No Surprise, But Lots of Delight: Phil Oates Named Middle School Principal


Surprise and delight–one of the Owl’s favorite terms from business school. It sums up how a company can just make someone’s day–a freebie, an upgrade, an extra that is unexpected and absolutely welcome. Well, the following announcement from Dr. Connolly, Superintendent of Weston Public Schools, contains ZERO surprise for the Owl and 100% delight. Phil Oates, current Assistant Principal at Weston Middle School, has been named Principal –taking charge when John Gibbons hands over the reins at the end of this school year.

You can read more about Phil here on the Owl, the most recent article is about his Assistant Principal of the Year award.

Congratulations, Phil; the Owl is just so fluffed and chuffed. Yeah, yeah, so the owlets will say: “no one cares, mom.”

Go ‘cats!


On March 2, 2023, we officially launched our search for the next Principal of Weston Middle School. We were fortunate to receive a very strong applicant pool, and after an initial review, we invited seven candidates to participate in a phone interview. The phone interviews helped us identify four top candidates, all of whom are current Middle School Assistant Principals in Massachusetts. An interview team, including Middle School parents, faculty members, and District administrators interviewed the four candidates on March 29th. Following the interviews, the team participated in a consensus-building process to select which candidates to advance to the final stage of the hiring process. 

We are excited to announce that the interview team voted unanimously to invite one candidate to advance: Phil Oates, current Weston Middle School Assistant Principal, and recent recipient of the Massachusetts School Administrators Association’s Assistant Principal of the Year Award. Midge Connolly will be appointing Phil Oates to be the next principal of Weston Middle School. 

Families are invited to meet Phil on Tuesday, April 11th at the Middle School Library from 5:45 – 6:30 PM. The meeting will also be available on Zoom, and we will share a Zoom link for online attendees next week.

Thank you for your interest in the Weston Middle School hiring process. 


Dr. Midge Connolly, Superintendent of Schools

Tim Heavey, Director of Human Resources

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