Student Retention Isn’t a Line Item. It’s a Mindset.

Smiley face exchanged between two hands, with green chalkboard behind it.
Smiley face exchanged between two hands, with green chalkboard behind it.

Enrollment Management//

September 8, 2025

Can our enrollment teams take lessons from my car dealership? Before you say no, read this.

Michael Christopher, ISM Consultant and Editor-in-Chief of Ideas & Perspectives

When a family enrolls at your school, it can feel like the end of a long journey — for them, and for your admission team. But in reality, it's just the beginning.

While educators rarely want to think of themselves as salespeople, or their school as a product to be sold, the truth is that every enrollment is, in a sense, a sale. Like any purchase, the real work of building loyalty happens after the contract is signed.

I was reminded of this recently when I brought my year-old car in for service at the local dealership. While I waited, the staff greeted me by name, offered me food and beverages, kept me informed about the progress of my car, and made me feel welcome. They even followed up with a personal note to ask about my experience. 

As a result, I now have a personal connection to the service department and the dealership. 

That experience made something clear: 

It’s not the “sale” that builds loyalty — it’s everything that happens after.

In her book Donor-Centered Fundraising, Penelope Burk relates a lesson for all of us (my substitutions in italics): 

Schools do not realize that the brand sells only once. Right after parents make those first gifts … they transition from interested outsiders to inside investors.” 

Understanding that transition is critical for us in schools and can determine whether we will be able to retain the students after their families have become insiders in our communities.

Unfortunately, I often find that the time, money, and effort schools put into recruiting students does not match the effort they devote to retaining them. The wisdom of Penelope Burk’s observation is that, once families become insiders, we must pay as much — perhaps more — attention to their relationship with the school as we do when we first recruit them.

When your Enrollment Management Team meets about retention strategies, consider the following:

Show the Love

Every campus visit is a chance to affirm a family’s decision to be part of your community. Is parking convenient? Are they greeted warmly by name? Are waiting areas comfortable and inviting? Whenever possible, offer families and visitors a glimpse into classrooms and student life so they can see your mission in action.

Be Our Guest Gif, from Beauty and the Beast

Say Thank You

Families should feel appreciated long after they enroll. How often do they hear from you outside of billing or formal updates? Regular, positive touchpoints — quick notes, photos, or stories that celebrate a child’s experience — reinforce their choice. Are parent-teacher conferences treated as opportunities to strengthen relationships, not just review progress?

Be at Your Best, Always

Think of every event — from athletic events to art exhibitions — as a showcase for your school. Do families feel welcome? Do the events run on schedule and deliver what they promised? Overall, how well do they reflect your school’s mission and values? 

Seinfeld Gif - excited characters hugging

Be Excited About the Future

To encourage retention, we have to show families what lies ahead for their child. When you communicate with current families, look for ways to preview the academic and co-curricular experiences that will come in the next grade or division. Do younger students get to connect with older peers? Do faculty know what’s happening beyond their own classrooms, and do they share the excitement?

Know Who’s Wavering

Stay attuned to signs that a family may be uncertain.  Check in with those who seem less engaged, and offer personalized support where you can. 

Note: This advice isn’t meant for the re-enrollment period alone. Proactive engagement  is a year-long proposition.

Gif of Lisa Simpson sweetly asking, Hi, How are you?

Share Tuition and Contracts with Care

Speaking of re-enrollment, we need to lead this process with celebration and anticipation. This is a chance to communicate what your school has accomplished in the current year and preview the achievements that will come next. Help your families see how their tuition dollars translate into student success.

On a logistical note: What is your re-enrollment process like — simple and straightforward, or unnecessarily complicated? Contracts should be clear, concise, and easy to complete.


In the end, retention isn’t a line item; it’s a mindset.

The schools that thrive are the ones that don’t win families over just once; they re-win them every day. 

Enrollment management doesn’t end with a signed contract; that’s merely the beginning of a long-term relationship built on trust, communication, and consistently great experiences. 

Just like the car dealership that made me feel seen and valued, our schools must go beyond delivering education — we must deliver belonging. 

When we approach every touchpoint intentionally and with warmth, when we treat current families not as transactions but as partners, we secure enrollment and earn advocacy.

In today’s competitive marketplace, that’s the most powerful marketing of all.


About the Author (H5)

Michael Christopher offers expertise in every facet of school advancement, from strategic planning and board operations to development, enrollment management, and marketing. As a co-organizer of ISM’s Advancement Academy, he works closely with school leaders to design strategies that align mission, resources, and community support. Michael is also the editor-in-chief of Ideas & Perspectives, ISM's flagship publication for members. 

Before joining ISM full-time in 2020 (after serving as an adjunct consultant since 2002), Michael led advancement at Lausanne Collegiate School (TN), Greensboro Day School (NC), and Holland Hall School (OK). In these roles, he rebuilt development programs, launched alumni engagement initiatives, created planned giving programs, instituted major gift efforts, managed successful capital campaigns, and coordinated image and identity projects that elevated each school’s profile.

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