From E-1 to CFO: Why Working Your Way Up Makes You a Better Leader Lessons from enlisted to officer to commander

Published: February 10, 2026 | By Gabriel Denny

I didn't commission as an Air Force officer. I enlisted as an E-1—the lowest rank in the military. For three years, I worked on aircraft, took orders, did the grunt work that keeps the mission moving.

Then I went to Officer Training School, commissioned as a Finance Officer, and worked my way to Major and Squadron Commander—leading 140 people and serving as CFO for a nuclear missile wing.

That journey—from bottom to top—taught me more about leadership than any MBA program could. Here's why.

You Learn What Actually Matters

When you're an E-1, you see the difference between leaders who talk about values and leaders who live them.

You see which policies make sense and which are bureaucratic garbage that wastes everyone's time.

You learn which leaders earn respect and which demand it (and fail).

The business lesson: If you've never done the work your team does, you don't really understand the problems you're asking them to solve. The best leaders have been in the trenches. They know what's hard, what's tedious, and what's broken.

You Understand What Motivates People

As an enlisted airman, I didn't care about the Wing Commander's strategic vision. I cared about:

Does my supervisor have my back?
Am I learning skills that matter?
Do I feel valued or like a cog in a machine?
Can I see a path forward?

Those questions don't change when you become an officer or a CFO. People want to feel valued, challenged, and supported—regardless of rank or title.

The business lesson: Most executives think comp and titles motivate people. They don't. Purpose, growth, and respect do. If you've been at the bottom, you remember what actually mattered.

You Earn Credibility the Hard Way

When I commissioned as an officer, I didn't magically become a better leader. But I had something most new lieutenants didn't: credibility with enlisted troops.

They knew I'd done their job. I understood their challenges. I wasn't some college kid fresh out of ROTC telling them how things should work.

That credibility mattered. When I gave direction, they trusted I understood what I was asking them to do.

The business lesson: Leaders who've never done the hard work struggle to earn respect. You can demand compliance, but you can't demand trust. Trust is earned—usually by proving you've walked the path your team is walking.

You See Both Sides of Every Decision

As a commander and CFO at Malmstrom, I made decisions that affected hundreds of people. Budget cuts, reorganizations, policy changes.

But because I'd been on the receiving end of those decisions as an enlisted airman, I understood their impact differently.

I knew what it felt like when leadership made changes without explaining why. I knew how frustrating vague direction was. I knew when a policy sounded good on paper but would fail in execution.

So when I made decisions, I communicated clearly. I explained the "why." I anticipated pushback because I'd been the one pushing back years earlier.

The business lesson: Leaders who've only been at the top make tone-deaf decisions. They don't understand how their choices ripple through the organization. Ground-up leaders do.

You Learn Humility (The Hard Way)

When you start at the bottom, you fail. A lot. You make mistakes, get corrected, and learn humility.

I've screwed up aircraft maintenance. I've been chewed out by senior enlisted leaders. I've had to apologize for errors and fix them.

That shapes you. It teaches you that rank doesn't make you infallible. It teaches you to admit mistakes, learn fast, and move forward.

Contrast that with leaders who've never failed publicly. They double down on bad decisions because admitting error feels like weakness.

The business lesson: The best leaders I know have failed spectacularly at some point. It made them better. Leaders who've never struggled often crack under real pressure.

You Build a Deeper Network

Because I came up through enlisted ranks, I built relationships across the entire organization—not just with officers.

When I needed something done as a commander, I knew who the key people were. I knew which senior enlisted leaders ran the real show. I knew how to navigate the system.

Leaders who only know other executives miss 80% of what's actually happening in their organizations.

The business lesson: The people closest to the work know where the problems are. If you only talk to VPs, you're getting a filtered version of reality. Ground-up leaders know who to talk to for truth.

You Appreciate Opportunity

When I was an E-1, becoming an officer felt impossible. Then becoming a major. Then commanding a squadron.

But each step felt earned—not given. I never took rank or position for granted because I knew how hard it was to get there.

That gratitude kept me grounded. It reminded me that leadership is a privilege, not a right.

The business lesson: Leaders who've had everything handed to them often take their teams for granted. Ground-up leaders remember what it took to get there—and they lead with gratitude.

The Bottom Line

Starting as an E-1 and working my way to Major didn't just shape my career—it shaped how I lead.

I understand what motivates people because I've been at the bottom. I earn trust because I've done the hard work. I make better decisions because I've seen both sides.

When you hire a CFO or fractional CFO, ask them: Where did you start?

If they've only ever been at the top, they're missing half the picture.

Want a CFO who understands what it's like to work your way up?

Let's talk or call (616) 881-6777.

About the Author

Gabriel Denny started as an E-1 in the Air Force and worked his way to Major and Squadron Commander. He served as CFO for America's largest nuclear missile wing, leading 140 people and managing a $125M budget.

Now he brings that ground-up leadership experience to growing businesses.

Key Leadership Lessons

Leaders who've done the work earn more trust
Understanding both sides of decisions makes you better
Humility comes from failing and recovering
Ground-up leaders build deeper networks
You can't fake credibility—you earn it