PDF Summary:The Dichotomy of Leadership, by Jocko Willink and Leif Babin

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. The Dichotomy of Leadership teaches you to master such dichotomies.

As former Navy SEAL commanders and corporate leadership consultants, Jocko Willink and Leif Babin have extensive hands-on leadership experience. In this guide, we’ll explain where Willink and Babin’s expertise overlaps with the ideas of other popular writers on leadership, such as Reed Hastings (No Rules Rules) and Ray Dalio (Principles). We’ll also offer actionable ways to put the authors’ ideas into action, whether you’re leading a team of professionals or just looking to discipline yourself.

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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.

How to Inspire Leadership in Others

In Turn the Ship Around!, retired Navy captain L. David Marquet also advocates for radical accountability at every level of your team. Marquet used this philosophy to transform the Navy’s worst-performing nuclear submarine into its best and incidentally trained a number of leaders who went on to achieve disproportionate levels of success throughout the Navy.

While Marquet acknowledges that lower-level leaders need to clearly understand their roles to successfully contribute to the mission (as Willink and Babin claim), he argues that it’s possible to give them an empowering mindset more directly. Marquet offers a number of strategies to inspire your team to embrace radical accountability:

• Teach your team to announce their intentions instead of asking for permission. By requiring his team to come up with plans before consulting their superiors, Marquet prompted them to take ownership.

• Give your team time to come up with solutions. Even if he had a potential solution to one of his subordinate’s problems, Marquet withheld it so his team could practice brainstorming and feel responsible for their success.

• Require your team to identify with the organization. Marquet required the submarine crew to introduce themselves to every visitor and welcome them to the ship. Acting as if they were proud to be part of the ship’s crew caused them to feel proud.

When You’re Not Managing Enough

At the same time, Willink and Babin argue that failing to keep a close enough eye on those working under you can be just as harmful as micromanagement. Don’t blame your team for doing something wrong if you were too hands-off to realize their mistake—that would be denying radical accountability. Instead, be vaguely aware of everything that’s going on in your team or organization.

(Shortform note: Willink and Babin imply that most undermanagement is due to carelessness, but there are other, stronger forces that discourage leaders from objectively overseeing their team, like motivated blindness. Often, leaders unconsciously turn a blind eye to problems in their organization because they’re secretly hoping that those problems don’t really exist. This is common when evidence that a problem exists isn’t definitive and can be explained away. For example, if a company’s website is unintuitive and ruins many potential sales, but fixing the problem would require a costly design overhaul, the company’s executives might convince themselves that the website is fine, even if experts tell them otherwise.)

Focus on the Big Picture

Another reason that not managing enough is harmful is that there are some tasks you just can’t delegate. Willink and Babin explain that because leaders don’t have to be focused on any one specific task, they’re uniquely able to manage the big picture. You can see how each of your team members’ tasks impact one another and how well the organization as a whole is accomplishing its mission. This gives you the perspective necessary to make decisions no one else can make. For example, if you’re coaching a basketball team, you may notice that the team is relying too much on one player and decide to make the other players practice without them. The players, focused on playing well, would be too close to the work to notice this issue.

(Shortform note: Even if a leader is initially the only one who can make certain big-picture decisions, this can’t last forever: All leaders eventually leave or retire. Therefore, if you’re truly focusing on the big picture and want your organization to continue succeeding for an indefinite future, you must train someone to eventually replace you. In Principles, Ray Dalio offers tips on how to train your replacement: Allow your potential successor to personally observe your leadership while working under you. Then, allow them to take some of your big-picture responsibilities before making the transition official so they can gain experience under your oversight.)

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.

(Shortform note: This dichotomy also applies to the way you manage yourself. Being the best you can be requires holding yourself to a high standard. However, if you push too hard and berate yourself for every little mistake you make, disciplining yourself will make you miserable—so you’ll be less likely to do it. For this reason, lowering the standards you set for yourself often makes it easier to discipline yourself and accomplish your goals.)

