The first few weeks of the daycare transition can feel like an emotional rollercoaster—for parents and children alike. While you’re watching for signs that your little one is settling in, it’s not always clear what healthy adjustment actually looks like. We spoke with Michaela LeRoy, Education and Development Specialist at Haven, the first fully licensed daycare in the U.S. to offer flexible childcare with on-site coworking and fitness, to understand what parents should really be looking for.

The early days of daycare transition: What actually matters

“Adjusting to a new school looks different for every child,” LeRoy explains. “Some may settle in within just a few days, while others may need several weeks to feel fully comfortable.” But there’s one crucial indicator that transcends individual differences: trust.

“One of the earliest signs of healthy adjustment is when a child can be comforted by their teacher(s),” she says. “This growing trust often shows up in small but meaningful ways, such as accepting help, exploring their new classroom, or seeking comfort from a teacher.”

The other early indicator? Simple curiosity. “Children begin noticing their surroundings and the friends around them, sometimes imitating what others are doing or showing interest through parallel play. Over time, they also begin to find comfort in the classroom’s daily routines, participating in familiar moments like snack time, circle time, and outdoor play.”

Here’s what might surprise you: “These signs may not always appear while a parent/guardian is doing drop off. Many children might still show distress at that moment, but typically once their parent/guardian leaves, they are able to be redirected and re-engage with their day.”

The home truth: What your living room reveals

While classroom behavior matters, LeRoy says some of the strongest adjustment indicators happen at home. She points to four key signs:

  • Talking About School A child comes home eager to share stories about what happened during their day.
  • Imitation A child asks for songs or stories they heard at school, or repeats phrases picked up from teachers and friends.
  • Excited to Return A child expresses how excited they are to go back to school to see their friends and teachers.
  • Natural Tiredness A child is more tired than usual after a full, stimulating day and can transition to bedtime more easily.

Understanding your child’s unique timeline

Every parent wants to know: how long is too long? LeRoy emphasizes that temperament plays a huge role. “A child’s temperament is the way a child responds to the world around them. There are three different temperaments: easygoing/adaptable, slow-to-warm/reserved, and highly sensitive/intense. Adjustment looks different for each one of these.”

She offers a clear example: “A child who is easygoing/adaptable might jump right into playing in their new classroom right after their parent/guardian leaves, without any tears. On the other hand, a child who is highly sensitive/intense might show adjustment in much smaller ways, like giving a little smile or quietly participating with friends.”

The timeline? “Most children begin to show positive signs of adjustment within the first two to four weeks. For children with a highly sensitive or intense temperament, it may take longer, sometimes more than a month, before those positive signs appear. It’s important to remember that adjustment happens in steps, not all at once.”

When words reveal connection

As children settle in, their language becomes telling. “When children begin to share details about their classroom experiences, it’s a strong sign they are building positive relationships at school,” LeRoy notes. “They may talk about activities they did with their teachers or friends, or proudly repeat phrases and actions they heard others use.”

The golden indicators? “They will most likely show excitement about returning to school, expressing how excited they are to see their teachers and friends again, sometimes even sharing what they plan to do together next time. Another meaningful sign is when children mention peers by name, or even by a special nickname, which reflects strong bonds and genuine social connections.”

Green flags in daily conversations

LeRoy identifies specific conversation patterns that signal healthy adjustment:

“When children consistently speak warmly about their teachers and friends, it’s a strong sign that they feel safe, supported, and connected at school. One green flag is when a child shares a specific experience with their teacher, like proudly talking about building a special block tower together or drawing a rainbow side by side.”

For peer relationships: “When a child mentions a peer by name and describes how they played together, it demonstrates a sense of social connection and belonging in the classroom. Similarly, when they express joy and anticipation about seeing their friends again, like saying they ‘can’t wait to play at school,’ it signals strong peer bonds and positive social adjustment.”

Supporting without overwhelming

How can parents encourage sharing without pressure? LeRoy has clear guidance: “One of the most important things families can do is speak positively about school. When children hear their parents or guardians describe school as a safe and fun place, they are more likely to open up about it.”

The key is in the questioning: “It also helps when parents/guardians ask simple, open-ended questions instead of questions that might lead to a negative response. For example, you might ask, ‘Who did you sit with at snack time today?’ or ‘What did you do during outside time?’ These kinds of questions invite children to share naturally without feeling pressured.”

And remember: “Conversations about school should be kept short and positive, giving children the space to talk while not feeling pressured.”

When intellectual curiosity blooms

Beyond social adjustment, LeRoy looks for the following signs of intellectual engagement:

  • Curiosity A child asks questions, experiments with toys and materials, tries new activities, and shows interest in how things work.
  • Focus A child stays engaged for longer periods of time with a specific activity or toy.
  • Creativity A child draws, builds, or creates projects that reflect their own ideas and imagination.
  • Love of Learning A child proudly shares their discoveries and creations with family, teachers, and friends.

Navigating drop-off and pickup

The daily transitions offer valuable information, but LeRoy advises strategic observation: “Parents and/or guardians can look for small cues as they drop off or pick up to get a sense of how their child is adjusting, things like their child’s body language, mood, or how they respond to their teacher.”

However, timing matters: “As much as they might want to know about how their child is doing in the classroom, it is important that they save all long conversations for a meeting with the teacher. A short and quick update as the child is being dropped off is okay, but the focus needs to be on the children.”

Her advice for smooth transitions: “It is important for parents and guardians to keep goodbyes short and sweet. Lingering in the classroom can make the separation harder for the child. When the goodbye ritual is brief, it reassures the child that school is a safe place.”

The social learning payoff

“Socialization plays a huge role in the early years of a child’s life, and school provides many opportunities to build these skills,” LeRoy explains. “Children often come home excited to talk about their new friends or share stories about what they did together at school. In the classroom, they learn important skills like taking turns, sharing, and helping others.”

The long-term impact is significant: “These trusting relationships are powerful. They shape how children view themselves, how they connect with others, and how they begin to understand the world around them.”

When to worry (and when not to)

LeRoy is clear about normal versus concerning behaviors: “When a child is starting at a new school, it is normal for them to cry or attach to their parents/guardians. These are normal responses to a new transition. Over time, these behaviors typically lessen as the child begins to show comfort and trust in their new environment.”

What’s concerning? “It is uncommon for a child to display ongoing concerning signs such as intense distress or withdrawal from peers and activities.”

Her philosophy on adjustment struggles: “Every child is different, and it’s important to remember that there is no ‘right’ timeline for adjustment. Some children may settle into their new school within a few days, while others may need a month or more to feel comfortable.”

“What matters most is not the exact number of days, weeks, or months it takes, but whether a child is showing small steps forward, like crying less intensely, calming down more easily, or beginning to engage in play and routines.”

The bottom line

LeRoy’s final wisdom for parents? Trust the process and maintain open communication. “If parents or guardians ever feel nervous or uncertain about how their child is adjusting, they should reach out to the teacher and the childcare director so that everyone is aware and can work together to support the child.”

Remember: adjustment isn’t about perfection—it’s about progress, connection, and gradually building the trust that makes daycare feel like a second home.