Lee’s Lieutenants: Leadership Lessons from the Civil War for the Battlefield and the Boardroom

May 8, 2017

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In the summer of 1862, the Army of Northern Virginia went into battle for the first time under its new commander, Robert E. Lee. In volume one of Lee’s Lieutenants, Douglas Southall Freeman provides a short and almost off-hand account of two of the actors in the drama that was unfolding. As the Confederates approached Union positions, two Confederate commanders rode their horses to the front of their attacking units. The first commander “rode along the front, and when the men cheered him he raised his hat. ‘Boys,’ he cried as he pointed toward the enemy’s position, ‘you can take it!’” The second commander is quoted as saying to his soldiers— “Drop your knapsacks and blankets, we are going to take that line. I am going to lead you.’”

Freeman provides a simple recounting of those moments, using them to give detail that enriches the scene and its participants. What is truly interesting about this small vignette, however, is that it can inspire a reflection on a matter of enormous significance to the idea of leadership. With the addition of two questions, this vignette can serve as a powerful tool for developing leaders. Here is the first question: As a result of what each commander said, which unit do you think performed better on the battlefield? There are three possible responses:

(a) The first unit.

(b) The second unit.

(c) The words of the commander were irrelevant to subsequent unit performance.

In my experience, as someone who has taught leadership to West Point cadets and corporate executives, most people choose answer (b) because they are attracted to the commander who said, “We are going to take that line. I am going to lead you.” People who prefer that answer think leadership matters more than most and believe the actions of leaders can have a direct impact on organizational performance.

The follow-on question is related: Why do most people tend to think the second commander was more inspirational? The answer is obvious because, at this point, we really only know one thing about the second commander: He clearly demonstrated to his soldiers he was willing to share in the mortal risk of fighting on a hellish battlefield. We also assume this willingness to share risk generated positive emotional energy on the part of the soldiers in his unit, which helped them perform effectively in battle. Thus, a consideration of this vignette can clarify several important assumptions related to leadership, and many of us learn that we hold two assumptions about leadership: First, that leadership matters and second, that the power of leaders depends, to some extent, on aspects of their character.

Freeman’s three-volume study of the Army of Northern Virginia, Lee’s Lieutenants, is filled with memorable insights into leadership. It was published during World War II and yet, in the words of noted Civil War historian James McPherson, “nothing written since equals them for insights into the problems and techniques of Civil War command, strategy and the evaluation of intelligence.” During the 35 months that Lee’s Army of Northern Virginia was in existence (from the summer of 1862 until its surrender at Appomattox in April of 1865), Freeman notes there were 47 soldiers who served under Lee as major generals and 146 soldiers who served under him as brigadier generals. Using a leadership canvas of this size, Freeman paints a picture that provides an astonishingly broad and vivid array of insights into some of the most fundamental aspects of leadership.

Leadership Matters

Effective leadership enabled the Army of Northern Virginia to punch above its weight. One of the most significant examples Freeman provides is that of Lee himself, who, unlike most of his Union and Confederate contemporaries, was able to build a unified, trusting and motivated command team that came closer to the ideal than most armies in history. Lee’s leadership ability in this regard should not be taken lightly. His opponents in the Army of the Potomac frequently acted less like an army and more like a collection of divisions that happened to be in the same place at the same time. The results for the Union were often disastrous. When writing of the dynamics between Lee and his command team, Freeman presents an interesting contrast regarding the influence that Lee was able to establish over his principal subordinates. During the course of the war, it was common for senior commanders to receive comments or criticism from Confederate President Jefferson Davis and from Lee about what they did or failed to do on the battlefield. Criticism from Davis frequently generated anger or resentment. By contrast, those on the receiving end of Lee’s disapproval then strove to meet his standards.

This leadership connection went beyond Lee’s relationship with his command team and extended far into the ranks of the army. In the desperate fighting in the Wilderness in the summer of 1864, Union forces under Ulysses Grant started delivering sledgehammer blows to Lee’s army. At one critical point, Lee himself began to lead a brigade into the thick of the fighting. The brigade refused to budge until Lee desisted and moved to a safer place. One of the Confederate veterans in the wake of this incident was heard to cry, “I would charge hell itself for that old man.”

Leaders Can be Developed

Freeman devotes most of his second volume to the fascinating leadership journey of Gen. Thomas “Stonewall” Jackson. This was the best evidence that Lee had a superior ability to identify, nurture and employ great leaders. Lee was not shy about using this ability and quickly molded the command team that he wanted during his first months of command after getting rid of division commanders who failed to meet his standards.

