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Insurgent Strategy at War
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Tuesday, March 29, 2022

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Insurgent Strategy at War

I've told you (over and over and over, I'm sure) how important insurgent strategic principles are in thinking, planning and acting in our information economy.  For thirty-some years I've been preaching the effectiveness of insurgent strategy in business and politics, particularly against entrenched incumbents in markets or in government. 

Every year, I claim those principles are more important now than ever before.  And for thirty-some consecutive years of this information age – year after year – I've been right (along with the many others who have supported this doctrine, most importantly for me Steven Jobs and Mike Murray at Apple Computer).

Now, in vivid reality and with still untold humanitarian consequences, we are seeing the effects of entrenched incumbent versus relentless insurgent in Ukraine on a digital world stage.


The Strategic Context of this War.

I want to address the overarching strategic contrasts and I'll be as brief as I can; I just want to offer a framework through which to view the daily events in Ukraine and Russia. And this framework may reinforce your own strategic instincts.

To be clear, "entrenched incumbent" is not only a definition of a leadership position (the political context), but also a matter of mindset, values and institutional religion – summed in the incumbent exhortation: "Think Big!"

Indeed, in most global markets, in addition to the one or two market leading businesses, we see scores more who act like/quack like the entrenched incumbent as if imitating them were the path to success. 

In NASCAR slip-streaming the leader benefits the following car, allowing it to save gas in the wake of the leader.  In business slip-streaming the leader has the effect of pushing the leader ahead by narrowing the differences in consumers' decisions.  Sameness in any category makes the leader's brand definition the category definition.  Think different!

This war is a classic a case of insurgent versus entrenched incumbent. It's David versus Goliath once again.  And once again, there is predictability in the entrenched incumbent's actions.  The insurgent's actions seem unplanned, yet they follow the form of successful insurgents through the ages.  

The entrenched incumbent believes in the inevitable force of its power, scope and superior material resources. 


The insurgent necessarily puts its faith in speed, mobility and its moral/emotional resources.

Putin was sure that the intimidation of 150,000 Russian troops massed on the Ukrainian border and his own vicious Chechen thug battalions as the point of the attacking spear would freeze the Ukrainians in fear and convince them to fold early in the fight.  This is typical of the entrenched incumbent.  They always believe that bigness will decide the contest.

For starters, Putin has vastly overestimated the power of his Russian army.  After all, though, he's not a military leader but a murderous spook.  While he may have dedicated ten billion dollars to military modernization, credible western sources estimate that about 75% of that money was swallowed up by corruption – it was basically stolen.  As a result, his is an army of confused and poorly trained conscripts with iffy weaponry and tangled supply lines. 

Further, Putin vastly overestimated the military prowess of the Chechen mercenaries he had intended to lead the invasion.  In attempting to take control of Antonov International Airport northwest of Kyiv as a key staging area in the first days of the invasion, a battalion of Chechen fighters were almost immediately wiped out by the Ukrainians and the Chechen General Magomed Tushayev was killed.  At first, the Chechens predictably denied Tushayev's death.  Then their terrorist leader, Ramzan Kadyrov, posted a video of him and fellow henchmen laughing and saying they would soon be, "Knocking on your door in Kyiv." 

The Ukrainians quickly posted proof that the bravado was actually posted to Telegram from the safety of a bunker in Chechnya.

In its use of broad-scale force, the incumbent often loses its sense of moral authority. 

The insurgent must use moral force to compromise the incumbent's size and resource advantages.  And the world loves the underdog.

The incumbent's actions, because they are so broad, speak much louder than words (the value of propaganda communications, or fake news, in this digital age is still overestimated by strategists, pundits and the media).  The world, outside of Russia and China, is watching the wanton destruction of Ukraine's cities and towns and murder of civilians.  And the watching world is not stupid. 

The moral call for action for this war was not made by Putin or his generals.  It was made by Volodymyr Zelenskyy in rebuffing President Biden's offer of sending a rescue plane for him as the Russians poured over the border.  "I don't need tickets.  I need ammunition."

It was a moral take-down of the attacking Russians and establishing the fierce insurgent spirit of the Ukrainians – not as victims, but rather as freedom fighters, spoiling for this fight.  It had a magnetic effect on those who would have sympathized with the Ukrainians, but now could be cheering them on, joining in emotionally. 

Indeed, the Zelenskyy presidency has been an assault on the incumbent corruption in his government and the existing image of the country.  One of his first acts was to remove the immunity from legal prosecution government members had previously enjoyed.  A next measure was for all cabinet members to remove his portrait from their office walls and replace them with pictures of their kids: "This is who we're fighting for!"

This is a war for Ukraine to redefine itself for its own citizens and for the world.  And, as Napoleon said, "Moral resources are three times as important as material resources in war." 

For his part, Putin made a meandering speech about his personal view of Russian history as a mandate for this "special military operation" that left most people scratching their heads. When was Ukraine ever a part of Russia?  Khrushchev was too much of a softie?  Huh?

