Failure can hurt. But when you’re a tech leader, failing to appreciate your team? That’s the kind of failure that doesn’t just bruise, it breaks trust.

I learned this lesson on the flight line of a fighter squadron.

The Wake-Up Call

As a young F-16 pilot, I was used to walking out to a jet that was fueled, inspected, and ready to fly. One afternoon, I got upset when my aircraft didn’t have as much fuel as I wanted for a training mission.

Was it a big deal? Not really. But I was in my own head and let the crew chief have it. I used foul language and was disrespectful.

Word got back to my commander, and he met me at the jet after my flight. He wasn’t happy.

“Captain Waldman, do you know what these young airmen do behind the scenes so that you can fly this jet?” he asked.

“Yes, sir,” I answered.

His response wasn’t pleasing: “You don’t have a clue. I want you to get up at 6 a.m. tomorrow and walk the flight line with these folks to see what they go through every day so that you can do the coolest job in the world.”

So I did. And that day changed my whole perspective on my life in that squadron.

Changing tires, crawling under jets, and refueling in 90-degree heat was a gut punch of humility. I saw the sweat, the skill, the precision those maintainers brought to the table. They weren’t just support crew, they were the lifeline of the mission. The unsung heroes who made sure I didn’t get shot down.

And I had never even bothered to learn their names. I was selfish, had an ego, and I was wrong!

Perhaps you can relate?

From the Flight Line to the CIO Office

In the world of IT, it’s easy to become siloed. You’ve got cybersecurity fighting fires. Infrastructure trying to keep legacy systems alive. Developers cranking out updates under unrealistic deadlines. And users? They’re pinging you at all hours with issues that sound like Greek to the business.

As CIOs, you’re piloting the digital jet, but how often are you walking the flight line?

How often are you showing up for the folks who keep your “aircraft” mission-ready?

How much time are you spending outside your “silo” getting to know those who support the mission of your organization?

Trust: The Currency of Leadership

Appreciation isn’t a nice-to-have. It’s a leadership requirement. Because in today’s high-speed, threat-heavy business environment, trust is your most critical currency.

And trust is tough to gain, but easy to lose.

When your sysadmin works through the night to restore a server, they’re not just saving data, they’re saving reputations.

When your data engineer builds a faster, smarter pipeline, they’re enabling decisions that drive millions in revenue.

And when your team feels seen, not just for what they do, but for who they are, they’ll push harder, stay longer, and perform better under pressure. 

They’ll also be more loyal which is a rare commodity these days in business.

It’s easy to talk digital transformation. To preach DevOps, AI, and agile. But none of that means a thing if you haven’t earned the trust of the people doing the work.

And trust is built on connection. It’s built on heart, compassion and respect.

It’s built on walking the floor, asking questions, sitting in on scrums, staying curious. It’s built on catching people doing things right and calling it out. It’s knowing your team’s names. Their goals. What fires them up. And what drags them down.

That’s what I mean when I say “walk the flight line.”

It’s not a metaphor. It’s a mindset. And it’s an action!

Your Leadership Challenge

The moment you start taking your team for granted is when the real problems sneak in. Missed vulnerabilities. Burnout. A resignation letter from someone you never thought would leave.

So, here’s my challenge to you, CIO:

• Walk the flight line this week. Literally or virtually.

• Ask the hard questions and really listen to the answers.

• Find one person behind the scenes and show them they matter.

Get to know the wingmen and wingma’ms who support the mission. Fill their jets with the most important fuel of performance: appreciation. Because leadership isn’t about knowing Java or juggling vendors. It’s about earning the right to lead by walking beside your team, not above them.

And if you’re willing to walk the line… they’ll follow you anywhere.