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Building Trust-Based Leadership: Military Insights for Modern Business Success
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In this 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.
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.
Links and Resources:
Website: www.outsiders-group.com
Command Post Cohort: www.commandpostcohort.com
LinkedIn: https://www.linkedin.com/in/craig-oglesby/
Today, I'm excited to welcome Craig Oglesby, Managing Member of Outsiders Group LLC and a leadership development specialist whose unique journey from military command to entrepreneurial success has given him remarkable insights into what truly drives high-performing teams.
Craig served over eight years as a U.S. Army Infantry Officer, including Company Commander roles where he led over 250 personnel in combat operations in Afghanistan, managing equipment valued at over $150 million.
Today, Craig focuses the belief that trust sets high-performing teams apart, and that communication and standards are two important skills for leaders to establish that trust. He holds an MBA from the University of Georgia, is a Lean Six Sigma Green Belt, and a PROSCI Certified Change Practitioner.
His consulting firm, Outsiders Group LLC, helps organizations solve the leadership challenges that keep executives up at night through his proven framework of trust-building communication and standards.
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