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.

Parenting With Only Necessary Rules

In 12 Rules for Life, Jordan Peterson uses this same logic for rules and discipline in his parenting advice. Like Willink and Babin, Peterson claims that you should impose as few rules as possible on your children, but when those rules are important, you should enforce them by any means necessary.

Many parents fail to effectively discipline their children because they’re afraid of becoming the kind of tyrannical disciplinarian that Willink and Babin describe. They don’t want to hurt their kids or earn their resentment. However, Peterson asserts that this lack of discipline harms children in the long run.

Likewise, Willink and Babin argue that as a leader, you know what rules your team needs to follow to accomplish their mission and should enforce them even if your team complains. Similarly, Peterson argues that parents know the rules to follow to flourish in society and should enforce them even if the kids resist. Peterson’s rationale is that if you fail to teach your children how to behave properly (especially in a social context), society outside of your household will punish them far more harshly than you. For example, if you don’t prohibit your child from hitting other children, they will be disliked by adults and other kids, leading to shame and alienation.

For the most part, this discipline doesn’t need to be heavy-handed. Willink and Babin’s advice to inspire your team to accept accountability applies to parenting as well. When your children reach a certain age, you’ll be able to explain why rules are important and motivate them to discipline themselves. However, when children are young, they won’t be able to understand some of your rules, even if you try to explain your rationale. For this reason, Peterson argues that in some cases, you may need to discipline by force. He cautions to exert only the minimum force necessary to correct your child.

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.

Fulfillment Through Training

In Flow, Mihaly Csikszentmihalyi argues that tackling increasingly difficult situations is not only the best way to improve your skills but also the way to live the most fulfilling, enjoyable life. He specifically distinguishes between “pleasure” and “enjoyment,” arguing that the enjoyment that comes with conquering a challenging yet satisfying task (like completing a SEAL team training exercise) is far more fulfilling than the pleasure of a sensory experience (like eating food or watching TV). He calls this experience of being fully immersed in an enjoyable task “flow.”

The problem that Willin and Babin diagnose in this section—a goal that’s too difficult—not only impedes your learning but also your overall happiness. If you face a situation that’s too challenging, the anxiety takes you out of flow. Likewise, if you’re working on a task that poses no challenge to you, you’ll get bored and won’t experience flow. If you find yourself in either of these situations, find a new goal that suits your current skill level.

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.

(Shortform note: In short, this dichotomy requires you to ask, “How much do I trust my beliefs?” In Thinking in Bets, Annie Duke advises to ask yourself this question not just when you’re making leadership decisions but all the time, for every belief you have. By viewing your beliefs as bets—risks that cost you something if you’re wrong—you’ll be less susceptible to cognitive biases and more likely to change your mind in light of new information.)

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.

The App That Allows Anyone to Lead

Like Willink and Babin, hedge fund manager Ray Dalio built his organization on the principle that good ideas can come from anywhere. In Principles, he describes designing his investment firm to be an “idea meritocracy” in which good ideas from anyone in the company can influence decisions at every level.

One way Dalio promotes this idea meritocracy is with an app he calls the “Dot Collector.” Dalio explains how this app works in a TED Talk: During a meeting, team members use their personal devices to give real-time feedback on whoever is presenting, adding comments and rating them on a scale from one to ten for a number of attributes. Anyone, even the newest hire in the meeting, can criticize anyone presenting ideas, even the CEO. Bridgewater’s leaders don’t just allow this feedback, they encourage it—it’s practically an obligation. By allowing anyone to question their decisions at any time via the Dot Collector, leaders at Bridgewater prove that they’re open-minded and earn the team’s trust.

Dalio’s company only hires leaders that fit the idea meritocracy culture—that is, those who can handle constant honest feedback. While Willink and Babin argue that you should mostly avoid criticizing your superiors to maintain a positive, productive relationship with them, Dalio proves that it’s possible to create an organization in which mutual criticism doesn’t strain relationships but strengthens them.

