Gettysburg Day 1: The Battle Was Won — The Position Was Lost
A continuing study in leadership by Terry D. Waldrop. Leadership accounts are from Waldrop’s first hand visit to battle sites with extensive study of tactics, decisions and timing.
September 7, 2026
There are times in leadership when confidence is absolutely necessary.
There are also times when confidence becomes dangerous.
Gettysburg is one of the best examples in history of what happens when a great leader, commanding a great organization, begins to believe too strongly in the formula that made him successful.
Robert E. Lee did not arrive in Pennsylvania as some confused commander who suddenly forgot how to lead. Quite the opposite. By the summer of 1863, Lee was arguably at the height of his military reputation. His Army of Northern Virginia had won significant victories, had repeatedly frustrated larger Union armies, and had developed an enormous belief in both itself and its commander.
That matters.
Winning changes how people think.
It changes how leaders think, too.
If you have coached long enough, run a business long enough, managed a hospital long enough, or led any organization long enough, you have seen it. A system works. Then it works again. Then it works a third time.
Before long, people stop asking why it works.
They simply assume it will.
That is where trouble usually begins.
Gettysburg was not simply a Confederate defeat. It was a case study in what happens when experience, confidence, incomplete information, unclear communication, and organizational momentum begin pulling in the same direction.
Sometimes that direction is straight off a cliff.
Winning Can Hide Problems
Lee had good reason to trust his army.
The Army of Northern Virginia had developed a swagger.
That word is appropriate.
Successful teams have it. Successful businesses have it. Championship programs have it. People walk differently when they believe they are better than the people across from them.
That confidence can be powerful.
It can also become a trap.
The Confederate army had learned that aggression frequently produced results. Lee had repeatedly taken chances that other commanders might not have taken, and many of those decisions had worked.
The problem with winning is that success can make yesterday's gamble look like today's strategy.
Those are not always the same thing.
I have seen coaches convince themselves that because something worked against one opponent, it would work against everybody. Nick Saban's Alabama teams could line up for years and physically overwhelm people. At some point, however, college football changed. Offenses changed. Personnel changed. Rules changed. Saban adapted because great leaders understand that yesterday's dominance does not guarantee tomorrow's results.
Organizations that refuse to adapt usually get introduced to reality in an unpleasant way.
At Gettysburg, Lee was operating on unfamiliar ground, deep in enemy territory, without the intelligence network he normally relied upon functioning at full effectiveness.
J.E.B. Stuart's cavalry was not providing Lee with the kind of timely information he desperately needed during the early stages of the campaign.
That should have mattered.
A lot.
Leaders make their worst decisions when they begin acting on what they think they know instead of what they actually know.
In sports, that gets you beat.
In business, it costs you money.
In healthcare, it can wreck an organization.
In war, it gets people killed.
The lesson is simple.
Confidence is valuable. Information is more valuable.
July 1: Winning the Wrong Battle
The Battle of Gettysburg did not begin as some perfectly designed confrontation between two armies.
It developed.
That point is important.
Confederate troops moving toward Gettysburg encountered Union cavalry commanded by John Buford. The fighting expanded as more troops entered the battlefield.
By the end of July 1, the Confederates had driven Union forces back through Gettysburg.
On the surface, that looked like success.
The Confederates had advanced.
The Union forces had retreated.
That is the kind of moment when leaders can become intoxicated by what the scoreboard appears to say.
Coaches understand this.
You can be ahead at halftime and still be getting your tail whipped tactically.
The scoreboard may tell one story while the game itself is telling another.
That is exactly what was happening at Gettysburg.
The Union army fell back onto tremendous defensive ground south of town. Cemetery Hill, Cemetery Ridge, Culp's Hill, and eventually Little Round Top formed one of the strongest defensive positions either army would occupy during the war.
The Confederates had won the immediate fight.
The Union had gained the better position.
Those are not the same thing.
That distinction should be written on the wall of every leadership office in America.
Activity is not achievement. Progress is not position. Winning a moment does not mean you are winning the larger contest.
"If Practicable"
After Union troops withdrew toward Cemetery Hill, Lee gave Lieutenant General Richard Ewell instructions to take the hill "if practicable."
Those two words have been debated for more than 160 years.
Did Lee intend a strong order?
Did Ewell interpret it too cautiously?
Would Stonewall Jackson have attacked?
Nobody can replay history.
That is not the most important leadership question anyway.
The better question is this:
Did the subordinate clearly understand the commander's intent?
That is the issue.
Leaders frequently make the mistake of believing they communicated something simply because they said something.
Those are two very different things.
Lee had enjoyed a remarkable relationship with Stonewall Jackson. Jackson understood Lee's aggressive instincts and frequently acted with enormous initiative.
Ewell was not Jackson.
Yet leaders sometimes communicate with the new person as though they are communicating with the old person.
That is a mistake.
Every coach has done it.
You explain something to a veteran player in five words because he has heard it for three years. Then you use the same five words with a freshman and wonder why he has no idea what you wanted.
That is not the freshman's failure.
That is the leader's failure.
Communication is not what the leader says.
Communication is what the other person understands.
That difference is enormous.
The Confederate command structure at Gettysburg repeatedly struggled with that problem.
Lee often communicated in broad terms.
His senior commanders possessed significant discretion.
That had worked before.
At Gettysburg, against a rapidly concentrating Union army occupying increasingly strong ground, ambiguity became expensive.