Incumbents are heritage-driven.  Their future strategy and sense of destiny are set in the past and in their past glory ("That's the way we do it, because that's the way we've always done it.").


Insurgents are vision-driven – with strategy designed to attain that vision of a better world.   

In an autocracy, as Russia has been for at least twelve of Putin's twenty-two years in power, the leader grows more and more impatient with disagreement.  It's an irritant. So, the autocrat winnows down his advisory circle to the "yes men," the sycophants who will not only agree with but celebrate his every idea and action.  We've all seen this same situation elsewhere in politics and in business over the years. 

Of course, eliminating contrarian thought creates incredible vulnerability for any institution.  Clarity seldom emanates from a bunker. Unadulterated bad news seldom finds its way safely to the BIG GUY's office.  The autocrat is eventually surrounded by dimwits and removed further and further from reality. 

In an autocracy and in most entrenched incumbencies, attitudes and values trickle down from the ultimate leader.  Vladimir Putin has stolen more money than anyone in the history of the world.  Therefore, Russia has a kleptocratic culture that permeates government and society.  At every step down the precisely-defined organizational lines of the bureaucracy, Russian "leaders" aim to get their share of the goods. 

Through this disastrous war, the Russian army has relied more and more on mercenaries.  This rent-an-insurgent concept has failed throughout history – true insurgents require a just fight, a moral war.  

The stunningly high mortality of Russian commanders in the first month of the war can be first attributed to this lack of moral purpose for their army.  Russia's conscripts are kept in the dark about their commanders' objectives and strategies – rather, they are expected to carry out every order without question.  In autocratic organizations workers at the lowest level seldom understand the institution's overall goals or strategies or their role in them.  Those young soldiers have had no idea what they were getting into or how to get out.  That draws their commanders dangerously closer to the front lines to provide the intimidation to keep them in the fight. 

These conscripts had been picked for this war from disparate and distant parts of Russia, so that the country wouldn't suffer the same degradation of public morale and support as in the Afghanistan debacle as the body bags came home (part of the "modernization" of the military has also been deployment of mobile crematoriums – no body bags).

The entrenched incumbent uses the bureaucracy as a form of institutional religion – charting the precise steps to advance, but also putting too much time and distance between detecting problems and devising solutions. 


Insurgents create an organization that is as flat and fast as possible, contributing to the insurgent advantages of speed and mobility.    

The bureaucratic maze of the Russian army is such that all strategic decisions must be passed up through the system; many, all the way to Putin. 

Ukrainian troops can generally make important spot decisions to answer to quickly arising challenges or opportunities.  When they see a tank convoy, trap it and kill it.  When they saw a tank transport ship portrayed on Russian TV as news of Russian advances in Berdyansk, they promptly set out to successfully sabotage and sink it. 

Although Russia has invaded Ukraine, a sovereign nation, the autocrat Putin believes this is fighting to rid mother Russia of a separatist insurgency and a key step in the restoration of Imperial Russia.  This is the mindset of the classic incumbent – domination is its heritage – and, therefore, its destiny.  The belief is what was, will be. "We are better than you.  That's why we will win."

It is fair to say that the United States has suffered this incumbent hubris a few times in its recent history.  And each time, it has led to failure and humiliation.  That is where Putin and Russia are headed now; and they don't have the U.S.' Scrooge McDuck vault of vast piles of gold to absorb the losses.  The Russian economy, even pre-Ukraine war, was no larger than that of Italy.   

Putin continues to define this war as not a war, but a "special military operation" to restore Ukraine to Russia; in his mind, "Back to the Future." 

The ferociously courageous Volodymyr Zelenskyy sees this as a definitive battle between two systems: democracy and autocracy.  He is vision-driven.  He refuses to let this be seen as a "proxy war" of the great powers.  Rather, he defines this battle as the first front of a new war for the survival of European democracy and the survival of Western political order and liberal democratic values.  He is fighting for the future, not for the past. 


The most fundamental contrast between entrenched incumbent and determined insurgent is the attitude toward change.

Incumbents hate change.  They see it as a threat and work to stamp it out internally and externally. 


True insurgents love change.  Change means opportunity with the molecules of the current order heated up and in motion.


As I write this, Russia is making a pivot in the form of restating its goals for the invasion, a tactical retreat.  Now, they see "victory" as securing their already established gains in the eastern and southern parts of Ukraine.  Of course, these changes destabilize Putin.  I know, I know, this cornered rat is desperate and has a nuclear arsenal at hand.  Still this particular rat is a narcissist and unlikely suicidal. 

It is impossible to say what the Ukrainians will do now and how or how much the West will help them.  Still, I hope and fervently pray that they can hold out for the unconditional surrender of Russia in this war. 

If they can last, they will win. God help them to last.  SM


33,000 Feet Over Somewhere: Preaching and Practicing the Discipline of Insurgent Strategy


Scott Miller








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