When we pick up our children from school, it’s almost automatic to ask, “How was your day?”

And just as automatically, the answers tend to fall flat: fine, good, okay, or sometimes nothing at all.

As adults, we can probably relate. When someone asks about our day, we don’t always feel like revisiting every detail, especially before we’ve had a chance to rest or reset. For children, this challenge is even greater.

In Montessori environments, children are immersed in experiences that are rich, complex, and often difficult to put into words. How does a young child explain the sensorial experience of carefully carrying each cube of the Pink Tower across the room? Or describe the quiet satisfaction of discovering that ten tens create a hundred square? Or articulate the subtle social negotiations that happen during community lunch?

Even for older children, language often lags behind experience.

Why “How Was Your Day?” Can Feel Like Too Much

As children move into the elementary years, they are also navigating peer relationships that are still very black and white. A single interaction can color their entire perception of the day. So their reports may sound overly simple: someone was mean, someone was nice, the day was bad, the day was good.

But often, the issue isn’t that children don’t want to share. Instead, the timing is off.

Research on children’s nervous systems helps explain why. When children walk out of school, their brains are often still in a state of high alert. Throughout the day they’ve managed noise, social expectations, concentration, corrections, and constant stimulation. Their nervous system hasn’t fully shifted out of “school mode” yet.

So it helps if we remember that we aren’t greeting children in their most rational state. 

Those first minutes after pickup are a transition, not a conversation window. When we jump in with questions too quickly, even well-meaning ones, we may unintentionally overwhelm our children’s nervous system, which hasn’t had time to settle.

Connection Before Conversation

In Montessori, we place great importance on transitions. We know children need time to move from one state of being to another, whether that’s arriving at school, moving between activities, or going home at the end of the day.

Instead of starting with questions, we can start with presence.

When we first see our children, a warm greeting that communicates “I’m happy to see you” goes a long way. Some children need a snack. Some need quiet. Some need movement, proximity, or simply space. This is not the moment to gather information. This is the moment to re-establish connection.

When families allow even 10 to 12 minutes of quiet decompression after school, through silence, music, or simply being together, children regulate more quickly. Evening stress decreases, cooperation improves, and children are more likely to talk voluntarily later on.

Rather than interrogating right after school. Try coexisting. This pause is deeply respectful. 

When Children Are Ready to Talk

Later, after your child has had time to settle back into your care, you may notice that conversation begins naturally. This is often when children share what mattered most to them, not what we might have thought to ask about.

When you do open the door to conversation, gentle specificity helps. Broad questions like “How was your day?” can feel overwhelming. Instead, try comments that invite reflection without pressure:

• “I noticed you seemed really focused when I picked you up.”
• “I’m here if you want to tell me about something you worked on today.”
• “What felt good about today?”

Just as important as the words is our availability. Putting down the phone, pausing the logistics, and showing with our body language that we are truly listening makes it safer for children to share.

Listening for Timing, Not Just Content

This approach applies across ages. Even adolescents benefit from what some call a “quiet landing” after school. When we honor timing, we’re less likely to walk into the emotional residue of the day and more likely to build cooperation and connection later.

In Montessori, we often say: regulation comes before reflection. Children don’t need us to extract their feelings. They need us to create the conditions where feelings can land safely.

Sometimes that looks like silence. Sometimes it looks like presence. And sometimes, after enough space has been given, it looks like a child finally saying exactly what mattered most.

So the question isn’t just “Do I listen to what my child says?” And instead becomes: “Do I listen for when they’re ready to speak?”

Curious to learn more strategies to support your child during transitions? Set up a time to come visit here in West Englewood, Chicago. We love to connect!