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The Dichotomy of Leadership:

Balancing the Challenges of Extreme Ownership to Lead and Win

Bibliographic Content

Jocko Willink & Leif Babin


St. Martin’s Press

Kindle, Hardback (320 pages), Audible (10hrs:34min)

Synopsis from Author

The importance of balance as a leader by the number-one New York Times best-selling authors of Extreme Ownership.

Every leader must be ready and willing to take charge, to make hard, crucial calls for the good of the team and the mission. Something much more difficult to understand is that in order to be a good leader, one must also be a good follower. This is a dichotomy - a Dichotomy of Leadership. It is, as authors Jocko Willink and Leif Babin explained in their best-selling first audiobook, Extreme Ownership, “Simple, Not Easy”.

Now, in The Dichotomy of Leadership, the authors explain the power inherent in the recognition of the fine line that leaders must walk, balancing between two seemingly opposite inclinations. It is with the knowledge and understanding of this balance that a leader can most effectively lead, accomplish the mission, and achieve the goal of every leader and every team: victory.

Using examples from the authors' combat and training experience in the SEAL Teams and then showing how each lesson applies to business and in life, Willink and Babin reveal how the use of seemingly opposite principles - leading and following, focusing and detaching, being both aggressive and prudent - require skill, awareness, understanding, and dexterity, all attributes that can be honed. These dichotomies are inherent in many of the concepts introduced in Extreme Ownership and integral to their proper implementation and effectiveness. Dichotomy is essential listening for anyone looking to lead and win.

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The Dichotomy of Leadership, Jocko Willink, Leif Babin

In most cases, rather than extremes, leadership requires balance. Leaders must find the equilibrium between opposing forces that pull in opposite directions. Being aggressive but cautious, disciplined but not rigid, a leader but also a follower - it applies to almost every aspect of leadership. Achieving the proper balance in each of the many dichotomies is the most difficult aspect of leadership. (pg xvi-xvii)

Summary of Book from War Is My Business

They wrote Extreme Ownership to teach the business world the importance of taking responsibility for organizational performance, training and development of junior leaders, long-term planning towards objectives, and improving communications; to name only a few issues. These elements of effective organization were lessons learned through their deployment to Iraq and subsequent training commands. If these were weaknesses for military organizations then they were likely weaknesses for businesses too. They taught their students to tackle these problems like their livelihoods depended on it, and many did put changes in place to improve them.

After the publication of Extreme Ownership, the authors, Jocko Willink and Leif Babin, began to notice a new problem arise amongst their students. While it fixed many of the problems businesses were seeing. Some took it to an extreme. Possibly as a consequence of the name Extreme Ownership containing the word “extreme.” Most things in the world require balance, but people either do too little or too much. Extreme Ownership was written for those that were doing too little in the way of leading their organizations. This book, The Dichotomy of Leadership, was a response to seeing people begin to take things to too far to the other end of the leadership spectrum.

This entire book is about balancing the various responsibilities of leadership. Every chapter, except the introduction, covers some type of issue that requires balance. Like their other books, they first discuss an experience they had while leading training evolutions or in combat in Iraq. These experiences lead into a discussion about a particular principle which in turn leads into an actual anecdote of teaching and applying this to the businesses of their clients. Usually, the business scenario occurs as a result of a student or organization taking a principle of Extreme Ownership to such an extreme that Jocko of Leif have to rein them in and balance them back out.

So, what issues, that require a leader to balance, are brought up in this book. Well, by looking at the chapter titles you know what dichotomy will be covered, except for Chapter 1 titled “The Ultimate Dichotomy” which covers the balance between looking out for the well-being of your people and organizational objectives. We will talk about the ultimate dichotomy in greater detail for this review, but will at least provide a layout of all the chapters so you have an idea of all that this book entails.

Book Layout

Introduction: Finding the Balance


Part I: Balancing People

Chapter 1: The Ultimate Dichotomy

Chapter 2: Own It All, but Empower Others

Chapter 3: Resolute, but Not Overbearing

Chapter 4: When to Mentor, When to Fire


Part II: Balancing the Mission

Chapter 5: Train Hard, but Train Smart

Chapter 6: Aggressive, Not Reckless

Chapter 7: Disciplined, Not Rigid

Chapter 8: Hold People Accountable, but Don’t Hold Their Hands


Part III: Balancing Yourself

Chapter 9: A Leader and a Follower

Chapter 10: Plan, but Don’t Overplan

Chapter 11: Humble, Not Passive

Chapter 12: Focused, but Detached

The Ultimate Dichotomy

It was difficult to grasp, the hardest and most painful of all the dichotomies of leadership: to care about your men more than anything in the world - so much so that you’d even willingly trade your life for theirs - and yet, at the same time, to lead those men on missions that could result in their deaths. (pg 19)

