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Your Leadership Legacy

Lieutenant Colonel Oakland McCullouch

The best leaders are the ones who have the sense to surround themselves with outstanding people and have the self-restraint not to meddle in how they do their jobs.” - Your Leadership Legacy, p. 79


I had the opportunity to meet Lieutenant Colonel Oakland McCullouch when I interviewed him for an episode of The Sourcing Hero podcast. The advantage that gives me is that I was able to hear every word of this book in his voice while reading. As a result, my review of his book, Your Leadership Legacy: Becoming the Leader You Were Meant to Be, is a mix of my response to his writing and my sense of who he is as a person.

The book is highly readable, perfectly structured to be read a few minutes a day (or all in one sitting) without any loss of continuity. It is also full of quotes from influential business and military leaders. The guide to everyone quoted in the book with a brief explanation of who they are/were on page 158 is helpful, and it demonstrates the broad range of thinkers that are reflected in the book.

McCullouch served in the U.S. Army for 23 years, spending time in Saudi Arabia, Iraq, Bosnia, and Kosovo before going on to work as the Associate Director of a food bank, Vice Chair for Military Affairs at the Mobile Area Chamber of Commerce, and a recruiter for the Army ROTC program at Stetson University in Florida. In every role and every organization he applied his best understanding of good leadership and picked up new lessons as well. His approach works equally well in military and civilian settings.

Leadership is not easy – and it is not about you. This book does an excellent job balancing big picture principles with detailed examples that prove them out. Vision and execution are equally important, and everyone has a role to play in solving a problem or making a solution work.

My favorite story in the book deals with micromanagement. In a life-and-death training situation most of us will never need to face, McCullouch had to take his boss aside and make him back off so the team could achieve their objective. Allowing people to succeed, not trying to ensure they succeed by hovering over them is the key.

There are also a number of firings in the book. Terminating employees is an unfortunate but necessary part of leadership. Each one caught me by surprise… not because I would have advocated to keep the person under the circumstances as they were described, but because McCullouch comes across as a caring and empathetic human being – in person and on the page. Employees who had to go are dealt with in a very matter-of-fact way that initially seems to conflict with McCullouch’s style. And yet, there is a consistency to his advice and approach that can’t be denied. Obstacles are an inevitable part of work, and it is a leader’s job to remove them. That is true whether the obstacle is a person or an external challenge.

If I had to characterize McCullouch’s leadership philosophy, I would say servant leadership with consequences. Expectations that leaders will work hard, dedicate themselves to the task at hand, and own their team’s good and bad results will not come as a surprise. But the clear care that underpins all of that may. People are at the core of good leadership – and if you do a good job as a leader, they will become your legacy. McCullouch is the kind of leader all of us want to work for, and now everyone can learn from.

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