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Six questions you need to answer when choosing a school

The most important questions aren't always the ones we think of first

 


How do I know which private school is right for my child? 


Meet schools in person, ask real questions, and find the best fit all in one afternoon.


Private School Expo - Fall 2025   Yes, I want to attend

 

When people begin looking at their private school options, they often begin by asking “What is the best school?” Which, as experts agree, is entirely the wrong question. You're not looking for the best school for someone else's child, you're looking for the best school for your child; you're not looking for the most celebrated school, you're looking for the right relationship. With that in mind, below are some of the questions, experts feel, parents should be asking.

To learn more, read our in-depth guide to the top questions to ask schools, and print this list of questions. You can also download our e-books on questions to ask private schools and choosing the best private school. Finally, read our experts' guide to choosing the right school.

“What’s most important to us?”

—Judy Winberg, education consultant

 

It’s a big, hairy question with many layers to it. It includes thoughts of who we are, of our cultural background, and of the kinds of people that we want our children to be. There are more prosaic aspects to it as well—location, academic approach, cost—and each family will rank these, and other things, differently. When the dust settles, values will be near or at the top of any list of priorities, just as they should be. The right school will reflect the ones that you hold most dear and that you wish to impart to your children.

“Is there anything the child wishes he or she could do in school
but hasn’t been able to?” 

Elaine Danson, education consultant
 

Ultimately, and choice of school is based in a sense of possibility. Hockey, travel, debate, theatre, technology, rowing with seals … if there is something that the child wants to do, there’s a school for that.  

“Is this a community you can imagine being part of? 

—Judy Winberg, education consultant
 

Each school is a community, one that is built around shared experiences, desires, and commitments. When you enroll at a school, the child becomes part of that community, of course, but you do too. You’ll be attending the campus from time to time, if not on a daily basis. You’ll likely be attending events within the school’s annual calendar. What are they? It’s good to know and to consider if they seem like the kinds of events you would look forward to. If not, it’s important to really ask yourself why. If so, that’s great to know. Because it’s a relationship you’re entering, and it needs to be positive one for all involved.

“Do the students look happy?” 

—Todd Orminston, head of school, Mount Snow Academy
 

Really. Do they look happy? Are they congregating, interacting with staff and faculty? When they approach the buffet in the dining hall, do they share a smile or a joke with the dining staff? How do they hold themselves as they walk between classes? You can’t learn if you don’t feel comfortable.

“Can you envision your child being successful at this school?”

—Judy Winberg, education consultant
 

Success doesn’t mean setting the foundation for a Nobel prize. It’s about students meeting their potential, and being pushed in supportive ways. It’s about learning who they are, and where they fit in the world. To do that, different students need different things. It’s important to know the ones that your child needs, and then find the environment that will best supply them.

“Does it feel right?”

—Judy Winberg, education consultant

 

It’s not about the class size, or the breadth of programming, or anything else we might look to—it’s about the child. Just as some children require an environment that will cater to their strengths, others will be best served by one that will build confidence and facility. While some students thrive in an active, collaborative environment, others work best in one that offers more structure. Often, simply joining a community that reflects their interests and their values can be transformative. 

For more information, read our guide on questions to ask preschoolselementary schools, and high schools.

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