The Dichotomy of Leadership by Jocko Willink and Leif Babin
- Book Summary

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This is my summary of ‘The Dichotomy of Leadership’ by Jocko Willink and Leif Babin. My notes are informal and tailored to my own interests at the time of reading. They mostly contain quotes from the book as well as some of my own thoughts. I enjoyed this book and would recommend you read it yourself (check it out on Amazon).


Dichotomy #1: Balance caring for your people with accomplishing the mission.

  • A good leader builds powerful, strong relationships with their subordinates. But while that leader would do anything for those team members, the leader must recognize there is a job to do.

  • If leaders develop overly close relationships with their people, they may not be willing to make those people do what is necessary to complete a project or task. They may not have the wherewithal to lay off individuals with whom they have relationships, even if it is the right move for the good of the company. And some leaders get so close to their people that they don’t want to have hard conversations with them - they don’t want to tell them that they need to improve. It’s hard. If you don’t do what you need to do - what you know you need to do - you aren’t helping anyone. If you don’t make the hard decision, you will be hurting the people you care about, not helping them.

  • If a leader is too detached from the team, they may overwork, overexpose, or otherwise harm its member while achieving no significant value from that sacrifice. The leader may be too quick to fire people to save a buck, thereby developing the reputation of not caring about the team beyond its ability to support the strategic goals.

Dichotomy #2: Find the right balance between taking all ownership yourself (micromanagement) and allowing your team to take ownership (hands-off leadership).

  • Micromanagement:

    • The micromanager tries to control every thought and action of each individual on the team. Micromanagement fails because no one person can control multiple people executing a vast number of actions in a dynamic environment, where changes in the situation occur rapidly and with unpredictability. It also inhibits the growth of subordinates: when people become accustomed to being told what to do, they begin to await direction.

    • Common symptoms that result from micromanagement:

      • The team shows a lack of initiative. Members will not take action unless directed.

      • The team does not seek solutions to problems; instead, its members sit and wait to be told about a solution.

      • Even in an emergency, a team that is being micromanaged will not mobilize and take action.

      • Bold and aggressive action becomes rare.

      • Creativity grinds to a halt.

      • The team tends to stay inside their own silo; not stepping out to coordinate efforts with other departments or divisions for fear of overstepping their bounds.

      • An overall sense of passivity and failure to react.

    • Corrective actions against micromanagement:

      • Instead of explaining what the mission is and how to accomplish it, the leader should explain the broad goal of the mission, the end state that is desired, and why the mission is important and then allow the team to plan how to execute the mission.

      • Monitor what is happening and check the progress of the team but refrain from giving specific guidance on the execution, unless the plan that is being formulated by the team will have extremely negative results.

      • If there is an opportunity when time and risk levels permit, a leader can step away from the team completely and allow it to plan and execute a mission on its own.

      • Stop being the “easy button.” If you answer every question, solve every problem, and make every single decision - why should your leaders think for themselves when they can just press the easy button and have you think for them and make the decisions for them as well? And they can blame you if something goes wrong because you made the decision.

  • Hands-off leadership:

    • Common symptoms that indicate when a leader is too hands-off with his team:

      • Lack of vision in what the team is trying to do and how to do it.

      • Lack of coordination between individuals on the team and efforts that often compete or interfere with each other.

      • Initiative oversteps the bounds of authority, and both individuals and teams carry out actions that are beyond what they have the authorization to do.

      • Failure to coordinate. While a micromanaged team might not coordinate with other teams because it doesn’t want to overstep its bounds, a team without good guidance may also fail to coordinate not out of fear but out of ignorance. In its efforts to solve problems and accomplish the mission, the team forgets that other teams might also be maneuvering and end up interfering with their efforts.

      • The team is focused on the wrong priority mission or pursuit of solutions that are not in keeping with the strategic direction of the team or the commander’s intent.

      • There are too many people trying to lead. Since everyone is trying to lead, there won’t be enough people to execute. Instead of progress, the leader will see discussion; instead of action, the leader will see prolonged debate; instead of unified movement, the leader will see fractured elements pursuing individual efforts.

    • Corrective actions:

      • Clear guidance must be given. The mission, the goal, and the end state must be explained in a simple, clear, and concise manner.

      • The team must understand the boundaries that are in place and what actions to take should it bump into those boundaries.

      • If multiple, simultaneous, overlapping efforts are being pursued, the leader must decide on and clearly implement the chosen course of action.

      • The team must be educated on efforts being executed by other teams so that deconfliction can occur.

      • If a team is paralyzed by too many people trying to lead - the classic case of “too many coaches, not enough players” - then the leader must assign and clearly delineate the chain of command, roles, and responsibilities of the team leaders and give them proper authority.

