Head of School Dr. Scott Gaynor first joined the staff of Stephen Gaynor School as a bookkeeper 30 years ago in 1994, while planning his next step in the finance world. But that plan was quickly put on hold as he fell in love with the school, and was compelled to leave the precision of finance for the joy of education. In honor of this exciting anniversary, Gazette editor Megan Bostaph sat down with Dr. Gaynor for an in-depth discussion about his time at Gaynor, and the journey he has taken along with the school as they both have changed and grown over the past thirty years.
What has your journey at Gaynor been like, from the very beginning to now?
My start at the school was, I wouldn’t say an accident, but I came here just as a landing spot between leaving a career at one bank and finishing up my MBA, and thinking that this would be a good place to reevaluate where I wanted to go next in the world of business and finance. But I came and I fell in love with this school, and there’s never been a day that I regretted that decision to leave [finance] and come work at Gaynor. I think my journey at Gaynor has been quite symbiotic with the school. I came here when I was very young, [when] we were a small school with an incredible mission, and I grew up here, for the past 30 years, maturing, growing, and adapting and learning, which feels very much like the same path as the school has taken.
Had you ever thought about becoming the Head of School?
No. I mean, I grew up with my grandmother [Dr. Mimi Michael] who started the school, and I grew up around the school, so I would come here on my vacations and even work here. My grandmother asked me before I graduated college if I wanted to come work at Gaynor, and I said with some level of confidence “no,” because my path in my head was in business and working at a financial institution. I always thought that that was the right path for me. And that’s why I would say it was very fortunate that I took that pause to rethink about what the path was going to be.
What does the role of Head of School at Stephen Gaynor School mean to you?
I was given a gift by Yvette Siegel-Herzog and my grandmother in the vision that they had for the school. I believe my most important job is the keeper of their vision, the person who is responsible for ensuring that the mission that they created to support children who learn differently in a highly individualized way is ongoing.
I still learn a great deal from Yvette every time I talk to her because she’s so adept at bringing me back to thinking about our core mission, who we are, and what has sustained us and allowed us to thrive and allowed children to thrive over six decades. So it’s very simple, but if you continue to use that lens to make decisions, whether they’re business decisions about facilities or curriculum programs or hiring someone, [you ensure] that they bring great success to this very simple idea that [Yvette and Mimi] had when they decided to start Stephen Gaynor School.
So that part of the job brings me great joy, and what makes being Head of Stephen Gaynor School so rewarding for me personally is the opportunity to speak with the students, whether it’s doing door duty, or watching our basketball team play, or how I just came back from the lunch room and got lost in conversation with a couple of students about basketball. [laugh]

Dr. Scott Gaynor with Stephen Gaynor School co-founders Yvette Siegel-Herzog (left) and Dr. Miriam Michaels (right).
I’ve learned that you are the third generation of Gaynor who have worked at the school. Does the idea of ‘legacy’ mean anything to you?
Yes, it does. It’s complex, it’s hard for me to untie my feelings for the school with the fact that my last name is on the school, and that I’m so proud that my grandmother and my parents were so involved in the school. But I can’t say that my emotional attachment to the school is any more than any other teacher or employee here at the school because, and this is what’s so great about Gaynor, we’re so mission driven, and the teachers and all the employees go above and beyond because they believe in this mission. So I don’t think I have a greater stake in [the school], I think a lot of people here have that and I just assume that everyone feels like they’re part of the Gaynor family, so the fact that I actually am part of the Gaynor family is a bonus. But I don’t want to diminish that everyone has that tie to the school. Especially the Chris Myers, the Sloan Shapiros, the Ruth Rachlins, the Joe Kaufmans who were here in those early days, they have it coursing through their veins just like I do, and they have the relationships with my grandmother and Yvette that I get to have. So, yeah, I don’t know if I answered your question or just made it more complex. [laughs] I’m really proud that my name’s on the outside of the school and that I have this connection to Stephen*. But as far as my love for the school, I can’t say that it would be any different [from anyone else’s].
*Stephen Gaynor, the school’s namesake, was Mimi’s son. He was a first year student at Cornell University in 1961 when he passed away in a car accident. When Mimi and Yvette started the school in 1962, they named it in Stephen’s honor.
Finally, what do you see for the school in the future?
We have this wonderful five year strategic plan, and it’s a terrific plan that really spotlights what we do well for the students who come here every day, and how to improve on that. At Stephen Gaynor School, we have a commitment to grow in our delivery of education for our children. So there’s the whole part of our strategic plan that’s dedicated to that [growth], and then there’s the other piece that I’m really excited about, and that’s the outreach. I think about school, the noun, the physical building and everything that goes inside of it, the teachers, the materials and everything like that. Then I like to think about school, the verb, the action part of educating children. And I think in the future, there’s such a great opportunity for us to help more children, not by growing bigger, but helping teachers become better at how they teach by partnering with public schools, partnering with organizations that serve Stephen Gaynor School. We have a number of areas of expertise, whether it’s the instruction of reading, executive functioning, self-advocacy, or any of those core academic skills that we teach so well, so [it’s important] to reach more children by helping more teachers learn these skills that are applicable, not even for children who learn differently, but for all children. All children need strong executive functioning skills, and we’ve proven that we’re pretty good at this, and we can help more children by training more teachers.
I’ve been thrilled with the work that Emily Barnes has done as Director of Outreach and Innovation. We’re so proud of the 17 years that we’ve been hosting the Community Learning Center here at Stephen Gaynor School, and this next step that Emily gets a great deal of credit for facilitating is the training of local public school teachers. And that speaks to my earlier point about strategic direction, that we have a great history of the CLC, but we can help so many more students if the teachers in these classrooms have these skills to support their students.