The Dichotomy of Leadership: Balancing the Challenges of Extreme Ownership to Lead and Win

by Jocko Willink

  “I didn’t have a good feeling about this one,” I said, appreciating his candid feedback.

  “Leif,” he continued, in brutal honesty, “if I wanted to get a bunch of my guys wounded or killed, this plan is exactly what I would do.”

  There it was. My suspicions were confirmed. I knew this company commander was a bold leader. He was aggressive and well respected. I knew that he would not—and did not—shy away from danger or risk. He and his Soldiers were the definition of courageous warriors. They had supported us on several high-risk missions that put his men in harm’s way. So if he was telling me this, I had better listen.

  I drove back across Camp Ramadi to speak with the leader of the special operations unit. After walking into his office, I told him what the National Guard company commander had said. I urged him to revise his plan and explore alternative routes to the target area. I stressed that the IED threat was a highly probable contingency for which he and his team needed to be prepared. But the leader of the special operations unit was unfazed, still confident in his plan.

  “Those National Guard guys,” he responded, “they’re risk averse. We roll in heavy with our armored vehicles and we’ve got massive firepower.”

  Special operations units such as this one, SEALs, and others had far greater training, better equipment, and a much larger budget for gear than the National Guard. Yet the National Guard unit, despite their lack of high-speed training and equipment, had accomplished a great deal on this toughest of battlefields. They had earned the utmost respect from us and the other U.S. units operating in the area. And the National Guard had something far more valuable than high-speed training and the latest gear: fifteen months of arduous combat experience in Ramadi. Because of that experience, from daily gun battles with insurgents to the devastating carnage of IED attacks, these National Guard Soldiers were now battle tested, combat proven, and still humble enough to respect the enemy and his capabilities.

  I continued to try to convince the special operations unit leader to come up with an alternative plan that included contingencies for likely scenarios or perhaps wait for a better opportunity to nab the high-value target. But I could not dissuade the leader from launching on the operation.

  I told him that our SEALs and Iraqi soldiers would not participate. I hoped that the lack of an Iraqi partner force might inhibit his ability to get mission approval. Unfortunately, they were granted permission to execute the mission, and despite the warnings, the special operations unit leader went forward with the operation. A few days later, in broad daylight—right in the middle of the day—they launched on the operation.

  They never made it to their objective.

  We learned later what happened: their convoy of armored vehicles had traveled only a short distance down the road on which they’d been advised not to drive when an IED exploded under the lead vehicle. With the heavy armored vehicle disabled and on fire, several of their troopers inside were wounded. Unable to abandon the vehicle or the men inside, they were pinned down under withering enemy gunfire for several hours as they waited for help. Finally, a nearby conventional army unit was able to respond and tow their vehicle. It was a miracle no U.S. troops were killed, though several were seriously wounded. But it was a close call and a humbling lesson that careful planning is essential. Had the special operations unit’s leader listened and thought through the likely contingencies, he never would have taken that route. Instead, he and his team would have come up with an alternative that would have prevented his men from being wounded and their vehicles destroyed and given them a much greater chance to successfully accomplish the mission.

  Principle

  Careful planning is essential to the success of any mission. In Extreme Ownership, chapter 9, “Plan,” we wrote that mission planning meant “never taking anything for granted, preparing for likely contingencies, and maximizing the chance of mission success while minimizing the risk to the troops executing the operation.” While the risks in combat are obvious, there are also significant risks in the business world. Livelihoods are at stake: jobs, careers, capital, strategic initiatives, and long-term success. Leaders must manage this risk through careful contingency planning for the things that can be controlled. But not every risk can be controlled.

  For planning, there is a dichotomy within which leaders must find balance. 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. Rather than preventing or solving problems, overplanning creates additional and sometimes far more difficult problems. Therefore, it is imperative that leaders focus on only the most likely contingencies that might arise for each phase of an operation. Choose at most the three or four most probable contingencies for each phase, along with the worst-case scenario. This will prepare the team to execute and increase the chances of mission success.

