Retention Risk: When Kids Trigger Parents

I found myself in a conversation with a small group of non-profit leaders at a networking event. When I shared that most of my clients are independent school leaders, one of my new acquaintances wanted to tell me about her experience as a parent at her child's independent school. This often happens, and I welcome it. I consider it informal research.

The parent, who I will call Jessica, is a parent of two middle school students who attend an independent school. She opened with a story about her profound disappointment in her son's English teacher. Last year, he was in an advanced English class and had a supportive, enriching, and genuinely fun experience. Sadly, the teacher retired, and the teacher hired to replace her, though highly experienced and credentialled, is not connecting with or challenging Jessica's son in English class.

Since she believes that the success of her non-profit rests in part on her ability to communicate effectively, Jessica is on high alert for anything less than excellence in the literary education that her son is receiving. I asked a few more clarifying questions. What was the evidence of poor teacher performance? How did her son describe his experience with the teacher? Had she approached the teacher about the unfolding situation?

This issue was triggering for her, and she had already jumped ahead and sent an email to the division head and scheduled a meeting with the Head of School. She did not meet with the teacher but planned to at some undetermined point. She was so agitated about the situation that she wondered if she could teach the class herself, albeit without any teaching experience. At the same time, she admitted that her son intuited that this was an issue that would immediately garner his mother's undivided attention. So, every day, he eagerly told her about every moment of the class, highlighting the parts that he knew would get the best reaction from Jessica.

The two other women in our conversation encouraged and supported Jessica, by telling me they have similar issues with their students who attend the local public school.

I admit Jessica's situation felt so familiar. I had done the same things: I felt triggered, overreacted, and failed to look at the situation as a teachable moment. I let my kids suck me into many situations that I believed could only be solved through my intervention and active management.

Inevitably, Jessica will push the issue forward, which will be a problem for the teacher, the division head, and the Head of School. The admin team will lump it into a bucket of parent concerns that may or may not rise to the top of the pile depending on what other significant occurrences are affecting the school that week. The teacher will feel marginalized and defensive, increasing the likelihood of a rocky year with Jessica's son. Jessica's issue has manifested in the first 90 days of school. My larger research on attrition indicates that problems that begin in the first 90 days that are not addressed and resolved within 2 months are more likely to lead to attrition.

The NAIS Trendbook 2024-2025 reported good news in enrollment. Member day schools reported that 65% were growing, schools had become more selective, yields were up, and the attrition rate was the lowest since 2019 at 7.9%. However, the May 2, 2025, NAIS snapshot reporting on concerns for heads of school showed “that about 46% of heads of school with fewer than 300 students reported that maintaining enrollment was one of their top challenges, compared to 35% overall.”

For smaller schools in competitive markets, stories like Jessica's constantly threaten their economic sustainability. What steps can school leaders take to help faculty, staff, and parents address issues more productively or, ideally, avoid them through better alignment?

For school leaders:

• Decide on the plan for meeting with all parents before or during the first 90 days of school. Who will generate the meeting?  Is this the responsibility of advisors, division heads, new teachers, veteran teachers, or the admissions team? Are the meetings in-person, via phone, or Zoom? If meeting with all parents in the first 90 days feels impossible, start with new families and families in a new division.

• At the end of the school year, learn the goals for the upcoming year from the perspective of parents and students. How will you distribute this information to teachers, advisors, or counselors in August?

• Ensure parents, teachers, and division heads know the escalation ladder for issues: start with the teacher. If there is an issue with a teacher, parents may lose faith in that teacher's competency and wonder how talking to him can help. Offer some talking points for both parents and teachers.

For parents:

• Know your triggers. Consider the sorts of things your child might tell you about school and how you would react to them. Are there non-negotiables? If so, talk with your child's teacher or division head so you are all on the same page.

• How can you raise resilient kids? Not every teacher will be awesome. Not every person in your child's life will like them or take an interest in their personal advancement. Not every workplace leader will note your child's worth, and some will get in the way of their professional growth. If you fight all the fights and relentlessly hold everyone accountable on behalf of your child, how can your child own their learning and success?

• Pick your battles. Decide which issues are worth empowering your child to navigate on his own and give him the tools to do that. Have his back, win or lose. What did he learn from either outcome? Decide which issues are beyond his power and necessitate your intervention to ensure his health and well-being.

The first few months of the school year are rich with possibility and hope for a wonderous year. It will be more wonderful if we plan for intentional conversations about goals, wishes, and fears with parents, students, teachers, and administrators and use what we learn to craft and elevate the level of excellence that can differentiate your school.

The author, Jill Goodman, is a consultant who works with independent school leaders to address budget concerns by increasing enrollment retention, building capacity in development, and enhancing leadership skills. Learn more about all services here.