Longstreet Saw a Different Battle
One of the most fascinating parts of Gettysburg is the disagreement between Lee and Lieutenant General James Longstreet.
Longstreet believed the Confederates should maneuver rather than repeatedly attack strong Union defensive positions.
Lee disagreed.
This is where leadership becomes complicated.
Good leaders do not always agree.
Strong organizations should not require agreement.
They require honest discussion followed by disciplined execution.
Longstreet believed Lee's preferred strategy was wrong.
Lee believed the Union army could be defeated where it stood.
That disagreement has become one of the central controversies surrounding Gettysburg.
My interest is not in assigning Longstreet sainthood or Lee stupidity.
Neither is appropriate.
The leadership lesson is more useful.
A leader must create an environment where trusted subordinates can challenge assumptions.
However, once the decision is made, the organization still has to execute.
That balance is difficult.
Too little disagreement creates an echo chamber.
Too much disagreement creates paralysis.
The best organizations operate somewhere in the middle.
I have always wanted people around me who would tell me when they thought I was wrong.
I did not always agree with them.
I certainly did not always enjoy hearing it.
There is a difference.
Leaders who only want agreement eventually surround themselves with people who provide it.
Then one day everybody agrees right up until the organization crashes.
Little Round Top and the Cost of Almost
The second day at Gettysburg produced another lesson the Confederates would pay dearly for.
Lee ordered attacks against the Union left flank.
The fighting was ferocious.
Places like the Wheatfield, Devil's Den, the Peach Orchard, and Little Round Top became some of the most famous ground in American military history.
The Confederates came remarkably close to breaking the Union position.
Close.
Leadership has very little respect for "close."
You either accomplish the objective or you do not.
That sounds harsh because it is harsh.
Organizations frequently comfort themselves with effort.
"We almost got there."
"We were close."
"We gave it everything we had."
That may make everybody feel better.
It does not change the result.
The Confederate attacks on July 2 demonstrated enormous courage.
They also demonstrated the limits of courage when strategy, timing, coordination, and terrain are working against you.
That is one of the great misconceptions about leadership.
People like to believe effort can overcome everything.
It cannot.
Hard work matters.
Courage matters.
Commitment matters.
But none of those things excuse bad positioning.
A badly positioned organization filled with highly committed people is still badly positioned.
Then Came Pickett's Charge
July 3 produced the decision that has become synonymous with Gettysburg.
Pickett's Charge.
Roughly 12,000 Confederate soldiers were ordered across open ground toward the center of the Union position on Cemetery Ridge.
It was magnificent courage.
It was also catastrophic.
The Confederates advanced nearly a mile under artillery and rifle fire.
Many reached the Union line.
Some briefly penetrated it.
Then the attack collapsed.
The losses were devastating.
Pickett's Charge has become so famous that it can distort our understanding of Gettysburg.
The charge was not the beginning of the Confederate problem.
It was the culmination of it.
That is a major leadership lesson.
Organizations rarely collapse because of one decision.
They usually arrive at the disastrous decision after a series of smaller decisions, assumptions, communications failures, missed opportunities, and refusals to change course.
By July 3, Lee had already committed emotionally and strategically to defeating the Union army on that battlefield.
That commitment mattered.
Leaders can become trapped by their own previous decisions.
Psychologists have terms for it.
Coaches have another one.
Stubborn.
Once a leader publicly commits to a course of action, changing direction can feel like admitting defeat.
It is not.
Sometimes changing direction is leadership.
The ability to say, "This is not working. We are doing something different," may be one of the most underrated leadership skills there is.
Lee had changed course before Gettysburg.
He would change course again afterward.
But on July 3, 1863, he did not.
Great Leaders Can Make Terrible Decisions
There is another reason Gettysburg deserves serious study.
It reminds us that greatness does not make anyone immune from mistakes.
Lee was unquestionably one of the most accomplished commanders of the Civil War.
That does not mean every decision he made was brilliant.
This is where modern leadership discussions often become silly.
We want people categorized.
Great leader.
Bad leader.
Genius.
Failure.
History does not work that way.
Neither does real leadership.
Great leaders make mistakes.
Average leaders occasionally make brilliant decisions.
The question is not whether leaders will be wrong.
They will.
The question is how quickly they recognize it and what they do next.
That applies to a football coach on Saturday afternoon.
It applies to a CEO watching numbers deteriorate.
It applies to a hospital administrator watching census collapse.
It applies to an athletic director watching a program deteriorate.
At some point the evidence starts talking.
Good leaders listen.
Bad leaders keep giving speeches about the plan.
The Gettysburg Lesson
The Confederate story at Gettysburg is not a story about cowardice.
There was plenty of courage.
It is not a story about incompetent leadership.
There were outstanding commanders throughout the Army of Northern Virginia.
It is a story about something far more valuable for modern leaders to understand.
A talented organization can lose.
An experienced organization can lose.
A highly motivated organization can lose.
A great leader can lose.
Success never eliminates the need for information, communication, adaptation, and judgment.
In fact, prolonged success may make those things even more important because success creates confidence, and confidence has a nasty habit of becoming certainty.
The Army of Northern Virginia arrived at Gettysburg believing deeply in itself.
Three days later, it began the long march back toward Virginia.
The courage had not disappeared.
The talent had not disappeared.
What changed was the result.
Leadership is ultimately judged there.
Gettysburg reminds us that past success earns respect.
It does not earn immunity.
And sometimes the most dangerous words a successful leader can believe are:
This has always worked before.