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Monday October 3rd

Tiffany Cheshire appointed principal of Guy B. Phillips Middle School

“Ms. Cheshire is a beacon of light,” Savada Gilmore, theater and creative writing teacher at Phillips Middle School, said.

Tiffany Cheshire poses for a portrait outside Guy B. Phillips Middle School on Tuesday, April 12, 2022. Cheshire was appointed principal of the school this month after serving in an interim role since October 2021.
Buy Photos Tiffany Cheshire poses for a portrait outside Guy B. Phillips Middle School on Tuesday, April 12, 2022. Cheshire was appointed principal of the school this month after serving in an interim role since October 2021.

On April 8, Tiffany Cheshire began her role as principal of Guy B. Phillips Middle School. 

Cheshire has worked at the school since August 2017, when she was hired as an assistant principal. She began serving as interim principal in October.

The Chapel Hill-Carrboro City Schools Board of Education appointed her as the school's principal at its April 7 meeting.

Cheshire has worked within CHCCS dating back as far as 2009, when she began her time in the district as a K-5 substitute teacher. She spent two years as an assistant principal in Alamance-Burlington Schools before coming back to CHCCS in 2013.

Over the years, she has served at CHCCS elementary schools, including Seawell Elementary School as a principal intern and at McDougle Elementary School as an assistant principal.

Cheshire said she has been able to maintain relationships with some of her former elementary school students. This year at Phillips, she said she has two students in her eighth grade class that she knew at McDougle Elementary.

“The fact that I've gotten to know them as students and people and their families over the last few years, I don't take that for granted," Cheshire said. "It's amazing to create relationships that are longer than just a few years.”

Savada Gilmore, theater and creative writing teacher at Phillips Middle School, said this emphasis on relationships is part of what makes Cheshire stand out. He said he believes she is a good fit to take on the role of principal.

“Ms. Cheshire is a beacon of light,” he said. “I can say that 100% unequivocally that she's going to have faculty, staff, students and parents’ best interests at heart.”

Gilmore is currently in his third year of teaching. He said he’s noticed an increase in faculty and staff morale since Cheshire started the position of interim principal.

As a new teacher, he said he has been able to thrive in his role because of Cheshire's support.

“I know that my strength is in working with people," Cheshire said.

Lisa Clarke, who has been teaching sixth grade science at Phillips for nearly 30 years, said Cheshire looked out for teachers' best interests when times were difficult — especially throughout the pandemic.

"It's like, ‘Oh, Tiffany, she's got your back,’” Clarke said. “And that's never been a question. In 29 years, sometimes you feel that, sometimes you don't. Tiffany let you feel that.”

Since the start of the pandemic, Cheshire had to handle a variety of challenges and accommodate teachers who have needed to work from home.

One of the challenges was high rates of staff turnover. Since her promotion, one of Cheshire's priorities has been filling these vacancies.

During the search process, she said she wants to focus on hiring candidates that are diverse.

"One thing that we've talked about is making sure that our staff reflects the students that are in it," Cheshire said. "So just making sure that when students look at our staff, they see someone who either physically looks like them or maybe believes similar things."

Cathryn Wirz, seventh grade math teacher at Phillips, said Cheshire has also been implementing restorative practices when mitigating student disputes, which has had a positive impact on the community.

“She does a lot with trying to reflect on situations,” Wirz said. “So if something happens with students or between students, she gets them together, having that restorative conversation so that we can prevent those issues in the future."

Cheshire also uses an open door policy, where parents or community members can visit her office whenever needed.

Chapel Hill-Carrboro Public School Foundation bookkeeper Shannon Grabowski, who is a parent of a Phillips Middle School student, said the policy has been helpful for members of the PTSA when they have questions.

“I feel like she'll advocate for everyone,” Grabowski said. “She doesn't pick a side. She’ll advocate for everyone to make sure that the best outcome happens.”

Cheshire said she imagines herself working with students and families for years to come.

“I hope that I can continue to build the relationships that I already have with schools all across the district," she said.


Tiffany Cheshire poses for a portrait outside Guy B. Phillips Middle School on Tuesday, April 12, 2022. Cheshire was appointed principal of the school this month after serving in an interim role since October 2021.


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