By Angela Sontheimer
Managing Director
Lincoln Leadership Institute at Gettysburg

In war, taking risks can cost lives. In the business world, risks may not result in actual causalities, but they can result in diminished resources, lost time, and decreased productivity.

To drive home this message — and to stress the importance of smart risk taking — we talk about risk taking in the context of the Battle of Gettysburg in our Transformational Journey from Gettysburg leadership experience.

One of my favorite examples is that of a conversation about risk between General Robert Lee and his first in command, James Longstreet, on the third day of the Battle of Gettysburg in July 1863.

Lee vs. Longstreet

History tells us that these two Civil War legends were discussing the details of what would become known as Pickett’s Charge (although its official name is Longstreet’s Assault).

Lee (pictured above) ordered Longstreet to lead a charge of approximately 15,000 men across a mile of open field to the waiting Union guns. Longstreet, convinced that the attack would fail, pushed back against his commander’s orders.

This is where risk comes into play in two ways.

1. Is the attack itself too risky and should Longstreet take the risk of contradicting a superior officer?

2. In a business environment should you speak up when you have doubts about the success of a new project or venture? How about if you are talking to the CEO?

In this case, Longstreet (pictured here) was convinced of the futility of the attack and let his boss know. In Michael Sharra’s classic, The Killer Angels, Longstreet states:

“Sir, I have been a solider all my life. I have served from the ranks on up. You know my service. I have to tell you now, sir, that I believe this attack will fail. I believe that no fifteen thousand men ever set for battle could take that hill, sir.”

He then goes on to list several reasons why he holds this opinion. In doing so, he makes a valiant attempt at influence leadership or in modern parlance, attempts to “lead up.” Longstreet takes the risk presented to him — he does confront Lee.

Lessons Learned

In our leadership program, we term these kinds of conversations “courageous communication” and feel they are an essential part of a healthy productive work place.

As subordinates, we need to find the courage to speak to our professional convictions no matter who is in the audience. As leaders, we also need to create an environment where it is ok to “talk back” to the boss.

In the case of Lee and Longstreet, Longstreet was right. The attack did fail and resulted in more than a 50% causality rate for the Confederates and combined losses of more than 7,000 Americans.

Our advice to you: Take the risk and have those tough conversations if your convictions tell you to do so. You never know what the results will be.

About Angela Sontheimer

Angela is managing director of Lincoln Leadership Institute at Gettysburg, where she is responsible for overseeing operations, marketing, and curriculum design. She is a graduate of Gettysburg College and holds a masters degree in leadership and liberal studies from Duquesne University.