As the war began, Jackson would not have been chosen by many people as a great battle captain. Before the war, he was an obscure math teacher at Virginia Military Institute who was savagely and routinely ridiculed by many of his students. In the first months of the war, he was held in low regard by many fellow officers. Even as Jackson began to achieve fame for his battlefield performance, he remained a very unusual leader. Those who study leadership today often distinguish between task-oriented leaders (get the job done) and relationship-oriented leaders (let’s build a great team). The usual conclusion is that leaders should strive to balance these competing tasks. Jackson was completely task-oriented and looked upon his soldiers strictly as a means to a greater end.

Jackson’s leadership persona was heterodox, yet he came to be revered by his men and implicitly trusted by Lee. How did this happen? The first time that Lee and Jackson worked together (in the Seven Days Battles during the summer of 1862), Jackson did not shine. When given an independent command, Jackson was constantly bedeviled by his inability to develop an effective command team. Freeman ends the first volume of Lee’s Lieutenants by summing up Jackson’s performance in the first year of the war:

That strange man Jackson, was he a mad genius, unable, unwilling to co-operate, or would he prove himself the right arm, perhaps the successor of the new commanding General?

There might have been doubts about Jackson in the minds of many, but Lee’s ability to trust his own judgment when it came to identifying and developing leaders was as valuable as it was rare. Lee could look past Jackson’s flaws and his occasional failures to see a subordinate of great promise. He nurtured Jackson, giving him increasing amounts of responsibility until the fateful day at Chancellorsville in 1863 when their relationship reached its apotheosis and Lee put the fate of his entire army in Jackson’s hands.

This occurred in the late spring of 1863 when the Union Army of the Potomac once again began to stir. In the maneuvering that followed, Lee and his army gradually found themselves facing the Union forces in the vicinity of Chancellorsville, Virginia. Although outnumbered, Lee and his army had no intention of sitting still and waiting for a Union attack.  Lee looked for ways of wresting the initiative from his enemy. He eventually decided to divide his army in order to carry out a devastating attack on the right flank of the Union army. Lee, with 14,000 soldiers, spent an entire day monopolizing the attention of 50,000 Union soldiers while Jackson, with 28,000 men, took concealed and little-known country roads in order to get into position on the Union flank. In the late afternoon of May 2, 1863, Jackson and his men fell like a thunderbolt on the unprotected right flank of the Union Army. The attack was a great success but, before the day was done, Jackson was mortally wounded by his own men in error while on a nighttime reconnaissance beyond the frontlines. Jackson would die of his wounds eight days later and when the two armies met two months later at Gettysburg, Lee would have to fight without Jackson. As Freeman put it, “Lacking Jackson, Lee could not win.  The price of victory at Chancellorsville was defeat at Gettysburg.”

The Traits that Make a Good Leader can be Deadly

In the case of Lee’s army, there was a powerful tension between leadership culture and command requirements. Commanders at all levels were expected by their soldiers and by their chain of command to be aggressive on the battlefield, indifferent to the dangers of combat and prone to leading from the front. All three of Lee’s primary subordinates (Jackson, James Longstreet, and James “Jeb” Stuart) commonly commanded from the front. As a result, Jackson was killed at Chancellorsville and Longstreet was seriously wounded almost exactly one year later and only a few miles from where Jackson was hit. Stuart was killed in hand-to-hand fighting the same week that Longstreet was wounded. This aggressive mentality permeated the officer ranks of the entire army. If we refer back to the two Confederate commanders who introduce this article, it is no coincidence that the first commander (“boys…you can take it!”) was Gen. Chase Whiting, who was quickly relegated to military obscurity. The second commander (“we are going to take that line.  I am going to lead you.”) was Gen. John Bell Hood, who rocketed to fame based on his relentlessly aggressive bravery on the battlefield.

At the beginning of the war, the Confederate high command assumed (in Freeman’s felicitous phrase) that the South was “opulent in leadership.” To their surprise, however, they quickly found out their supply of competent general officers was limited and the consequences of command attrition were devastating. After only one year of combat, Lee discovered that one of his biggest problems was finding enough competent senior officers. Freeman notes:

[F]or the first time attrition at the level of brigade command was threatening dangerously the organization of the army.  Some of the most reliable veteran regiments might be rendered ineffective because they would not be well led.

