First-year Chaparral Elementary School Principal Ann O’Connor is in a good place. “It’s been fantastic,” said Claremont Unified School District’s newest head administrator.

“I just love the school. And the staff and the parents really do like each other. It’s a wonderful, warm place to be. I couldn’t ask to be in a better place.”

Ms. O’Connor spent the past 14 years at Sycamore Elementary, first teaching kindergarten, and then a second/third grade multi-age class. In an unintended bit of symmetry, she spent the previous 11 years teaching second- and sixth-graders at Upland’s Sycamore Elementary, and in staff development in the city’s school district office.

All told she’s been in education for 27 years as a teacher, administrator and now as a principal. It’s a long tenure for anyone, but considering she’s just 49, she’s poised to have a 40-plus year in education.

“I’ll be here as long as they’ll keep me,” she said. “I don’t have any plans to go anywhere. I’m really enjoying it. It’s a been wonderful.”

Her style is less stern headmaster and more congenial, trusted confidante. “I get in classrooms as much as possible,” she said. “And it’s not like they’re changing their behavior when I’m there. It’s a very natural fit. When I come in they’re comfortable. I’m also visible on the playground. They feel they can come to me.”

She met her husband, Claremont High School Principal Brett O’Connor, while she was teaching in Upland. The couple married relatively early and hit the ground running, having three sons in close succession.

“We came to Claremont because we wanted to put our kids in the Claremont schools.” Their boys all went to Sycamore, El Roble Intermediate and CHS. Now 22, 21, and 19, they’re all in college.

“I guess it’s a fairy tale come true,” Ms. O’Connor said.

A native of Mission Viejo, she’s a 1991 graduate of San Diego State University, where she earned her bachelor’s degree in education. She went to work shortly after, and in her spare time earned her master’s in educational administration from Cal State University San Bernardino in 1996.

Switching roles from teacher to principal can be problematic, but Ms. O’Connor seems to have made the transition gracefully.

“The pressure’s different,” she said. “I’m still dealing with students on a daily basis, but I’m looking at the overarching picture.”

Some educators miss the day-to-day, direct interaction with students when they move into administrative positions. Ms. O’Connor’s management style has helped quell that potential downside.

“I am out there to greet the kids every morning, and I’m in the classroom quite a bit, so I still feel like I’m getting a kid fix,” she said. “I still see them grow and change.”

One challenge has been the array of issues that inevitably arise with 650 students, their parents and caregivers looking to her for leadership.

“Your day is never what you think it’s going to be,” Ms. O’Connor said. “Things come up all day that you need to take care of as they come. I see it more as being a problem solver. Sometimes we just have to work through it until we can find a place where the parents, faculty and staff are happy.”

She takes a whole child approach to students’ issues, helping to “make them as well rounded as possible,” she said. “It’s about helping them to be the best they can be.”

Her varied background has prepared her well for being in charge. She’s been part of many CUSD committees, including the Common Core Steering Committee and District Technology Leadership Team. She is trained as a trainer of trainers in Thinking Maps and Robert Marzano’s Strategies that Work. She’s provided staff development trainings in curriculum design and classroom management.

While in Upland she was also instrumental in training and management. She’s also freelanced as a consultant, training administrators, teachers and instructional aides in K-12 schools in all subjects as well as in classroom management and lesson design. She’s also trained principals.

“It’s not that different,” Ms. O’Connor said of the difference between teaching and being Chaparral’s principal. “You make yourself available, and set aside the time that parents need to communicate with you, and when they come to you you make sure that you get back to them in a timely manner.”

Her new job, with its expanded hours both during school and in the summer, wasn’t an option when her kids were young. The O’Connors decided she would stick to teaching until their boys were off at college. Now that she’s free from packing lunches, attending kids’ school events and tackling the mounds of laundry produced by three athletic teenage boys, she can afford to spend the extra time away from home.

“I love teaching and am passionate about students and giving them the best I have every day,” she said. “I am now ready for a new challenge. Now that our youngest son is in college, the time is right for me to take the next step in my career and I couldn’t be happier.”

One does wonder what kind of shop talk she and Mr. O’Connor—two CUSD principals—share over the dinner table.

“We don’t really do too much of it,” Ms. O’Connor said. “We do talk a little bit of shop, but no more than when I was teaching. It does help to keep things in perspective and just for balance and someone to bounce ideas off. He knows the culture of the community.”

That empty nest, when a formerly raucous, bustling home is suddenly quiet, can also be a tough adjustment. Characteristically, Ms. O’Connor said her family is doing just fine.

“It’s actually been nice,” she said. “You kind of have time to remember why you got married and what you love about each other. It is great having the kids home though, and we love having them here, but when they’re back at their colleges or universities Brett and I pick up where we left off.”

—Mick Rhodes

mickrhodes@claremont-courier.com