Upping the Ante on Re-enrollment

I’m seeing too many schools send a warm tuition notification letter followed by a standard, impersonal contract package a week later. No personalization, no excitement, just a transactional moment that could have been a real connection. I get it. You've got technology constraints, timing challenges, and a massive amount of work, but this moment is too important to let slip by.

Re-enrollment is more than a formality; it’s an opportunity to reinforce your school’s value proposition and remind families why they belong in your community. If knowing every child and family is core to your school’s identity, then your re-enrollment experience should reflect that. And before you say, “But we’ve already sent contracts!”—I’m here to tell you, it’s not too late. 

Simple Ways to Up the Ante on Re-Enrollment

Spotlight What’s Ahead: One school I work with is using their weekly newsletter to build excitement with a “Things to Look Forward to Next Year” feature. Each grade level contributes a quick highlight:

📌 “In 5th grade, look forward to our outdoor education trip to [location] where we’ll see our classroom learning come to life.”

📌 “In 11th grade, look forward to guest speakers on [topic], supporting you as you begin to consider what comes after high school.”

Personalize the Contract Package: Another school is embedding this messaging into their contract cover letter, reinforcing the incredible experiences families are signing up for. (Literally, this is just the email that goes to families with links to the contract and other info).

A Handwritten Touch: A third school is sending handwritten notes to families in the mail—a thoughtful surprise that lands a day or two after the contract goes out.

Celebrate the YES! Don’t stop when the contract is returned.

💡 Use Valentine’s Day as inspiration—send a heart-shaped cookie home with a note: “We love that you’re coming back!”

💡 Make it visible. Hold up a big banner at car line that says, “We ❤️ our Smith School families!”

This moment is more than paperwork, I see it as a chance to affirm, celebrate, and delight the families who choose to stay.

What are your favorite re-enrollment touches? I’d love to hear! Reply and share your ideas. 🎉

A Meaningful Pause

It is easy to slide right from the school year into summer mode - whether that means a continuation of your work, a vacation, or just adjusting to a new schedule. I want to remind you of the power of a meaningful pause. Without this intentional moment, it is too easy to just keep moving and forget to stop, celebrate, reflect, and look forward.

Try this as a sort of guided meditation: Bring to mind the school year that has just passed. See it as a timeline stretching out in front of you. As you walk along this timeline, notice the significant moments and experiences.

Reflect on your accomplishments. See the faces of the students you’ve impacted, the colleagues you’ve collaborated with, and the challenges you’ve overcome. Allow yourself to feel pride and gratitude for your dedication and hard work.

Acknowledge any moments of stress, frustration, or difficulty, and imagine releasing these moments. Release any residual tension or worry, knowing that you have done your best, and knowing that others have done their best, too.

Then, focus on the positive experiences. Remember the joy in students’ faces, the laughter shared with colleagues, and the moments of personal or professional growth. Allow gratitude to fill your heart and radiate through your entire body.

Now look ahead to the summer months. Set an intention for this time. Mine is to stay present as my family embarks on a big adventure. Perhaps for you it’s intentional rest, reading some great books, picking up a hobby, or spending more time outside.

I am grateful for the past year, for the growth and challenges, and I am open to the positive experiences that summer will bring. I wish the same for you.

A Community Atmosphere As a Retention Tool

Photo courtesy of Matthew Soule

In my last blog post, I wrote about integrating a retention mindset. As we approach end-of-year gatherings, I thought I’d reflect a bit on how the Small Boarding School Association has me as a loyal fan (i.e.: “a returning family” and one who refers others!).

I went to my first SBSA conference in 2018. That was an infamous event, where there were bank robbers, a snow storm, people in their PJs at the opening keynote, and so on. I was incredibly impressed by the team at Stuart Hall School in Staunton, Virginia and the SBSA Board. The event was seamless, and I’ve been trying to get back to this conference ever since. Well, 2024 was finally my year!

In March, I headed to Birmingham, Alabama and Indian Springs School to present at the conference. A huge shout-out to the conference organizers and our hosts at Indian Springs. The experience prompted me to reflect on the hallmarks of exceptional events, and more broadly, the way we can influence the “user experience” with our schools.

There are so many ways we interact with stakeholders every day. Assembly where parents are invited. Advancement events. Phone calls with current parents when they call the front desk to report an absence. Parent-teacher conferences (the ultimate retention event!). End-of-year celebrations of learning. Awards events, if your school conducts these. Consider how you want community members to feel and work backwards when designing experiences and interactions.

A conference such as SBSA is a concrete, time-bound example of how we want to show up for our communities, but we can use it as a case study. The way I felt at the conference is how we want all people at our schools to feel.

What made the SBSA conference so easeful, professional, and valuable:

1. Clear communication: Pre-conference communication was timely and clear. When I emailed with a question, I got a response seemingly immediately.
2. Focus on attendee needs: Naturally, there were welcoming remarks, acknowledgements, awards, and announcements, but these felt genuine and warm, and helped me feel connected to the event as opposed to a guest at someone else's show.
3. Logistics and comfort: On site, signage was perfect. People were available to direct us when we were confused. Food was plentiful and delicious. Snacks were out and easily accessible.
4. Over-delivering: There were some surprise-and-delight moments. A no-cost coffee truck appeared one day. There were lovely flowers outside every presentation room. 
5. Pacing: I did not feel rushed. There was time between sessions to connect with people as well as find my way to my next thing.
6. Inclusive: People appeared genuinely interested in meeting each other and mixed easily and comfortably among the group. 

