TACKLING UNCERTAINTY

Leading with What Matters Most

In the complex world of K-12 operations, the ability to bridge the gap between the school boardroom and the community is a rare skill. Enter Drew Schlosberg. With a 45-year career spanning journalism, marketing, and educational consultancy, Drew has spent decades as a primary bridge-builder in San Diego. As the former spokesperson for The San Diego Union-Tribune and current CEO of Drew Schlosberg & Associates, he brings a unique “outsider-in” perspective to K-12 leadership. Today, we sit down with the founder of XTRA Weekly and host of the Future Pathways: Superintendents Unplugged podcast to discuss how district leaders can navigate the juggling act of modern school administration, community relations, and innovative curriculum development.

From an operational standpoint, what’s the most common unseen hurdle district leaders are facing in 2026?

Without question, what is happening in D.C. with all the federal cuts. Programs are funded one day and suddenly gone the next. Districts build plans around funding that disappears almost overnight, and that creates chaos.

Regardless of what side of the aisle you’re on, when programs that serve Hispanic students, minority students, and low-income families get cut, the impact is real and immediate. These aren’t isolated groups—these programs support students across the board.

How are the strongest leaders responding to that uncertainty?

The best leaders don’t lead from the noise. They pay attention to what’s happening, but they stay focused on what they can control.

Our kids don’t wake up thinking about what’s going on in D.C. They’re coming to school for 182 days a year, and that’s where leaders have to stay focused. You deal with the other stuff, but you don’t let it distract you from the mission.

What role does collaboration between districts play right now?

In San Diego County, the superintendents actually work well together. All 43 districts collaborate, share ideas, and support each other. That’s unusual.

When leaders work together, especially in smaller or isolated districts, it makes a huge difference. They don’t always agree, but they listen, they communicate, and they figure things out together.

There’s growing public skepticism about the value of education. How should districts respond?

Superintendents need to learn how to be great marketers and great communicators. In the 21st century, if you’re not telling your story, someone else is telling it for you.

You have to communicate value. You have to show parents and communities how you’re preparing their kids for what comes next—whether that’s college, a career, or something in between.

What should schools be emphasizing beyond test scores?

Test scores are a measure. They’re not the measure.

When kids feel like they belong, when they’re engaged and interested, learning accelerates. Belonging costs nothing. Saying a student’s name, asking how they’re doing—that matters.

We know from research that when kids are in nurturing, welcoming environments where they can explore and take risks, they thrive.

“The best leaders don’t lead from the noise. They pay attention to what’s happening, but they stay focused on what they can control.”

-Drew Schlosberg

How important is student interest in learning?

When you get a kid interested in something, their cognitive ability goes off the charts.

That’s why you’re seeing programs like auto mechanics, construction, and skilled trades coming back. These are sophisticated careers, and students in those programs often outperform others because they’re engaged and applying real-world skills.

How should districts think about preparing students for the workforce?

Most parents want the same thing: They want their kid to be a critical thinker, a problem-solver, and someone who can adapt.

Schools need to work with chambers of commerce, workforce development groups, and local businesses. That’s how you show students—and parents—what the real world looks like and how education connects to opportunity.

What’s your advice to leaders navigating AI in schools?

You can’t ignore it. It’s here. There’s absolutely a place for AI in the classroom. The key is learning from people who use it well, setting boundaries, and using it to stimulate thinking.

If you’re talking about career pathways, students are going to be asked about AI in interviews. We owe it to them to help them understand how to use it responsibly.

If you had to sum it up, what should leaders stay focused on?

Pay attention to the noise, but don’t lead from it. Focus on kids. Focus on belonging. Focus on preparing students for what comes next. If you do that well, a lot of the other stuff works itself out.