Reflections on #Leadership: Asking the Right Questions

The future operating environment, with its complex threats and increased tempo, will demand that future Army professionals be comfortable with uncertainty, be able to adapt quickly to fast-paced events, and possess emotional maturity and professional judgment in decisionmaking.[1]

Since the Army Operating Concept: Win in a Complex World was published in 2014, military leaders have been inundated with the idea of complexity. But how should we prepare to overcome complexity? How can leaders improve their ability to understand, visualize, and describe this environment to enable decision making? How should we adjust our planning to account for this complexity? In the past, the military has largely focused on new or improved processes and technology to account for historic lessons learned, but will this be successful in the future? There are many ways to prepare for a complex world, but improving cognition through inquisitiveness should be chief among them.

When discussing leadership today, few people would put inquisitiveness on the list of leadership skills necessary to be successful. A military leader is expected to be an expert at leading his unit in combat, epitomized by the age old fundamentals—shoot, move, and communicate. These fundamentals are undoubtedly required for tactical success, but veterans of recent conflicts are equally aware that tactical victories do not always translate into strategic success.

The military’s uneasy relationship with questions is one of the most significant problems.

If we believe the answer to this challenge is to develop a new process, we should consider the flexibility of that process. A widely accepted phrase throughout the Army is the fact that many solutions are METT-TC (i.e., situationally) dependent.[2] The book A More Beautiful Question concurs when it states that “answers are relative.”[3] How well are we preparing our leaders to create flexible solutions to complex problems?[4]

Leaders must be capable of evaluating doctrine, tactics, and standard operating procedures to determine what may effectively solve the problem at hand. If the existing ideas are insufficient to solve the problem, leaders must alter existing processes or find new processes to achieve their desired results.

Nothing outlined thus far should come as a surprise, but it is not easy to be an agile leader. So what are some of the obstacles that leaders must overcome? The military’s uneasy relationship with questions is one of the most significant problems. This unease stems from tactical necessity, cultural power distance between superiors and subordinates, and each leader’s individual expertise.

Many situations require prompt action and decision making from leaders, and disciplined adherence to orders from subordinates. A perfect example is during a firefight. When lives are at stake, soldiers need to react quickly and follow orders to defeat the threat, or risk being defeated themselves. Combat is not usually the best time to ask questions.

Tactical necessity, in part, contributes to the military’s high cultural power distance as well.[5] Some in positions of authority falsely believe that they must have the answer to all the questions. Studies by Tony Wagner and Warren Burger, innovators in education and business respectively, suggest that this is an artifact from the United States’ industrial age education system.[6] Ultimately, this cultural bias tends to create an environment where questioning is discouraged.

Some leaders also discourage questioning because they desire to be recognized and known as experts. We all want to know and have the skills necessary to be successful in our respective fields. However, studies show an inverse relationship between expertise and the ability to ask questions.[7] This is not to suggest that we should avoid becoming experts, but we should balance expertise with a healthy dose of skepticism to ensure our thinking is sound.

Leaders are comfortable with questions in some situations, especially controlled environments. For instance, command climate surveys and collaborative planning between superior and subordinate leaders are controlled in that the leader sets the tone for what questions are asked and what feedback they use or incorporate. Another example is the coaching methodology used by many observer coach/trainers. Although they share doctrine, tactics, techniques, and procedures to assist their counterparts, observer coach/trainers are encouraged to ask questions as part of the reflective coaching process as well.[8]

What is going on? What should the environment look like? What are the obstacles impeding progress towards the desired end state? What broad general actions will resolve the problem?

Some of the Army’s doctrinal processes encourage us to ask questions too. The Army design methodology lays out a series of questions to help us understand, visualize, and describe our environment, problems, and potential solutions. The questions are: “What is going on?,” “What should the environment look like?,” “What are the obstacles impeding progress towards the desired end state?,” and “What broad general actions will resolve the problem?” Doctrine expands upon the Army design methodology process to include example questions and techniques for questioning, but ultimately leaders must refine these root questions based on specific situations to help commanders and staffs frame complex problems and envision solutions

Unfortunately, the Army design methodology is not usually introduced to military leaders until they attend their captain’s career course or intermediate level education. Is this too late? Should we be introducing the Army design methodology, or maybe just encouraging questioning sooner? Examining the conflicts in Iraq and Afghanistan, we are likely to find that analyzing our environment through design methodology questions helped leaders at all levels understand and direct actions within their area of operations. So how are we preparing leaders to ask these questions and the questions that will follow?

