The Dichotomy of Leadership: Book Overview

This article is an excerpt from the Shortform book guide to "The Dichotomy of Leadership" by Jocko Willink and Leif Babin. Shortform has the world's best summaries and analyses of books you should be reading.

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What is Jocko Willink and Leif Babin’s book The Dichotomy of Leadership about? What is the key message to take away from the book?

The Dichotomy of Leadership is Willink and Babin’s follow-up to 2015’s Extreme Ownership, which argues that a leader should take responsibility for all their team’s mistakes and do everything they can to improve the team’s chance of success. The principle of Extreme Ownership serves as the foundation of Willink and Babin’s argument throughout The Dichotomy of Leadership.

Let’s explore five dichotomies that the authors believe every leader should strive to balance at all times.

The Dichotomy Of Leadership: Balancing The Challenges Of Extreme Ownership To Lead And Win

If you want to accomplish anything on a large scale, you have to learn to lead a team. What makes leadership difficult, however, is the fact that every quality of a good leader becomes a hindrance when taken to the extreme: At a certain point, courage, discipline, and empathy all become deficiencies like recklessness, rigidness, and emotional paralysis. Thus, leadership requires a delicate balance of various dichotomies: You must be compassionate yet pragmatic, humble yet confident, bold yet cautious. In The Dichotomy of Leadership, former Navy SEAL commanders and corporate leadership consultants Jocko Willink and Leif Babin will teach you to master such dichotomies.

The Philosophical Roots of the Dichotomy of Leadership

Willink and Babin are far from the first to suggest that the ideal course of action lies between two extremes. Most people know this concept as the “golden mean,” a phrase coined by the Roman poet Horace. The golden mean is a prominent idea in many ancient philosophies

– The Greek philosopher Aristotle uses the golden mean as the cornerstone of his entire system of ethics.

– In Confucianism, the golden mean is the subject of the “Doctrine of the Mean,” a central philosophical text written by Zisi, the grandson of Confucius. 

– In Buddhism, the golden mean is known as the “Middle Way” and emphasizes one specific dichotomy: the balance between indulgence in sensual pleasures and self-inflicted suffering.

Background: Extreme Ownership Requires Balance

The principle of Extreme Ownership serves as the foundation of Willink and Babin’s argument throughout The Dichotomy of Leadership: Leaders are entirely responsible for finding the balance with the greatest chance of success in every dichotomy of leadership.

Dichotomy #1: Care About Each Individual, but Make Sacrifices for the Group

The first of Willink and Babin’s dichotomies we’ll discuss is the balance between serving the individual and serving the group. We’ll begin by explaining this balance in greater detail, then describe two specific instances of this dichotomy: first, when you have to lead the people you care about into danger; and second, when you have to cut someone you care about from the team.

Willink and Babin assert that you should care about every member of your team as if they were part of your family. A tight-knit emotional bond between team members is one of the most powerful assets you can have to accomplish your mission. Mutual trust and support allow each member of the team to perform at their best, and feelings of camaraderie are a potent source of motivation.

However, even if you care about your team more than anything, a leader must inevitably make decisions that put individual team members in harm’s way for the sake of the mission. Willink and Babin assert that this dichotomy is integral to the idea of what it means to be a leader. It’s why many people see leadership as a burden—many leaders struggle with a guilty conscience over the decisions they have to make.

The Team Will Get Hurt

Leadership requires pushing your team into dangerous environments. Willink and Babin learned this lesson in the warzone of Ramadi, Iraq, but they argue that it’s equally true in the workplace. Workers will make mistakes and feel ashamed and receive feedback that bruises their egos, and they may at some point need to be fired.

Willink and Babin argue that as a leader, your job is to accept radical accountability and minimize these unpleasant dangers whenever you can. Try to provide your team members with everything they need to thrive, whether that be additional training or other kinds of special attention. Furthermore, don’t overwork them to the point of misery—on the contrary, make the job as pleasant as possible for them, as long as they’re contributing to the success of the mission.

However, Willink and Babin offer a warning: Don’t let your emotional connection to your team members cloud your judgment. Sometimes, the right decision requires you to let your team get hurt—for instance, if your company is struggling financially, you may need to lay people off to survive. The whole point of forming a team is to accomplish a worthy mission. If you allow your feelings for someone on your team to ruin the mission, you fail the entire team and waste their collective efforts.

To Coach or to Fire?

One potent form of this dichotomy occurs when cutting someone from your team. Willink and Babin assert that you want every member of your team to feel unconditionally supported. However, they point out that if you let a single struggling member drag the rest of the team down, you’re doing everyone a disservice.

Willink and Babin emphasize that in the majority of cases, you should try as hard as you can to coach struggling team members until they improve and meet your team’s standards. Part of radical accountability is accepting responsibility for your team members’ shortcomings. If they fail, begin by assuming you’re not mentoring them well enough.