  It is important, however, that leaders manage the dichotomy in planning by not straying too far in the other direction—by not planning enough for contingencies. When leaders dismiss likely threats or problems that could arise, it sets the team up for greater difficulties and may lead to mission failure. At every level of the team, leaders must fight against complacency and overconfidence. Nothing breeds arrogance like success—a string of victories on the battlefield or business initiatives. Combat leaders must never forget just how much is at stake: the lives of their troops. Business leaders, too, must never become callous with the livelihoods and careers of their employees and associates or the capital invested. Each risk requires careful evaluation, weighing, and balancing the risk versus the reward—the benefit to the team and to the strategic mission of a successful outcome. Careful contingency plans that are focused are key to managing such risks and achieving victory. It is difficult to balance the dichotomy between these two extremes. But it is critical for every leader to understand that in order to be successful, he or she must plan, but not overplan.

  Application to Business

  “I don’t believe we have fully looked at the contingencies,” said the chief operating officer (COO). “I’ve voiced my concerns. But they don’t seem to be taken seriously.”

  Jocko and I sat in the COO’s office. We were there to kick off a Leadership Development and Alignment Program for the company’s senior executive team and midlevel managers. The company had delivered a string of successes in recent years, owing in large part to a smart and aggressive leadership team eager to establish the company as a major player and take on the dominant competitors in the industry. The company’s successes drove an additional capital raise, which they had recently secured. As a result, the company now had the resources to invest in expansion.

  Victory upon victory had built confidence in the company’s executive team and its department leaders—and none were more confident than their CEO. The CEO was determined to grow, and he had no shortage of grand ideas. The company’s COO urged more caution and a careful evaluation of the risks involved.

  “What risks are you most concerned about?” Jocko inquired.

  “We are trying to grow in multiple directions simultaneously,” the COO responded.

  “Launching a single subsidiary company is expensive and carries risk,” the COO replied. “We are launching two different subsidiary companies at the same time. We are also expanding the corporate office, hiring dozens of new administrative staff, and locking in a long-term lease on three more floors of the corporate headquarters building. That’s over a hundred more offices and a significant long-term expense. These plans seem to make sense right now, but if the market takes a downturn or we have a significant manufacturing problem, all those plans would be in jeopardy.”

  “Well, those are real possibilities,” I said. “It sounds like your team is in need of some detailed contingency plans.”

  “Look,” the COO continued. “I’m willing to accept that we will have to take some risks as we expand.
But we need to think about how to handle those risks. I’m concerned that we are overleveraging ourselves.”

  “Why do you think the CEO is pursuing these initiatives concurrently?” I asked.

  We had worked with a number of companies in rapid expansion mode. Some had aggressively launched new initiatives that achieved extraordinary results. Others had taken on too many simultaneous risks that burned huge amounts of capital with little return, and they had to pull back and pursue a more careful growth strategy.

  “I get that there are significant opportunities in each of these efforts,” the COO answered. “I am all about the need for us to grow and expand our market share. But we really haven’t done the contingency planning you’re talking about—and that’s the problem. Look: If the market took a downturn or we had a major recall of a product, and one of these subsidiary companies failed, the loss would be significant but it wouldn’t be catastrophic. But if both of these subsidiary companies failed simultaneously, it would be a major blow to our company’s bottom line. It might shut the whole thing down.”

  With careful contingency planning, the CEO and the company’s leadership team would have taken steps to mitigate such a possibility. If they focused their efforts to launch only one subsidiary initially, and once its success was established launched the next one, that would be a much safer bet.

  “What about the additional administrative support?” I inquired. “Is that something you feel isn’t needed?”

