Skip To Main Content
How Private School Leaders are Preparing for the Year Ahead & Strategizing for Success
Claire Hollowell

Ready or not, it’s time to dive into another school year. We sat down with three private K-12 school leaders at a Virtual Poolside Chat to discuss what the year ahead will look like for them, how they plan to meet enrollment goals, and where they’re shifting their strategies. Read on to get more of their insights, or watch the full webinar on-demand at any time. 

Meet the Panelists: 

Panelist for how private school leaders

Lessons Learned in the Past 

Q: What is one lesson you learned during the pandemic that you will bring forward with you into the coming year? 

Yuri: One of the biggest lessons I took from the previous year is “always have a backup plan.” Things can always change. Even just recently when we thought we were all set and things were looking pretty rosy during the summer months and as we headed into a new school year, things changed again and COVID cases started spiking. We’ve had to adapt and make some changes already. It’s vital to communicate, be flexible, and expect the unexpected. More than just plan A, you need a plan B and a plan C. That’s definitely one of the key lessons that I’ve learned over the past year and will certainly take into the upcoming school year.

You have to make sure your head is on a swivel. Even though you’re focused on the thing that’s right in front of you, you also have to know where you’re headed next.

Stacy Glaus, Chief Strategy Officer, Breck School

Stacy: We have all pivoted so much in the last year. That’s definitely a lesson that I know we will all carry forward. But one thing that stands out for me is finding time to make sure that you’re not just thinking about the crisis in the moment, but that you’re making mission-aligned decisions and innovating beyond just the crisis at hand. I’m really, really proud of the way my communications team and our entire leadership team at Breck were able to do that. Launching a new schedule in this new academic year, thinking about enrollment, and having our admissions at the highest point we’ve had in several years, we’re really just trying to make sure that we keep our eyes focused and not let the pandemic dominate all of our time.

Rik: When I think about lessons learned, my mind goes to the idea that community and connection matter most. This moment of crisis has also revealed heroism in so many ways. And when we boil down our purpose as independent school educators to what’s at the heart of it, our decisions are guided by what’s best for our students. Mission matters more than ever right now — what your school’s purpose is and what you stand for. Grace and gratitude are big too. We’re human beings. And in this moment having gratitude and expressing and acknowledging grace is critical. 

Strategy Shifts & Planning For The Year Ahead

Q: How has your school’s approach to retention changed for the new school year? Are there any new retention initiatives that you plan to undertake? 

Stacy: In terms of retention for new families, we’ve been thinking about it from a three-year perspective. We had new families enter in the 19-20 school year who never experienced a full school year at Breck. The same is true for 20-21, and now the 21-22 school year. We’re really looking at how we engage those families with very intentional strategies. I met with our advancement team to go through the events and activities that are directed towards them. You also want to think through things that might be new to them since many families may not have experienced a traditional school year with you. Take the time to explain what homecoming means, what it means to go to a back-to-school night, or how parent-teacher conferences run. Spending time on that right now at the beginning of the school year will yield great benefits as you enter into re-enrollment season in January. 

“As the Director of Enrollment Management, I’ll often tell my colleagues that I shouldn’t be the last person to find out when a student is struggling. I should probably be the first or at least second person to find out because everything impacts enrollment and we want to make sure that those students are having a positive experience. If a student is in need of assistance we want to have a plan in place to help them.”

Yuri Francis, Director of Enrollment Management, Stony Brook School

Yuri: We want to continue some of the basic initiatives we’ve put in place over the years, which is largely focused on communication with the key division heads, whether it’s our upper school director, middle-school director, athletic director, or Academic Dean. We want to make sure that we are staying on top of what’s going on with our students. 

It’s important for my office to be aware of what’s going on with each individual student on campus. Communication across the division heads is vital. Some of the other important factors include trying to follow up with our families during the school year, typically via a survey early in the school year for new families that are joining the school, and then throughout the year for our returning families, just to get a feel of how they’re doing and how their experience is going. 

Something new that we’re planning to do this year is to create a parent ambassador program. We already have our student ambassador program going, but we really wanted to have one for our parents. Another thing we’re doing is capitalizing on those first six weeks before the weather changes. We want to get our students outside, having fun, running around. And hopefully, they’ll be able to do that without masks since they’ll be outside. Many of our boarding students weren’t able to join us last year on campus. So this will be the first time for many of our students to experience the entire community back together. That’s definitely important for us and I think it’ll help us with retention efforts.

Q: How are you planning on running events this year? Will you host virtual, hybrid, or in-person campus admission activities?