However, if it becomes obvious that the struggling team member isn’t able to improve, you’re obligated to cut them from the team. Willink and Babin explain that this is also a form of radical accountability—doing what needs to be done for the good of the entire group. You’re protecting the rest of the team from the consequences of their potential mistakes. And more than likely, you’re doing what’s best for the one who’s struggling—they’ll be happier working on a team better suited to their abilities.

Dichotomy #2: Take Responsibility for Your Team, but Don’t Do Everything

The second dichotomy we’ll discuss is the balance between hands-on leadership and prudent delegation. Willink and Babin assert that because a leader can’t do everything, the best way to take responsibility for your team’s success is to endow other people with responsibility. However, if you delegate all your responsibilities and assume that someone else is solving every problem, you could be unknowingly steering your team toward disaster.

First, we’ll examine the dangers of micromanagement and the benefits of delegation. Then, we’ll examine the other side of the dichotomy: the problems that arise when a leader is too distanced from the work.

Don’t Micromanage

Willink and Babin explain that some people misunderstand the concept of radical accountability, using it as an excuse to assume direct responsibility for as many tasks as possible—micromanaging their teams.

The authors condemn micromanagement primarily because micromanaging your team members discourages them from taking responsibility for the broader mission. If your team members sense that you want to control everything, they’ll do nothing but wait around until you give them specific directions. By disincentivizing them from coming up with creative ideas and getting things done on their own, you stunt their personal growth and hurt the team’s potential for success.

Willink and Babin assert that any excessive reliance on accountability checks from above is a form of micromanagement—for example, a supervisor in a restaurant whose only job is to ensure that food is being prepared correctly would be micromanaging. Such time-intensive micromanagement wastes the time of your upper-level leaders.

Every Member of Your Team Should Be a Leader

Instead of direct supervision, Willink and Babin suggest a more self-sustaining form of accountability: Every member of your team should feel internally motivated to hold themselves and each other accountable for their work. In other words, on the ideal team, all members would see themselves as a leader and accept radical accountability for the entire team’s mistakes.

How can you make this happen? Willink and Babin argue that the best way to inspire your team members to accept radical accountability is to explain how their jobs contribute to the mission’s success. In most cases, the problem isn’t that your team doesn’t want to try hard to succeed—they simply don’t see how their effort makes a difference to the team’s overall success or failure. If you make it clear how each member of your team supports the mission, you’ll make it easy for them to care about what they’re doing. This is far more effective than watching over their shoulder 24/7.

Dichotomy #3: Maintain High Standards, but Don’t Push Too Hard

The third dichotomy we’ll discuss is the balance between demanding high performance and nurturing your team’s growth. Willink and Babin argue that since you’re accepting radical accountability for your team’s overall success or failure, it’s your responsibility to ensure that every team member is performing at a high standard. However, if you push your team too hard, demanding absolute perfection, you’ll destroy your team’s morale and hinder their performance.

We’ll discuss two instances in which leaders ask too much of their teams: first, when leaders impose too many strict rules, and second, when leaders make training too difficult.

Only Enforce the Necessary Rules

The first way leaders push their teams too hard is by establishing and enforcing too many rules. Willink and Babin explain that many leaders falsely assume the best way to discipline a team is to force them to be disciplined about everything. For example, they enforce strict rules limiting the number of bathroom breaks per work shift or demanding absolute silence during a presentation, in hopes of strong-arming the team into being focused on the mission at all times. Wielding authority like this is counterproductive—enforcing rules your team knows don’t really matter will only cause them to resent you.

That being said, Willink and Babin are adamant that to maintain high standards, you must be willing to enforce the important rules, even if the team complains. As a leader, your big-picture perspective gives you a clearer sense of what’s important than the more specialized team members below you. Don’t let your unwillingness to upset the team keep you from enforcing the rules you need to—you can’t afford to compromise on what really matters.Willink and Babin explain that the fewer rules you impose, the more your team will respect the important rules you do enforce. For this reason, let your team work the way they want to, even if you’d prefer them to do it differently. Allow them to have some fun. When you do lay down rules, always clearly explain your rationale so the team fully understands why they’re important. This will motivate them to follow the rules and keep themselves accountable.

Challenge Your Team to Help Them Grow

The second way leaders commonly push their teams too hard is by putting too much pressure on them during training. Willink and Babin argue that deliberate training is necessary for a team to reach its full potential because facing consistently difficult challenges is necessary to improve. Using this logic, the authors claim you can train a team with no direct experience to do anything by putting them in increasingly difficult training scenarios.

However, the authors warn that if you place your team in situations that are too difficult for their current skill level, you’ll demoralize them. The team won’t improve and will resent you for making them needlessly suffer. Instead, slowly expand your team’s comfort zones by placing them in situations that are challenging, but not overwhelming.

Dichotomy #4: Defer to Others, but Trust Yourself

The fourth of Willink and Babin’s dichotomies we’ll discuss is the balance between trust in others and confidence in your ideas. The best leaders can take advice as well as they give orders. Being a leader doesn’t always mean telling people what to do—often, other team members are better equipped than you to make the right decisions. However, if you’re too reliant on others and lack confidence in your leadership, you may end up following others’ lead in situations where you know better.