The takeaways are clear and actionable immediately:

1. Communicate early and often. Respond promptly.
2. Focus on what really matters to your community as opposed to what matters to you.
3. Creature comfort is impactful in having people feel welcomed and relaxed.
4. Find ways to add some sparkle to your gatherings. At my wedding 20+ years ago, ice cream sandwiches magically appeared in the later part of the evening after many guests had left. People still talk about that!
5. Find the balance between keeping things moving and allowing grace and space in any schedule.
6. Be proactively friendly. Avoid the tendency to stick with who you already know. A sense of belonging is vital if we expect families to return and to recommend our school to others.

As we enter into end-of-year events, these ideas can help guide some of your planning. Again, start with how you want people to feel. These suggestions are not "big boulders" that make a gathering successful. Rather, these are the details that separate good from truly remarkable.

By the way, the conference in 2025 is going to be local to me, and I am already inviting others to it and blocking the time on my calendar. A raving fan, indeed!

Integrating a retention mindset

I recently had a powerful coaching conversation with a client school about a typical end-of-year event that is taking place this month. It's an event where lots of current families will be present and learning will be on display. School leaders inherently understood the importance of such an event. It needs to run smoothly, show off the program, and generally "feel good." But they were surprised when I said the event should be looked at as a massive retention opportunity. This prompted a broader conversation about the more general need for a “retention mindset,” and where and how that might be more integrated into school life.

When I say “retention mindset,” I simply mean taking the perspective that every interaction we have is an opportunity to reinforce a family’s decision to be at our school. Internal marketing is another way to think about this, if it’s more comfortable to you in those terms.

Most school leaders naturally are aware of the importance of school gatherings, communications, and day-to-day interactions in making sure that families are having a good experience (translating to retention), but I think many are not taking the next leap in seeing every interaction as a retention opportunity. This is a slight mindset shift that can reap huge rewards. The details are where this comes into play most.

End-of-year events are an ideal time to remind families of the value they are receiving from your school. An event running smoothly is the base level of what’s needed. Aside from that, what are the small touches you can include to share value? For example, perhaps you have student art on display on purpose during end-of-year gatherings. Could you add a student-led gallery walk, explaining the assignments that are on display? Many schools host a “future peek” type of event for families to see what’s coming next year. Could that be followed up by a handwritten note by a teacher for the following year, expressing how excited they are to have the student in their class? Is there an opportunity to celebrate student accomplishments that are mission-aligned for your school, so that families are seeing the “product” they can anticipate as their children grow up at your school? This goes beyond next-school and college placement. These moments are powerful reminders of the value-add families receive by being part of your community.

Classroom newsletters are another great example. Leaders know that they are important and need to be executed well, but are not necessarily thinking of them as retention tools. How could a classroom newsletter be re-thought or slightly tweaked to serve as a stronger retention tool? This could be as simple as including a highlighted area that shares a particularly special moment in the classroom each week. Parents of older children typically lose sight of the day-to-day work of school. Is there a way to integrate more photos of older students with narratives describing their activities as part of regular school communication?

Beyond these specific examples, I encourage you to consider how every event, communication, and interaction is a retention opportunity in that faculty, staff, board members, and other key volunteers are always reflecting your school and what it stands for. A quick moment in the school lobby may not feel like a big deal to you, and you certainly don’t need to awkwardly parade someone through the gym showing off winning banners when all they asked was for a quick calendar reminder on something. However, every moment of connection matters, and the extra few minutes you spend to really connect have an impact.

Retention efforts that focus on the student rather than parents have a slightly different flavor, but the mindset is the same. How can we use seemingly normal moments to remind the student why they are at our school?

This is a school-wide effort and one that may take some time. Start with looking at your year-end traditions. Is there a small change or two you could make? Don’t be afraid to experiment. We are talking about low-stakes, high-impact changes. Let me know what you try!

Paths to Success

It's been another busy season, with schools trying to solve enrollment challenges from all angles. One school I’m working with is trying to fill a 9th-grade class in a market with less than 300 students who are of the appropriate age, capable of paying 50% of tuition, and within a reasonable commute time. Meanwhile, another school is struggling to fill kindergarten spots in an area with plenty of students and financially able families, but with a saturated market leading to unpredictable yield and quickly disappearing waitpools as schools scramble to fill spaces. These are both seemingly insurmountable barriers.

In essence, there are two main issues at play. Firstly, declining markets are prevalent in many areas, resulting in smaller applicant pools. Secondly, in markets with higher populations, there seems to be an oversupply problem, resulting in qualified candidates receiving multiple offers and unpredictable, and in many cases, low yield. We all know this is not sustainable. 