Stacy: I actually have the distinct honor of leading our COVID compliance team here at Breck. I can say with excitement that we are looking forward to returning to a much more normal in-person-style event season for this year, but we also recognized the great gains that we experienced in being pretty much fully remote last year. We’re entering into a hybrid model. We will have some in-person events and some virtual events. We’re excited to welcome families back to campus this year in a way that we weren’t able to last year. Our admissions team took time to rethink our processes a little bit and think through what was really valuable before and what we did last year that had traction. We remain committed to making research-informed decisions as part of our COVID compliance team. And we will continue to do that throughout this upcoming year. 

Yuri: We’re looking at a combination approach. We’re planning for one in-person open house, followed by a series of virtual open houses. We’re also hoping to host students on campus for a class visit date throughout the school year. We’re fortunate in some respects that we’re over-enrolled, so we’ll have to see if our classes can accommodate visitors. We will wait a few weeks into the school year to make that decision. If we’re unable to accommodate in-person class visit days, we’ll do them virtually as we did last year. We’re not going to do much of any travel, but we are going to focus those travel dollars and funnel them into digital marketing.

Rik: We’re coming back together and we’re wicked excited to get everybody back in person. We actually got to that at the end of last year, which is wonderful, and then over the summer as well, but it took courage and it took planning and thoughtfulness. We’re very excited to have in-person events. We’re blessed to have a 50-acre campus and can utilize outdoor spaces for admission events. We often talk as a leadership team about COVID keepers, like the hybrid approach and the use of a virtual open house. Those were a great addition to our work. For those families who lead busy lives and may or may not be able to get to the open house on a given day, they can still hear from teachers and get information on the school on their own time and schedule.

Q: A lot of communication has been dominated by COVID. How do you make sure you’re communicating your school’s value to new families and giving families a reason to become returning families? 

Rik: The concept of really getting to know each individual family is big. We’re an all-boys K-8 school. We take great pride in traditions like our morning handshake. They’re going to want to stay because we’re going to shine our light in this moment and deliver on our mission and on our promise. We often say if we could just get more folks to understand, appreciate, and know a Princeton Academy experience, then we would be able to build our community in that way. Well, now we have a chance.

One other piece is collaboration. This is not one person’s job. Retention means delivering in the classroom. Retention means having a great playground and athletic field and stage and making sure they’re all positive experiences and provide growth opportunities for the children. Then I go back to communication. That’s the key for families who are new to an independent school. Think through how you are communicating with them, how frequently, and with what level of quality, so that they can understand what their child’s experience is, especially in a time when there may be still a bit of a separation between where parents and families are and their knowledge of what’s happening in the building. 

How private school leaders - coffee and notes

Staying in Touch with Families Throughout the Year

Q: Do you have any recommendations on how to keep parents informed and connect with them throughout the year to ensure that their expectations are being met and allay concerns before they become bigger issues? 

Yuri: A year or two ago we worked on improving our communication by focusing and limiting the number of different communications that go out to our entire community. There’s one communication that goes out Friday afternoon from our assistant head of school that includes all of the important details and events and news within our community. We certainly let our families know to be on the lookout for this communication because everything they need to know will be in that one email. We want to make it easy as opposed to them getting inundated and receiving too many messages.

The other thing that is extremely important for getting a read on how parents are feeling throughout the year, is our advisory program. Our advisees meet with their advisor once a week. Advisors play a key role in looking out for students. They can help us stay abreast of what’s going on in their life both from an academic perspective, and also from a social, emotional, and wellness perspective as well. 

“The head of school should be the chief storyteller. It must start with her or him, and run through the entire school.”

Rik Dugan, Head of School, Princeton Academy  

Rik: This is the core right here. This is the key essential component, how we communicate with our families. In those advising communications and teacher communications, communicate good news. Communicate when a child does something great. Amidst times of crisis and stress as a parent there perhaps is nothing better than getting an individual one-on-one communication about something amazing your child did. Those little touchpoints are huge. 

We have two weekly communications. Every Friday I write a letter to our community alternating with our assistant head of school, Paris McLean, and it’s a storytelling letter. Maintaining the voice of the institution is critical in these moments because it is also being balanced by the operational side. You should be communicating transparently to build trust. If there’s a COVID positive case and you need to quarantine a group, if that’s all the messaging that families are receiving, then their experience takes on only that life and tone. But we know that there’s joy and vibrancy and beauty and color and diversity in our schools that also need to be communicated. 

Balancing storytelling with the necessity of crisis communication is vital. We’ve focused so much of our communication and our conversation of course, on COVID, but we should also address the other important things happening at this time. We want to continue to amplify and advance the imperatives of justice, equity, diversity, and inclusion. We have to continually ask how we can lead the way from a communication standpoint and an enrollment piece. Every communication in a virtual world is an asset. Every letter from a school leader, every open house that’s virtual can be shared, forwarded, and used in a way that really leverages your story. 

