• Private Schools
• Advice Guide
• Choosing a School

With so many schools offering different environments, teaching styles, and philosophies, the process can feel overwhelming. For Barbi Benjamin Levitt and Michael Levitt, the decision to move their daughter—and later their son—out of the Hebrew school they had attended since nursery into different private schools was an emotional one. Yet in retrospect, they say that with the right support and thoughtful research, they were able to find schools that matched their children’s academic, social, and emotional needs.

How do you begin by understanding your child?

The first step in choosing the right school is determining what kind of learning environment your child is most likely to thrive in.

“Before thinking about the features of any particular school, begin by looking at your child’s needs, strengths, and personality,” explains educational consultant Judy Winberg.

“I can still remember the psychologist telling us that Jessica needed to be in a different school—now.”

For the Levitts, this meant recognizing that Jessica’s current environment wasn’t working. “Just after Christmas in her Grade 2 year, students were asked to present a book; while many classmates read at levels 4 or 5, Jessica was still at level 1. She came home in tears,” Barbi recalls.

They sought help from an educational psychologist to gain clarity on Jessica’s learning profile. “If you’re considering an evaluation or aren’t sure whether it’s needed, ask your pediatrician to guide you,” advises Elaine Danson, educational consultant and former principal at Montcrest School.

The assessment gave the Levitts an objective view of her cognitive strengths and areas needing support. “She had an unidentified learning disability and wasn’t absorbing material,” Barbi says.

Though painful, this insight allowed them to move forward. They realized the familiar Hebrew school path they had envisioned might no longer suit Jessica’s needs.

TIP: Former school experience doesn’t guarantee future fit. Always prioritize your child’s unique needs over tradition or nostalgia.

How do you make your initial school list?

With a deeper understanding of your child, the next step is to define your criteria—both for the child and your family.

The Levitts prioritized schools with small class sizes so Jessica could receive more attention. They also sought a welcoming coed environment and a transitional program that would let her catch up without feeling stigmatized.

Other factors many parents consider: your child’s interests and talents, extracurricular offerings, alignment of the school’s values (religious or otherwise), and classroom educational tools like technology. As Danson says, “Ask: what’s working now, and what’s missing?”

TIP: Don’t overlook your own needs. Distance, transportation, schedule, and family logistics all matter.

How do you begin evaluating schools?

Once you have a preliminary list, dive deeper. Many parents start with school fairs like Our Kids Media’s Private School Expo in the fall, and via school websites and directories.

While peer recommendations are useful, Winberg cautions not to overvalue them: “One child’s positive or negative experience doesn’t guarantee the same result for yours.”

She also suggests looking beyond rankings such as those by the Fraser Institute. “Ratings in isolation tell only part of the story,” she says.

TIP: Most schools maintain robust websites. Use directories like OurKids.net school profiles to compare features side by side.

What should you know about the application process?

From interview strategies to submission tips, you’ll want to familiarize yourself with each school’s admissions process. Find our overview in our admissions guide and deeper insights via expert admission advice.

Why should you visit potential schools?

After narrowing your list, schedule school tours. Admissions teams typically host tours or shadow days to help families experience the culture firsthand.

“A school visit is your chance to align expectations: yours vs. the school’s,” says Cathy Lee, Director of Admissions at Bodwell High School. “Then evaluate fit.”

Winberg advises observing classrooms: “Are students engaged? Do teachers facilitate learning or sit behind desks? Look at the parking lot culture and community feel. Could you see yourself belonging here?”

Danson recommends asking about parent‑teacher communication, staff qualifications (especially for students with special needs), financial stability, and leadership continuity.

This is your chance to ask unfiltered questions. After all, your child will attend here five days a week—make sure you understand the philosophy, policies, and expectations.

“When we toured two schools, one had mostly boys in its class. We didn’t think it would suit Jessica,” Barbi says.

Jessica spent a trial day at Crestwood School. “By noon, people knew her name. By afternoon, the admissions director said she would flourish here,” Barbi recounts.

Though it was midyear, Jessica transferred right after March break. Today in Grade 5, she’s thriving—academically, socially, and emotionally.

“It really does come down to happiness,” Winberg says. “If your child is happy, success follows—regardless of curriculum.”

TIP: Arrange trial or observation days for your child before committing.

The Levitts’ son Casey later faced his own choice among UCC, Crescent School, and The York School. After tests, visits, and conversations, Casey accepted the spot at York. “He loved it from day one,” Michael says.

“Trust your gut: does this feel like the right fit?” Winberg advises. “If so, move forward.”

TIP: Avoid assuming there is only one perfect school. Keep options open and consult our expert guide to finding the right school.