After 22 years at Wilton High School, including the last 15 as principal, Dr. Robert O’Donnell is reflecting on the changes, challenges and successes he’s seen and had as he prepares to turn the page on a 38-year career in education.
O’Donnell, who will retire at the end of this month, said his passion for education began long before he arrived in Wilton. It started when he was studying French and German as an undergraduate at the University of Connecticut.
“I had very good educational experiences myself in high school and in college, and I thought, ‘If I go into teaching, I can help kids learn languages and expose them to culture and travel and the values thereof,’” O’Donnell said during a phone interview Monday.
He found he had a gift for working with students in multiple settings — in the classroom, on athletic teams and in student government.
“I got to be a student council advisor and a faculty advisor and teach kids languages, and I just loved it,” he recalled. “So I thought, ‘Well, education’s for me. I’m going to keep going.’ Then I eventually went into administration, and it’s been a very, very rewarding career.”
His colleagues agree, and say O’Donnell’s impact on the school community over the years has been profound. At a recent Board of Education meeting, School Superintendent Kevin Smith gave an emotional speech in honor of O’Donnell, describing him as a leader who viewed the district’s success as going beyond rankings and statistics.
“He’s been the rock of Wilton High School. When the waters become rough, Bob provides reassurance. When difficult decisions need to be made, he approaches them thoughtfully and with integrity. When students or staff need support, he’s there with compassion, wisdom, and a steady hand,” Smith said. “His leadership, as you know, has never been out loud or self-promotional. Instead, it is characterized by humility, consistency, kindness, and that steadfast, rock-solid commitment to all the people he serves.”
Now moving on to the next chapter, O’Donnell reflected on several accomplishments he is proud of, while always quick to point out that every one was a team effort.
He mentions the school’s wide-ranging list of courses as an example, pointing to 50 new course additions over the past 10-12 years.
“The work that we’ve done here as a team — and it’s always a team in education — the work to establish a very, very strong academic program for students where they have multiple courses and programs to find something that they’re interested in and something that they’re passionate about in addition to the required courses,” O’Donnell said. “We’ve got a very, very unique and full program of studies here.”
He also listed the school’s block schedule format, which was introduced in 2019, as something that has helped both students and teachers.
The schedule has students attending four classes every day instead of seven, allowing more time for each class. Four lunch waves and miniature labs, for science classes, were also launched.
“So there are fewer transitions, longer periods where teachers can go deeper. And I think that’s something that’s been good for staff, students, and families,” O’Donnell said. “And it allows students to just not be rushed all the time. And I think that’s been a success as reported by the survey work by a lot of our constituents here.”
O’Donnell has also witnessed the introduction of social media and artificial intelligence (AI) into the lives of high school students, both of which have presented challenges and opportunities.
“I think it’s important not to be afraid of whatever, whether it’s social media or AI or technologies, because it’s the way the world is developing, and that, of course, intersects with education,” O’Donnell said. “So, social media — there are ways to positively leverage social media in terms of promoting your programs or sharing information with groups of students, and that’s all positive.”
But O’Donnell said educators have to address social media’s adverse effects on students in school too. One way Wilton handled this was by implementing an all-day in-school ban on cellphones in October 2024. Wilton was one of the first districts in the state to do such a ban, O’Donnell said.
“I think that’s been a good thing to say to kids, ‘Listen, for six-point-something hours a day, you’re going to be off your cell phones, and you’re going to be present, you’re going to be interacting with each other, you’re going to be communicative, you’re going to look somebody in the eye,’” O’Donnell said. “And that has been a game changer here. While not perfect, I do think this is going to help our … Wilton kids, in the long run.”
The proof, he said, was in what the kids have shared about the change.
“We’ve had a lot of very positive feedback from them, that while they didn’t want to lock their phone away or put it in the car, they realized pretty quickly that the level of interpersonal communication and connectedness that we thrive on in schools has been really augmented by the lack of cell phones,” he said.
At least while they are in school, students don’t have to worry about someone taking a video or a photo of them, he added.
“I mean, social media, it’s part of our world, and it’s not something we can completely eradicate, nor should we. But I think when we either restrict it or try to use it in measured approaches, it can be better,” O’Donnell said.
Wilton Public Schools this week announced that James D’Amico will step into the principal’s role after O’Donnell retires on June 30. D’Amico has been principal of New Fairfield High School for the past seven years.
As for what advice he would give his successor, O’Donnell said to continue letting the staff do their work and embrace the community made up of parents and students — all components that have made Wilton one of the premier high schools in the country.
“The ethos in Wilton is, we do anything we possibly can for our kids. And then, trust the adults. Hire really good people and develop them and realize that they have amazing expertise and let them accentuate their expertise because they’re so skilled in what they do. They’re not teachers and staff that need to be micromanaged,” O’Donnell said. “We hire people and we support them and we let them do their really, really good work.”
He added that Wilton parents have always been good partners for the district.
“They are here for the schools. They’re heavily invested,” O’Donnell said.
Although he has some mixed emotions about leaving education, O’Donnell is coming around to the idea of retirement more as June 30 approaches. He’s looking forward to spending more time on his hobby of working on and driving antique cars as well as cycling and golf.
“I intend to fully retire and just have some more time to do the things that I want to do in life that are a little bit different,” O’Donnell said.
