The Brand Called You

Leadership Beyond Titles | LTC (R) Oakland McCulloch, Author, 'Your Leadership Legacy'

Nov 26, 2025
Lieutenant Colonel Oakland McCulloch, a leadership expert and author, shares insights from his 23 years in the U.S. Army. He emphasizes that true leadership transcends titles and is rooted in trust, character, and purpose. Oakland discusses the importance of servant leadership, humility, and learning from failures. He also highlights the need for clear communication and warns against micromanagement, advocating for empowerment instead. His vision for future leaders revolves around curiosity, a strong desire to serve, and leveraging technology.
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ANECDOTE

From Team Captain To Combat Leader

  • Oakland McCulloch learned leadership early through sports and school roles which led him to choose a military path.
  • His deployments taught him that taking care of people is the key to mission execution.
ADVICE

Leave The Rank At The Door

  • Put your ego aside when moving from military to civilian roles and start rebuilding trust from scratch.
  • Earn respect by listening, adapting your communication, and learning the organization's culture.
INSIGHT

Legacy Is Leadership Passed On

  • Legacy is mostly what you pass on to the next generation of leaders, not your job accomplishments.
  • Developing others multiplies your impact across organizations and generations.
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