On May 11, 2023, the second season of the Enrollment Management Association’s (EMA) Impossible Questions Podcast began with a special crossover episode. Ari Betof joined host Christina Dotchin, vice president of member relations at EMA, as episode co-host on her Enrollment Spectrum Podcast. Christian Donovan, head of school at Friends School of Baltimore, joined as the special guest before coming on board with Betof as the Impossible Questions Podcast co-host for the second season.
This second season opener featured a summary highlighting especially interesting themes the podcast explored in its first season. Throughout that season, the hosts explored questions such as “How do experienced enrollment leaders learn about unfamiliar markets?” and “How should we involve others in conversations about enrollment?” Both these episodes featured Donovan, bringing his expertise to bear as a guest when Betof and first-season co-host Hans Mundahl had thrown him a number of messy, impossible questions.
Experience and background
Dotchin began by anchoring the conversation in the diverse experiences that Betof and Donovan bring to the table. Betof is a co-founder and partner at Mission and Data, an EMA strategic data partner, and a nationally recognized expert on financial sustainability and organizational stewardship for independent schools. In addition, he has served as an independent school trustee, head of school, chief advancement officer, director of enrollment management, and in other key roles.
Donovan is currently the head of school at the Friends School of Baltimore, an independent Quaker school. He also bases his insights on his previous work in enrollment management, strategic initiatives, and college counseling at a variety of schools. He previously served as assistant head of school and director of strategic research at Head Royce School in Oakland, California, following eight years as that school’s director of enrollment management. He has also worked in counseling and admissions roles at Athenian School in Danville, California, also in the Bay Area. Donovan is an EMA founder and faculty leader who has been instrumental in moving forward the EMA’s Future Leaders program.
Fun fact: Betof and Donovan have known each other since their student days at George School in Newton, Pennsylvania, then spent seven years working together in enrollment management and integrated institutional advancement at the school. Donovan is currently a member of the George School board of trustees.
“You just begin”
This crossover episode emphasized that school leaders don’t have to know the answer to every impossible question—the inquiry and the journey in themselves can become valuable learning experiences.
So, the first impossible question for Donovan in this episode was: What do you do when you’re asked an impossible question? What paradigm of leadership do you apply?
As a current head of school, Donovan thinks about this question frequently. He’s constantly on the lookout for a “metaphorical magic bullet” that will cause everyone to say, “Of course. That’s the answer!” But, he said, “I’ve never found it.” He asked if his co-hosts remembered the 2015 Matt Damon movie The Martian. At the end, Damon’s character describes to a group of students how he found his way home after being marooned on Mars: “You just begin.”
That phrase had a big influence on Donovan. He explained that, when faced with a messy, impossible question, the way forward is to “solve one problem at a time.” Then, once enough problems are solved, it’s possible to find the way home. The value—and the possibility of achieving a true “Aha!” moment—lies in steadfastly working on the problem.
Building on context
Noting Donovan’s experience at schools of different types and sizes, Betof asked how impossible questions manifest in different contexts.
A similar problem, Donovan said, can play out very differently depending on the environment. The common factor that leads to success for school leaders is to get to know the school community. For example, at the time of this episode, he’d been in the Baltimore area for less than a year. He found its independent school community very different from that of the Bay Area. Baltimore is “oversaturated” with choices for families choosing an independent school, and there are “smaller, more nuanced” ways that things like financial aid and merit scholarships play out in the Baltimore market.
Donovan spent his first year trying to understand this new context. He remembered that there are always two responses to a challenge. The first is figuring out how to handle the immediate problem in the moment. The second is learning how to grasp the bigger picture that the challenge represents. Much of that bigger picture involves context. In addition, making a choice for the short-term can lead to consequences that make long-term issues more difficult to resolve.
Finding the truth together
The three hosts agreed that one of the joys of podcasting is the chance to learn from people who have thought deeply about the issues the Impossible Questions Podcast tackles. Donovan related this to the Quaker principles that both George School and the Friends School of Baltimore are built on. It’s a “philosophy of continuing revelation” in which no one has a monopoly on truth, but where people collectively share knowledge and insights and find truth together. This philosophy is about working through the interesting questions that are present from the start, but also finding other important questions that germinate from those conversations.
Listen to the full episode on Apple Podcasts or the EMA’s website. There, you’ll also find a wealth of other information about EMA’s programming and professional tools, including the Strategic Enrollment Management Spectrum mentioned in this episode.
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