When everything is going right, be thinking about where things can go wrong

“What is some advice you would give to a leader who has a hard time letting go of the reigns and delegating to others?”

‍It’s human nature to get comfortable with success. Victory breeds confidence. Successive victories multiply that confidence which can lead to complacency. When leaders and teams get complacent, they fail to thoroughly plan for contingencies since the potential for challenges and obstacles seems far-fetched. However, this mindset sets the team up for disaster.

Two weeks ago, shares of Apple Inc., a longtime sure bet for investors, plummeted on the announcement that quarterly revenue was at least $5 billion short of expectations. The selloff of Apple shares that ensued erased nearly $75 billion in market value. Since its peak last year, Apple lost $428.74 billion in market cap. In October 2018, when Apple became the first U.S. company to reach $1 trillion market capitalization, Apple was considered one of the most rock-solid investments anywhere and a precipitous decline seemed almost unimaginable.

Last week, the most dominant NCAA Division I college football team of the last decade, the University of Alabama Crimson Tide, suffered a devastating 44-16 loss to the University of Clemson Tigers in the college football national championship game. Clemson, the underdog, dominated every aspect of the game. It was the worst loss for Alabama since Head Coach Nick Saban arrived in 2007. Clemson’s rout of the Crimson Tide, who had dominated every other team they faced, was a shock to college football fans and commentators alike. But it appeared most shocking to the Alabama’s players and coaching staff. They may have expected a tough game, but they likely did not expect a blow out. Contingencies that seemed highly improbable can become reality precisely because the team did not anticipate them and were therefore unprepared.

Such examples illustrate just how difficult it is to plan for contingencies and prepare for obstacles when everything is going right—when the expectation of victory is all but assured.

This presents a constant challenge for military units on the battlefield, where lives are at stake. In Chapter 6: “Aggressive, but Not Reckless” of The Dichotomy of Leadership, Jocko wrote about what military historians have long referred to as “the disease of victory.” The disease of victory occurs on the battlefield when a military unit’s success breeds overconfidence. Leaders and teams begin to overestimate their own tactical prowess and underestimate the capabilities of their enemy. When many operations have taken place without experiencing a worst-case scenario, the assumption becomes that the worst-case scenario won’t happen. Proper contingency planning begins to wane and the team’s mental and physical preparation decreases which negatively impacts the team’s performance. What leaders need to understand is that in reality, every iteration of success actually increases the probability of such a worst-case scenario happening.

As operations officer (one of the senior leaders) at a SEAL Team, I visited training sites to observe our front line leaders, the task unit commanders and platoon commanders, leading

their teams in training. The training was designed to be difficult in order to challenge leaders and prepare them for the immense challenges of combat. Upon arrival at the training site, I would check in with the task unit commanders and platoon commanders and ask how their training was going. The worst answer I could hear was: “We’re crushing it.” That answer told me that they were simply in denial of performance struggles or that they had not yet truly been tested. That attitude set the team up for failure. When significant and unexpected challenges were encountered, the team was unprepared to meet those challenges and failure often ensued. The best leaders, when asked how training was going, would answer: “We’re doing some things well. But we have a lot to work on.” Those leaders were positive, but humble. They didn’t allow themselves and the team to become overconfident and they didn’t get complacent. When the obstacles came, the team was far more prepared and, as a result, far more successful.

This isn’t just bad behavior by choice. Complacency caused by successive victories is human nature and something to which all of us are susceptible. For a leader that wants to continue to win, it is crucial to be aware of this tendency. The disease of victory is real. When everything is going right, that is when it is most difficult—yet most important—to take a step back and analyze where and how things might suddenly go wrong. That way, both leaders and teams are fully prepared to meet the inevitable challenges and obstacles that arise in order to sustain victory.