For most of his Air Force career, retired Lt. Gen. Brian Kelly thought about how to get the right people into uniform, develop them and keep them there.
Today, as president and CEO of the Military Officers Association of America, he spends much of his time thinking about what happens to those people after they leave.
Increasingly, Kelly sees those as parts of the same continuum.
I believe strong national defense comes from strong people, Kelly told Military.com in a recent interview.
And for Kelly, taking care of those people shouldn’t suddenly become more complicated when they take off the uniform.
His vision is straightforward: When a service member becomes a veteran, the federal government should already know who that person is, have access to the records documenting that service and be prepared to help connect the new veteran with the benefits he or she may have earned.
Instead of forcing veterans to figure out a new system on their own, Kelly believes technology and greater cooperation between the Defense Department and Department of Veterans Affairs could eventually allow the government to come to them.
And a new executive order suggests that system may be getting closer.
Making the Handoff Seamless
President Donald Trump signed an executive order Sept. 8 directing the Defense Department and VA to overhaul how military personnel and medical records are shared between the departments.
The order requires the departments within 180 days to establish updated technology and policies allowing the permanent and ongoing sharing of Official Military Personnel Files and Service Treatment Records from the time someone enters military service through the period when that person requires VA benefits.
It also calls for new digital tools, including artificial intelligence and other emerging technology, aimed at creating a single source to help veterans apply for and access benefits and employment opportunities.
VA Secretary Doug Collins said the changes could eliminate weeks of waiting for veterans applying for health care and financial benefits. The VA estimates improved records sharing could cut another 20 to 30 days from processing times for recently separated service members.
We want to make the transition from military to Veteran status as seamless as possible, Collins said when the order was announced.
That goal closely resembles the future Kelly described to Military.com.
Kelly said a transitioning service member should eventually be able to reach the VA and hear, essentially: The government already has your information. It knows what benefits you may be eligible for. It knows what medical conditions are documented. Now, what else do you need?
“You are now in the VA system,” Kelly said, describing what that future interaction might look like.
The larger change, he said, would be making the government more proactive rather than requiring veterans to initiate every part of the process themselves.
“For the VA to get that automatically picked up and be proactive with [the veteran], and not reactive to [the veteran], would be a game changer for the veteran community,” Kelly said.
More Than Disability Claims
Much of the public discussion surrounding veterans benefits focuses on disability compensation and the claims process. Kelly said the opportunity is broader.
“Claims are, and people focus on the claim piece, but there’s lots of other aspects of VA and veteran benefits,” Kelly said, pointing to housing, education and other benefits earned through military service.
The Sept. 8 order takes a similarly broad approach.
In addition to improving the flow of records between the military and VA, it directs changes to the Transition Assistance Program and other workforce programs.
The goal is to connect departing service members with specific job opportunities, training or apprenticeships before separation and link them with government veterans representatives who can assist with applications for health care, disability, home loan, education and other benefits.
MOAA has publicly welcomed the effort, saying it plans to work with VA and other stakeholders on improving the Pentagon-to-VA records handoff and expanding transition and career support.
For Kelly, the issue isn’t about assigning blame for a system that has developed over decades.
He noted that the Defense Department and VA are separate federal departments with different missions, structures and measures of success. The opportunity, he said, is to align those systems more closely around the person moving between them.
Forcing the VA and the Defense Department]into greater cooperation is to the benefit of the veteran and the veteran’s family, Kelly said.
People Aren’t Easily Replaced
Kelly’s focus on that transition reflects a broader view of military personnel that developed during his 33 years in uniform.
Before retiring in 2022, Kelly spent 3½ years as the Air Force’s deputy chief of staff for manpower, personnel and services, overseeing policies affecting the service’s workforce. He previously commanded the Air Force Personnel Center. He became MOAA’s president and CEO in January 2023.
His experience inside the personnel system taught him that people cannot be treated like another piece of military equipment or a budget line that can quickly be reduced and restored.
Kelly pointed to the Air Force’s experience during the sequestration-era force reductions. The service cut roughly 29,000 people, he said, and eventually grew back toward its previous size. But rebuilding headcount did not immediately rebuild experience.
Kelly recalled cases in which a squadron eventually had more people than it had before the reductions, while its average experience had fallen from about 9.8 years to about 4.2 years.
“You can’t replace that very well,” Kelly said.
Unlike a private company, the military generally cannot go into the civilian labor market and hire someone with 15 years of experience as an Air Force officer, senior noncommissioned officer, military pilot or other specialist. Those people have to be developed over time.
You need to be very cautious and very careful about how fast you move those levers and what you do because it’s not easy to replicate and recreate, Kelly said.
That challenge may become even more important as the military prepares its workforce for rapidly changing technology and a different kind of potential future war.
An 18-Year Expert Takes 18 Years
Kelly said military personnel systems ultimately have to follow military strategy.
When strategy changes, so do the skills and capabilities the services need. Recruiting, training, development and retention eventually have to change with it. But there is an unavoidable lag.
The senior NCOs, lieutenant colonels and colonels leading today’s force entered the military years before many of today’s technologies and strategic demands existed.
“If you want your whole force to be harmonized, you don’t do it in 18 months,” Kelly said. Then he put the challenge more simply.
To grow an 18-year expert in your new strategy takes 18 years.
That long view helps explain why Kelly now talks about veterans benefits, military compensation, recruiting, retention and transition as connected pieces of a larger system.
MOAA represents more than 350,000 currently serving officers, retirees, veterans, families, caregivers and survivors, and Kelly said his role now gives him greater freedom to advocate for that community than he had while serving within the military chain of command.
But he said the desired outcome isn’t fundamentally different.
Kelly wants the Defense Department to succeed in recruiting people, providing them a strong experience while they serve and taking care of their quality of life. And when those people leave uniform, he wants the VA positioned to continue that support.
“We don’t have a different outcome that we want from those folks,” Kelly said. “But we might have differences in what we think are the priorities.”
The Sept. 8 executive order won’t eliminate every complication veterans encounter when leaving military service. Some benefits will still require applications, evidence and eligibility determinations, and the order gives agencies months to build or modify many of the systems required to carry out its goals.
But the direction aligns with the model Kelly described: a military and veterans system that carries information forward with the service member instead of asking that person to start over after leaving uniform.
For Kelly, that would represent more than a technological improvement.
It would mean the government increasingly recognizes military service as a continuum from the day someone enters the force, through the years spent developing expertise, to the benefits and support that follow when that service ends.
And the veteran would no longer have to navigate that transition alone.
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