MacArthur 2017 1st Place Award Winner

Epic Fail

Why Leaders Must Fail to Ultimately Succeed

Maj. Timothy Trimailo, U.S. Air Force

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Sgt. Gregory Padilla (second from left) gives a status report to 2nd Lt. Randy Jozwiak (left) during a live-fire exercise 20 July 2015 as part of Northern Strike 15 on Camp Grayling Joint Maneuver Training Center, Michigan. Padilla is a team leader and Jozwiak is a platoon leader assigned to the 1st Battalion, 126th Cavalry Regiment. (Photo by Sgt. Seth LaCount, U.S. Army)

When a reporter asked him how it felt to fail a thousand times, Thomas Edison replied, “I didn’t fail 1,000 times. The light bulb was an invention with 1,000 steps.”1 For Edison, failure was not just an option but a requirement for eventual success. Without the many setbacks he faced during the invention process, Edison would not have learned from his mistakes and ultimately bring a commercially viable light bulb to mankind. Unfortunately, modern society tends to downplay failure, deny its occurrence, or experience shame when others recognize it first. In adolescent sports, for example, league organizers hand out participation trophies to all the participants rather than embracing the fact that some people win and others lose. Even some of the most prestigious universities in the United States are reluctant to give underperforming students failing grades.2 Upon graduation from these institutions, these students are unprepared for the cruel, unforgiving realities of the world.

Those in control of these adolescent sports leagues and universities are impeding the development of these young people due to their distortion of the line between success and failure. Simply put, today’s society is coddling the Nation’s future leaders and setting them up for later, more significant, failure by not letting them experience failure early in life.

The modern trend of failure aversion is also prevalent in the military. Commanders and mentors are not allowing junior leaders to fail early on in their careers. This phenomenon is likely due to several factors. First, the military is a difficult and unforgiving business that involves death and destruction, so an aversion to risk and failure is an expected byproduct. Second, senior leaders experience an enormous amount of scrutiny by the Department of Defense, Congress, and public opinion, causing them to micromanage junior officers more than ever before to preclude failures that they perceive might reflect badly on them. Additionally, military leaders are often “type A” personalities who demand maximum control over operational variables.

Consequently, some of these senior leaders often punish even minor failures with severity, sometimes degrading the potential for future promotion for otherwise promising young leaders. Much like in the civilian world, this zero-tolerance failure policy is hurting the next generation of leaders in the military by stifling initiative and making them risk averse. They either have not been allowed to fail and recover early on in their careers, or they leave the military based on limited promotion opportunities stemming from a previous failure from which they perceive they cannot recover. Moreover, in a world of increased external scrutiny and access to new micromanagement tools through new technologies, the institutional trend toward failure avoidance and fear of admonishment for failure is only becoming more pronounced.

This is extremely unfortunate, however, because leader development requires some failure. Failure that occurs in the proper context allows individuals to learn from mistakes, promotes resiliency and moral courage, and builds the capacity to balance risk and reward in future decision making under the more serious conditions of actual operations, including combat.

Fail and Learn Early or Fail Big Later

In September 2013, the commandant of the Marine Corps fired two general officers for failure to “exercise the level of judgment expected of commanders of their rank” after fifteen insurgents breached security at a base in Afghanistan and destroyed numerous aircraft.3 The validity of the decision to relieve these commanders and the character and experience of the officers in question is beyond the scope of this essay, but avoiding this type of failure at senior levels should be a primary goal as the military develops its leaders.

Unfortunately, this example likely will not be the last major failure by a senior American officer. Whether it be a method for interacting with subordinate troops, the selection of an appropriate tactical mission task during operational planning, or the management of a unit training plan, failure as a junior leader in such endeavors provides the necessary experiential forum for trial and error. As leaders rise through the ranks in the military, they build a personalized set of tools to leverage as the problems they encounter become more complex.

