The Dichotomy of Leadership (Commentary)

This is a review and commentary of the book from Jocko Willink and co-author Leif Babin

Angel Mondragon
12 min readFeb 11, 2019


These commentaries serve dual purposes. The last time I attempted to read a book a week; I succeeded. Despite having gone through 52 books that year, I retained no more than 5% of the literature. I quickly realized I had the wrong goal. I was focusing on the number of books instead of the lessons to be absorbed. Burning through books had a nominal positive return and mainly was a waste of energy. So, this time I want to go through the books while taking copious notes and critically analyzing the entries to find where its lessons can be implemented across a wide spectrum of our day-to-day life.

The Dichotomy of Leadership accounts both Jacko’s and Leif’s experiences in war as supplementary tools to illustrate how the particular principle of the chapter is relevant to the civilian application. The book highlights the complicated dichotomies located in a leadership position. Additionally, the book is presenting a guide on how to become a balanced leader, if you implement into your strategy with discipline.

We can start interpreting the book with the title:

Dichotomy — /dīˈkädəmē/


A division or contrast between two things that are or are represented as being opposed or entirely different.compensation

Leadership — /ˈlēdərˌSHip/


The action of leading a group of people or an organization.

The tile is direct and deliberate. Unlike many titles from books I’ve read in the past, this one cuts out the fat and is notably descriptive of the contents ascertained in the text. Each word joined articulately forms the main topic of the book; two contrasting things that are entirely different, found in leadership. This presents the style of both storytelling and teaching that Jocko employs with instruction on his core principles of leadership. If you are not familiarized with Jocko and his stoic form of dialogue check out this here:

Extreme Ownership | Jocko Willink | TEDx UoN


The analysis of each book will be tailored to how the information is being presented. In The Dichotomy of Leadership, each chapter contains a particular principle that Jocko and Leif emphasize. My intention is to itemize each dichotomy in detail.

“The foremost requirement in leadership is humility” — Jocko.

This is the core mantra of their supplementary book, Extreme Ownership, and the core principle for becoming a great leader. This phrase can be found in each principle moving forward.

The book begins with narratives from the two authors and discusses their prequel book, “Extreme Ownership”, which supplements this, but can be read independently. They also talk about the “rules of combat,” which encompasses the dichotomies listed below. Here are the Rules of Combat:

  1. Cover and Move — simply refers to team work. Smaller teams work within larger teams and sometimes conflict arises, resulting in safety problems. The leader must quell the friction between teams, promote working and supporting each other, and remain focused on the mission.
  2. Simple — is all about taking the complexities of safety. If your employees are confused about their work and the attendant safety steps, Extreme Ownership requires you to ensure your team fully understands their role and contribution to the success of the mission.
  3. Prioritize and Execute — involves remaining a step or two ahead of real-time problems to avoid failure. As Willink notes, “taking on too many problems simultaneously will likely lead to failure at them all.”
  4. Decentralized Command — refers to the number of people one can manage — six to ten, according to the authors. Leadership needs to be distributed down through the teams along with the safety responsibilities. Team members must know what they need to do, and why they are doing it. Senior leaders maintain “situational awareness” by constantly communicating with their subordinate team leaders and back them up even when bad decisions are made.

When you are reading the dichotomies and principle of this book below. Look back at these Rules of Combat to understand with the main purpose of the principle is aiming to address.

The Dichotomies Found In Leadership

We’ll just jump right into the meat of the book. These principles are delivered by a story from combat and a story from a civilian application, primarily business. I will omit from telling the stories and go straight to the principles for now. I may address the stories in the application section below. Enjoy!

1. Leadership vs Followership —

As a leader you must take extreme ownership on everything that happens in the mission and to the team, but also know when to be lead with decentralized command. Senior leaders must develop junior leaders to learn how to make critical decisions autonomously, and fully understand why they are doing something. They must also know the parameters in which they can make decisions. It is the leaders’ duty to empower and trust junior leaders. Junior leaders in return must display confidence that they clearly understand the strategic mission. Senior leaders must implement an environment of frequent communication and trust between subordinates in addition to tactical training to prepare junior leaders for such a role.

Take Away: The balance lies in knowing when to lead and how to effectively lead or being too hands-off. Too much autonomy without proper training can result in junior leaders making poor decisions, failing to achieve the strategic objective.

