MyWingman, LLC was established when retired U.S. Army Colonel Dr. Burl Randolph Jr. transitioned from military service into the corporate world and recognized a critical gap. Many business leaders are expected to operate at a high level without ever being formally trained to lead at scale. After more than three decades in the military, including three deployments in Iraq, and earning a doctorate in management with a focus on organizational leadership, he now supports executives using the structured, mission-focused leadership principles developed during his service. “Leadership can be simple, but it’s not easy,” he says, “It comes with no instruction manual, but that doesn’t mean it cannot be learned.”
According to Dr. Randolph, many newly appointed CEOs step into complex challenges equipped with data but without the leadership development required to navigate them effectively. He encounters this gap regularly. Rather than allowing leaders to remain uncertain, he works to guide them toward clarity and decisive action. “People say you don’t know what you don’t know,” he says. “I disagree. You do know what you don’t know; that’s why they’re called questions. Ask them early, and often.”
Dr. Randolph advises leaders to categorize challenges into two groups: those within their control and those that must be endured. External disruptions such as economic downturns, government interruptions, and global crises must be managed and navigated. Internal issues such as cultural misalignment, unclear responsibilities, and escalating costs can be addressed directly. His initial approach with any organization is to implement systems that provide real-time visibility into performance. “If you are still running a 500-person firm on pen and paper, the realities of today will hit you like a truck,” he says. He adds that many executives have never been prepared to lead large organizations in the first place.
“If you think about it, the military has CEO schools,” he says. “While it does not literally teach you to run a business, it teaches many of the skills and core competencies today’s corporate leadership needs.” From junior enlisted roles to senior command positions, he explains that military leaders are trained to scale responsibility effectively. “Officers often follow a rule that one leader should not directly manage more than ten people,” he says. “In the business world, that structure scales upward where a front-line manager leads around five direct reports, a plant manager oversees four line leaders rather than forty operators, a regional leader manages a small group of plant heads and a deputy, and a CEO leads a compact circle of executives and regional managers who carry information upward and downward with clarity and speed.”
Each MyWingman, LLC engagement begins with a complimentary one-hour consultation, followed by a Pre-Contract Interview. During this session, Dr. Randolph assesses two essential qualities: openness, defined as a willingness to engage in honest dialogue, and vulnerability, defined as the ability to acknowledge areas that require improvement. “If we can’t talk straight,” he says, “no contract will save us.” Once a foundation of trust is established, Dr. Randolph develops a leadership coaching plan based on the Randolph Roadmap for Inspired Leaders. This plan integrates practical execution strategies with long-term vision and legacy development based on the person’s leadership level.
Dr. Randolph describes leadership growth through three key components: counseling, which establishes expectations; coaching, which enhances capability; and mentoring, which transfers knowledge and experience. When leaders openly recognize their own limitations, he notes, it encourages teams to do the same, creating an environment focused on continuous learning.
Another challenge he frequently observes is that organizations often promote individuals based solely on performance. High-performing sales professionals, engineers, and technical specialists are frequently elevated into leadership roles without being equipped to lead effectively. Dr. Randolph believes this approach can limit organizational success. His work focuses on addressing this gap by preparing leaders to manage and guide teams, not simply contribute individually. “The result,” he says, “is an organization that moves up and to the right without burning out your best people in the process. There’s a good reason why the military promotes based on potential, not just performance.”
He emphasizes that early engagement allows organizations to intentionally shape their culture, establish strong communication structures, and prevent leadership breakdowns before they occur. “Competitors can copy your product, your pricing, even your processes,” Dr. Randolph says. “They cannot copy leadership clarity when it’s been forged the right way.”
For Dr. Randolph, leadership is not an inherent trait reserved for a select few, but a discipline that can be developed, refined, and sustained over time. Through MyWingman, LLC, a leadership and management advisory firm informed by military principles and adapted for corporate environments, he helps executives define their purpose, execute their mission, and build a lasting legacy. “You won’t rise to the level of your goals if you fall to the level of your systems,” he says. “My job is to make sure your systems and blind spots don’t fail you when it matters most.”
