Jermaine Gassaway: A checklist for parents choosing school leadership

• Jermaine Gassaway, a superintendent and public education advocate, outlines what parents should look for in school and district leaders before enrolling their children.

Why leadership is the first thing to check

North Carolina, USA, Oct 03, 2026, ZEX PR WIRE — Parents often start a school search by looking at test scores or building tours. Jermaine Gassaway says that misses the bigger question: who is running the school, and how do they lead.

“A building can look great and still have weak instruction,” Gassaway says. “The leader sets the tone for everything else. If you skip that part of the search, you’re missing the most important piece.”

Gassaway has worked as a teacher, a principal, and a superintendent. That range gives him a view of leadership from more than one seat, and he says the questions parents ask should change depending on what they can actually observe.

What to ask before you tour the building

Gassaway suggests parents start with a short list of questions for any principal or superintendent they meet.

How do you measure growth, not just scores. A single test score tells a parent almost nothing about whether their child is improving. Gassaway says leaders who can talk about growth over time, not just a snapshot, are paying attention to the right thing.

How often are you in classrooms. A principal’s visibility in classrooms is a signal of how closely they track teaching day to day. Gassaway says parents should ask directly how often the leader observes instruction and gives feedback to teachers.

What happens when a student falls behind. Every school has students who struggle. Gassaway says the real question is whether there is a clear plan, with specific support, for those students, or whether it is left to chance.

How do you support new teachers. Turnover affects children directly. Gassaway says parents should ask how new teachers are coached in their first year, since that shapes whether a child gets a stable classroom experience.

Red flags parents should not ignore

Gassaway points to a few signs that should raise questions, even if the rest of a school visit goes well.

A leader who cannot describe how they use data. If a principal talks only in generalities about student progress, Gassaway says that is worth a follow-up question.

A staff that seems unsettled or unclear on expectations. Gassaway says parents can pick up on this just from talking to teachers or reading how a school communicates with families.

No clear answer on discipline or support plans. Parents should expect a straight answer on how the school handles behavior and academic struggles, not a vague reassurance.

What good leadership sounds like

Gassaway says strong school leaders tend to talk in specifics. They can describe how a reading program works, not just that the school “cares about literacy.” They know their staff by name and can speak to strengths and gaps on their team. They treat parent questions as normal, not as a challenge to be managed.

“You can tell a lot from how a leader answers a hard question,” Gassaway says. “Do they get defensive, or do they give you a real answer. That tells you how they’ll treat you once your child is enrolled.”

A short list parents can bring to a school visit

Gassaway recommends parents keep it simple: three or four questions, asked directly, with room to follow up.

• How do you track whether students are growing, not just passing.

• How often are you in classrooms, and what do you look for.

• What is your plan when a student is behind grade level.

• How do you support teachers who are new to the school.

He says the answers matter less for their polish and more for their specificity. “A leader who knows their school will have real answers,” Gassaway says. “A leader who doesn’t will talk around it.”

About Jermaine Gassaway

Jermaine Gassaway is a superintendent based in Charlotte, North Carolina. He is a former teacher and school principal, and the author of “Unopened Books: Multiplying the 2%” and “When You Arrive: A Children’s Book About Racism.” He is a graduate of Johnson C. Smith University and has worked in public education for more than a decade.