A quick historical example of the ultimate dichotomy:

One of the most famous incidents that occurred during the First World War, for the Americans, was the exploits of 1-308th Infantry “The Lost Battalion” led by Major Charles Whittlesey. During the Meuse-Argonne Offensive from October 2nd through the 7th of 1918. Major Whittlesey’s battalion was isolated as a result of German counterattacks forcing friendly units to his flanks to fall back. They were cut off from supplies, constantly attacked, subject to friendly and enemy artillery fire, and suffered many casualties during their encirclement. The Germans offered the Americans the opportunity to surrender in light of the situation:

...The suffering of your wounded men can be heard over here in the German lines, and we are appealing to your humane sentiments to stop. A white flag shown by one of your men will tell us that you agree with these conditions. Please treat Private Lowell R. Hollingshead as an honorable man. He is quite a soldier. We envy you. -The German Commanding Officer

Major Whittlesey, however, refused to surrender his men. They continued to resist until a relief force came on the night of the 7th of October. During that hellish five days, of the original 554 men that made up “The Lost Battalion,” only 194 were still fit to fight with around 107 killed, 190 wounded, and 63 missing in action. They sacrificed much to accomplish their mission as ordered, and that bravery and sacrifice were commended. Major Whittlesey was even awarded the Medal of Honor alongside six other Soldiers and more than 30 would receive the Distinguished Service Cross.

That is the story that most people know. What most people don’t know is that Whittlesey would commit suicide by throwing himself overboard in 1921 while en route to Havanna. While we can’t be certain of the reasons, we do know that Whittlesey suffered great mental anguish for those that died and suffered due to his decisions. He was racked with what-ifs and questioned what he could have done differently - even questioning if surrender may have been the better option to ensure more of his people would survive to see the end of the war. The Germans surrendered a month later anyway, did he need to sacrifice his men by resisting and carrying on with his mission- he probably thought.

That is the ultimate dichotomy of leadership that Jocko and Leif talk about in their book. That a leader needs to care for their people while simultaneously putting them in danger for the sake of the mission. They speak of the sacrifices that their own Navy SEALs made while carrying out their orders, and the anguish such a conundrum causes in a leader. And this is what they teach to their students.

In business, leaders treat their people well, not just because happy and satisfied people with high morale perform better, but because they develop strong relationships. Business leaders can develop concern for their employees - family, financial situation, aspirations - to such an extent that it directly impacts business decisions. This can be both good and bad. Good in that caring for the impact on employees builds a happy workforce that is loyal to management, but bad in that strong feelings for employees can be detrimental to the objectives of the business when decisions must be made.

The primary goal of business is to generate a profit, at the very least, while providing their goods and services. Profit is necessary to keep the business functioning. Without profit, the business may go into the red and everyone’s livelihoods may be at risk. Management may care so much for their employees that they are unable to make the necessary tough calls (shut-down underperforming departments or fire a number of employees) to get the business back into the black. Sometimes sacrifices must be made to meet mission objectives. It is a difficult decision for leaders to make, but no one said being a leader was easy.

This situation reminds me of an old saying,

A ship in harbor is safe, but that is not what ships are built for.

Attributed to John A. Shedd

Final Thoughts

Of the three books put out by Echelon Front that I have talked about, or at the least, the ones with the most appropriate content for War Is My Business: Extreme Ownership, Leadership Strategy and Tactics, and (this one) The Dichotomy of Leadership; it is this one that I find the most valuable. While Extreme Ownership began the discussion of personal accountability and responsibility for results required of leaders, and Leadership Strategy and Tactics provides their perspective to numerous leadership dilemmas, The Dichotomy of Leadership provides an expanded look at many of the same topics covered in both in the pursuit of balance. As a result, if you had to pick one book, I would say that The Dichotomy of Leadership may be the best.

Knowing when to be strict, and when to be lax. When to build up subordinates, and when to cut the fat. When to plan for contingencies, and when to move forward with the plans you have so far. All of these leadership issues require balance, and for many of us that are in leadership positions, we are racked with uncertainty of how to act. Being too heavy-handed or being too soft on a particular dilemma is a concern, because not only do we not know what the immediate effects might be but more importantly we may not be able to see what good or bad precedents we are creating. This book, I feel, provides the greatest value since it helps provide a perspective on relatable and common issues in both military organizations and in the business world that we all struggle to determine. Questions about what to do without clear answers.

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