Lakeside’s 2025-2026 school year has been defined by a single proverb: the only constant in life is change. From the first days of September all the way through the day you read this article, an  unprecedented shift has seemingly arrived every month. Lakeside’s community has seen the implementation of a new phone-free policy, an updated assembly setup, and a pilot program for schedule modifications, to name but a few. Yet the change announced on Wednesday, Feb. 11 has overshadowed all others: Kai Bynum, head of school since July 2022, stepped down from his position with immediate effect.

“Serving as head of school has been a remarkable privilege,” Dr. Bynum wrote. “Our community has made so much meaningful progress together: launching Lakeside’s strategic plan … completing the T.J. Vassar ’68 Center … evolving the school’s approach to community health and safety.” 

“Even as I found the work deeply fulfilling and invigorating,” he continued, “the demands of serving as head were proving incompatible with the realities of my health.”

Given his health challenges, Dr. Bynum already had a reduced presence on campus throughout the year. He had not been visible at Lakeside since November, when he began a medical leave of absence to finish recovering from a surgery he underwent in June.

“During my medical leave, I turned the mirror of awareness and perspective on myself and realized what I needed to do,” Dr. Bynum wrote. “Though the decision is a heavy one, it is accompanied by a sense of peace.”

Mr. Boccuzzi Steps Into Interim Head Role

In conjunction with Dr. Bynum’s message, Board Chair Sean O’Donnell ’90 released his own statement. Along with reflecting on Dr. Bynum’s “vision, passion, and deep love and care for our community,” Mr. O’Donnell outlined how Lakeside’s board and administration will handle the transition process. Notably, he announced that Ryan Boccuzzi will serve as Lakeside’s interim head of school from February 2026 through June 2027.

“It was a real mix of emotions,” said Mr. Boccuzzi, reflecting on Dr. Bynum’s exit. “We knew that Dr. Bynum was making the right decision for him to take care of himself … I was very happy that he was prioritizing himself to make sure he’s going to be well and in good shape.” At the same time, “it’s really hard to have [the head of school] step away mid-year and to think about what that means for leadership.”

Mr. Boccuzzi explained that the board and administration considered multiple options before naming him to the interim head role. “There’s a whole industry of ‘interim heads of school,’” he said. “And so we were asking, ‘Is that the right thing for Lakeside right now?’” He noted that searching externally for an interim head would have brought significant disruption: “needing to interview and hire an interim head of school, [then] the entire community needs to meet that head of school, and then that new head of school leaves in a year and a half … That’s so many transitions, and we were able to do it in a simpler fashion.” Ultimately, he and the rest of the school’s leadership decided that “we can do this ourselves, internally, and spread out the work.” 

As interim head, Mr. Boccuzzi hopes to carry forward the initiatives launched by Dr. Bynum, including the execution of the “Hope in Action” strategic plan. “‘Cultivating a school community that inspires and empowers all our students and educators with the will to seek joy, to be hopeful, and to transform the world with care,’” he said, quoting from the “Hope in Action” webpage. “That’s something Dr. Bynum talked about a lot, and I think it really is a good statement as to how we should be trying to live our mission … we don’t need to wait for a new head of school for that. We can start thinking about what we can do in our curriculum right now to get things moving in that direction.”

Mr. Boccuzzi also aims to make full use of the perspectives, experiences, and connections that he has gathered in his time at Lakeside. “I hope I’m going to be able to rely on the many relationships I’ve built over my four years here,” he said. “Because I think if you’re talking about pushing things forward and creating more joy, creating more of a sense of hope, treating people with care — you have to know people to do that.” 

“What I’m most excited about,” he added, “is that I think I know our school well enough at this point to say ‘Where do we need to put our attention to make sure that we’re doing this in the best way possible?’” 

The Search for a New Head of School

Beyond securing stability for the present, Lakeside must also prepare for the future. Now, the process begins of finding a new long-term head of school to replace Dr. Bynum.

