Senior U.S. Air Force leaders are embracing and promoting the concept that if their Airmen are not failing, then they are, more than likely, not moving forward.

They believe pushing the envelope is necessary to keep the U.S. Air Force dominant and the occasional failure should be viewed by supervisors not as a negative, but as part of a greater positive.

In this series, we hear senior Air Force leaders give examples of how taking calculated risks and failing throughout their careers taught them valuable lessons, propelled them to future success and made them better leaders.


Dr. Will Roper, Assistant Secretary of the Air Force for Acquisition, Technology and Logistics

As the Air Force’s Service Acquisition Executive, Dr. Will Roper oversees Air Force research, development and acquisition activities with a combined annual budget in excess of $40 billion for more than 465 acquisition programs.

Dr. Will Roper, Assistant Secretary of the Air Force for Acquisition, Technology and Logistics reflects on an experience that shapes his view on taking risks in the United States Air Force. Video // Peter Ising

He promotes the concept of “Fail Fast, Fail Forward” as a foundational culture shift necessary to keep the U.S. Air Force dominant.

This philosophy is manifested in his promotion of rapid prototyping and funding innovative ideas through Air Force Pitch Day and AFWERX’s Spark Tank.

Roper believes that by spending money to develop fledgling technologies and ideas quickly, and then prototyping them rapidly, flaws are found much earlier in the development process.

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Dr. Will Roper, assistant secretary of the Air Force for acquisition, technology and logistics, speaks to a crowd of small businesses, venture capitalists, and Airmen during the Inaugural Air Force Pitch Day in Manhattan, New York, March 7, 2019. Air Force Pitch Day is designed as a fast-track program to put companies on one-page contracts and same-day awards with the swipe of a government credit card. The Air Force is partnering with small businesses to help further national security in air, space and cyberspace.

U.S. Air Force photo // Tech Sgt. Anthony Nelson Jr.

This method avoids committing to the huge cost of the much longer traditional system and weapons development and acquisition where flaws are only found years and hundreds of millions of dollars later. Then the Air Force is stuck with that flawed system for decades.

However, in order for “Fail Fast, Fail Forward” to work, Roper believes the Air Force must adjust its attitude towards risk.

He points out that his own success actually points to a persistent flaw in the Air Force’s tolerance for risk – people are only rewarded for taking a risk that pays off. Roper insists that to foster an innovative culture, people must be rewarded for taking a good risk in the first place.

“Why are the people who succeed the only people we cite when we talk about risk taking as a virtue?” Roper said. “I’m trying to be very mindful with Air Force program managers and people taking risk that they get their evaluation and validation for me at the point that they take the risk.”

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