwhelming rejection of Putin’s  “referendums” in eastern Ukraine at the United Nations.

The larger question surrounding Ukrainian morale may, in fact, come from beyond Ukraine’s borders as partners in Europe may find themselves squeezed between supporting Ukrainian sovereignty or choosing lower gas prices following a series of tense elections and in the midst of a cold winter.

What impact does potentially reduced support have on the morale of the Ukrainian troops?

Sun Tzu’s second question is “Which of the generals have the most ability?” The meaning of this question is just about as obvious as its answer. 

Few topics have received as much attention as the incompetence of Russian leadership through the course of this conflict. The early stages of Russia’s advance were slowed by logistical problems which have only become more severe as the conflict has dragged on. More recently, Russian military officials were duped into a dramatic shift of forces to the southern front which enabled the UA to reclaim a significant amount of territory in the north of their country in mid-September. The Ukranians have exploited the failures of Russian leadership by targeting individual Russian commanders- numerous Russian military officers have been taken out in targeted strikes. This crisis in Russian leadership is amplified by reports that Putin himself has taken on an increasingly large role in military planning- a troubling sign for those with a keen historical memory.

The next question is one of the more straightforward- we are told to ask “With whom lie the advantages of the heaven and the earth?” Sun Tzu reminds us to consider the basics of battlefield terrain.

The Ukranians continue to benefit from their densely forested defensive positions and have made a nightmare of river crossings for any would-be advancing Russian forces. The clear advantage goes to the Ukrainian defenders on this matter, and given the nature of this question, it should be little surprise that little has changed here since our first assessment.

Fourth, Sun Tzu tells us to consider “On which side is discipline most rigorously enforced?” 

Discipline might be more rigorously *enforced* on the Russian side, but even with that in mind there is little doubt that the men and women serving in Ukraine’s defense have behaved in a far more disciplined and orderly way. While there are regular stories of Russian soldiers refusing to carry out war crimes or sabotaging their local commanders, Ukrainian artillery forces have shown themselves capable of autonomous strikes with a deployment time that puts America’s own efforts to shame. 

It is a sad reality that war brings out the worst of people, and both sides of the conflict have allegedly committed numerous war crimes- however the clear advantage in both military and humanitarian discipline lies with the Ukranians. 

Sun Tzu’s fifth question is quite direct, “Which side has the stronger army?” While Putin’s forces retain the advantage in both manpower and equipment, the Ukranians have made novel use of weapon systems and have reduced the impact of Russia’s larger conventional force.

The main strengths of the Russian military, as has been the case since the Second World War, are a large population and heavy artillery- however Putin has struggled to bring both of these factors to bear. The impact of Russia’s large population is muted by the misinformation effect that the war in Ukraine is simply a “special military operation”, and Russian heavy artillery has been slowed by the aforementioned difficult terrain and ineffective leadership.

Ukraine has countered the Russian artillery that has managed to reach the front with tactical nimbleness and an iron chin. The Ukrainian army has deployed light drones, like the Bayraktar, personale sized anti-tank weaponry, like the Javelin, and more recently HIRAS artillery pieces that have greater range and out maneuver their Russian counterparts. It has become a pattern for the United States and other partner nations to supply Ukraine with more advanced weapons at a defensive pacing- but this has not stopped Ukraine’s defenders from using weapons systems in impressive and creative ways.

The Russians retain the advantage of the conventionally stronger military, but Ukraine has outperformed expectations on this measure, perhaps more than any other.

Next, Sun Tzu asks “On which side are the officers and men more highly trained?”

While the Russian army has its advantage in size, the Ukrainian army appears far better trained on both an individual and collective level. It is difficult to get an accurate assessment of how well trained combatants are without being on the ground, but reports have suggested that “mobilized” Russians have been sent into combat with very little training and minimal equipment. 

From an outsider’s perspective little has changed here from the beginning of the conflict- the perception being that the Ukrainian Army was well trained through its ranks, while the training of Russian soldiers would quickly fall off after an initial surge.

Finally, Sun Tzu asks his seventh question “In which army is their greater consistency in both rewards and punishment?” In many respects, this question calls back to the themes posed by the fourth question regarding discipline.

From the Ukrainian perspective rewards and punishments are perfectly clear- the reward for success is national sovereignty and international admiration, while the cost of failure would be seeing meaningful portions of their nation annexed by a bullying neighbor.These rewards and punishments are perfectly consistent in that they are each non-exclusionary. All Ukranians would benefit from continued sovereignty, just as all Ukranians would suffer Russian colonization. 

From the Russian point of view things are less clear, and for many conscripted Russians the “reward” for participating in the conflict is largely avoiding the “punishment” that would come from ignoring their conscription. There are also some, and perhaps many, enlisted Russian fighters who have consumed enough Kremlin propaganda to believe that they are truly “de-nazifying” Ukraine; this would certainly come with the perceived (if unfounded) reward of fulfilling one’s military duty against an “evil” enemy. 

The individual with the most to lose or to gain through continued fighting is Putin himself. Putin likely understands the impact that this conflict will have in shaping his legacy, and his ability to manage those “rewards” and “punishments” without escalating the conflict will be absolutely pivotal in the coming weeks and months. 

When making projections back in March, I suggested that “ the Ukrainians have three clear advantages- a “sovereign imbued with moral law”, “the advantages of heaven and earth”, and “greater consistency in both rewards and punishments”. (While) Putin’s invading force has one clear advantage- its superior size.“ The remaining three matters – good generalship, discipline, and training were each considered toss-ups.

So far, it appears that the conflict has largely played out in accordance with Sun Tzu’s calculations with Ukraine’s outperformance in the remaining three categories leading to their relative military successes. Much of the conflict is yet to unfold, but the Ukrainian side has comfortably succeeded in avoiding the complete annexation of Ukraine by the Russian military.

The Spanish American philosopher, George Santayana observed that, “Those who cannot remember the past are destined to repeat it.” Mark Twain said, “History doesn’t repeat itself but it often rhymes.”  And, Winston Churchill paraphrased Santayana in a 1948 speech to the House of Commons when he said,”Those who fail to learn from history are destined to repeat it.”  Perhaps we should consider ourselves fortunate that Vladmir Putin appears to have forgotten to read his copy of Sun Tzu’s classic work while determining his war effort. If Putin had done his essential reading, however, he might have remembered one of Sun Tzu’s most important lessons- simply knowing when it is best not to fight.


Peter Scaturro is the Director of Studies at the Foreign Policy Association.