The United States’ civilian education system has come under scrutiny for failing to teach inquisitiveness.[9] Nicholas Murray argues in a recent War on the Rocks article that the professional military education system is no different.[10] This shortcoming might stem from the difficulty of grading advanced cognition.[11] In an environment defined by time constraints and fairness, many educators and evaluators use multiple choice or fill in the blank assessments to measure understanding and check the block rubrics to measure how students or subordinates apply prescribed processes. It is more difficult to measure the skills of analysis, synthesis, and evaluation. However, these higher cognitive functions are precisely the skills we need to win in a complex world, and they require questioning and inquisitiveness.

Celestino Perez Jr., Department of Joint, Interagency and Multinational Operations, Oct. 30, 2012 (Prudence Siebert/Fort Leavenworth Lamp)

Many have proposed ideas for how to succeed in today’s complex environment. For example, Celestino Perez suggests that the military should increase its political literacy to understand causal relationships in conflict.[12] Meanwhile, BG(R) Huba Wass de Czege believes that leaders should develop hypotheses and test them to advance towards end states.[13] The common denominator seems to be the assertion that leaders who ask the right questions will be successful. Furthermore, when a leader creates an environment where she encourages her subordinates to question as well, she’ll be capable of harnessing her organization’s collective brainpower, which is much greater than hers alone.

Military culture may have an uneasy relationship with questioning, but given the complex environment we face, leaders must both develop and encourage inquisitiveness to be successful. Leaders should not delay questioning or inquisitiveness until they become more senior. The last fifteen years have placed increased demands on the decisions made by junior officers and teaching all leaders to ask good questions will enable the Army to succeed in the future.

Gary Klein is a U.S. Army officer and a member of the Military Writers Guild and the Defense Entrepreneurs ForumThe views expressed in this article are those of the author and do not reflect the official policy or position of the U.S. Army, the Department of Defense, or the U.S. Government.

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Header Image: U.S. Army Maj. Gen. John W. Nicholson Jr., 82nd Airborne Division commanding general, listens to questions from a U.S. Military Academy cadet training with the division at Fort Bragg, N.C., June 27, 2013. (U.S. Army Photo)


[1] Department of the Army, TRADOC Pam 525-3-7, The U.S. Army Human Dimension Concept (Government Printing Office, 2014), 17.

[2] Mission, Enemy, Troops, Terrain, Time, and Civil (METT-TC) is an acronym used to describe the Army’s mission variables.

[3] Warren Berger, A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas (New York, NY: Bloomsbury USA, 2014), 159.

[4] Department of the Army, TRADOC Pam 525-3-1, The U.S. Army Operating Concept: Win in a Complex World (Government Printing Office, 2014), iii.

[5] Stephen J. Gerras, Leonard Wong, and Charles D. Allen, “Organizational Culture: Applying A Hybrid Model to the U.S. Army” (U.S. Army War College, November 2008), 14–16.

[6] Warren Berger, A More Beautiful Question, 44–50, 165–174.

[7] Ibid., 13.

[8] OCTs use a range of skills to coach their counterparts, but two of the most common are to provide advice or ask leading “why” questions to help their counterpart learn and reflect from their experiences.

[9] Tony Wagner, The Global Achievement Gap: Why Even Our Best Schools Don’t Teach the New Survival Skills Our Children NeedAnd What We Can Do About It (New York: Basic Books, 2008), Ch.1.

[10] Nicholas Murray, “Rigor in Joint Professional Military Education,” War on the Rocks, February 19, 2016,

[11] In 1956 Benjamin Bloom outlined a taxonomy for categorizing the cognitive skills of knowledge, comprehension, application, analysis, synthesis, and evaluation, which are listed from the lowest to the highest level.

[12] Celestino Perez, Jr, “Strategic Discontent, Political Literacy, and Professional Military Education,” The Strategy Bridge, January 14, 2016,

[13] Huba Wass de Czege, “Operational Art Is Not a Level of War," Small Wars Journal, March 14, 2011,