Building Trust-Based Leadership: Military Insights for Modern Business Success

Dec 11, 2025

In this compelling episode of Cutting Through the Clutter, host Cyndee Woolley welcomes Craig Oglesby, managing member of Outsiders Group LLC and leadership development specialist, whose eight-year journey as a U.S. Army infantry officer—including company commander roles leading over 250 personnel in Afghanistan—has shaped his revolutionary approach to building high-performing teams. 


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Craig shares his proven framework centered on a deceptively simple yet powerful truth: trust is the invisible force that separates good teams from exceptional ones. Like Wi-Fi, you can’t see it, but you definitely know when it’s not working. Through candid conversation, Craig reveals how leaders can establish and maintain trust through intentional communication and clear standards, even in today’s digitally-driven workplace where remote teams and social media complicate genuine connection. 

The discussion moves beyond theory into practical application, exploring how one-on-one conversations build trust over time, why communicating purpose prevents teams from “making up their own stories,” and how to set standards that empower rather than control. Craig introduces the concept of “left and right limits”—like navigational buoys that define safe waters while allowing flexibility—giving teams space to maximize their potential within established boundaries. 

From addressing the shift in communication styles across different eras to leveraging after-action reviews for continuous improvement, Craig offers actionable strategies for closing out 2025 strong and positioning your organization for growth in 2026. Whether you’re managing a small team or leading a geographically diverse organization, this episode delivers the practical wisdom you need to build authentic trust and unlock your team’s true potential. 

Perfect for: Business leaders, entrepreneurs, team managers, military veterans transitioning to civilian leadership roles, and anyone seeking to strengthen organizational culture through trust-based practices. 

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