Another reason early failure facilitates learning from mistakes can be derived from an analysis of the alternative. In some instances, a record of continual success taken for granted can breed eventual failure since meaningful learning often does not occur under circumstances of persistent success. For example, Italian motorcycle company Ducati began racing bikes on the competitive racing circuit in 2003. After some initial success attained by applying learning from early poor race results, the engineers failed to continue looking at race data to incrementally improve their bike design for future races.4 As Francesca Gino and Gary Pisano point out, initial success for Ducati limited the incentive to continue organizational learning, causing the company to later fail due to an accrued culture of complacency.5 As applied to military leader development, this vignette illustrates the natural condition of success. Simply put, too much success can lead to overconfidence and lethargy, which in turn hinders continual learning and improvement. In contrast, leaders must embrace the concept that learning from failure is an inevitable necessity for continual improvement and performance optimization.

The final aspect of failure as a catalyst for learning is that it helps leaders identify the indications and warnings of failure before it occurs in the future. Kathy Malloch and Tim Porter-O’Grady assert that highly successful leaders are preoccupied with failure because this preoccupation makes them focus on the minute details and address indicators of failure quickly and decisively.6 Failure provides a means of analyzing all aspects of the individual and the organization to help identify the critical factors that lead to failure. By analyzing these indicators after an unsuccessful event, the leader can identify similar indicators in the future to proactively avoid failure. With reference to the previous example of the two Marine generals in Afghanistan, it is possible that learning from tactical mistakes at the junior level could have helped those individuals pinpoint indicators of a base breach ahead of time to avoid failure on such a large scale.

There is a caveat to the argument that leader development should encourage learning from failure at the junior level. The focus should not be misconstrued as an effort to ensure junior leaders fail but rather on providing them with an environment that tolerates mistakes in a context where those mistakes lead to self-assessment, learning, and correction to avoid future failure. As philosopher George Santayana asserted and Winston Churchill later reiterated, “Those who cannot remember the past are condemned to repeat it.”7 While failure is necessary for deep learning to occur, those who do not actively learn from mistakes will be far more likely to repeat them. Consequently, for the military officer, failure in the proper context and environment should be regarded as an opportunity to learn from mistakes, avoid the pitfalls of perpetual success, and identify warning signs of future failure on a larger scale.

Fail, Recover, Repeat

In addition to learning from mistakes, overcoming adversity and bouncing back from failure is an important step in the development of a leader. As two scholars in leadership, Warren Bennis and Robert J. Thomas observe, “the skills required to conquer adversity and emerge stronger and more committed than ever are the same ones that make for extraordinary leaders.”8 The way in which a developing leader reacts to difficult situations directly correlates to that individual’s ability to overcome adversity in the future. These experiences provide the leader with a newfound understanding of self and an increased ability to deal with future hardships. However, if growing leaders are not given a chance to bounce back from adversity because they are shielded from failure, they remain untested and are more likely to confront difficult future situations in negative ways. In other words, these leaders are not developing what Bennis and Thomas refer to as “adaptive capacity,” because they do not have the opportunity to do so.9 On the other hand, leaders who develop this capacity and build individual resilience are far more likely to promote that behavior within their subordinates and units as they climb the organizational ladder.

In addition to building individual resilience, failure as a junior leader also helps develop moral courage. A key aspect of moral courage is the ability to admit mistakes without fear of humiliation and shame.10 The willingness to admit mistakes is an unnatural quality, especially for the stereotypical competitive leaders within the military. That being said, the ability to adapt and overcome failure as a junior officer helps build the confidence needed to be comfortable enough to admit mistakes later in a leader’s career. As Peter Olsthoorn asserts, the unit cohesion that builds physical courage in the military is the same element that makes individuals more likely to blindly conform and, thus, less likely to exude moral courage.11 Moreover, the emphasis of unit success combined with the tendency toward modulating individual failure is hindering the development of moral courage in growing military leaders. While team building and unit cohesion are critical to operational success, senior leaders must also focus on developing individual qualities in subordinates to include moral courage.

Critics of the argument that failure early in one’s career breeds resilience and moral courage might assert that these traits are inherent in, or absent from, every individual and are not qualities that can be developed. Traditional Nicomachean ethical principles, for instance, assert that one can learn most skills but cannot acquire moral virtues above and beyond what is already inherent in the individual.12 While each human being certainly possesses some level of individual morality and resilience, the trials and tribulations of failure during formative years can assist in building the aptitude for these traits and the willingness to employ them in the future. The military needs its leaders to overcome failure early in their careers to develop individual resilience and moral courage. These abilities not only assist leaders in the conduct of future personal behavior but also in encouraging these traits in subordinates, which fosters a culture of practicing moral courage.

