Are You A Leadership Rough Rider?
In the annals of American history, few figures loom as large as Theodore Roosevelt, the 26th President of the United States. His bold leadership, unwavering determination, and adventurous spirit captured the imagination of a nation. Roosevelt has long been one of my favorite historic politicians thanks to his conservation initiatives. I recently spent some time in San Antonio (shout out to the 24-242 5th Platoon and Menger Hotel folks), where I learned in greater detail one chapter of his life that further exemplified his leadership qualities - this time recruiting and leading the Rough Riders during the Spanish-American War.
In the spring of 1898, tensions between the United States and Spain reached a boiling point, ultimately leading to the Spanish-American War. Roosevelt, then Assistant Secretary of the Navy, resigned from his position to join the fight. Eager to prove their valor, Roosevelt and a diverse group of volunteers - cowboys, Native Americans, Ivy League athletes, and adventurers - formed the 1st United States Volunteer Cavalry Regiment, famously known as the Rough Riders. San Antonio, Texas, became a crucial staging ground for their training and preparation. On July 1, 1898, Roosevelt mounted his horse (named Little Texas) and led the Rough Riders, the black soldiers of the 9th and 10th cavalry, alongside several thousand members of the 5th Corps of the US Army up Kettle Hill (and San Juan Hill) in Cuba, routing the Spanish leading to the Spanish ceding Cuba, Guam, Puerto Rico and the Philippines in the Treaty of Paris.
Sifting through the sands of history from the Menger in San Antonio, I was struck by the fusion of statesmen, soldier, cowboy, and conservationist. While perhaps contradictory in some regard, I came away with some timeless leadership insights that remain as relevant today as they were over a century ago.
Knowing what is right doesn’t mean much unless you do what is right ~Roosevelt
Leadership Lesson 1: Embrace Team Diversity
Roosevelt understood the strength that diversity brings to a team. The Rough Riders were a motley crew, drawn from different walks of life, yet united by a common cause. By embracing experiential diversity and individual attributes, Roosevelt created a cohesive unit where each member felt valued and respected for what they brought to the team. Concurrently, they fought alongside the 9th and 10 cavalry and the 5th Corps in common goal despite differing experience. Today, leaders can learn from this lesson by recognizing the unique perspectives and talents that individuals from diverse backgrounds bring to the table. Embracing diversity isn't about ticking boxes; it's about leveraging the richness of varied experiences to drive innovation and success.
When you are at the end of your rope, tie a knot and hold on. ~Roosevelt
Leadership Lesson 2: Lead by Example
Throughout their training in San Antonio and later on the battlefield, Roosevelt led by example. Despite his privileged upbringing, he willingly endured similar hardships and challenges as his men. Whether charging up San Juan Hill or sharing their meager rations, Roosevelt showed solidarity with his troops, earning their admiration and loyalty. In modern leadership, the principle of leading by example remains paramount. Leaders who roll up their sleeves, work alongside their team, and demonstrate integrity inspire trust and motivate others to give their best.
It is hard to fail, but it is worse never to have tried to succeed. ~Roosevelt
Leadership Lesson 3: Adaptability and Resilience
The campaign of the Rough Riders was marked by adversity and uncertainty. From logistical challenges to fierce combat in the sweltering heat of Cuba, they faced obstacles at every turn. Roosevelt's ability to adapt to changing circumstances and maintain resilience in the face of adversity was instrumental in their success. That included having to dismount their horses and leave them behind when making the final charge up Kettle Hill. Today's leaders operate in an environment of constant change and disruption. Those who cultivate adaptability and resilience, who can pivot when necessary and inspire their team to persevere in the face of challenges, are better equipped to navigate uncertain waters and achieve their objectives.
Do what you can, with what you have, where you are. ~Roosevelt
The legend of Theodore Roosevelt and the Rough Riders endures as a testament to the power of bold leadership, camaraderie, and resilience. From the dusty plains of San Antonio to the hills of Cuba, their story, while not perfect, offers timeless lessons for leaders in any era. By embracing team diversity, leading by example, and cultivating adaptability, we can adopt the lessons from Roosevelt to inspire and unite our teams toward shared goals. As we face the challenges of the 21st century, let us remember the words of Teddy Roosevelt himself: "Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to rank with those poor spirits who neither enjoy much nor suffer much, because they live in the gray twilight that knows not victory nor defeat."