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AI Picked 25 Books Military Leaders Should Read

by Jasper AI (with oversight from Joe Byerly and Jack Hadley)

A Note from Joe and Jack: Recently From the Green Notebook leadership has been playing with artificial intelligence (AI) tools for artwork, branding, and social media posting. To assess the capabilities of one specific AI tool, Jasper, we asked it to recommend books to military leaders. We simply told it, “Write a list of 25 books military leaders should read and tell us why we should read them.” Here’s what Jasper said.

The military is an institution where leaders are developed through experience and training. However, one often overlooked aspect of leadership development is reading. Reading is essential in lots of areas of life, but it is especially important for military leaders. Not only does reading inform the reader and teach them new skills and knowledge, but it also helps cultivate critical thinking skills and the ability to deal with complexity and uncertainty. In this post, we will be sharing 25 books every military leader should read and why they should read them.

1. The War of Art by Steven Pressfield: This book explores the idea of resistance and how it can hold back individuals from achieving their true potential. By overcoming resistance through determination and discipline, military leaders can become more successful.

2. The Leadership Challenge by James Kouzes and Barry Posner: This book provides a framework for leadership based on five key practices: modeling the way, inspiring a shared vision, challenging the process, enabling others to act, and encouraging the heart. These practices can help leaders achieve success in any military setting.

3. On War by Carl von Clausewitz: Considered a definitive classic on military strategy, On War provides insight into the nature of conflict and how military leaders can handle it.

4. Start with Why by Simon Sinek: Military leaders should read this book to understand the importance of a clear purpose and how it can motivate and inspire followers.

5. The Art of Possibility by Rosamund Stone Zander and Benjamin Zander: This book offers a new perspective on leadership and how to create a positive, innovative environment in which military teams can thrive.

6. The Seven Habits of Highly Effective People by Stephen R. Covey: This book provides valuable lessons on how to achieve success through habit formation and personal development. Military leaders can benefit from incorporating these habits into their daily lives.

7. The Unforgiving Minute by Craig M. Mullaney: This memoir details the journey of a young Army officer and the challenges he faced during his deployment in Afghanistan. Military leaders can learn from Mullaney’s experiences and apply some of his coping strategies in their own deployments.

8. The Art of War by Sun Tzu: One of the most influential books on military strategy ever written, the Art of War offers timeless wisdom on strategy and the art of conflict.

9. Extreme Ownership by Jocko Willink and Leif Babin: This book developed from the experiences of two Navy SEALs who led special operations teams in Iraq. Through their stories, Willink and Babin teach valuable leadership lessons applicable to any military setting.

10. The Lean Startup by Eric Ries: Military leaders can apply the principles of the Lean Startup process to their own decision-making and risk management strategies.

11. Leaders Eat Last by Simon Sinek: This book explores the idea of servant leadership and how leaders can create a thriving culture by putting the needs of their followers first.

12. The Long Gray Line by Rick Atkinson: This book is a detailed history of the United States Military Academy at West Point. Military leaders can learn from the experiences of past cadets and apply the lessons to their own leadership development.

13. Outliers by Malcolm Gladwell: This book examines the reasons why some individuals attain extraordinary success and how military leaders can apply similar thinking within their own organizations.

14. The Power of Positive Leadership by Jon Gordon: This book teaches readers how to harness the power of positivity to build strong teams and foster productive relationships.

15. The Mission, The Men, and Me by Peter Blaber: This book explores leadership in special operations teams and how leaders can achieve success by putting the needs of their teams first.

16. Endurance by Alfred Lansing: This book tells the tale of the ill-fated expedition led by Ernest Shackleton to Antarctica. Military leaders can draw on Shackleton’s resourcefulness, perseverance, and leadership skills for inspiration.

17. The Innovator’s Dilemma by Clayton Christensen: This book explores the idea of disruptive innovation and how military leaders can address the challenges arising from rapid technological changes.

18. The Dichotomy of Leadership by Jocko Willink and Leif Babin: This follow-up to Extreme Ownership explores the complexities of leadership and how leaders need to balance competing demands to achieve success.

19. Band of Brothers by Stephen E. Ambrose: This book tells the story of Easy Company, 506th Regiment of the 101st Airborne Division, U.S. Army, during WWII. Military leaders can learn from the experiences of these soldiers and apply their lessons to their own teams.

20. Red Team by Micah Zenko: Military leaders can learn from this book about the importance of critical thinking, risk assessment, and planning for contingencies.

21. Team of Teams by General Stanley McChrystal: This book offers valuable insights into the importance of adaptability and collaboration in military leadership.

22. Shoe Dog by Phil Knight: This memoir details the founding of Nike and the challenges Phil Knight faced along the way. Military leaders can learn from his story about persistence, innovation, and teamwork.

23. Thinking, Fast and Slow by Daniel Kahneman: This book explores how the mind works and provides insight into decision-making strategies. Military leaders can benefit from adopting some of these strategies in their own decision-making processes.

24. The Prince by Niccolò Machiavelli: Although this book is controversial, it provides insight into the importance of leadership in times of crisis and the delicate balance between power and ethics.

25. The Elements of Style by William Strunk Jr. and E.B. White: This book is a classic guide to writing clearly and effectively. Military leaders can benefit from its lessons in order to communicate effectively with their teams, peers, and superiors.

Were AI’s Recommendations Any Good?  

Joe and Jack here again. From our perspective, as moderators and editors at FTGN, this is a solid list of book recommendations. Collectively we have read most of these books and recommended them to friends (and our audience!). Most strikingly, none of these 25 recommendations are obviously wrong choices. This experiment is another example of the ways AI can enrich our intelligence and extend our consciousness; but this is new territory, and it’s a bit scary. 

Here’s the problem: we have no idea where Jasper pulled this information from. As we tested the different writing prompts on various subjects over the course of the week, and Jasper produced some brilliant pieces (some even in Joe’s writing voice), we found multiple errors. The only reason we were able to identify Jasper’s missteps was because we were familiar with the material we were asking it to produce.

While we appreciate Jasper’s attempt to educate us, AI doesn’t give us an out. It doesn’t allow us to be intellectually lazy. If anything, it requires more of us. As the military continues to test the power of AI-enabled decision-making, leaders need to be able to step in when the algorithm is wrong. 

Leaders must continue to prepare their minds to think critically. Lucky for us, Jasper has prepared a great starter list of professional reading recommendations to enrich our mental models, to better understand people and how to lead them, and to learn how to deal with the complexity of the modern world. We hope you start with this list, and then develop your own and share it. We also hope that you share that list with friends and colleagues. We both believe that books are one of the greatest investments we can make in our personal and professional development. 

If you are looking for more reading suggestions (by an actual person), check out our Monthly Reading List Email. Joe has been recommending 3-5 books a month with thousands of subscribers since 2017. His recommendations range from new releases to books that are thousands of years old and he always shares why he thinks you should read them too. 

Also, check out some of these other popular reading lists we’ve published over the years:

Jasper is an AI service that generated the main body of this text during a free trial period. Joe Byerly is the founder of From the Green Notebookand the coauthor of My Green Notebook: “Know Thyself” Before Changing Jobs. Jack Hadley is the Editor-in-Chief at From the Green Notebook.