The Thin Gray Line between
Success and Failure

Learning from failure and developing resilience and moral courage in the face of adversity are extremely important in leadership development, but military leaders must ultimately take risks with nearly every decision they make as senior leaders. Army doctrine states that accepting prudent risk assists commanders in seizing an opportunity to gain and maintain the initiative on the battlefield.13 In other words, the Army embraces the fact that military operations involve risk and leaders must take acceptable amounts of risk to facilitate success in conflict. The ability to identify prudent risk, however, is a skill developed as a junior officer. Aside from thorough analysis, the most effective way to truly understand what risk is prudent and acceptable is to cross the line into unacceptable risk at some point. When a leader takes an unacceptable risk, failure is far more likely to occur. This experience further reinforces the leader’s ability to discern prudent risk from unacceptable gambling and employ informed judgment to make critical decisions on the battlefield.

The goal of accepting prudent risk is to increase the probability of harnessing great reward. Risk is often viewed as negative and something people should avoid, but thoughtful, habitual risk-taking is actually a requirement for high-level success.14 Tim Kane refers to this quality in leaders as the “bias for action” that entrepreneurs possess, or a desire to proactively and carefully take risk to maximize returns.15 The only way to garner maximum reward in any business is to take a risk. In the military context, leaders who take prudent risk on the battlefield are the ones who enjoy the greatest successes in conflict as well. As Gen. David Perkins asserted at a 2013 Army Mission Command Symposium, retaining a position of advantage on the battlefield is difficult since that advantage is always relative to the enemy and is always temporary, since the enemy is constantly adapting to the evolving operational environment.16 In other words, prudent risk-taking is a requirement for waging warfare in the modern era. However, if military leaders do not take risk, experience failure, and learn from mistakes early on in their careers, then they will not fully understand the characteristics of prudent risk-taking and will never fully harness the vast rewards available through taking risks. Put another way, risk-taking and failure can buy down future risk. Military leaders earn their paychecks by effectively managing risk and maximizing the chances of success.

An alternative point-of-view on risk and failure is that the violent nature of military operations requires leaders to minimize risk at all costs to avoid failure and subsequent loss of life. The media and the American public criticized American military leaders after the intervention in Iraq in 2003 for deploying too few personnel and for not having a reasonable plan for the post-war stability effort.17 According to the critics, these leaders had miscalculated the risk involved in this type of military effort. However, this example does not validate the assertion that risk should be avoided at all costs. On the contrary, it proves that misunderstood risk is dangerous, but prudent risk-taking can garner high payoffs. While the merits of the campaign in Iraq are not the subject of this essay, the argument is that leaders must take a risk in the face of less than perfect information, and that miscalculations of risk early in their careers can inform the balance of risk and reward to enhance judgment later as a senior leader. If this balance is learned through failure at earlier stages, senior leaders can avoid loss of life to gain and maintain a position of relative advantage in military operations through informed decision making and the management of prudent risk.


Leader development requires some level of failure. It allows leaders to learn from past mistakes, it builds individual resiliency and moral courage, and it develops the capacity to balance risk and reward in decision making to promote future success. Learning from mistakes is a human requirement, but it is necessary for leader development as well. It facilitates personal growth and helps leaders understand and visualize success and the warning signs of failure, but it also reduces the complacency promoted by a perception of inevitable perpetual success. Failure can also breed resiliency and moral courage, because it teaches the leader to overcome adversity, acknowledge mistakes, and come out the other side of difficulty with new self-actualization, confidence, and toughness. While these qualities are inherent in each person from birth, they are also taught through trials and tribulations. Finally, the military profession requires leaders who can accurately balance risk and reward. Without risk-taking, there is no return on investment, and military leaders must embody that entrepreneurial spirit in order to seize an opportunity and maintain the ever-changing position of relative advantage over the enemy. On the other hand, the key to effective risk-taking is analysis and prudency. All three of these points illustrate why military leaders must fail early in their careers to be effective organizational leaders at higher echelons.

