Leadership

An excellent study on leadership. This book examines how Abraham Lincoln built and led a cabinet made up of his political opponents, transforming them from rivals into a unified team during the nation’s most perilous years. Drawing on deep historical research, Doris Kearns Goodwin shows how Lincoln’s empathy, patience, and political skill enabled him to manage clashing personalities, navigate intense partisan divides, and preserve the Union through the Civil War.

Former Delta Force officer Pete Blaber’s reflection on leadership and decision-making under extreme conditions. Drawing from combat missions and unconventional operations, Blaber distills principles like “Don’t get treed by a Chihuahua” and “When in doubt, develop the situation” to emphasize adaptability, situational awareness, and putting people ahead of rigid plans. I liked Blaber’s “saturate, incubate, illuminate” framework for decision-making: First, flood your mind with every piece of relevant information. Then, give it time and space to work in the background. Finally, act on the insight that surfaces, often unexpectedly, once the mental connections lock into place. Sort of a way to deliberately use “shower thoughts” or the sorts of insights we have when casually contemplating complex ideas. 

MSG (Ret.) Paul Howe, a former Delta Force operator, shares hard-earned lessons in leadership and training forged in combat. Drawing from over 20 years of military experience, including the Battle of Mogadishu. Howe delivers a clear-eyed guide for building resilient teams, designing effective training, and leading under extreme conditions.

Rich Diviney is a thoughtful guy and a deep thinker, with experience at NSWDG that you won’t hear him talking about publicly, but that provides a lot of the basis of his writing. In this concise, science-backed handbook, he outlines a framework for staying calm, focused, and effective in high-pressure situations. He covers things like regulating and focusing your body’s stress response, breaking down chaotic situations into manageable steps (aka segmenting), and building trust through “dynamic subordination”, where leadership shifts fluidly according to who has the best vantage point.

This book can be read as a leadership-focused sequel to Daniel Goleman’s Emotional Intelligence. Where Emotional Intelligence lays out the framework for how self-awareness, self-regulation, empathy, and social skills shape human interaction, Primal Leadership applies those ideas directly to the practice of leading teams and organizations. Taken together, they show why the most effective leaders must be strategic thinkers, and emotionally attuned to the people they lead.

Part memoir, part business philosophy, this book tells the story of Patagonia’s founder, Yvon Chouinard. A climber and craftsman who never aspired to run a company, Chouinard built Patagonia around values that prioritize the environment and employees. He explains how the company’s culture (flexible schedules, environmental activism, quality over growth) grew out of his own life as a climber, surfer, and environmentalist. The book is equal parts autobiography, manifesto, and field guide for anyone trying to build a business without losing their principles.

This book reframes organizations as networks of small tribes (natural groups of 20–150 people) whose strength defines the broader culture. Drawing from a decade-long study of over 24,000 individuals across two dozen companies, Logan, King, and Fischer‑Wright identify five cultural stages through which tribes evolve, from “Life sucks” to “We’re great.” The authors provide a roadmap for leaders: assess your tribe’s stage, use specific leverage points to elevate it, and establish a culture where collective potential drives both well-being and business results. The bit about distinguishing between dyads and triads in organizational communication is extremely useful - basically, seek to eliminate road blocks that interfere with clear, direct communication.

When Captain David Marquet took command of the USS Santa Fe, a submarine ranked lowest in operational performance and crew retention, he recognized that traditional top-down leadership would only sustain failure. Instead, he introduced a “leader–leader” model that replaced rigid hierarchy with decentralized decision-making. Marquet empowered his crew to say “I intend to…” instead of asking permission, supported them with clarity and competence, and shifted authority to where information lived. Within a year, the Santa Fe became one of the Navy’s highest-performing submarines, with record retention and morale levels. Marquet’s ideas pair well with Jocko Willink and Leif Babin’s Extreme Ownership and The Dichotomy of Leadership. Where Extreme Ownership emphasizes taking full accountability as a leader, and The Dichotomy of Leadership explores balancing competing tensions (discipline vs. initiative, confidence vs. humility), Turn the Ship Around! shows how those same principles can be extended to entire teams through distributed authority.

Written by the legendary San Francisco 49ers coach, this book distills Walsh’s philosophy of leadership and performance into lessons that go far beyond football. At the heart of his approach was what he called the “Standard of Performance,” a detailed set of expectations for behavior, preparation, and execution that emphasized discipline, consistency, and professionalism at every level of the organization. Walsh believed that if you set the right standards and lived by them, outcomes like wins and championships would follow as a natural consequence. It’s less about motivational speeches or dramatic halftime turnarounds, and more about the patient, systematic work of building a culture of excellence.

