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The Best Leaders Ask Great Questions

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When I was early in my leadership journey, I thought being an effective leader was about having all of the answers and knowing what to do when others didn’t.  This may be the case in a time-limited crisis like close-quarters combat, but what about the other 99% of the time? I used to think that asking questions was indicative of incompetence or an unacceptable degree of ignorance.  We’ve all had that experience where we wanted to ask a question but didn’t because we were afraid we’d look stupid.  As I matured as a leader, I observed that a major component of leadership was asking great questions, which means asking the right questions at the right time.

One subset of people in leadership positions ask questions to which they already have the answers or know there is no way to know the answer.  These inquisitors are either testing their subordinate or seeking to make themselves appear superior.  They don’t ask questions to promote greater understanding, they seek to bolster themselves by tearing down the people around them.  This creates an environment of fear and shame that harms organizations.

Another group of leaders are the ones who haven’t yet figured out the right questions to ask.  They either ask questions from curiosity that serve no constructive purpose, or they haven’t yet figured out that the phrasing of the question drives the type of answer they receive. One of my first leadership lessons as a squadron commander was in handling a disciplinary case.  I mistakenly asked my legal advisor if I could do something.  The answer came back, no I could not do what I wanted.  Frustrated, I went to my boss who listened to me patiently and explained that the question I ask will affect the answer I get.  She then asked me how I might rephase the question to get a more helpful answer.  Illuminated, I went back to my office and called back my legal counsel to ask how I could do what I wanted to do legally.  The answer, as you might imagine, was very different.  My legal teammate went became my partner in problem solving, helping me to achieve an outcome that met my intent.  From that point forward I’ve been especially thoughtful about the questions I ask.

The final and best set of leaders who harness the power of questions to build up their teams and cultivate understanding.  A well-phrased question allows an individual to consider aspects they may not have considered, which facilitates growth.  Questions that make people think like the one my boss asked me all those years ago.  A question that not only spoke to the problem at hand, but to any entire world of possibilities.  If she had simply handed me the answer, she would have missed an opportunity to make me grow.  The wise leader also is confident enough to ask the “stupid” questions, knowing that there are others who are wondering the same thing but lack the courage to ask.  A leader who takes the time to read the room will know what questions need to be asked and when.  There is no end to the people who will thank you, either out loud or silently, for asking the questions on their minds.  Your leadership by example will encourage others to ask questions which will strengthen the psychological safety, the ability to learn, and ultimately the performance of your organization.  If you want to be a great leader, what questions should you be asking?

Authored By: Jason Lamb, Managing Director

Jason Lamb

Jason is the United States Space Force's Talent Strategist. In this role, he is actively involved in crafting and executing the United States Space Force’s human capital strategy and plans. A nationally recognized thought leader in leadership and talent management, he advises Space Force senior leadership on how best to acquire, develop, engage, assess, promote, and employ its military and civilian members. Prior to his current position, Jason served over 25 years in the Air Force as an intelligence officer and retired in the rank of Colonel.

In uniform, Jason served with distinction in a variety of intelligence, staff, and command assignments in deployed combat environments, geographically dispersed organizations across the globe, and in the United States. As an intelligence group commander, he led over 650 personnel in eight units spread across four continents supporting everything from national decision making to time-sensitive tactical operations.  Jason has deployed in support of Operations SOUTHERN WATCH, IRAQI FREEDOM, and ENDURING FREEDOM. During his career, Jason was recognized as the Air Force’s Intelligence Officer of the Year, graduated number one from his Air War College class, was awarded the Bronze Star in Afghanistan, and twice awarded the prestigious Legion of Merit.

While those accomplishments are noteworthy, he is perhaps best known for leading a significant culture shift in the Air Force and across the Department of Defense beginning with a series of articles he published under the pseudonym “Col Ned Stark.”  In those articles, Jason highlighted significant organizational culture and leadership alignment issues, provided root cause analysis, and offered innovative solutions resulting in the Chief of Staff of the Air Force offering him a senior position on his staff.  To the surprise of many, Jason chose to end his fast-track career and retire instead so that he could coach and engage with broader audiences.  The Space Force reached out to Jason to architect an innovative new approach toward talent management and leadership development that would ensure the long-term alignment of the newest armed service’s mission and values.  The result was The Guardian Ideal, described by the Chief of Space Operations as the single most important accomplishment of the Space Force to date.

Jason understands how to create and develop high-performing teams of teams.  He knows how to uncover organizational misalignment and dysfunction to craft tailored solutions that improve workforce retention and performance.  Jason is a proven leader and solver of wicked and complex problems.

Jason graduated from the U.S. Air Force Academy with a degree in International Relations with a minor in Japanese.  He holds four advanced degrees in organizational management, national security policy, and strategy.  Additionally, Jason is an International Coaching Federation-certified professional coach with an additional certification as an Energy Leadership Index Master Practitioner.  He resides in Colorado with his wife and daughter.

Victory Strategies is a Veteran Owned Business.