“Who loves them unconditionally?”

“These children have amazing teachers here, amazing coaches, advisors, deans — adults who teach them and work with them,” said Ioanna Bailey, Drayton Dormitory dorm parent. “They care for them by mentoring them, challenging them and guiding them. But at the end of the day, they need to be loved unconditionally. That’s what I try to do.

“When I see them each night, I’m there to say, ‘You did the best you could today and that’s great. I’m proud of you.’”

Working at a boarding school is more than a job — it’s a lifestyle choice. And it’s not one that Ioanna Bailey ever thought would be for her.

Living with — and supervising — a bunch of teenage boys? No, thank you, Ionna thought. She and her husband Mike were recent empty-nesters, having launched two sons into the world. She had a vibrant career in the fashion industry in Manhattan and traveled overseas regularly. It was a cosmopolitan life that she loved. 

Admittedly, though, she was getting tired of the fast pace. And Mike was not a big fan of the Big Apple. So when he was presented with the opportunity to work as athletics director at George School, Ioanna agreed to give it a try — on one condition.

“I thought I’d retire,” she said. “I’d take time to read, relax, reconnect with friends. But I was not going to get involved in the George School community.”

And for the first two years, that’s what she did. Mike was busy in his new role, and Ionna stayed home. Then Odie LeFever, a longtime George School employee, befriended her and "introduced her to everything at George School with a lot of kindness and grace,” Ioanna remembered. Odie invited her to attend Meeting for Worship. 

“Just because I love you, I’ll come,” Ioanna told Odie. She had doubts about her own ability to sit in silence. “But I loved it right away, and I began going to Meeting every week with Odie.”

That opened the door to George School for Ioanna. Next, she met Shari Rossmann, who was the director of student activities. They shared a love of cooking, and Ioanna began helping Shari prepare food for the students.

“That was a little step into the George School Light,” Ioanna said.

The final moment of transition came when Dean of Students Erin Sio asked Mike and Ioanna to serve as dorm parents in Drayton. At the time, Mike was transitioning to a new role as director of George School Day Camp and head coach of the track program. 

He remembered, “Erin approached us and said, ‘We really need good dorm parents, and you and Ioanna would be so good for these kids. Is there any way we can talk you into that?’”

Mike agreed to serve as interim dorm head, and Ioanna worked with him as dorm parent. Right from the start, their approach worked, and soon the “interim” part of Mike’s title fell away.

“We are both passionate people,” Mike explained. “My background is in competitive athletics; Ioanna is a nurturer. We show our care and love in different ways.”

Ioanna instantly fell in love with her students, and both she and Mike felt grateful that, at this stage of their lives and careers, they had time and energy into building their dorm community. Ioanna found herself checking in on “her boys” most nights, whether it was her assigned duty night or not. 

“Somebody may need a shirt ironed, or will have a girlfriend over and I’ll want to keep an eye out,” Ioanna said. “Sometimes I have to remind someone to clean up. Sometimes I can tell by one of the boy’s mannerisms that they are distraught, so I’ll say, ‘Come sit over here, let’s talk.’ This is their home; they are in different rooms, but still, we are all in the same house.”

They acknowledge every individual birthday, even those that fall outside of the school calendar. Balloons, decorated doors and celebration. The whole dorm sings “Happy Birthday” to each student on their special day, a tradition so ingrained in the Drayton experience that alums have even returned on occasion to celebrate their birthdays in the dorm.

Both Ioanna and Mike recognize what can be learned through communal living, and while their teaching approaches differ, they are united in that they choose not to sweat the small stuff. Rather than focus on rules and regulations, they focus on guiding the students toward the positive behaviors that strengthen their dorm community. It opens doors to deeper conversations and creates a truly home-like atmosphere.

Mike holds weekly Sunday gatherings in the dorm, where the group may focus the conversation on the importance of cleaning out the sink after shaving, which often leads into broader life lessons.

“When kids come to talk with me about their lives, it lights up my life,” he said. “But I recognize that I am not their parent. I share my view, but I’ll say, ‘You need to talk with your folks about this.’”

Ioanna gently prompts the behavior she wants to see from the students. “If the garbage needs to be emptied, I simply walk to the garbage can and begin taking the bag out. And every time, several kids jump up and say, ‘No, no, no, Ioanna, I’ll do that.’ They are eager to be helpful.”

“It’s not just the food. It’s that moment that makes it sort of magical. It’s because you make it in front of them, and you hand it to them with love.”

Food — and particularly homemade crepes, her specialty — is Ioanna’s love language. “It’s not just the food,” she said, “even though it is hot and yummy. It’s about the moment when you hand it to them and exchange a few words. ‘Let’s take a picture and send it to your mom.’ Or, ‘How was your day today?’ It’s about making sure they feel seen. It’s that moment that makes it sort of magical. It’s because you make it in front of them, and you hand it to them with love.”