HANSCOM AIR FORCE BASE, Mass. – As the acting program executive officer for Digital prepares to retire after more than 30 years in the Air Force, he discussed seizing opportunities and building connectedness.
Col. Riley Pyles joined the Air Force through the ROTC program in 1994. His father had served in the Air Force for more than 34 years as a chief master sergeant, and pushed his son to attend college and get a commission.
“When I was in ROTC and filling out what was then called the dream sheet with five Air Force Specialty Codes, I wasn’t sure what I should do,” said Pyles. “Two of my father’s previous bosses, retired base commanders from Ramstein [Air Base, Germany], recommended that I check acquisitions. I’m so glad I got that recommendation because 30 years later I’m still smiling.”
He noted that was his first time being mentored, but said he’s been fortunate to have amazing mentors throughout his career, including his very first supervisor in the Air Force, who is still his mentor today. Pyles strives to take what they have invested in him and pay it forward.
“In general, my leadership style is to work things behind the scenes and to allow others to shine,” he said. “My mantra has been if I take care of my people, by default they end up taking care of me. My job is to enable them to effectively tackle the mission to their utmost ability, and ensure they don’t have to deal with the churn of the bureaucracy.”
Pyles also encourages personnel to take advantage of opportunities that come their way. He started his career in the C-17 program office at a time when the program was capped at 40 aircraft because of the performance of the prime contractor and the aircraft. Under the leadership of then-Brig. Gen. Ronald Kadish, who selected senior leaders for the program office and picked then-2nd Lt. Pyles to be in his Commander’s Action Group, the program was turned around.
“I got to be part of and experience working with General Kadish and other senior leaders saving the program,” Pyles said. “I got to see [the program] excel and watch over the years as more than 270 were produced across the Air Force and for multiple partner nations.”
Pyles also served as the AF Space Command representative to the Air Force Association Junior Officer Advisory Council. He said he was lucky to be selected across all the company grade officers for the volunteer opportunity. Pyles and representatives from other major commands canvassed the CGO population on quality-of-life issues that helped inform AFA for their annual reports to congress.
Pyles also recalled a pitch he made to then-Maj. Gen. Rowayne Schatz, about a multi-year procurement buy for the C-130J, during a ferry flight Schatz was piloting.
“This was probably the weirdest place I ever made a pitch,” he said. “It was one of several opportunities to engage with senior leaders about why the multi-year procurement was a good thing for Air Mobility Command and AF Special Operations Command, and it led to the DOD [Department of Defense] saving over 500 million dollars, improving buying power, and helping AMC and AFSOC with their missions.”
The departing PEO also talked about getting people together, especially outside of the office. Pyles noted that, while he moved up the ranks, he wanted to ensure subordinates would still approach him. He told a story when the Air Force first had personnel do group physical training and his deputy senior materiel leader belonged to an outrigger canoeing club and had the team go and learn how to row/canoe, showcasing how every position, no matter how strong, if they’re not in sequence, can potentially tip the boat.
“Getting to know people on a personal level breaks down barriers and makes a team better and I carried that going forward,” he said, noting that he regularly joins his directorate’s group PT sessions, including encouraging civilians to participate. “Out on the field, all barriers are broken down and we can connect including mentoring and coaching on a level we might not be able to do [elsewhere].”
He talked about the activities that Hanscom AFB offers that allow people to unite, including the commander’s cup, gatorball tournaments and the sporting activities between the four major base organizations that take place on ”First Fridays.” Pyles said he hopes those types of events continue.
Speaking to personnel from an Advanced Tactical Acquisition Corps cohort recently, he was asked why he served 30 years, and credited the Air Force’s “unique culture.”
“We say it’s a wingman culture - wingmen look out for each other and in my experience that’s absolutely true,” Pyles said. “It can’t be an anomaly; I’ve served in so many different locations, units, with so many different people, but at each landing spot I’ve felt part of an extended family where I’ve been welcomed and given the opportunity to reach the highest of heights. The people have made me want to come to work every day, want to give 100 percent – had they not been as amazing as they were there was no way I would have served 30 years.”
He said he’s been pleasantly surprised at the opportunities that have been presented to him following retirement, but said he hasn’t made a decision yet and is looking forward to a month or two of downtime. Pyles said he will be staying in the area at least until his children finish college.