So, I’ve been wondering how we can approach these issues from new angles. The NAIS Jobs-To-Be-Done research identifies problems that families want us to solve, offering a platform for creative thinking to meet needs while setting ourselves apart from the competition or attracting new families. This is a great starting place if you haven’t considered it already.

Most decisions of all kinds, to me, feel like a choice of a path as opposed to "right" or "wrong." Perhaps educational decisions are partially driven by parents seeking to pave pathways to success for their children, and their choice of school reflects these pathways, which can be quite narrow. They are trapped in a “right” or “wrong” or “better” and “worse” mindset as opposed to a more neutral, one-is-different-not-better-than-the-other mentality.

We're often bombarded with stories of individuals who have followed a linear trajectory: excelling academically, climbing the corporate ladder, or achieving fame and fortune through a particular talent or skill. While these narratives are undoubtedly inspiring, they represent just a fraction of the countless routes one can take towards success. For every CEO who rose through the ranks of a Fortune 500 company, there's an entrepreneur who started a thriving business from their bedroom. For every bestselling author with a string of degrees, there's a self-taught writer who honed their craft through sheer determination and passion. 

Emerging non-traditional educational models, such as coding boot camps, entrepreneurship programs, and online learning platforms, are increasingly popular, putting another obstacle in our way as we attempt to advance our missions.

We face seemingly conflicting challenges: families have a narrow definition of success, creating a narrow funnel to our product, yet there's a market need for educational options catering to broader pathways to success.

To address these challenges, we can do a few things. In a very competitive market where everyone is talking about the same benefits, a unique definition of success, and demonstrations of that success, may be compelling. And/or we can broaden our market appeal by thinking creatively about our programs in order to deliver different kinds of success to families who are not already considering our schools.

These ideas require willingness to take a couple of risks. It's through daring to innovate and explore new avenues that we can truly shape the future of education and better serve our students and communities, as well as ensure the health of our schools.

Three Quick Tips for Smoothing the Way for Applicants

In the last several months, I’ve done a lot of thinking about the admission process from the family point of view, as my own daughter applied to independent high schools last year. Among the things I learned (and I learned a lot!), a few items struck me as “low-hanging fruit” to help families feel more invited into the admission process.

The key question is “Does the process reflects the mission and values of our school? And, further, does the process reflect the experience a family or student can expect should they enroll? This is hardly low-hanging fruit, but worth pointing out nonetheless. These are great questions for a leadership team or enrollment management team to discuss.

1. Double check that reminders do not arrive to a family on the weekend before a Monday event or appointment. If the family is left with questions, they have no one to reach out to before they are expected to participate in whatever the event is. (We know that we are likely checking email for exactly this reason, but a parent doesn’t necessarily know this!)

2. Details about any type of visit are essential to helping a family feel comfortable. What to wear? Should students bring a backpack? Water bottle? Lunch? Snack? Will a current student greet the student visitor? Will there be coffee and greeting for parents, or it a drop-off? Visits are high-stakes for the family and there is so much unknown by them that we take for granted. We know we will take great care of the family, regardless of how they show up. But the family is walking into a strange environment.

3. Rather than steering folks toward a general email address (info@… or admissions@…), try to find a way for families to email a person, even more so if you are a school dealing with high volume. That may seem counter-intuitive, but especially for schools where the process is naturally impersonal due to so many people, any effort to personalize is appreciated!

These quick changes will help families feel more prepared and welcomed into your community. Let me know what other easy tricks you have to smooth the way!

Survey Timing Considerations

Many schools do survey research to learn about why families do not choose to enroll after an admission offer (we’ll call these “declining families”). Often this work is done in the late spring, but I have recently been asked a few times about whether it’s too late to do the work now, in the middle of the fall. “It depends,” of course, but here are some considerations.

What will you do with the information you gather? For example, are you trying to explain low yield to the board? Or are you making a case for needing more financial aid? Is your team considering a program change that this data will inform? Different desired outcomes will inform time-sensitivity, as well as the formulation of questions.

Did you attempt to survey this group earlier? If so, you might consider a personal email with a link to a much shorter survey that acknowledges the earlier communication. Or, depending on the actual list of people, you might reach out personally to just a few and ask if they’d be willing to hop on the phone for a few minutes.

Are you worried about low response rates? My general rule of thumb is that some data is better than no data at all. It is nearly impossible to get statistically significant results in schools because our sample sizes are just too small. I wouldn’t worry about low response rates as long as the development and implementation of the survey is not too time-consuming for your team.

When is it just too late? When surveying families who have left your school (attrition), I don’t think it’s ever too late. Families who have something to say will often appreciate the opportunity to share. For the declining families, though, I’d say it’s probably not worth doing after November 1. By that point, families are embedded in their new school and are probably not thinking a lot about their experience with you anymore. Having said that, I do think that if you take the uber-personalized approach and reach out to people one-on-one for specific reasons, you might get good feedback at any time. It’s just about asking the right questions and framing the conversation effectively.

The bottom line is that survey research is an extremely valuable tool as you assess and understand the family experience with your school at various points in the journey. Timing is very important, but it’s not the only consideration when deciding whether to embark on the work.