2. Caring Deeply for Troops vs Placing them in Risky Situations —

This principle highlighted to need for realistic training. It is incumbent upon the leader to mitigate risk when training, but the training must not be so risk-averse that the team does not receive the proper preparation needed to accomplish the overall mission. As much as you care for you wo/men you must accomplish your duty as a leader and achieve success with the mission. That includes placing your team at risk, and it “very well could cost peoples lives” therefore requires some cover and move. The dichotomy lies between being too detached from your team where no one respects you because you only care about the objective; or placing too much care for the team and as a result, the overall objective suffers because you are afraid to place the team at risk.

Take Away: Train hard but train smart. Prepare but don’t overstrain. You must prioritize the mission, both compassionately and logically.

3. Taking Too Much Ownership vs Not Taking Enough* —

This is the main dichotomy most administrative authority faces. The problem with micro-management is simple: It is impossible to control everything, it inhibits the growth of subordinates, initiative fades and eventually dies, as does creativity and bold action. The team becomes “thoughtless” and only takes action upon receiving orders. The “hands-off” leader is no better. The team receives no clear objective or direction. Contrary to the micro-managed team, hands off subordinates have too much creativity, planning strategies beyond their boundaries, abilities, and competence. The “troops”, instead of moving towards the strategic goals, organized, now execute random action which often conflicts directly with other team members tasks and the overall objective.

Symptoms to look for in a micro-managed environment:

  1. The team shows a lack of initiative,
  2. Members only take action when directed,
  3. Members do not seek solutions to problems, instead they “sit and wait” for solutions to be presented,
  4. Even in an emergency a team will not mobilize and take action.

Symptoms to look for in “hands-off” management:

  1. Lack of vision,
  2. Lack of coordination form individuals on the team initiative oversteps the bounds of authority,
  3. The team is focused on the wrong priority mission,
  4. Too many people trying to lead equates to more discussion and less action.

Take Away: The balanced goal is to give the troops the guidance needed to execute while simultaneously acquiring the freedom to creative make decisions and lead. Don’t become the “easy button” in meetings, allowing you to think for them and them to blame you.

4. Set Boundaries vs Not Setting at All —

This particular dichotomy focuses on “leadership capital”. Leadership capital is the recognition that there is a finite amount of power that any leader posses. It is easy for a leader to “foolishly” spend this capital on trivial and strategically unimportant items. Such capital can only be built only through action. The leader must display confidence and build trust in that “they have the long term good for the team” with the mission in mind. A great leader knows how to prioritize standards that cannot be compromised by holding the line firm, while simultaneously allowing “slack” in other less critical areas of the mission. This is where implementing the WHY or reason for holding the line is vital for the leader to do.

Take Away: Explain WHY it will help the mission while explaining what happens if the standard is not met, as a consequence. There are tasks that require to have a line held FIRMLY while other more trivial items are less important, thus can have slack.

5. Training vs Giving up —

“Give up?” You may be asking. This dichotomy emphasizes the opposing forces of being a proficient trainer. As a leader, it is your mission to “train, coach, and mentor” you junior leaders to the best of your ability so that the members of the team can perform to the highest of the standards, or at the very least the minimum standard. The dichotomy is that the leader must also know when a member does NOT have what it takes to get the job done. “As the leader continues to pour [resouces] into one non-performing individual other members of the team … are neglected … and can begin to question the leader’s judgment.”

Take Away: The performance of the team trumps the performance of an individual. The balance is between developing individuals but prioritizing the team.

6. Risk vs Reward —

This one is straight forward. Does the outcome greatly outweigh the risk involved? Being “default aggressive” is not only a great mentality to have, but should be your default setting when strategizing a plan. Playing offense is the best defense, but that does not mean you should not mitigate risk. This principle used two parallels stories, one in a military context other in business. Both stories shared similar attributes to characterize the sources to catalyze the negligence of risk. A string of good luck combined with arrogance led two leaders in separate circumstances to nearly “cost the mission”. They were gambling, and they failed to take a logical perspective at the high probability of failure.

Take Away: Be aggressive with risk mitigation; calculated risk.

7. Too Much Accountability vs Not Enough Accountability —

This principle discusses how accountability can be used as a tool in leadership but often is overused; or worse, improperly executed. Implementing accountability as a leader encourages members of the team to remain disciplined and complete their set objectives. However, like many other tools, accountability can be abused in the form of micromanaging or lose value over time. In addition to losing value, when the manager is not available for direct oversight the task may or MAY NOT get completed. This problem is also true for the opposite end of the spectrum of a culture without any accountability. Here tasks are hardly completed and no repercussions are deployed. The solution for balanced accountability is simple. To be a balanced leader you must express the WHY completely. Explain why what they are doing matters and is important to the overall objective and to them personally.

