When enrollment falls short, the instinct is often immediate. We need more marketing. We need more inquiries. We need more applications. But marketing isn’t always the real problem.

In this episode, I sit down with Tom Sheppard, Founder of 20 More Students, to talk about how independent schools can better diagnose what’s really happening when enrollment numbers start to shift. Tom argues that today’s schools are facing a convergence of forces, from changing family expectations and new school models to affordability, specialization, and questions around return on investment. Simply asking the enrollment or marketing office to “do more” may not solve the underlying issue.

Together, we explore how enrollment, retention, marketing, program, data, and the family experience all intersect, and why sustainable enrollment requires a much broader institutional conversation.

In This Episode, We Discuss:

• Why the first question after “We need 20 more students” should be “What are we actually trying to solve?”
• What marketing can and cannot fix when enrollment is struggling
• Why schools may need to rethink the traditional generalist model in an era of specialization
• How Millennial families are changing conversations around value and ROI
• Why retention should be proactive rather than reactive, and what eighth-grade attrition may be telling schools about their high school experience
• How teachers can help families see value through everyday conversations about their individual child
• Why strong, longitudinal enrollment data matters, and what to do if your school doesn’t have it yet
• One number, one conversation, and one family question schools can use to better understand their enrollment health right now

Tom closes with a reminder that while the challenges facing independent schools are real, he remains optimistic about schools that are willing to work across departments, ask difficult questions, and rethink what the independent school model can become.