Dr. Webb Winslow Celebrates KUA Career, Looks Forward To Retirement

FS: Hi Dr. Webb, thanks for meeting with me.

RW: My pleasure, Forest.

FS: How long have you been working as a teacher?

RW: This is my thirtieth year.

FS: How many have been here at KUA?

RW: This will be my thirteenth year at KUA.

FS: How’d you first find KUA?

Dr. Webb in the history office in 2003.

RW: When I was working at Milton Academy, my job had evolved from teacher, coach and dorm parent to teacher, coach, dorm parent and administrator. At that time I was looking for a full-time administrative job and one of the places that was interested in me was KUA. I came up here to interview and see the campus and immediately knew that this would be a good place for me. The most notable thing I remember was passing kids on the sidewalk and they were actually smiling. They offered me a job as Academic Dean, which I did for six years and then left KUA to work as Head of School at a few other schools. I returned in 2012 to finish my career as a teacher.

FS: And why’d you ultimately choose to be a teacher instead of an administrator?

RW: Originally, I left my previous career to complete my doctorate and needed a job. It just so happened that I did an interview for the Dean of Faculty at Andover as a favor and in the process I ended up deciding to take the job for a year. I became increasingly interested and that one year turned to another year, and another year, and then I decided that I liked that as a career path.

FS: What have some of your favorite memories been?

RW: My favorite memories have mostly been tied to kids’ successes. For instance, when a kid comes in not confident in their abilities and then you see them convinced that they are pretty good at that subject — those are the moments that most teachers really live for. I have been lucky to have quite a few of those moments here. The sense of community here is stronger than any other I have seen. It’s been a good place to work.

Dr. Webb’s faculty photo in 2001.

FS: Have you been looking forward to retirement?

RW: Yes, but for me retiring probably isn’t what many people think of as retiring. I’m already looking at several opportunities to go back overseas and help programs that teach kids develop. The one thing that I am certain on is that retiring will include moving to a warmer place. For me, it’s less of a retirement and more of a transition to new things.

FS: Do you have any advice for the students and faculty here?

RW: For faculty, I think they already know this, but love the kids and be endlessly hopeful. And kids, be honest of what you need to work on and seek out your own initiative and the willing help of your community.

FS: Where do you see KUA in ten years?

RW: Probably about the same size, and with even more reasons to be proud of itself, whether that is academic, athletic, or theatrical. Probably the one item I think we will continue to improve is the completeness of the experience for the students at this school. This school is a completely different place than it was when I arrived here in 2000. It’s on an upward scale and I think the recent endowment shows a lot about the potential we have in this school.


KUA wishes Dr. Webb a happy retirement and thanks him for all of his years of dedication and service to the school.

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