Take Away: If the why is clearly expressed and understood an intrinsic desire to stay accountable can self-manifest. As a leader do not use this an excuse to become complacent and passive. You must still conduct some over-accountability post completion to make certain that quality has not dissipated.

8. Over Planning vs Under Planning —

This particular dichotomy is rather important as it requires the leader to have confidence in knowing in what areas they excel in, while simultaneously have the ability to acknowledge their lack of experience. Overplanning appears to be the default setting for many when strategizing an operation. Overplanning allows for the leader to think of various negative outcomes and attempt to overcome those outcomes; or outright avoid them altogether, if possible. However, the sequence of events hardly ever go directly to plan. It is the leader’s obligation to be reflexive and have the ability to respond and adapt to the changing situation. Therefore, planning on a microscopic level was not only a waste of time but could cause confusion when a mission does not occur as anticipated.

Take Away: Flexibility trump minute details when it comes to planning. However, you must ALWAYS plan for likely contingencies (3–4).

9. Submerged in Details vs Too Far Removed —

This is the last dichotomy that I found in the book. The principle is for a leader to detach from trivial details and take a step back so that the leader can see the “bigger picture”. Here a leader can see areas that need focus thus prioritize and execute. Yet, a leader cannot be too detached that they do not know was is “going on with the team”.

Leif used a story from SEAL training as his analogy while talking to a group of c-level executives. In the story, Leif was told by a previous commander to be in the back of the “train inside the kill house”. When training with jock, he asked Leif why he was positioned there. He continued to ask if he could see the front. The answer was a no, therefore he was unable to know what was happening. Jocko would proceed to say that Leif was unable to remain in the back either. Instead, he needed to be positioned somewhere in the middle whereas a leader he could observe both ends of the spectrum without being slowed down by the details. There, he was able to see the bigger picture and make prioritized tasks, with the mission in mind.

Take Away: The details are necessary to understand each members’ position so that you can plan accordingly, develop to improve and conduct oversight to ensure quality.

“If you care for your team first an utmost, then you will absolutely win. That is the goal. To place your men and the mission ahead of yourself. That is how a leader can truly win at all costs.” — Jocko


Preferable to building an opinionated conclusion I rather take the teachings of the book and attempt to find areas in life where the lessons can be applied. Jocko and Liefs experience in combat helped them become amazing leaders. Those skillsets were transferable in the business field when they built Echelon Front, a consulting agency used to maximize the output of the managerial staff in business. Listening to the stories as each parallel narrative taught an invaluable lesson on leadership I also thought of the application of these principles outside of the military and business sector. Here is what I have gathered, and here is where I myself have implemented.

Application in Life

The application of this book is not exclusively reserved for leaders in a business or military context. Instead, the core principle of being a balanced leader can be practiced across various circumstances in life. If we take a high-level perspective at the role of a leader we can deconstruct the characteristics that create the archetype and where those characteristics can be applied. These roles can be parents, teachers, managers, pastors, siblings, and spouses. However, I want to dive into how this book directly applied to my life, and can potentially be applied in yours.

If you do not know, I am the CEO of our financial service company PlutusX. I also hold C-Level roles in various other entities, where I am not directly a “leader”. I have have had a real struggle with wanting to become a fair, fun, yet stern and productive leader. Finding that balance has always been a difficult task for me. I read several books on leadership although none truly assisted me with my performance as this book has. Coming from a computer science background, and more specifically data science I wanted to quantify these metrics to keep my self in “check”. This is the first week of implementation. As I gain more data I can better asses how to become a balanced leader. Although this particular book contained tremendous amounts of substance it is still one-dimensional regarding the tools needed to become a great leader.

After reading the book I quickly realized that these dichotomies help us become balanced leaders with our team, but the overall psychology of the leader is of equal importance. Throughout this book journey of mine, I will be reading various books, including “The Righteous Mind” and many others to assist me in supplementing this book to become a comprehensive leader.

Once again, this type of leadership transfers over to other areas of life, not just work, and not just military. This is not an excuse for you to assume that this book does not apply to you directly. You must take initiative to apply these teachings in your day-to-day life. I myself will implement these lessons in my life to become a better: significant other in my relationship, a better friend, and a better overall human being to others.

So, I challenge you to find where you can apply this book in your life — GET SOME!

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Written by: Angel Mondragon.



Angel Mondragon

Take advantage of trends, Artificial Intelligence developer, Blockchain Enthusiast, TA Trader. Curious mind and infamous communicator.