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Phillips Middle School principal Tiffany Cheshire wins CHCCS principal of the year

Tiffany Cheshire sits outside of Guy B. Phillips Middle School on Tuesday, April 12, 2022.

On April 12, Guy B. Phillips Middle School principal Tiffany Cheshire walked into a meeting with her supervisor. She was told there were people who wanted to speak with her about Phillips' performance — and she was prepared for something pretty contentious.

But, when she came around the corner for what was supposed to be her meeting, she saw students lined up and down the hallway.

Still not knowing what the commotion was about, she started to jog.

"If I've got a tunnel of people, let's have some fun with it," Cheshire said.

She was completely surprised when she walked into the gym and saw Chapel Hill-Carrboro City Schools Superintendent Nyah Hamlett standing before her. Hamlett then announced that Cheshire had won the district's Principal of the Year award and brought out her husband and two children.

“I try to make sure I still got something left for them and I’m not completely empty from pouring into other kids at school… Our priority is making sure that our kids also feel like they're important to us and their priority,” she said. “Them getting to be there and getting to see that meant the world to me.”

Cheshire began working in education in 2005 as an elementary Spanish teacher. She then went to get to get her master's in school administration from UNC.

While she was in graduate school, she worked as a substitute teacher and a principal intern. After she graduated, she served as an assistant principal in the Alamance-Burlington School System. She began working at Phillips in 2017 as an assistant principal and became principal in 2022.

Allison Crosetto is the school social worker at Phillips and was there when Cheshire started as an assistant principal. She said Cheshire is the epitome of a leader and makes community outreach a priority. She said as a social worker, that has been incredible for her. 

"She's gonna have my back and she trusts me, which is a really hard balance for somebody to have in their employees, but I feel that daily," Crosetto said. 

Cheshire said one of her favorite parts of her job is that regardless of what the day looks like, she gets to connect with students.

“It feels like every single day is different in a good way,” she said. “I really like the variety and I love the connection that I get with kids and staff.”

Austin Tortorici, a sixth grade science teacher at Phillips, said Cheshire leads with a people-first approach. He said she empowers staff to take the lead on things, such as discussing school policies with all who are involved in the decision before generating them.

One of Phillips' assistant principals, Glenn Estacio, has been working with Cheshire for almost two years. Phillips was the only middle school in CHCCS to exceed growth in student achievement last year, which Estacio said is a combination of the work of the whole school and a testament to Cheshire’s leadership.

“I feel like for me, this is kind of a combination of the growth and the work that Phillips has put in for the last few years,” Cheshire said. “It's not really about me, it's really about all the people around me that have been able to get me to this position, everybody working hard.” 

Phillips' other assistant principal, Shanice Harrington, said working with Cheshire is a pleasure. 

“Part of the reason why I really wanted to work with Ms. Cheshire under her leadership is because she always has just a bubbly personality, no matter what room she walks into,” Harrington said.

Cheshire said she doesn’t think this award will change anything for her directly, but it does mean that all of the school's work has been recognized. She said she hopes people see Phillips and want to work there, that people move into the community and want to send their children to Phillips.

@DTHCityState |

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