Dichotomy #3: Don’t be too lenient, but also don’t become overbearing.

  • Don’t confuse the idea of “taking care of your people with allowing them not to work as hard. You must set high standards and drive the team to achieve those standards, but you cannot be domineering or inflexible in matters of little strategic importance.

  • Carefully evaluate when and where to hold the line and when to allow some slack. Leadership capital: there is a finite amount of power a leader possesses. As a leader, you only have so much authority that you can spend, and you need to choose wisely where you apply it.

  • Overbearing: imposing harsh discipline, screaming at people, and crushing the morale of the team. No one wants to follow such leaders. They might accomplish an immediate task, but in the long run, the team’s growth will be smothered.

  • When a leader must hold the line and enforce standards, it must always be done with the explanation of why it is important, why it will help accomplish the mission, and what the consequences are for failing to do so. It must never be done with the attitude of “because I said so.”

Dichotomy #4: Do everything you can to develop and improve the performance of individuals, but fire underperformers when it’s necessary.

  • A leader must do everything possible to help develop and improve the performance of individuals on the team. A leader must also understand when someone does not have what it takes to get the job done.

  • Most underperformers don’t need to be fired, they need to be led.

  • When all avenues to help an individual get better are exhausted without success, then it is the leader’s responsibility to fire that individual so they do not negatively impact the team.

  • Human beings have limitations; not every person on a team will be suited for a particular job. Some people might need a less technical position. Some people can’t handle stress. Some might lack the creativity to come up with new ideas or solve problems. This doesn’t mean they are worthless - it just means the leader needs to utilize them in a position where their strengths are fully capitalized. The leader is still trying to maximize the potential of every individual.

  • Don’t be too quick to fire - but don’t wait too long.

Dichotomy #5: Place yourself and others just outside of your comfort zone, but don’t go too far.

  • If training is too easy and doesn’t stretch the capabilities of the participants, their improvement will be minimal.

  • If training overwhelms the team to a point where its participants can no longer function, it greatly diminishes the lessons they will learn from it.

  • While training must make the team, and especially leaders, uncomfortable, it cannot be so overwhelming that it destroys morale, stifles growth, and implants a defeatist attitude.

Dichotomy #6: Be aggressive/proactive, but never reckless.

  • Don’t passively wait to be told what to do, proactively seek out ways to further the strategic mission. Understand the commander’s intent, and where you have the authority to do so, execute.

  • For decisions that are beyond your pay grade or above your authority, still make a recommendation up the chain of command to solve problems and execute.

Dichotomy #7: Be disciplined, but not rigid.

  • Balance the strict discipline of standard procedures with the freedom to adapt, adjust, and maneuver to do what is best to support the overarching commander’s intent.

  • As SEALs, we had SOPs for just about everything we did: the way we lined up and loaded our vehicles, our vehicle and foot patrol formations, the methodologies we used to clear buildings, the way we handled prisoners and dealt with wounded SEALs - the list goes on and on. But those SOPs didn’t constrain us on the battlefield. On the contrary, they gave us freedom. The disciplined SOPs were a line to deviate from, and we had the freedom to act quickly based on those procedures.

Dichotomy #8: Hold people accountable, but don’t hold their hands. (same as the micromanagement one)

  • While a leader wants team members to police themselves because they understand why, the leader still has to hold people accountable through some level of inspection to ensure that the why is not only understood but being acted upon.

  • The balance between the troops understanding the why mixed with intrusive accountability provides the best possible outcome for a team.

  • There are cases when accountability should and must be used. If a subordinate is not performing to standard, despite understanding why, despite knowing the impact on the mission, and despite being given ownership, then a leader must hold the line.

  • Use accountability as a tool when needed, but don’t rely on it as the sole means of enforcement. A reliance on heavy accountability consumes the time and focus of the leader and inhibits the trust, growth, and development of subordinates (aka micromanagement).

Dichotomy #9: A good leader must also be a good follower.

  • In order to be a good leader, you also have to be willing to follow. Leading does not mean pushing your agenda or proving you have all the answers. It’s about collaborating with the rest of the team and determining how you can most effectively accomplish your mission all together.

  • It is the weakest form of leadership to win an argument through rank or position.

  • Be willing to lean on the expertise and ideas of others for the good of the team. Be willing to listen and follow others, regardless of whether they are junior or less experienced.

  • A good leader must be a good follower of their own senior leaders. One of the most important jobs of any leader is to support your own boss.

