How Grant Leveraged Failure in the Civil War

This article is a sidebar continuation of ideas raised in “Failure Is Not Optional: Why Project Failure Is OK.”

In understanding failure, the most effective analogue for me has been in looking at the life of Ulysses S. Grant and the conduct of the Civil War under Lincoln, especially after the president appointed Grant head of the Union armies. The Overland Campaign of 1864-65 was of particular importance, not only because it led to Union victory, but also for what it said about Grant’s character in the face of disaster.

For both Ulysses Grant and Abraham Lincoln had known disappointment and failure. The stories of their failures are often overstated, especially in the case of Lincoln. What one finds when the exaggerations are removed is that when either of these men suffered a setback, rather than treating it as a tragedy or permanent failing, they incorporated the lessons to be found in that setback and pushed on. It is this character they recognized in each other and that brought them together.

The defining moment in the case of the Overland Campaign of 1864, in my opinion, happened in the aftermath of what is called the Battle of the Wilderness. Over 23,000 men died or were wounded during this bloody three-day battle. The Union army in particular sustained significant losses. The difference on the day after the battle is that instead of withdrawing back to Washington, D.C., as previous Union generals had done when facing stalemate and staggering losses, Grant turned Lee’s flank and proceeded on to Richmond, which he viewed as the strategic center of the campaign and—with Sherman’s actions in the deep south—the strategic center of the war. He did this several times during the campaign: fighting Lee to a bloody stalemate as each turning movement was met by counter-maneuver, Lee—having lost the initiative—being forced to synchronize his movements to Grant’s in a deadly dance.

The difference between Grant and his predecessors—all of whom were better military tacticians and more highly respected—is that Grant didn’t waiver in the face of setback. His predecessors had not known failure and therefore did not know how to deal with it. When they experienced it they quit the field.

For Grant had done the math—the strategic and tactical position of the Union Army compared to the Army of Northern Virginia—and believed that while the respected Lee could strike lethal blows, he couldn’t route his army if he stayed the course of the plan and absorbed minor tactical defeats, learning from them. His thinking is best summed up when, after the battle, his generals speculated on Lee’s next move. He replied tersely: “I am heartily tired of hearing what Lee is going to do. Some of you always seem to think he is suddenly going to turn a double somersault, and land on our rear and on both our flanks at the same time. Go back to your command, and try to think what we are going to do ourselves, instead of what Lee is going to do.” He was focused then on his own actions based on the goal and what had been learned during the day.

His contemporaries, rivals, and enemies called him Bloody Grant the Butcher and accused him of being a drunkard. Given the meat grinder that was the American Civil War—the world’s introduction (though no one realized it at the time) to modern warfare—it is a wonder that he didn’t drink all of the time. For the war of maneuver that Grant developed would soon morph into a precursor of the trench warfare that marked World War I fifty years later in the siege of Petersburg and Richmond.

I believe Grant was able to withstand such disappointment, horror, and criticism because, unlike many of his contemporaries—and unlike Lee—he often expected things to go against plan, and he had developed a means of absorbing and incorporating these circumstances when they did. He then developed a new plan and pushed on, following his strategic vision. He didn’t believe in inerrancy and often saw error in himself and in his subordinate generals in very stark and bloody terms.

Of course, no project managers in the IT field have to assess risk and failure in such immediate circumstances involving life and death or existential threat. Our decisions, however, can have real-world implications that can affect the lives of others.

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