Dear Vets: Are You a Good Leader?

Dear Vets — are you a good leader?

I’ve asked myself that question many times. More often than not, the honest answer is: I don’t know.

From entering West Point at 17 through ten years of active service, leadership was the air we breathed. It was taught, reinforced, evaluated, and expected. Even if we simplify leadership to inspiring others to do their best work toward a shared objective, the military’s version operates very differently than corporate leadership. And to be clear, even in uniform, I had plenty of room to improve.

What surprised me was how much harder leadership became in civilian life.

Why?

Because civilians have choice. They choose to work for you. They choose whether to stay. And they can choose to leave at any time. Gallup reports that 75% of employees leave because of their managers — poor leadership is the number one reason people quit.

In the military, that option doesn’t exist. There’s built-in stability, a strict hierarchy, shared values, and the UCMJ enforcing order and accountability. Corporate leadership operates without those guardrails.

The best corporate leaders I’ve observed don’t rely on authority. They lead with empathy. They build trust. They set clear expectations and hold people accountable without fear. They listen — actively. They seek to understand, not just to be understood. They create environments where transparency is normal and ownership is expected. And, critically, they’re humble.

Being strong in any one of these areas is hard. Being competent in all of them is harder. Miss too many, and you’re no longer leading — you’re running a hobby club, a social circle, or a well-intentioned team without direction.

Late last year, one of the businesses I’m involved in faced a major inflection point. Performance issues and compounding challenges put real pressure on the organization — including the very real possibility of missing obligations. The stress was palpable. (Entrepreneurs, you know the weight: worrying about payroll can feel heavier than a firefight — but that’s another conversation.)

It wasn’t until existing leadership transitioned out that we were able to reset, chart a new course, and rally the team.

We’re not out of the woods yet. But this quarter, I spent deliberate time focused on the fundamentals: people, culture, systems, and clarity. With the support of key consultants and committed team members, we made meaningful progress quickly. People now understand where they stand, what’s expected, and where we’re headed. That clarity has allowed us to identify gaps, fix what’s broken, and start building for the future.

The progress didn’t come from heroics. It came from applying the leadership principles above — imperfectly, but intentionally.

So am I a good leader?

I’m getting better. At least, I hope so.

The improvements weren’t driven by me alone. They came from an executive team willing to be honest, make hard calls, and take ownership together.

I try to stay intentional about learning. I reflect. I ask uncomfortable questions of myself. And I stay committed to improving.

Lately, I’ve wondered if leadership is like humility. The more you think about how to be humble, the more elusive it becomes. If humility requires thinking less about yourself, then obsessing over it defeats the purpose, doesn’t it?

Maybe leadership works the same way.

For now, that’s enough. Adjust your bearings — but keep moving.

Press on,
Freddie J. Kim

If this resonated, join Azimuth Check: Adjusting your bearings after honorable service — a monthly reset for leaders adjusting their bearings after honorable service.

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