    • Disagree and commit. Even if you disagree with the decision, you must execute the plan as if it were your own. Often, for natural leaders who are eager to step up and take charge, it may be a struggle to follow a leader who is less competent, less aggressive, uncharismatic, or uninspiring. Regardless, when lawful orders from the boss or higher chain of command conflict with a leader’s ideas, a subordinate leader must still be willing to follow and support the chain of command. Failing to do this undermines the authority of the entire chain of command, including that of the defiant leader.

    • Failing to follow also creates an antagonistic relationship up the chain of command, which negatively affects the willingness of the boss to take input and suggestions from the subordinate leader, and hurts the team.

    • You should strive to have the same relationship with every boss you ever work for, no matter if they are good or bad. Whether they are an outstanding leader whom you admire, a mediocre leader who needs improvement, or a terrible leader for whom no one on the team has respect, you must strive to form the same relationship with all of them.

Dichotomy #10: Plan, but don’t overplan

  • Careful planning is essential to the success of any mission. Leaders must consider the risks they can control and mitigate those risks as best they can through contingency planning. When proper contingency planning doesn’t take place, it’s a failure of leadership.

  • Not every risk can be controlled. You cannot plan for every contingency. If you try to create a solution for every single potential problem that might arise, you overwhelm your team, you overwhelm the planning process, you overcomplicate decisions for leaders.

  • Focus only on the most likely contingencies that might arise for each phase of an operation. Choose at most the 3 or 4 most probable contingencies for each phase, along with the worst-case scenario.

Dichotomy #11: Be strategic about when you push back up the chain of command.

  • Leaders must be humble enough to listen to new ideas, willing to learn strategic insights, and open to implementing new and better tactics and strategies. But a leader can also not be passive. When it truly matters, leaders must be willing to push back, voice their concerns, stand up for the good of their team, and provide feedback up the chain against a direction or strategy they know will endanger the team or harm the strategic mission.

  • Carefully prioritize when and where to push back. Leaders have an obligation to support their chain of command and carry out the orders that came from above.

  • Pushing back against an order or task from the boss should be the rarest of exceptions and definitely not the rule. To go against the chain of command when you don’t have to is unnecessary and unwise. If challenging and questioning orders becomes routine, junior leaders damage their relationships up the chain of command, which undercuts their ability to push back against direction from above when it truly matters.

  • In Task Unit Bruiser, we didn’t complain about the little things that others might have pushed back on. Instead we understood that there were important reasons for these administrative requirements and got them done. When they asked us to complete paperwork, we did it - on time and well-edited, quality work. When they asked us to take photos of our Iraqi soldiers in training and on combat operations, we did that and strove to do it better than anyone else. When the task group asked for serialized inventory lists of all equipment before departing on operations, we took the extra time and effort and made that happen. In doing the seemingly small things well, we built trust that strengthened our relationships with our chain of command and enabled us to challenge an order in the rare circumstances when there truly was a strategic detriment to our mission and increased risk to our troops.

Dichotomy #12: Stay focused, but detached.

  • Your position should be somewhere in the middle, with the bulk of your forces, close enough to the front to know what is going on, but far enough back that you aren’t in the weeds doing the tactical work.

  • You can’t be in the back, because you don’t know what’s happening up front. If you don’t know what’s going on, you can’t lead.

  • You can’t be all the way up front, because then you’re too far into the tactical details to provide proper command and control.

‘The Dichotomy of Leadership’ also covered many more insightful topics. You’ll find them below in alphabetical order.

Disagree and commit

  • Napoleon: Every general-in-chief who undertakes to execute a plan which he knows to be bad, is culpable. He should communicate his reasons, insist on a change of plan, and finally resign his commission, rather than become the instrument of his army’s ruin

Leadership

  • Leadership seldom requires extreme ideas or attitudes. The opposite is true: leadership requires balance.

  • Humility is the most important quality in a leader. Be humble or get humbled. Check your ego, accept constructive criticism, and take ownership for your mistakes.

  • Good leaders are rare; bad leaders are common. That is just the way of the world, even in an organization as highly screened as the SEAL teams.

  • Explaining the why. In a perfect world, every employee would care deeply about the profitability of the company they work for. But these folks have other things to care about. Husbands and wives. Kids. Soccer games. Bills and cars and mortgages and the game on Friday night and the broken water heater and the kid heading off to college. They have a ton to care about - and like it or not, the profitability of the company is not high on their list. They have to understand the why - but that why has to have a thread that ties back to them, to what is in it for them.

Managing your boss

  • The relationship to seek with any boss incorporates three things:

    • They trust you.

    • They value and seek your opinion and guidance.

    • They give you what you need to accomplish your mission and then let you go execute.

Strategy

  • Keep plans simple. While it is sometimes tempting to utilize more complex or convoluted tactics, always choose the most straightforward course of action so that everyone on the team knows exactly how to execute the plan.


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