Leadership Isn’t Always Liked — But It Should Always Be Right

Early in my career as a young supervisor in the Air Force, I was handed a challenge that would shape how I viewed leadership from that day forward. It wasn’t a tactical issue. It wasn’t mission-related. It was personal. And it was complicated.

One of my Airmen had gotten himself deep into financial trouble. Before he was married, he was balancing over twenty credit cards and department store accounts. It sounds crazy, but he had it under control, until marriage added another layer of expenses and spending. Things spiraled. Fast.

By the time he came to me, the debt had taken over his life. In the military, financial irresponsibility is a serious offense. I had already seen the consequences firsthand; my very first supervisor had been discharged because of debt. So I knew what was at stake.

But I also knew this young Airman had potential. So instead of writing him off, I sat down with him. We got him into the financial management program, started closing credit accounts, and created a plan. It wasn’t quick, but it was working.

Then something unexpected happened; he received assignment orders to Hawaii.

Now normally, that kind of news would call for a celebration. But with the cost of living in Hawaii and the state of his finances, I knew this wasn’t a reward; it was a trap. Sending him there would have put him right back into survival mode. Worse, it could’ve meant the end of his military career.

So I did my homework. I discovered that under the right circumstances, a unit commander could cancel an assignment. The report date was still nearly a year away, so we had time, but I needed support.

Not long after, I was called into a meeting with our unit commander and superintendent. They wanted to talk about my subordinate’s situation, and more importantly, what I planned to do about it.

I laid it all out: the progress we’d made, the steps taken, and the harsh financial reality of living in Hawaii. Then I said something I knew might not be popular:

“If we send him, he won’t make it. And we’ll be handing another unit a problem that started with us. Let us finish what we started; cancel the assignment and give him a real chance to recover.”

And here’s the part of the story that still sticks with me: they listened.

Despite my rank and limited time as a supervisor, the commander and superintendent heard me out. They didn’t dismiss my voice because of my position; they respected it because I brought a thoughtful, people-first solution to the table. And in the end, they acted on my recommendation. The assignment was cancelled, and the Airman stayed under our wing.

Now, he wasn’t happy about it. In fact, he was downright angry. He thought I’d sabotaged a dream assignment. But I wasn’t trying to take anything from him. I was trying to protect his future; even if he couldn’t see it in the moment.


The Leadership Lessons

There are a few lessons in this story that I still carry with me, and that I try to pass on to the leaders I train today:

1. Leadership means doing what’s right…not what’s popular.
There will be times when leading your people means telling them “no,” or redirecting them from something they want. If it’s not good for them, your job isn’t to agree…it’s to lead.

2. True leadership requires long-term thinking.
Had we sent him to Hawaii, the short-term excitement would’ve come at the expense of long-term damage. I wasn’t focused on making him happy in the moment; I was focused on protecting his future.

3. Good leaders don’t just make decisions…they listen first.
What our commander and superintendent did that day was a powerful lesson. They invited a young, relatively inexperienced supervisor into the room, not to report, but to be heard. And then they acted on what I shared. That kind of trust builds stronger teams, and smarter decisions.

Not every leadership decision ends in applause. Some end in frustration, confusion, or even resentment, at least for a time. But real leadership isn’t about being liked. It’s about doing what’s right, even when it’s hard.

And sometimes, it’s about being the only one in the room willing to say what no one else wants to hear, because the people you lead are counting on you to protect what they can’t yet see.

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