Your First Executive Civilian Job Will Surprise You—In All The Wrong Ways
Why do senior military leaders struggle in their first civilian job? You would think that someone who has led thousands of people in a fleet, a brigade or a division, made life and death decisions (literally), and managed billion-dollar operations would transition into a civilian job and crush it.
That is not what happens.
In fact, some of the most successful military leaders I’ve worked with struggle the most in their first civilian role—which surprises the hell out of their spouses.
Their struggle is not because they lack ability. Not because they aren’t “a good fit”. Not because they are “still wearing their rank.”
Senior leaders struggle because they’re using a military map to navigate civilian territory
Which is strange.
Because the map looks right.
What goes wrong
1. Senior military leaders think they are being hired for their leadership.
In the military, leadership is a word that contains a host of meanings—taking up responsibility at a staggering level. Being chosen from among outstanding peers for the most significant jobs. Having the experience and skill required to make big decisions quickly, confidently and accurately.
Yet in the civilian world, leadership is not what they want from major commanders. Leadership is only part of the package. Visibility, relationships, and internal navigation matter just as much—and often more.
2. Senior leaders underestimate civilian culture shock. Really.
When you have spent your adult life moving all over the world to master a new job in a few days, moving into the civilian world seems like just another assignment.
But it is not.
This is not just a new job. It is a completely different system.
Expect unclear expectations. Shifting priorities. A matrixed organization where you have three different bosses who don’t seem to know each other. Expect Bizarroland.
3. Senior leaders expect their experience to make sense.
You think they hired you because they understand what you did in your job at scale.
Nope.
They hired you because someone who worked with you in the past vouched for you at the right moment. They mentioned you at the end of a meeting. They sent their boss your resume and suggested that when Allison leaves next summer, you would be a good fit.
Civilian organizations don’t inherently understand what your career actually entailed. They don’t know what your capabilities are in the civilian environment. And at first, neither do you.
What successful transitions do differently
Too many military leaders think the unwritten rules they operated under are still they unwritten rules that apply in the civilian world. They think the reward is jumping in at a leadership level the first day
This is the part that drives civilian CEOs crazy. “I wish they would take a few months to learn the system before trying to lead it,” a defense executive told me at a dinner recently.
What does that even mean?
Instead of assuming authority, in a successful transition:
§ You study how decisions are truly made at the new company, not how people say they are made.
§ You observe who has influence and how often that influencer is usually part of the EA mafia.
§ You see what kind of power and control longevity gives to certain unleaderly leaders.
§ You figure out the crushing burden of profit and loss.
§ You identify what success in all its loveliness truly looks like.
Here is the part no one tells you
Even if you had the most successful military career in the history of the world, the first civilian job will shake your confidence in yourself. It will make you privately question whether you belong and make you doubt what your military career prepared you to do.
Left unchecked, this is how you become one of those guys with dead eyes.
Where I come in
This is why I do the work I do with senior military leaders and their families. This isn’t glorified resume writing. It is not reading off a list of coaching questions and asking “How does that feel?” or “Where do you carry that in your body?”
This executive coaching is about helping you understand the system you are walking into. It is translating your experience into a value proposition that lands. It is you and your spouse making decisions that set up your true generational wealth.
If you are within 12 months of transition—or already in your first civilian role and wondering why it feels harder than expected—schedule a conversation. We’ll figure out what’s actually going on—and what to do about it.