First, we’ll examine the argument for setting your ego aside and following someone else’s lead. Then, we’ll discuss the exceptions when it’s best to fight for what you believe is best.

Know When to Let Others Lead

Willink and Babin explain that part of radical accountability is basing your plans on the best ideas, no matter who came up with them. Often, this means trusting someone with specialized experience more than your intuition, even if you technically outrank them.

According to Willink and Babin, some leaders cling to their ideas because they want to appear confident to their team. This has the opposite effect: Overconfidence in your decisions will only cause your team to doubt you more. If, instead, you show humility by willingly adopting a plan from one of your subordinates, your team will see that you honestly want to succeed and have their best interests at heart.

Willink and Babin argue that you should not only defer to the leaders serving under you but also to the leader in charge of you: your boss. Every time you fulfill your boss’s expectations without complaint, you earn their trust and make them more likely to respect your opinion in the future. This is extremely helpful for the mission—an adversarial relationship with your boss makes everything harder. For this reason, even if you think an order from above is pointless or unnecessary, execute it as if it were your idea.

Know When to Fight for Your Ideas

On the other side of the dichotomy, you face different problems when you become too deferential to the plans of others. If you’re positive that following someone else’s plan will lead to disaster, you have a duty to fight for your ideas. Willink and Babin argue that sometimes, you’ll know something your boss doesn’t and realize that following their orders would be a serious mistake. Alternatively, several team members below you may push back against a plan that you know is best. If you cave to external pressure and accept a bad plan because others want you to (perhaps because you know no one will blame you when the plan fails), you’re not accepting radical accountability.

Similarly, encourage team members under you to fight for the ideas they believe in. Willink and Babin note that your team will likely be hesitant to push back when you give them orders, so specifically instruct them to do so for the greatest chance to find the best plan.

Dichotomy #5: Rush Forward, but Be Careful

The final dichotomy of Willink and Babin’s that we’ll discuss is the balance between forceful action and cautious risk management. Find a way to rush toward your goal as ruthlessly as possible while maintaining the presence of mind to guard against careless mistakes.

We’ll first examine the benefits of purposeful aggressive action as well as some of the more subtle dangers of failing to act, like the risk of overplanning. Then, we’ll warn against the dangers of acting too hastily and incurring unnecessary risks.

When in Doubt, Do Something

Willink and Babin recommend building the momentum to achieve your goal as quickly as possible. In most situations, doing anything, even embracing an imperfect solution to a problem, is better than doing nothing. This is because problems often get worse the longer you take to solve them. Proactive action now makes things easier down the road.

The authors explain that doing nothing but waiting around for orders is the opposite of radical accountability. There’s always an action you can take to further the mission. If you don’t have the authority to do something, make a direct recommendation to someone who does.

It’s Possible to Be Too Careful

As Willink and Babin explain, aggressive action is necessary because excessive caution and planning cause more problems than they solve.

Willink and Babin point out that if you try to prepare for too many potential dangers, you risk confusing your team (and yourself) with needlessly complicated contingency plans. Additionally, Willink and Babin assert that dedicating too many resources to a plan in case something goes wrong comes with drawbacks. 

For example, imagine you have to give a presentation at work. You’re worried that you’ll forget an important point and decide to write down your entire speech on notecards. During the presentation, you struggle to sort through your stack of notes on the spot. By preparing for the worst, you’ve sabotaged yourself. 

If you frequently trap yourself in situations like this, you can regain balance by actively deciding to plan less. The authors suggest limiting yourself to planning for three or four of your most likely obstacles, as well as your worst-case scenario.

Don’t Take Unnecessary Risks

However, on the other side of the dichotomy, don’t let the pressure to rush forward force you into a fully avoidable catastrophe. Before you make any decision, Willink and Babin advise you to take a moment to weigh its risks versus its rewards. In most cases, there’s a way to take aggressive action without risking disaster. Come up with a plan to get the most done while risking as little as possible.

According to Willink and Babin, one sign you’re not taking enough time to consider risks is if another team member, especially someone with experience, tells you you’re being reckless. Use this as an opportunity to re-examine your decision-making process. Another time to be particularly cautious is after a victory, when you’re most likely to feel overconfident. In cases like this—whenever you feel more eager than usual to take risks—make it a habit to slow down.

The Dichotomy of Leadership: Book Overview

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Here's what you'll find in our full The Dichotomy of Leadership summary :

  • How to master the many different dichotomies that make a great leader
  • How to successfully lead others and yourself
  • How good qualities can become detrimental when taken too far

Darya Sinusoid

Darya’s love for reading started with fantasy novels (The LOTR trilogy is still her all-time-favorite). Growing up, however, she found herself transitioning to non-fiction, psychological, and self-help books. She has a degree in Psychology and a deep passion for the subject. She likes reading research-informed books that distill the workings of the human brain/mind/consciousness and thinking of ways to apply the insights to her own life. Some of her favorites include Thinking, Fast and Slow, How We Decide, and The Wisdom of the Enneagram.

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