  “I understand the need for additional administrative support,” the COO replied. “We’ve had a number of requests from our department heads for more support. I understand that. But taking on a multiyear lease of expensive office space large enough for a hundred additional offices is, I think, excessive. Why can’t we just expand to a single additional floor instead of three? Who knows what the economy will look like a year or two from now? This company has only seen good times. We haven’t been around long enough to experience hard times. What if the economy takes a turn for the worse and we lose significant business? Our company will be on the hook for these additional salaries, and even if we let employees go, we will still be locked in to the long-term lease for empty offices and burning major capital that we may not have.”

  His concerns sounded reasonable. It was clear that he wasn’t totally risk averse, but he knew things might not go as planned and he urged caution about the level of risk the company was taking and the lack of steps taken to mitigate that risk. This was precisely the reason that planning for contingencies was so critical to mission success.

  “When we were in combat,” I told the COO, “it was crucial to carefully evaluate risk and develop contingency plans for the things that were likely to go wrong. Once we analyzed those risks, we recognized that there was much we could control to reduce risk. Contingency planning helped us take the steps necessary to prepare for the uncertainty of outcomes during combat operations. And that’s no different for you or your team here.

  “In Ramadi, when we went into enemy-held neighborhoods where the threat was extremely high,” I said, “we took steps to mitigate risks from attack. The roadside bombs or IEDs were the biggest threat, so in the worst areas, we didn’t drive. We walked in via foot patrol. We set up sniper overwatch positions in buildings, where the chance of enemy attack was high, and we set up multiple positions that could support each other. Planning for these contingencies helped us manage the risk—even extreme risk in that environment.”

  Jocko added: “You might think that in the SEAL Teams, we are all Big Tough Frogmen who run to the sound of the gunfire no matter what. And for many situations, that is exactly what we did. We have to show courage under fire and be willing to risk our lives. But we can’t be foolish. We can’t take needless risk that prevents us from accomplishing our strategic mission and endangers our troops,” Jocko continued. “As leaders, we have to do that smartly by mitigating the risks we can control. Careful evaluation of the risk enables us to develop contingency plans so we can execute in the most effective manner to accomplish the mission with the least amount of risk to our troops.”

  Jocko explained to the COO that in training, we put SEAL leaders to the test to humble them and hopefully prevent them from having to learn such lessons in combat when real lives were at stake.

  “We utilized a ‘kill house’ to practice maneuvering through hallways, entering doors, clearing rooms. We often conducted such training using simulated fire with paintball or Simunition rounds against role-players—SEAL instructors or volunteers acting as the bad guys or opposing force,” Jocko said.

  Jocko described how many of the scenarios were designed to lure the SEAL unit into a dire situation, where the leader must step back and analyze the risk.

  “In one such scenario,” Jocko said, “our SEAL instructor staff would place a bunkered ‘enemy’ machine gun position covering a long hallway, where the role-players simulating bad guys could engage the SEAL platoon from a protected position from which they couldn’t be easily hit by the SEAL assault force trying to clear the building. The SEAL leader would send two shooters forward down the hallway toward the enemy fire. The two SEALs would encounter devastating fire, the sting from dozens of paint rounds hitting their bodies at high speed. The instructor staff would put them down—they’d be told to lie on the floor of the hallway simulating that they’d been killed. The SEAL leader would usually send two more of his SEAL shooters forward. The results from attacking a hardened position would inevitably be the same: two more SEALs ‘killed.’ Then the SEAL leader would send two more shooters, until the hallway was littered with dead—thankfully only simulated dead.”

  “That’s when we would have to step in,” I added, “and ask the SEAL leader: ‘Do you think this is a good idea to continue sending more of your troops to their death?’ When the leader responded in the negative, I explained that charging forward into enemy gunfire was courageous but foolhardy. It would only result in the destruction of his entire force. And worse, they were no closer to accomplishing the mission of eliminating the threat and clearing the house. I instructed him to contingency plan—to think of another way to attack the problem: ‘Can you send two of your SEAL shooters outside the building and attack from a different direction? Is there another entrance, a window or doorway, where we can attack the enemy from behind?’ I would ask.”

