340th shirt wears many hats

  • Published
  • By Debbie Gildea
  • 340th Flying Training Group Public Affairs

Traditional Reserve Citizen Airmen tend to be busy with civilian and military career responsibilities, as well as the day-to-day tasks that are part of life. Apparently that isn’t busy enough for people like 340th Flying Training Group First Sergeant Senior Master Sgt. Samuel Caballero, who effortlessly wears spouse and teammate, civilian businessman, Reserve Citizen Airman, educator and trainer, and “first shirt” hats while squeezing in ample time to help potential leaders find their footing.


Caballero and his wife, both members of a Hispanic professional development organization Prospanica, work together to help promote self-development within the San Antonio business community. 


Caballero, former Association for Talent Development - San Antonio Chapter president, earned his Master of Arts degree in management from Webster University. His wife, former president of San Antonio’s Prospanica, earned her Master of Business Administration through the University of the Incarnate Word. Thanks to their leadership roles in the business community coupled with their extensive education and experience, they were uniquely positioned to be able to see a need, develop a solution and act.


The Need: Many people don’t know what it means to lead, or how to become a leader, and many don’t know how to have a positive impact on people - how to leave a positive legacy.


The Solution: Caballero, his wife, the leadership team of Prospanica and Barbara Greene with Greene and Associates put their heads together and developed the Emerging Leaders Series, a multi-module education series that covers a variety of characteristics commonly found in strong leaders. Modules cover emotional intelligence, finding one’s strengths, values-driven work and more.


The Action: With a plan in hand, the husband-wife team and the other team members facilitated the inaugural Emerging Leaders Series course in 2016. The intensive, six-month program wrapped up in 2017. Their second series ended in May 2018, and a third is slated to begin toward the end of this year.


What is an emerging leader, and who is this program for? It would be an understandable assumption that “emerging leaders” are young adults entering the workforce, but that’s not necessarily so, Caballero said.


“When we first started looking at identifying our target audience we realized that an emerging leader can be someone who just graduated college and is managing or leading several team members. But we also had strong interest from managers and supervisors with many years of experience who weren’t aware of the impact of their action - or inaction,” he explained. “So, in essence, an emerging leader is someone who is beginning to recognize their leadership presence, and who realizes the positive impact they would like to make, and the legacy they want to leave behind.”


Caballero, a traditional Reservist who enlisted in 1990, has earned two associate degrees, a bachelor in urban studies, the management master’s degree, professional manager certification, and is a certified professional in learning and performance. He also completed every level of enlisted professional military education, including the Air Force Senior NCO Academy and the Senior Enlisted Joint PME Part I and II.


His skills and abilities have resulted in selection for military quarterly and annual awards and civilian professional development awards, and he’s been recognized for coaching and mentoring, and as a certified professional in learning and performance.


With such a resume, it’s no surprise that he is engaged in growing leaders outside of the military. The surprise is that he does it for free.


“I’m not paid to facilitate the program - we do this pro bono - but I love being part of ELS,” he explained, adding that being able to participate is payment enough. He also offers other workshops on a pro-bono basis on topics like building a support system, communicating for mutual understanding, establishing goals, time management and more.


With 28 years of professional uniformed service behind him, the “Shirt” has developed a host of skills (and highly-sensitive intuition) thanks to struggles and challenges he’s experienced in the civilian and military workplaces.


“I have used my experiences from when I was not at a mature level to help me understand my emotional intelligence, and to recognize that sometimes I based decisions on emotion rather than logic,” he said.


Coming to understand himself and internalizing lessons learned over the years from his mentors and coaches combined with vast military training instructor and first sergeant experience have helped him develop his own distinctive coaching and mentoring skills.


"I always go back to the desired end result, and remember that I got here through people. The focus is on how we treat people; understanding how they want to be treated and what drives them. That impacts how we connect with them and how they connect with us,” he said.


Being able to use all of his experiences, successes and failures, and all of the lessons the Air Force and fellow Airmen have taught him to help others grow has been its own reward, and it is the decades of instruction, corrective guidance, encouragement and mentorship that have given him the strength and strategic perspective necessary to be able to effortlessly wear so many hats