This is a novel, but it has been required reading for generations of military officers because of the way it illustrates two starkly different models of leadership. It follows Sam Damon, a selfless professional who leads through integrity, courage, and loyalty, and contrasts him with Courtney Massengale, an ambitious careerist who prioritizes personal advancement over principle. Spanning from World War I through Vietnam, the book shows how each man’s choices ripple across decades of war, peace, and politics. It’s long, but worth the time; reading it will give you a lens through which to judge leadership styles you’ll encounter in the real world, and to reflect on which path you want to follow yourself.

General James Mattis, one of the most respected Marine leaders of his generation, lays out the leadership lessons he learned across a forty-year career. The book is structured around three phases of his life: as a direct leader of Marines in combat, as an operational commander shaping campaigns in Iraq and Afghanistan, and as a strategic leader responsible for entire regions and alliances. The through-line is his insistence on reading, reflection, and clarity of intent as the foundations of command.

This book distills the culture and leadership philosophy of the New Zealand All Blacks, the most successful rugby team in history. Kerr draws out the habits, values, and practices that built their dynasty, from the insistence on humility (“sweeping the sheds”) to the focus on collective purpose over individual glory. The lessons apply directly to business, the military, and any environment where trust, accountability, and character determine success more than raw talent. If you want a practical guide to shaping a culture that lasts beyond individuals, this is one of the best texts available.

Retired U.S. Army General Stanley McChrystal distills the leadership lessons he learned while commanding Joint Special Operations Command in Iraq and Afghanistan. Faced with insurgents who adapted faster than the U.S. military’s traditional hierarchical structures could respond, McChrystal realized that efficiency was no longer enough. To succeed, organizations had to become adaptable, networked, and resilient. He describes how he broke down rigid silos, fostered radical transparency, and empowered small, decentralized units to act with autonomy while still remaining aligned to a shared mission.

This has a lot of principles that can be applied well beyond football. It’s about Bill Belichick, the famously private and detail-obsessed coach of the New England Patriots. The book traces Belichick’s path from his father’s coaching career at the Naval Academy through his own rise in the NFL.

Most books by SEALs are a cliche at this point, but Jocko’s stuff is solid and focuses some of the most fundamental principles found in SOF that can be surprisingly uncommon in the rest of the world. His central premise is, like many of things that really matter, simple in theory and difficult in practice: leaders must take absolute responsibility for everything in their world. Failures can’t be blamed on subordinates, circumstances, or chance; only owned, learned from, and corrected. Willink and Babin illustrate this through direct combat stories paired with business-world applications, showing how principles like decentralized command, simplicity, and discipline create stronger teams. Read these in order, from Extreme Ownership, to Dichotomy, to Strategy and Tactics. And, if you’d like a contrasting view of the culture in the SEAL teams (including Jocko's unit) without all the self-mythologizing, read Code Over Country by Matthew Cole.

If Extreme Ownership lays out the principle that leaders must take responsibility for everything in their world, The Dichotomy of Leadership explores the balancing act required to apply those principles well. Leadership is full of tensions: being aggressive without being reckless, leading with confidence without arrogance, caring for your people without losing sight of the mission. Jocko and Leif show how leaning too far in one direction can undermine a leader’s effectiveness, and they illustrate each dichotomy with stories from combat and business.

This book serves as a field manual for leaders at every level, from small teams to large organizations. The format is straightforward: real-world problems are posed for everything from dealing with difficult subordinates to balancing discipline with flexibility, and answered with concrete guidance rooted in the principles of humility, accountability, and decentralized command. It reads less like theory and more like a playbook, making it one of the most directly actionable leadership books on your list.

Also mentioned in our complexity category, this is a foundational book on applying systems thinking to organizations. Senge introduces the concept of the “learning organization,” where teams build shared vision, reflect on mental models, and use feedback loops to adapt to complexity rather than resist it. It’s a book that bridges theory and practice, showing leaders how to shape cultures that continually learn and improve. While it’s aimed at business leaders, the principles apply just as well to military teams, coaching, and any environment where people must operate together in dynamic, uncertain conditions. It’s a good companion to Black Box Thinking.

Also in our thinking category, this book uses experiments and case studies to show how people consistently mismanage complex systems ranging from cities, to ecosystems, to economies; because they oversimplify, ignore feedback loops, or try to control variables they don’t understand. The result is often unintended consequences and system collapse. It’s a close look at human psychology under pressure, making it a valuable companion to Thinking in Systems by Donella Meadows. It helps explain why even well-intentioned leaders can make disastrous choices when they fail to grasp complexity in its full scope.