September 16, 2025
by Stephen T. Messenger
In the bloodiest battle of the Civil War at Gettysburg, Confederate General Robert E. Lee had to make a decision that would change the course of the war. It was a paralyzing choice, one where there was no right answer, and a decision which would have a significant impact on the future.
We will face high-stakes decisions in life, and when we do, it’s not enough to trust instinct alone. We must actively seek counsel, embrace uncomfortable perspectives of others, and rigorously test our assumptions to prevent blind spots from driving us toward disaster.
The Third Day at Gettysburg
On July 3, 1863, General Lee ordered what would become known as Pickett’s Charge, a massed assault of nearly 12,500 Confederate soldiers advancing across open fields toward entrenched Union forces on Cemetery Ridge. The charge was meant to break the Union line in one decisive blow, but instead it became one of the most infamous failures of the war.
Nearly half of the attacking force became casualties in less than an hour, with entire brigades shattered by Union artillery and rifle fire. The failed assault forced Lee to retreat from Gettysburg, ending his invasion of the North and marking a decisive turning point in the war.
General Lee could have walked away from this fight, but he didn’t. In hindsight, the decision to attack appears reckless, but it reflected several critical failures in his decision-making approach at that moment.
First, Lee relied heavily on his own instincts and past battlefield successes rather than seeking full counsel from his subordinates, many of whom had serious reservations about the attack. His reluctance to fully invite dissenting perspectives narrowed his options and reinforced his own belief that the Union center was vulnerable.
Compounding this was an incomplete intelligence picture. Lee underestimated the strength and readiness of Union defenses and overestimated the exhaustion of his opponent. The fog of war is always present, but Lee’s decision illustrates the danger of acting on assumptions without validating them through reliable reconnaissance and multiple perspectives.
Finally, he underestimated the toll his own forces had endured over two days of brutal combat, pushing exhausted soldiers into an assault with little chance of success.
These combined factors led to catastrophic losses and marked the high-water mark of the Confederacy.
Dealing with Hard Decisions
Last week, I visited the Gettysburg battlefield and saw the ground of Pickett’s Charge. It was roughly three-quarters of a mile across uncovered, open terrain. Our day was a little cooler and less humid, we were well fed and hydrated, and zero cannons were pointing at our position. It was still intimidating. So, what was Robert E. Lee thinking?
General Lee prior to Gettysburg had a 4-0-1 winning record in the Civil War, and he was running circles around the Union forces. But on this battlefield, he had no shortage of challenges. He never had a complete picture of the field, faced coordination problems among some subordinate commanders, and struggled with army-wide communication.
These factors contributed significantly to his defeat at Gettysburg, a turning point that weakened Confederate prospects. Just as Pickett’s men marched into the teeth of Union fire, leaders today can march their teams into disaster if we act on unchecked assumptions.
Trap #1. Trust Only Our Instincts. We should surround ourselves with wise counselors and solicit their advice. None of us are as smart as all of us. Even if we don’t agree, having conflicting opinions help us shape better decisions.
General Lee was calling the shots himself. It worked for him before, but the scale and complexity of Civil War battles were increasing. Meanwhile on the other side of the lines, his opposing General, George Meade, was seeking advice from all his senior leaders… and won.
Trap #2. Assume We See the Whole Picture. We’ll never know everything, but it pays to gather as much info as we can and use it to make our decision. By putting out feelers, asking questions, challenging assumptions, and collecting intelligence, we have the ability to make better choices.
When Lee ordered Pickett’s Charge, he made several assumptions that the Union Army would fold under a 12,500-man assault. But his assumptions were wrong. His opponent Meade also lacked a full picture, but he learned more by waiting for the attack than attacking into the unknown.
Trap #3. Let Confidence Be Overconfidence. Especially with a track record of success, we tend to trust ourselves more than we should, more so when we’re tired. Yet every day is an opportunity to start fresh and reassess where we’re at. Confidence is great! Overconfidence is dangerous.
On Day Three, the last day of Gettysburg fighting, General Lee thought his troops were strong enough for this three-quarters mile-long assault over open ground into withering fire… and win. They were exhausted, dehydrated, and overextended. It was a valiant attack but ended with a devastating loss.
It’s Our Decision to Make
When we have tough decisions to make, it’s worth thinking about the traps. First, include wise counsel and don’t rely solely on intuition, even if it’s great. Second, gather as much information as possible. Finally, be confident, but realize we have blind spots.
Tough decisions will always come, but if we slow down, seek counsel, and challenge our assumptions, we’ll stand a better chance of avoiding our own Pickett’s Charge.
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