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Read Anything Good Lately? My Top 5 List of Favorite Books

Reading has always been a favorite pastime of mine, for both business and pleasure. Each year, I typically make a list of the books that impacted me the most.

But amidst all the disruption and seemingly constant uncertainty of 2023, I have been returning to some of the books that were fundamental in shaping my leadership approach. This eclectic list is a selection of the top five influential books that have had a profound impact on me, with insights and perspectives that continue to challenge my thinking.


So many books, so little time. ~ Frank Zappa


The List

Zen and the Art of Motorcycle Maintenance, by Robert Pirsig

This iconic book first made a tremendous impact in the 1970s, with college students in the post-Kerouac era. I also discovered this philosophical masterpiece in college in the early 1990s. It opened my mind to the idea that we can break free from thinking in only the two typical worldview dichotomies: black and white. It showed me how we can transcend into the humanism of the “gray.”  Reading this as a young man came at a pivotal time in my life, and it changed my view of the world, leading me to constantly question my thinking, as well as the thinking of those around me. Now 35 years later, I still consider this to be, across genres, my favorite book of all time.


The Fountainhead, by Ayn Rand

To me, The Fountainhead is another incredible work of fiction and philosophy. Considered a modern classic, this book has often been found in the “back pocket” of artists for the past 50-plus years. What I find interesting is how the book can be interpreted and used by people in so many ways— from a fierce, libertarian foundation where the idea is paramount to a strength of will, to where creators persevere and fight for their passions. What really resonated for me in this book was the notion of integrity: It provided for me the confidence and fortitude to not only stand up for what I believe, but to also recognize how you must find, or create, a tribe to make it happen. Despite its focus on intense, rugged individualism, I learned that leaders must stand for something and be willing to fight through “the noise” to see their vision realized.


The Dichotomy of Leadership: Balancing the Challenges of Extreme Ownership to Lead and Win, by Jocko Willink & Leif Babin

This is one of the best leadership books I have ever read. Written by two former Navy Seals, it contains military examples, but the lessons within it go much deeper. Each chapter focuses on fundamental dichotomies that provoke leaders to consider how they would apply or relate to them. For example, one chapter discusses “when to lead and when to follow,” which really challenges, in the most profound way, how leaders coach and lead through development in succession planning to strengthen their overall team members’ performance. The dichotomies presented in the book are devices that allow the reader to dive deep into the gray area between extremes, which engaged me in reflection and in its practical actions and applications throughout the book.


About Face: The Odyssey of an American Warrior, by Col. David Hackworth

This autobiography, by one of the most decorated soldiers in U.S. history, describes Hackworth’s evolution and realization as a maverick leader, with the intrigue, complacency, and politics that existed in the post-World War II U.S. Military. Hackworth, a journalist and Army Colonel, served through several wars, including World War II, Korea, Vietnam, and Delta Force. He one of those leaders who went into Vietnam and realized that he had to adjust his thinking and approach to succeed. This book was my first introduction into “complacent thinking,” and how various leaders responded to simple acts that created massive disruption—often leading to massive failures.


Team of Teams: New Rules of Engagement in a Complex World, by Gen. Stanley McChrystal

McCrystal’s book begins with a simple thesis: How do you take a 3,500-person organization and get it to operate like a small team: with agility, adaptability, and innovation? As a historian, I’ve always been struck by the ways that corporate leadership and team management often follow lessons from the military when in combat. McChrystal led a joint special operations command in Iraq in the mid-2000s and is credited with being a key factor in changing the direction of that failing conflict. There were many paradigm shifts and realizations that he and his team went through in order to apply an innovative team performance model, and I still use lessons from this book in my coaching practice. I am also fascinated how a three-star General, who had served for many decades in the military, had the humility to recognize when he needed to change his thinking and then engage and trust his staff at all levels of command to become a constant learning organization.


Honorable Mention

The Scout Mindset: Why Some People See Things Clearly and Others Don’t, by Julia Galef

Scouts see things around them more clearly and make better judgments. This engaging book encourages us to take off our blinders and shares the psychology of building the capability of the Scout mindset within your team, so you can adapt more quickly through informed decision-making.


What I’m Reading Next

Power Failure: The Rise and Fall of an American Icon, by William D. Cohan

I am looking forward to reading this definitive account of the remarkable rise – and the incredible fall – of the General Electric Company.  I am intrigued to learn more about how it became an iconic American company and how its leadership failed in the past several decades.


Have you read any of these? I’d love to hear from you and welcome any recommendations on your favorite old and new books, fiction, and non-fiction! Please send me an email or message me on LinkedIn.



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