To ease and streamline this search process, Lakeside has chosen to collaborate with the educational recruitment firm Carney, Sandoe, & Associates. CS&A is a major player in the world of faculty and administration recruitment, having recently helped to facilitate head of school appointments at schools located in Connecticut, Missouri, and New York, among others. 

Notwithstanding the wide scope of their work, CS&A’s representatives asserted that their process of selecting candidates will be tailored closely to Lakeside’s environment. “It’s exciting to partner with such a vibrant and intellectually engaged school community,” said CS&A consultants Karen Whitaker, Darryl Ford, and Devereaux McClatchey, who corresponded with Tatler via email. “Lakeside is a national leader in education in so many ways, and it’s a privilege to work alongside such a wonderful group of educators and families.” 

To deepen their understanding of Lakeside, CS&A’s consultants sent out a community-wide survey and made campus visits on March 25 and 26. They noted that the survey “helps us refine our recruitment efforts, in terms of understanding what sort of leadership style and background could be most effective,” while the campus visits “helped us better understand Lakeside’s culture, values, and priorities.”

After analyzing the survey responses and considering the information gleaned from their visit, CS&A’s consultants wrote a “position description” summarizing the role of a Lakeside head of school. This position description will be used to initiate conversations with available candidates, which could take the form of brief Zoom calls aiming to provide an insight into “their experience, leadership style, and interest in Lakeside.” As the pool of candidates narrows, the consultants will also conduct more comprehensive in-person interviews. They will then introduce top contenders to Lakeside’s own search committee (a group chaired by board member Melinda Lewison ’90 and composed of several adults from throughout the community, including English teacher Avery Downing). 

The process seems relatively simple on paper, but CS&A’s consultants note that confidentiality considerations can make it more complex. “One of the bigger challenges in head searches for a school of Lakeside’s caliber is that many of the top education leaders request that their interest remain confidential, so that it does not jeopardize their standing in their own school community,” they said. “And yet, certain community members would like to have more visibility with respect to the finalist candidates.” 

“We have to trust the [search] committee to do good work,” Mr. Boccuzzi noted, “because we all won’t necessarily get to know every candidate they’re getting to see.”

CS&A’s consultants plan to introduce promising candidates to the search committee in late spring or early summer, with the actual appointment decision occurring between June and October. The new head of school will then begin work in September 2027. 

Mr. Boccuzzi looks forward to working with the new head of school, helping them integrate into the established community while simultaneously learning from their unique perspective. “It’s fun to have new eyes in a situation,” he said. “I’m really looking forward to a head of school coming in and asking questions like, ‘Wait, why do we do this thing that way?’ And you’re like, ‘I don’t know why we do it that way. We’ve just always done it that way.’” He hopes that such questions will foster reflection that helps Lakeside continue its journey of growth.

The Only Constant in Life is Change

An era comes to a close; another era will soon begin. 

Despite his mixed emotions surrounding Dr. Bynum’s exit, Mr. Boccuzzi remains excited and hopeful for the future. “I feel very lucky. I’ve worked at four different schools. I’ve been a part of a number of different leadership teams. I’ve never worked with a team that’s as strong as the team we have right now at Lakeside. And it’s been really fun, even in just these first two months … to get to work with this group in a way that feels like we’re stewarding the school well through this transition point.” 

“All change brings opportunity,” he remarked. 

This story of change is far from over. As the head of school transition continues, Tatler will endeavor to provide the community with crucial information, context, and analysis. In this first installment of what will surely be a long-running series of articles, let us end with a quote from Dr. Bynum’s exit announcement: “This community has given me so much joy and care. Lakeside’s students and their teachers truly have transformed my world and provided me with a powerful sense of hope for the future. Thank you.”

Thank you, Dr. Bynum. Lakeside can only hope that your successor, whoever they may be, espouses the same “vision, passion, and deep love and care” that you have consistently shown this community.