Dr. Kaine Osburn knows his succession planning is unconventional, but the Wilmette native believes his novel approach to his final year as superintendent will help him achieve one of his greatest goals: leaving Avoca School District 37 in a better place than he found it.
After five years at the helm, Osburn will retire from his role as the district’s top administrator at the end of this school year, yet he will depart knowing his successor, Dr. Sandra Arreguín, will have already been on the job for more than a year.
When a superintendent leaves a district, school boards typically appoint the heir apparent near the end of or after their tenure. Osburn said a typical transition didn’t sit right with him, noting that he approached the District 37 School Board as soon as he knew retirement was on the docket.
“The idea of me just leaving and letting people figure stuff out without being in the best position to do so really bugs me,” Osburn said. “So when I made the decision (to retire), I went to the board early, and I said, ‘I know now that I’m not coming back … do you want to bring somebody in earlier than usual who can work side-by-side so that the transition can be as smooth as possible?’”
The School Board turned Osburn’s vision into a reality, approving the hiring of Arreguín earlier this year as superintendent-elect for this current school year and the district’s new superintendent for the 2024-’25 school year.
“The board was willing to look at an unorthodox transition process so that it could ensure implementation and sustenance of the District’s newly adopted mission, Portrait of a Graduate, and strategic plan,” Dr. Sumit Dhar, president of the District 37 School Board, said in a press release issued earlier this year.
“These articles are reflections of the desires, goals, and aspirations of our community,” Dhar continued. “Dr. Arreguín’s biography and experience align with our community’s values and goals, and we are confident she will contribute to and sustain our high standards.”
Arreguín commenced her District 37 career earlier this summer, immediately starting to work alongside Osburn. And Arreguín’s early time in the district is more than a shadowing experience.
The experience this year, Osburn said, has allowed Arreguín to take on a “definite portfolio of work to do, so she’s not just shadowing, she’s doing the work. She’s leading committees and leading initiatives,” he added.
“Every day that she and I and the team here work together; it just makes me more and more excited,” he said. “We’re such a small team and to bring in new blood, it’s exciting. She gives us insights we didn’t have.”
Arreguín comes to Avoca after serving as the assistant superintendent for curriculum and instruction at Niles Township High School District 219 for the past five years. Prior to that, she worked at Township High School District 113, which consists of nearby Highland Park and Deerfield high schools.
Arreguín’s roles at District 113 included chair of the world languages department, director for English learners, and the assistant superintendent for curriculum, instruction, and assessment. She has also been the principal of Northwood Junior High School in Highland Park.
“The mission of the district centered around curiosity, growth, and diversity is completely aligned to my personal values and core beliefs as an educator,” Arreguín said in a press release earlier this year. “I am excited for our future work together to serve the students, families, and staff of Avoca.”
Osburn’s final career stop is one he’ll forever cherish
Taking on the superintendency at District 37 was a homecoming for Osburn that felt like a fitting next step in his career in education.
Osburn, who grew up in a family of educators, started out as a high school English teacher, carrying out his passion for writing and teaching. He spent the majority of his teaching days at Niles West High School, where he found leadership opportunities that eventually led him to consider a future as a school administrator.
After a few years in administration, Osburn became the principal at Niles West. He served in the position for six years before becoming a deputy superintendent in Naperville.
Osburn then took on his first superintendency, becoming the top administrator at Lake Zurich School District 95. There was no shortage of priorities to tackle in the district when he arrived. Osburn led the district through the passing of a large-scale referendum that included more than $100 million in capital improvements.
His role in District 95 could have been his final stop, Osburn admitted, but then the superintendent position at Avoca opened, and the New Trier High School alumnus could not pass up the chance to return home in 2019.
“I still lived in Wilmette and the idea of working in the community where I lived was very enticing,” Osburn said. “And another thing that was true is that I had started my career in high school, and then gone to a K–12 district — and the idea of going to a K-8 district was really exciting also because I found that, with all due respect to my high school friends, elementary school is really where all the magic happens, where all the big changes occur.
“I felt like I could come to a school district and build really good relationships and get to know people and we could make a lot of great changes for the betterment of our kids,” he added.
Osburn described some of the highlights during his five years at the helm of the district as “foundational pieces” that will directly align with his goal of leaving the district in a better place than he found it.
One of the key initiatives related to that is the district’s work on fostering what he described as a “rigorous collaborative culture” among staff.
“Our staff’s impulse is to be very collaborative, they want to work together and we work hard to give them rigorous tools so it’s really effective collaboration,” he said, adding this will become “one of the strongest points about the district.”
Osburn also led the district through one of the toughest challenges the educational landscape has ever faced: the COVID-19 pandemic. He applauded the district’s board of education for its support throughout the pandemic, noting that its backing was crucial in the district making it through the pandemic’s peak as “best we could.”
“Our board of education was very supportive and they understood that whatever decision I was going to make was going to make at least half of everybody unhappy,” Osburn said. “So they just said to me, ‘Listen, keep us informed, answer our questions, keep doing the research and make the best decision you can.’”
The main focus of the remainder of Osburn’s tenure is the district’s ongoing consideration of its facilities and the potential upgrades needed for a “sustainable future.”
In 2022, a facilities and finance committee dove into the district’s finances and buildings and recommended that the board of education take action to ensure both can be sustained long-term. The school board is now in the process of working with the community to review which of three options has the most support.
The options under consideration are:
- Conducting maintenance to service operations, enhance security, renovate and add minor additions for an improved learning environment;
- Building a new elementary school on the Marie Murphy property to replace Avoca West while also refurbishing portions of the junior high;
- Building a new PK-8 school on the Marie Murphy property to replace Avoca West and Marie Murphy.
As previously reported by The Record, the School Board could make a facilities decision as soon as December or it could delay one until the spring.
One other accomplishment that Osburn holds dear to his heart is on the personal side of education.
“When I came here, I really looked forward to knowing every kid and every family and every staff member, and knowing something about them that could be helpful to our relationship and making their experience better, and I would say that I’ve gotten really close to that and it’s one of the things that makes getting up and coming here everyday amazing,” he said.
As Osburn’s tenure with Avoca comes to a close, “he’s very grateful” to be ending his career here, and there is plenty about the district that he will miss. At the top of that list are two of the aspects of education that he’s always loved: talking with students and talking with teachers.
Osburn has never been the type of leader to consider his legacy, and true to that nature, he believes the most effective, great leaders tend to put their egos aside.
He does have a hope for how the District 37 community will recall his superintendency though.
“Just remember me for who I am, which is an intense, focused and committed person who wanted the best for our students and our staff and the best from our students and our staff,” he said. “And that will be enough if that’s what they remember. That will be plenty.”
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Martin Carlino is a co-founder and the senior editor who assigns and edits The Record stories, while also bylining articles every week. Martin is an experienced and award-winning education reporter who was the editor of The Northbrook Tower.