Today’s operational environment is complex, dangerous, and unforgiving. Joint doctrine asserts that “the commander is the central figure in operational art, due not only to education and experience but also because the commander’s judgment and decisions are required to guide the staff through the process.”18 Today’s military leader requires education, experience, and judgment that feeds reasonable decision making. Unfortunately, today’s leaders are not allowing their junior officers to take prudent risk and learn from failure at lower echelons. While this practice might improve chances for successful operations today, it hinders the growth of the junior leaders who will be charged with defending the Nation in the future. Those officers must experience and learn from failure today to become more resilient, more confident in their moral courage, and more adept at balancing risk and reward in future operations. Just as Edison responded to a reporter about his failures on the path to inventing the light bulb, the military leader is also an invention with a thousand steps.


  1. Pauline Estrem, “Why Failure is Good for Success,” Success magazine, 25 August 2016, accessed 30 August 2017,
  2. Michael Zuckerman, “Failing to Fail?,” Harvard Magazine online, 23 December 2013, accessed 23 August 2017,
  3. Rajiv Chandrasekaran, “Two Marine Generals Fired for Security Lapses in Afghanistan,” Washington Post online, 30 September 2013, accessed 23 August 2017,
  4. Francesca Gino and Gary Pisano, “Why Leaders Don’t Learn from Success,” Harvard Business Review, April 2011, accessed 23 August 2017,
  5. Ibid.
  6. Kathy Malloch and Tim Porter-O’Grady, The Quantum Leader: Applications for the New World of Work (Burlington, MA: Jones and Bartlett Publishers, 2005).
  7. George Santayana, The Life of Reason; Or The Phases of Human Progress (New York: Charles Scribner’s Sons, 1920).
  8. Warren G. Bennis and Robert J. Thomas, “Crucibles of Leadership,” Harvard Business Review (September 2002), 39–40.
  9. Ibid.
  10. William Ian Miller, “Moral Courage and Civility,” chap. 16 in The Mystery of Courage (Cambridge, MA: Harvard University Press, 2000).
  11. Peter Olsthoorn, “Courage in the Military: Physical and Moral,” Journal of Military Ethics 6, no. 4 (2007): 270–79.
  12. Ernst M. Conradie, Morality as a Way of Life: A First Introduction to Ethical Theory (Cape Town, South Africa: Sun Press, 2006).
  13. Army Doctrine Reference Publication 6-0, Mission Command (Washington, DC: U.S. Government Publishing Office [GPO], 2014 [Change 2]), 1–4.
  14. Anne Kreamer, Risk/Reward: Why Intelligent Leaps and Daring Choice Are the Best Career Moves You Can Make (New York: Random House, 2015).
  15. Tim Kane, Bleeding Talent: How the U.S. Military Mismanages Great Leaders and Why it’s Time for a Revolution (New York: Palgrave Macmillan, 2012).
  16. David G. Perkins, “Understanding Mission Command,” YouTube video, from the 2013 Association of the United States Army symposium, posted by “USArmyCAC Fort Leavenworth,” 29 October 2013, accessed 23 August 2017,
  17. Paul Yingling, “A Failure in Generalship,” Armed Forces Journal (1 May 2007), accessed 23 August 2017,
  18. Joint Publication 5-0, Joint Operation Planning (Washington, DC: U.S. GPO, 11 August 2011), XIX.

Maj. Timothy Trimailo, U.S. Air Force, is a staff officer with the Secretary of the Air Force Legislative Liaison Office in Washington, D.C. He holds a BS in political science from the U.S. Air Force Academy and an MBA from the University of Nebraska. His assignments include space operations and acquisitions tours at Schriever Air Force Base, Colorado; the Space and Missile Systems Center, El Segundo, California; and the National Reconnaissance Office, Chantilly, Virginia. Trimailo is a 2017 graduate of the U.S. Army Command and General Staff College, Fort Leavenworth, Kansas.

November-December 2017