  “We watched the lightbulb go off in that SEAL leader’s head as he realized that not only could he do this but he absolutely must do this if he was to succeed as a leader,” said Jocko. “It is a leader’s duty to mitigate the risk you can control.”

  “I struggled with those same problems in the same type of difficult training scenarios,” I told the COO. “In the moment it was difficult to see what needed to be done. But when I recognized this, I realized that we could perform much better if we took the time to develop careful contingency plans. If, before we even launched on the operation, I thought about how we might best react to a likely scenario, I could more easily make that decision when I encountered it. Even better, if I briefed the team on what to do in the event we encountered such a scenario, they were ready to execute and the team could do so even without immediate direction.”

  “But best of all,” Jocko added, “when SEAL leaders thought through a likely contingency—like a bunkered enemy machine gun position in the house—and carefully planned how to handle that situation, they came up with alternative ways to get the mission accomplished while reducing the risk to the SEAL assault force. This meant they might enter the building from a direction that the enemy role-players hadn’t anticipated and catch them off guard. When this happened, the SEAL platoon decimated the enemy fighters, accomplished the mission, and didn’t lose a single man.”

  “That’s where you need to be,” I said. “All business ventures will inherently carry some element of risk. Thorough planning, understanding and creating action plans for likely contingencies, will help you mitigate that risk. While you can’t plan for everything—and you shouldn�
�t get bogged down with too much planning—you must still use solid planning to mitigate the risks you can control. Finding the balance between planning and overplanning is critical, and it sounds like right now you need to lean toward more planning so that you are fully prepared to react properly should some of these possible contingencies occur.”

  With that, Jocko and I encouraged the COO to lead up the chain of command and put together a comprehensive plan that included a clear assessment of the risks and the contingency plans to help mitigate them. The COO moved forward, aggressively planning to achieve the CEO’s goals, but with thorough contingency plans in place to ensure the highest probability of long-term mission success.

  The “ammo table”—ammunition storage in the Charlie platoon mission planning space, which also served as the Task Unit Bruiser Ready Room. SEALs are taught from day one that violence of action and superior firepower are what wins in a gunfight. Task Unit Bruiser agreed.

  (Photo courtesy of the authors)

  CHAPTER 11

  Humble, Not Passive

  Leif Babin

  ROUTE MICHIGAN, SOUTH-CENTRAL RAMADI, IRAQ: 2006

  Everyone in the convoy was on edge as our Humvees rolled through downtown Ramadi on the main road, known to U.S. forces as “Route Michigan.” It was broad daylight, and as insane as it might seem, despite the frequency of violent attacks, there were some locals along the roadside and civilian vehicle traffic on the road.

  Every pothole, every piece of trash that littered the road, might be an IED delivering fire, shrapnel, and death. The frequent bomb craters and charred remains of vehicles along the roadside were a grim reminder. Ambushes, too, were a huge threat. Insurgent fighters with RPG-7 rockets and belt-fed machine guns might be concealed in nearby buildings, ready to unleash an attack at any moment.

  Our SEAL turret gunners manned their heavy machine guns and scanned relentlessly for threats. They stood with chest and head exposed through the roof of the Humvees above the vehicles’ armored plates. Each turret had armor protection on three sides but still left the gunner vulnerable. Those of us inside the vehicle also kept a sharp eye out for any potential attack as best we could through the thick, dust-covered glass of the armored windshield and windows. But the best protection for the turret gunners—our convoy’s best defense—was our posture: ultra-aggressive, weapons pointed in all directions manned by vigilant gunners, ready and eager to unleash the fury at the first sign of a threat. We aimed to make any potential attackers hesitate, to think twice about whether they wanted to suffer the consequences, and wait for an easier target. The muj1 were keen to talk about martyrdom, but they never wanted martyrdom on our terms. The possibility that they might be slaughtered before they could do any real damage to us was a substantial deterrent.