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.

(Shortform note: Crucial Conversations offers tips on how best to challenge someone else’s plans. First, create a comfortable space for conflict to take place: Ensure that both of you feel respected and agree on the mutual purpose you’re trying to achieve. Then, begin your discussion by identifying the facts you both agree on before investigating where your views differ. This helps avoid a common pitfall of high-stakes debate: People often end up arguing furiously over minute details without realizing that they mostly agree. Not only does this waste time, but it also makes debaters feel like enemies instead of teammates.)

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.

(Shortform note: The Practice of Adaptive Leadership makes the case that leaders should pay special attention to contrarian team members who question leadership decisions at every opportunity. The authors claim that most organizations silence or fire these contrarians, as they’re often unpleasant to work with. However, if you instead encourage them to speak up, you can tap into an endless source of honest feedback.)

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.

(Shortform note: You could also frame this dichotomy as the need to find the right amount of courage—not too little, but not too much. Aristotle argued that people who lack fear entirely are just as immoral as “cowards” who fear everything. You need courage to take action, but it’s just as necessary to fear things like temptation and failure so you can work to avoid them.)

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.

Today’s Economy Rewards Employees Who Take Action

Willink and Babin’s advice to always look for some way to advance the mission is particularly beneficial to employees in today’s workforce. In Linchpin, Seth Godin argues that in today’s economy, the only way for a worker to thrive is to take the initiative to execute original ideas instead of following instructions. This leads to success because the contributions with the greatest potential value are those your organization isn’t already asking for.

Businesses need “linchpins” who execute original ideas because the alternative is mass stagnation. When an organization is full of people who simply follow instructions, only solving problems someone else forces them to solve, the problems they’re ignoring at work get worse: If your business isn’t actively innovating, other businesses will inevitably copy your product and produce it faster and more cheaply.

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 Just Plan, Plan to Improvise

In Blink, Malcolm Gladwell illustrates Willink and Babin’s point by showing how slow, rational deliberation fails when plans become too overwhelming. He cites the 2002 Millennium Challenge, a training simulation in which a large military force meant to represent the US army failed to defeat a smaller force playing the role of an enemy state. Gladwell explains that the US team failed because they spent too much time collecting massive amounts of intelligence on the enemy and required several levels of officers to painstakingly analyze every decision before taking action. Their overcomplicated systematic planning caused more problems than it solved.

In contrast, Gladwell argues that a balance of planning and improvisation is necessary to succeed. To do this, logically determine a broad strategy in advance, then enable your team to make instinctive, split-second decisions when handling details in the moment. The smaller team portraying the US’s enemy succeeded by employing this strategy: They outlined a plan to aggressively overwhelm the US team, then released control and allowed their officers to find the best way to accomplish this in battle.

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.

(Shortform note: In The Black Swan, Nassim Nicholas Taleb argues that instead of measuring your risks by comparing the odds of success with the odds of failure, you should compare the bounds of success with the bounds of failure. In other words, avoid situations where it’s possible to suffer significant losses, even if the odds tell you you’re almost certain to succeed. For example, if you’re traveling to India, you should get vaccinated for typhoid before you go, even if you’ll only be there for a couple of days—there’s a low chance you’ll contract the disease, but it’s worth it to limit the possibility of severe damage.)

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.

(Shortform note: In Think Like a Rocket Scientist, Ozan Varol agrees that it’s easy to act carelessly without realizing it. Varol argues that one way to combat this is to imagine that you’re perpetually losing, even if you’ve achieved wild success. He cites a study that found basketball teams who were slightly behind at halftime had a greater chance of winning the game—losing made them try harder. Instead of waiting for a teammate to tell you you’re making a mistake or waiting until you’re victorious to slow down, convince yourself that you’re making a mistake right now and look for errors to confirm this belief.)