Questions to Ask Before Toddler Starts Preschool

Knowing what questions to ask before toddler starts preschool can make all the difference in finding the right fit for your child. Whether you’re choosing a Montessori toddler program or preparing for that emotional first drop-off, knowing what to ask helps ensure your child is supported, respected, and set up for success from day one.

A Montessori Guide to Feeling Prepared, Not Overwhelmed

Choosing a toddler or preschool program is a big milestone, but it often comes with a million unknowns. Whether your child is starting in a Montessori classroom or a traditional early childhood setting, knowing the right questions to ask can make the transition smoother for everyone.

Use this list to help guide conversations with your child’s school, build confidence, and set your child up for success from day one.

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👩‍🏫 Classroom & Teacher Access

• Will there be an opportunity to meet the teachers and tour the classroom before the first day?
• Is this visit scheduled individually or in a group setting?
• Will my child have a designated cubby or locker for extra clothes and personal items?
  • What should I bring to keep at school (e.g., extra clothing, diapers, wipes, etc.)?
• Are there any parent-teacher conferences during the year? How often, and in what format?

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📅 Daily Schedule & Activities

• What does a typical day look like for my child?
• How long is the morning work period?
• How often do the children go outside, and for how long?
  • Will my child need any weather-related gear to keep at school (e.g., sunhat, rain boots, jacket)?
• Does the school offer any enrichment classes (e.g., music, Spanish, art, chapel, or wellness)?

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🧴 Daily Care & Health Needs

• Can I send diaper cream for my child’s teacher to apply if needed?
• Can I also provide insect repellent or sunscreen for extended care days?
• Do teachers assist with reapplication during the day?
• Are there any product restrictions (fragrance-free, nut-safe, etc.)?

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🥪 Meals, Snacks, & Water Bottles

• Do I need to provide snacks? If so, for which parts of the day (morning, extended care)?
• Does the school provide lunch, or is there a catered option?
• Are there specific guidelines for snack containers, lunchboxes, or bags (e.g., short handles, easy-open)?
• Should I send a reusable water bottle daily? Are there rules for size, labeling, or material?
• Is the school nut-free or peanut-free?
• Should I label all of my child’s belongings—including clothing, water bottles, containers, and comfort items?

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😴 Nap Time Routines

• What time is nap, and how long does it last?
• Do I need to provide linens (sheet, blanket, pillow)?
• How often are nap items sent home to be cleaned?
• Can my child bring a comfort item (like a pacifier or soft toy)?
  • Should it stay at school or go home daily?

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📱 Communication with the School

• Does the school use an app or online platform for daily updates and parent messages?
• How do I notify teachers if my child is absent, has an early pickup, or needs more supplies?
• How frequently should I expect to hear from my child’s teacher or school?

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🚗 Drop-Off, Pick-Up, & Carpool

• How does drop-off work?
  • Do I stay in my car, or walk my child to class?
  • Who helps children out of the car if drop-off is via carline?
• How is pickup handled at the end of the day?
• What if I’m running late or need to pick up early?
• How do I communicate changes to pickup plans?

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🌿 Classroom Support & Supplies

• Does the classroom have a wishlist or list of needed items?
• Are donations (like tissues, wipes, or extra clothing) welcomed throughout the year?
• Are non-toxic indoor plants or flowers welcome in the classroom? (Montessori teachers often love this—but always ask first!)

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🧺 Additional Helpful Questions

• Are there clothing recommendations? (e.g., closed-toe shoes, no overalls, easy-on pants for independence)
• Are indoor shoes required?
• Is there a checklist for what to bring on the first day?
• How can I support my child emotionally as they transition into school?
• If my child is transitioning out of diapers, how does the school support toilet learning?
  • Are there expectations for readiness?
  • Should I send extra underwear, wipes, and pants?
• Are there diapering preferences I should follow?
  • (For example: Do diapers need side tabs for stand-up changing?)

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🧡 Final Thoughts

Asking these questions ahead of time helps prevent first-day stress and shows your child’s teachers that you’re a proactive and respectful partner in their care. Montessori environments are built on communication, observation, and trust—starting with you.

Want a printable image of this checklist? [Download it here.]

Or a PDF version [Download it here.]

🔗 Extra Support for Your Toddler’s Transition to School

Looking for more help preparing your child for this big step? Here are some of our most helpful Montessori-aligned resources:

Topic	Helpful Link
🧺 Toilet Learning	Montessori Toilet Learning Guide
🥾 Clothing & Shoes	Best Montessori Shoes for Toddlers
🥪 Meals & Lunch Gear	Back-to-School Gear for Toddlers