Is Your Leadership Approach Making Your Organization Worse? 

Are your current top performers driving away your future leaders? Is your organization stuck in a vicious cycle of toxic leadership that's eroding company trust and culture? Oakland McCulloch, retired Army Lieutenant Colonel and leadership expert, shares hard-earned wisdom about breaking these destructive patterns and building organizations where both people and results perform well. 

In this compelling conversation with host Damon Lembi, Oakland draws on over 40 years of experience to examine why current leadership approaches are falling short and what needs to change. He makes a passionate case for servant leadership while acknowledging the critical importance of driving results. Through vivid stories from his military career and civilian consulting work, Oakland provides practical guidance on building trust, developing future leaders, and creating winning cultures - all while avoiding the pitfalls that trap many well-intentioned leaders. 

 This Episode Covers: 

• Why many organizations are trapped in a toxic cycle where poor leaders drive out good emerging talent, leaving only mediocre performers who perpetuate bad leadership practices 
• The critical balance between caring for people and driving results - and why you don't have to sacrifice one for the other 
• How to build trust through intentional relationship-building and why leaders must trust their people as much as people trust their leaders 
• Why keeping high-performing toxic employees destroys organizational culture and trust 
• The importance of getting back to a "winning culture" while maintaining integrity and values 
• Practical approaches to delegation and empowering teams while maintaining accountability 
• How to develop emerging leaders through proper training and role alignment 

Episode Highlights: 

(00:00) Introduction to Oak McCulloch – Damon introduces Oak, highlighting his career and passion for servant leadership. 

(01:30) The State of Leadership Today – Oak discusses why accountability and responsibility are often missing in modern leadership. 

(05:00) Servant Leadership in Action – Oak shares lessons learned from mentors who emphasized putting people first. 

(09:00) Balancing Accountability and Results – Oak explains how leaders can achieve success while fostering a people-focused culture. 

(12:33) Avoiding Micromanagement – Oak provides advice on delegating effectively and empowering teams to take ownership. 

(17:00) The Power of Trust – Oak emphasizes the importance of building trust within teams and shares his 360-degree trust framework. 

(21:30) Lessons from Military Leadership – Oak discusses how his experiences in the Army shaped his leadership philosophy. 

(33:18) Building a Legacy of Leadership – Oak offers advice on mentoring future leaders and fostering long-term impact. 

About Oakland: 

Oakland McCulloch draws on over 40 years of high-stakes leadership experience across military and civilian sectors to help organizations develop stronger leaders and build more effective teams. As a retired U.S. Army Lieutenant Colonel, he led teams in combat operations, peacekeeping missions, and disaster relief efforts before successfully transitioning to civilian leadership roles. Oak has helped commission over 600 Army officers and received 31 military service awards, including the Bronze Star. His 2021 book Your Leadership Legacy and international speaking engagements focus on practical, actionable principles drawn from his extensive experience building and transforming organizations in both military and civilian environments. 

Resources Referenced: 

Your Leadership Legacy: Becoming the Leader You Were Meant to Be by Oakland McCulloch  

We Were Soldiers Once...And Young: Ia Drang The Battle That Changed the War in Vietnam Hardcover by Harold G. Moore and  Joseph L. Galloway (referenced in the discussion of General Hal Moore) 

Oakland McCulloch on LinkedIn 

Oakland McCulloch's website 

Podcast Contact Information:   

Website: www.learnit.com 

Email: podcast@learnit.com 

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