Overconfidence, Ambition, and Irresistible Failure

“General Lee, sir,” a teary-eyed George Pickett declared, “I have no division.”

The despair in his voice was palpable. The awful reality of his failure to break the Union line at Gettysburg had incapacitated him. He stood in shock, shoulders slumped, seemingly lost.

This is the one scene that I remember vividly from Gettysburg, the epic Hollywood dramatization of the famous Civil War battle. I went to see it at the theater with my best friend, Rob. Man, that was a long movie; it even had an intermission! But we gutted it out as if we didn’t know how the story ended. And just in case you don’t know, the good guys won.

But back to the scene with Pickett and Lee.

On the third day of the battle, the commander of the Confederate forces, General Robert E. Lee, had decided to pit a large portion of his army against what he supposed was a weak point in the Union Army’s lines. But to get to that point, Confederate soldiers had to cross nearly a mile of open field under the watchful eyes of their foe — quite the ambitious objective. At risk of oversimplifying the details of the battle, I’ll summarize it for you like this: Lee was overly confident in his Army and believed it would carry the day. But a series of factors caused Lee’s assault to go awry and the attackers, most notably Pickett’s division, suffered tremendous losses in front of a terrific defense put up by the Union forces. The attack failed miserably.

Most concerning is the fact that Lee knew the attack was failing; he could watch it all unfold. And this failure didn’t happen fast. After all, Lee’s army had to walk for a mile across an open field while being cut down by unrelenting Union firepower! Yet, solidly confident in his army’s ability, Lee let the attack continue. Despite the reality of what he was seeing, he let the failure happen. Seemingly, Lee’s overconfidence had made failure irresistible. Lee and his army never recovered from the loss.

Interestingly, I sometimes see the same thing happen (on a different scale) in many organizations wherein leaders have set ambitious goals. In most cases when things don’t go as expected, leaders make adjustments to their plans. But situations wherein leaders are overly confident in their teams or the plans they’ve implemented to accomplish their goals, they often miss the failure that’s happening right in front of them. When things don’t happen as expected, these overly confident leaders don’t make necessary adjustments to their plan. Worse, they often double down, as if to reinforce the failure. They’re so confident in their team and their plan that failure becomes irresistible. Sadly, when the failure comes it is sometimes so great that the organization struggles to recover from it. Too much money, time, and energy has been lost.

What happens in the wake of organizational failure plays out just like the scene in the movie. As soldiers flee the battlefield, Lee, mounted on his horse, rides to Pickett’s side. “General Pickett, sir,” he says, “you may reform to the rear of this ridge and set up defensive positions.” Standing in despair, Pickett simply stares off into the distance.

“General Pickett, sir,” Lee continues, “you must look to your division.”

“General Lee, sir,” says Pickett with tears in his eyes, “I have no division.”

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Overconfidence, Ambition, and Irresistible Failure was originally published in Horizon Performance on Medium, where people are continuing the conversation by highlighting and responding to this story.