Reading is Invaluable for Leaders

I realize that no one ever became a good fastball hitter by reading a book about baseball. Similarly, one can’t become a good leader by simply reading. Yet reading and reflection can be a valuable part of the process that people use to develop themselves as leaders. Reading about leaders can illustrate truths about leadership, it can demonstrate effective leader behaviors, and it can uncover the challenges faced by leaders (as well as the solutions to these leadership challenges).

To illustrate the value of reading about leaders, consider the leadership journey of just one of Lee’s lieutenants. During the course of his three-volume history, Freeman follows the career of John Bell Hood and. we learn an important truth from his leadership journey. As noted, we initially meet Hood in the first volume as a brigade commander exhorting his men to follow him as he leads a charge against the Union lines. In the second volume, as a division commander, he distinguishes himself yet again on the bloody battlefield of Antietam. Freeman writes that the consensus of the army was that “of all the officers under Longstreet, the most likely to be a great soldier was Hood.” In the third volume, Hood leads his division in a spectacular attack at Gettysburg, and is promoted to lieutenant general. As it turns out, he is given operational responsibilities that are beyond his capabilities. In the summer of 1864, he takes command of the Army of Tennessee with the mission of defending Atlanta against Gen. William Tecumseh Sherman’s Union forces. By September of 1864, Hood lost Atlanta. Two months later, he lost his entire army in the battles of Franklin and Nashville. In large part, these failures occurred because he relied on the aggressive tactics that had brought him success as a junior officer.

Reflecting on Hood’s career provides powerful lessons for young leaders. From Hood’s example, we learn the successive levels of leadership (tactical, operational and strategic) are very different from each other and each requires its own unique competencies. Freeman notes one of the lessons of the Civil War: “It was plain that a man would not of necessity be a good general because he had been an excellent captain.” Successful tactical leaders might be tempted to think their success has prepared them adequately for the demands of strategic leadership. A consideration of Hood’s career demonstrates the fallacy of this assumption. This insight is an important one for people who want to assume responsibility for their own leader development process. The lesson here is that developing oneself as a strategic leader needs to begin long before one actually becomes a strategic leader.

People who want to create their own individual, proactive leader development program will benefit from a realization that reading about great leaders can promote the habit of reflection, and this habit is useful in several respects. Warren Bennis frequently speaks of leadership crucibles, which are events of such heightened interest or importance that they serve as milestones in a leader development journey. Experiencing moments of great danger, risk or complexity are illuminating moments for young leaders, but it is not enough to experience a crucible—one must have the ability to reflect on the lessons learned and use these reflections to gain insight. Management scholars (such as Henry Mintzberg) note that top leaders have a bias for action rather than reflection, so the ability to engage in meaningful reflection is a skill that requires practice to master. Reading about the challenges, trials and triumphs of great leaders, such as we see in Lee’s Lieutenants, can help develop the ability to reflect in a meaningful way and, as such, is a productive part of a leader development program.

Leadership from the Battlefield to the Boardroom

Thinking back to our introductory leadership diagnostic, it is plain that the Confederate high command belonged to the group that thought leadership mattered and had a very deliberate and often successful way of developing it — to a point. It is also plain that they failed to understand the distinction between tactical and strategic leadership. This assumption had disastrous consequences. Confederate generals would often act like captains on the battlefield with deadly results.  In addition, the high command, assuming they had a steady stream of strategic leaders, never developed formal development programs for budding strategic leaders. They gradually ran out of qualified generals.

The business world, and organizations in general, ignore these leadership lessons at their peril. Many organizations today also assume that leadership development is a low priority because the marketplace will provide a steady stream of strategic leaders. They fail to understand that when leaders parachute into new organizations, their managerial expertise survives intact but their leadership influence does not. That is because the competencies and character traits demanded of great leaders are grounded in the specific culture, values and mission of their organization.

We see from Lee’s Lieutenants that assumptions about leadership have consequences.  Acting on valid assumptions about leadership means you can benefit from sustained competitive advantage. Acting on faulty assumptions about leadership means you will find yourself in a rural Virginia farmhouse surrendering your army to Ulysses Grant.


Mike Hennelly served in the U.S. Army for 21 years where he qualified as an Army Ranger and certified as an Army strategist.  Later, as a civilian with a Ph.D in strategic management, he taught strategy to MBA students at two different universities and then spent seven years teaching strategy and leadership to cadets at West Point.  Since retiring from West Point, he provides seminars on strategic leadership to executives of some of the world’s largest companies.

Image: Painting by Charles Hoffbauer, Virginia Historical Society

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