What strategy secret can you learn from great military leaders?




Successful strategy is about surprise.

Running straight at a problem when it’s well established is suicide. Throughout military history frontal assaults against prepared defenses have failed.

Via How Great Generals Win:

From the beginning of organized warfare, frontal attacks against prepared defenses have usually failed, a fact written large in military history for all generals to see… great generals strike where they are least expected against opposition that is weak and disorganized.

History says you need an element of surprise. Almost all successful attacks have hit enemies from the rear, from the flank, or anywhere it is not expected:

Because enemy response is so unpredictable, commonplace or mediocre generals often do not understand the full significance of flank or rear attacks and, usually because of strong enemy resistance, find themselves drawn or provoked into a direct strategy and frontal attacks, which are rarely decisive. One of the factors that make a general great, and therefore make him rare, is that he can withstand the urge of most men to rush headlong into direct engagements and can see instead how he can go around rather than through his opponent. One reason such generals are few is that the military profession, like society as a whole, applauds direct solutions and is suspicious of personalities given to indirection and unfamiliar methods, labeling them as deceptive, dishonest, or underhanded.


B. H. Liddell Hart epitomizes much military wisdom in two axioms. The successful general, he says, chooses the line or course of least expectation and he exploits the line of least resistance.

If you’re a little David against a big Goliath, it’s definitely about surprise. You need to break the rules to win.

When underdogs play by the rules, they lose 72% of the time. When they break with established strategy and innovate, they win 64% of the time.

Via Power:

As Malcolm Gladwell has insightfully noted, the rules tend to favor—big surprise—the people who make the rules, who tend to be the people who are already winning and in power. Gladwell described research that shows how playing by the rules—following conventional wisdom—in arenas ranging from sports to war favors the already more powerful, while doing things differently and following an unconventional strategy permits even heavily outresourced underdogs to triumph. In every war in the last 200 years conducted between unequally matched opponents, the stronger party won about 72 percent of the time. However, when the underdogs understood their weakness and used a different strategy to minimize its effects, they won some 64 percent of the time, cutting the dominant party’s likelihood of victory in half. As Gladwell noted, “When underdogs choose not to play by Goliath’s rules, they win.” So, if you have all the power you want or need, by all means not only follow the rules but encourage everyone else to do so too. But if you are still traversing your path to power, take all this conventional wisdom and “rule-following” stuff with a big grain of salt.

So how do you engineer surprise? Deliberately mislead the enemy.

In his classic The Art of War, Sun Tzu said “All warfare is based on deception“:

  • “Hence, when able to attack, we must seem unable; when using our forces, we must seem inactive; when we are near, we must make the enemy believe we are far away; when far away, we must make him believe we are near. Hold out baits to entice the enemy. Feign disorder, and crush him.”
  • “Attack him where he is unprepared, appear where you are not expected.”
  • “The whole secret lies in confusing the enemy, so that he cannot fathom our real intent.”

Deception is key. You’d be smart to heed the words of The Godfather: Keep your friends close — and your enemies closer.

Research shows dominant leaders really do exactly that:

Three experiments supported the hypothesis that dominant leaders seek proximity to ingroup members who pose a threat to their power, as a way to control and downregulate the threat that those members pose.

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What three things can we learn about strategy from the greatest generals of history?

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What can we learn from Sun Tzu’s Art of War?


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