Stacy: The phrase I use most often is “no surprises.” We talked earlier in this discussion about using the people closest to you whether that be faculty or staff member, as your word of mouth marketers. They are your closest lever to those families, to those students. And so in terms of communications, especially for COVID one thing that I worked really hard on last year was bringing our faculty along. Every week we had a faculty meeting with our COVID compliance team and our consulting physician to say, here’s what we know, here’s the direction we’re headed, and this is the plan right now. And so when we entered faculty workshop week, faculty had already been talking about it and word on the street was that Breck really was owning this opportunity to lead.

How private school leaders - notebook

Q: How frequently do you survey your families to see how they’re doing or track any problems that might arise?

Stacy: We typically survey our new families midway into the fall, right around mid-October. We also have new family coffees. One at the end of August, another one in September, and then we send the survey out in October. After that our admissions team meets again with the new families who participated in the survey to check in and see how they’re doing. That feeds into an advancement model where we have the opportunity to explain to them what the annual fund is, which launches in November. In terms of response rates, we aim for 60 to 70% participation. You want new families to give their feedback and have that personal connection. 

Rik: We survey regularly, and our journey of surveying is something that we continue to assess. When we were transitioning to remote we were surveying nearly bi-weekly. I do new parent coffees with each family and we have larger group gatherings to get feedback. And then we regularly do an NPS survey in the spring. We use the NPS algorithm of really one or two questions: how likely are you to promote our school/ would you recommend it to another family. I believe that gleaned good data for us as well. And I would say that faculty and staff should be included in that surveying process as well. And perhaps even students, depending on the age group.

Yuri: For surveying families, October is ideal, maybe November at the latest. In terms of the response rate, I think anything over 60% is pretty good and if you’re able to get 80% participation that’s outstanding and that’s what you’re looking for. 

Breaking Down Silos & Building a Dynamic Duo

Q: Admissions and marketing often work in silos. What is one thing that you would recommend to help break down barriers and encourage collaboration between admissions and marketing? 

As a school leader, I have to take responsibility and accountability first and foremost for making sure that our leaders are empowered to lead. I consider it my responsibility.

Rik Dugan, Head of School, Princeton Academy  

Rik: We’re blessed here. Our director of enrollment management and director of marketing communications work in partnership. The office of marcomms here at Princeton Academy was something that we actually created over the past several years. It didn’t exist prior. It’s allowed the professionals, frankly, to redefine what enrollment management and Marcomm look like in synergy. As a head of school empowering leaders to lead experts and professionals who know their craft better than anyone, creating space and time for that synergy to occur is key. I meet individually with each member of our leadership team as well. Create space to ensure that silos don’t form. 

Yuri: We don’t have a dedicated marketing team at our school. Our director of advancement and I share those responsibilities. We try to partner up and meet at least once a month to talk about different initiatives and bounce ideas off of each other. Even if we did have a marketing team in-house, trying to meet at the very least once a month or even biweekly is a great way to start to break down those walls and silos. You want to understand what everyone is working on and know what your calendars look like. Talking about goals is also very important because you can help one another out and make progress towards your goals together. 

Stacy: At Breck, we operate under a model of shared leadership, and sometimes shared leadership means that things take longer. We need to know what advancement is doing and advancement needs to know what admissions is doing, and communications needs to know what they’re all doing, and it’s not easy and it’s not perfect. It’s not perfect, but I hope that you have the ability to have a high trust relationship with those leaders across departments. And I’m grateful that I have that here at Breck, and I consider our leadership team members, my great friends. You have to be able to have conversations that are tough but also be able to celebrate the wins and be able to go to admissions or to go to our head of school and say, look at what we accomplished together. Those things are really, really important.

Rik: It’s also important to acknowledge the collaborative nature of diverse thoughts. Innovation takes all of us. We all have a pie with many slices and the overlap and the intersect may be on somebody else’s slice, but that’s not the totality of your job. For example, somebody who’s overseeing communications at a school during COVID is also having oversight of health and wellness communications and mission-critical communications. Honor and respect the shared space and see it as an opportunity for diverse collaboration of ideas. 

The start of a new year is always the perfect time to revisit your approach to and strategies around communication, retention, admissions, enrollment, and more. To get more tips, tricks, and strategies to use in the year ahead, watch the full webinar on-demand.

Connor Gleason Headshot


Connor has spent the last decade within the field of marketing and communications, working with independent schools and colleges throughout New England. As Finalsite’s Web and Marketing Manager, Connor plans and executes marketing strategies and digital content across the web. A former photojournalist, he has a passion for digital media, story-telling, coffee, and creating content that connects.

Explore More Recent Blogs

Subscribe to the Finalsite Blog

Love what you're reading? Join the 10k school marketers who get the newest best practices delivered to their inbox each week.

Request a FREE
website report card

Want feedback on your school or district's site? Get a free website report card, generated by an in-house website expert, sent right to your inbox.