The biggest benefit of hiring veterans isn’t discipline or an ability to follow orders.
It’s that every veteran arrives having already been through a deliberate, sequential leadership development system. One that trained them to communicate clearly under pressure, hold a standard, learn from failure through structured after action reviews, and develop the people around them.
Most organizations hire that capability without recognizing it and then leave it unused because they onboard veterans exactly the way they onboard everyone else.
I’ve lived and experienced this personally. So has Daniel Grochowski, a fellow West Point graduate, former Field Artillery officer, and founder of Five & Fly.
His experience was so challenging and enlightening that he built a company to solve the problem he found. Today, his company builds and manages SkillBridge programs and has assisted more than 500 transitioning service members, with a 90% placement rate.
What follows is what we learned and what any operations leader can do with it.
What the Military Actually Builds in Its Leaders
Civilian hiring managers tend to picture a veteran as someone reliable under pressure and good at taking direction. That picture is accurate, but it misses the most valuable part.
The military doesn’t just train people to do a job. It installs a set of leadership tools and repeats them until they become instinct, regardless of rank, branch, or specialty.
The after action review (AAR) is the clearest example. After a training event, a mission, or any hard stretch, the team stops and works through four questions: what was supposed to happen, what actually happened, why the two differed, and what changes next time. No blame, no speeches. Just learning, captured before anyone moves on.
Communication is the second example. People are often surprised when I tell them that most of what a pilot does is talk on the radio. Learning to physically fly the aircraft is the easy part. The hard part is knowing who to talk to, when, how, and why. Daniel described artillery the same way: if an officer ever has to pick up his own rifle, the coordination he was responsible for has already broken down. Leadership works the same way. The majority of it is communication, and veterans have practiced it in environments where getting it wrong carried real consequences.
Why Veteran Leadership Gets Lost in Translation
If veterans bring all of this, why does it so often go unnoticed?
Part of the answer is the transition itself.
Daniel left the Army in 2020 for a remote role at a tech startup after following the advice most service members heard at the time. He quickly realized that the things that had defined him, including West Point, Division I football, and evaluations that ranked him at the top of his peer group, meant nothing in his new environment. Nobody was being unkind about it. The civilian world simply doesn’t have a way to read those signals. The result was a real identity crisis, one Daniel says (and I can attest to) most transitioning service members face in some form.
The resumé is the second problem. A top-block officer evaluation or a leadership role over dozens of soldiers doesn’t translate onto a sheet of paper in a way a civilian recruiter can weigh. Veterans arrive with confidence built from years of success while facing a steep technical learning curve in a new industry. That combination can read as overconfidence from the outside which feeds skepticism in both directions.
And the third problem is less obvious: the loss of proven leadership infrastructure. Inside the military, the leadership systems are just how things work so service members take them for granted. Many only realize how valuable the tools were once they’re working somewhere that doesn’t have them.
The Most Common Reason Companies Fail to Leverage Veteran Hires
The most consistent failure Daniel sees on the employer side is assumption.
Organizations have operated the same way for years, and people inside them naturally expect every new hire to think the way they do. When a veteran brings a different way of approaching problems, the difference often gets read as friction instead of value.
Five & Fly’s fix is simple and deliberately structured. For the first 90 to 120 days after a service member joins an organization, the Five & Fly team holds a check-in every 30 days with both the hiring manager and the new hire. The manager is pushed to actually evaluate how the person is developing. The new hire is asked what isn’t making sense yet. Then the two conversations are brought together.
Over time, the hiring manager and the veteran start having those conversations on their own, as part of their normal rhythm. That’s the real goal.
The 85% Rule: A Practical Framework for Hiring Veterans Into Leadership Roles
Daniel’s hiring approach for veterans comes down to one idea: hire for the 85% you can’t teach, then teach the 15% you can.
Here’s how it works in practice:
- Define the 85%. Character, aptitude, mindset, and transferable leadership skills. These take years to build and are nearly impossible to train into someone in a quarter. Screen hard for them.
- Budget three to four months for the technical 15%. Industry knowledge, your equipment, your systems, your terminology. If a strong candidate can’t learn that within a quarter, the problem is usually in your onboarding, not the hire.
- Plan three to four quarters ahead. Programs that give you access to transitioning service members need runway. When one VP was asked what his hiring needs would look like a few quarters out, the honest answer was that nobody had looked that far. Organizations that routinely think three or four quarters ahead are the ones that win the talent they want.
- Build in structured check-ins. Use the 30-day, two-sided rhythm described above for at least the first 90 days so assumptions get surfaced early instead of becoming turnover.
This framework runs directly against the way many small and mid-sized organizations hire. The typical pattern is reactive: someone leaves, parts need to ship, and the seat has to be filled immediately. Once cost of goods sold and overhead are covered, the margin left over rarely feels big enough to justify hiring ahead of need. But reactive hiring over-weights the technical 15% and under-weights the 85%, and the organization ends up back in the same place a year later.
How the DoD SkillBridge Program Gives Manufacturers an On-Ramp to Veteran Talent
The Department of Defense SkillBridge program lets eligible service members train or intern with an approved civilian employer during their final 180 days of service while continuing to receive their military pay and benefits.
How much of that window a service member can use now varies by rank and branch. For an employer, it’s an extended opportunity to see how a candidate performs before making a hiring commitment.
The need is significant. By Daniel’s count, roughly 200,000 service members leave the military every year, while only about 3,500 opportunities lead directly to employment. This is exactly why structured programs matter, and why employers that plan ahead can reach talent their competitors never see.
What This Means for Every Leader on Your Team
I often use a simple picture with senior leaders: a pilot pushing the coffee cart down the aisle means nobody is at the controls. When a VP is constantly doing a director’s job, or a manager is doing a supervisor’s job, nobody is flying the plane. Senior leaders are there to think two to five years down the road, and the only way they get that time back is when the levels below them are staffed with people who can run their own teams.
Veterans are one of the best sources of those leaders available. But the larger lesson applies to every supervisor you have. The military produces capable leaders because it treats development as a system: repeated tools, clear standards, structured reflection, and deliberate progression. Most organizations are hiring the output of that system without building anything like it themselves.
Building that structure for every supervisor you have, veteran or not, is what we do at Operation Lead. You can start with The Leader’s Preflight Checklist at operationlead.com/checklist, or schedule a call to learn how our system works.
If you want a SkillBridge pipeline of your own, start a conversation with Daniel’s team at fiveandfly.com.
Let’s Lead,
Craig
