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The Head's Assistant: Circle of Trust

Wednesday, February 8, 2017  
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By Christina Mimms, SAIS

A head’s assistant wears many hats: board liaison, calendar master, event organizer, human resources manager, travel agent, and even security guard. While the exact responsibilities vary from school to school, the qualities of the person remain much the same – school heads need someone who is responsible, flexible, and, most importantly, trustworthy.

For Kathy Corwin, executive assistant to Dr. Leonard Kupersmith, head of Christ Church Episcopal School in Greenville, SC, her job may include “anything from A to Z,” she said. “I look at my role as customer service, internal and external.”

She organizes information for the school’s board meetings, monitors the head’s budget and his calendar, coordinates interviews for high-level positions at the school, and organizes faculty/staff events. Corwin also is second in line for emergency management communications.

“I keep a big to-do list but I don’t marry myself to that list,” she said. “God has put me in this position to teach me flexibility. Each day brings its own challenges and needs.”

One need that all head’s assistants hold dear is confidentiality. As someone who likely attends board meetings, sets up meetings with high-level sources, and even serves as a sounding board to faculty and staff members facing a personal challenge, the head’s assistant must be discreet and silent much of the time. “It’s a sacred position at the school,” Corwin said. “You carry so much confidential information.”

Often when people seek a meeting with the head of school, they must turn to the head’s assistant first. “The office of the head never closes, but the head isn’t always available,” said Dr. Michael Ehrhardt, head of Cary Academy in Cary, NC. “The assistant needs to be available and supportive so that people know they can come in and seek advice and guidance.”

The head’s assistant also knows that any day can go haywire. A snow day, a canceled meeting, students becoming ill on a field trip, or a water main break near campus can derail a carefully planned schedule. “It’s important to present a calm and professional demeanor,” Ehrhardt advised.

When problems develop, often the head’s assistant serves as the messenger to inform others of the issue. The person may be the first to know or even the first responder in a situation. “Often we are operating very quickly and don’t have time to get a full story,” Ehrhardt said. “I appreciate my assistant’s [Kim Fogleman] ability to brief me.”

Assistants hold a lot of important and sensitive information – organization and sensitivity are key. "The administrator’s assistant may know more about the inner-workings of the organization than anyone else in the school, perhaps even the head," said SAIS President and former Head of School Dr. Kirk Walker. "But while they may be privy to a host of sensitive information, they must operate under a standard of confidentiality stricter than that of the head. There is only one person to whom they can share their information and only one person to whom they report. It is a tough job, and sometimes a lonely one."  

Operating in a high-intensity and high-energy area of school life can be draining at times. Some days feel like a whirlwind. The head’s assistant enjoys few breaks but “you have to take care of yourself,” Corwin said. “You need to give yourself time away. You are a limited resource.”

Corwin received an appropriate Christmas gift last year – a sign that reads, “You can do anything but not everything.”

When Laura Benzing first started as assistant to Dr. William George, head of Asheville Christian Academy in Asheville, NC, she quickly realized she could easily become overwhelmed. After attending the SAIS Summer Institute for the Head’s Assistant, she learned from others about setting boundaries. “Keep communication open so you know the expectations and don’t be afraid to ask for what you need,” Benzing advised. She set some rules for herself as well. “My boss can email me any time but I only answer at certain times,” she said. 

She deeply values their relationship, as well as her position, which includes serving as the assistant to the board and all human resources work, from employee background checks to contracts to benefits. “I know everyone by name and I love the interaction with the faculty,” Benzing said.

Corwin’s office is located in the lower school at CCES, guaranteeing her some smiles each day. “I love hearing the interactions of the students and the patience of the teachers,” she said. “The sweetness and the sense of safety the children feel is evident.”

Head’s assistants, and any administrators, would be well advised to spend time outside of their offices when possible. Students’ and teachers’ friendly faces can be a great resource for stress relief. Finding a support network helps as well.

“There are great opportunities for head’s assistants with professional organizations,” Ehrhardt said. “There are pressures unique to that role and they need a peer group to talk with about issues, as well as professional development for technology and other training.”

Assistants also appreciate being recognized, as oftentimes people who work behind the scenes are overlooked. Corwin and Benzing both report they have very supportive bosses. “It’s a really important role on multiple levels that we don’t always get to celebrate,” Ehrhardt said. 

School heads may want to go ahead and mark their calendars for Administrative Professionals Day on April 26. “It’s the one thing I have to remember!” Ehrhardt laughed. “She reminds me about everything else.”

For more information about the SAIS 2017 Institute for the Head’s Assistant, June 20-21 at Emory Conference Center in Atlanta, visit  

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Institute for New Heads
June 13-15, 2018 | Peachtree Corners, GA
An informative program preparing administrators for a successful transition to headship.

Institute for Heads
June 19-22, 2018 | Asheville, NC
This energizing and nurturing retreat offers an opportunity for thoughtful dialogue and engagement with colleagues on key issues facing heads of school and their spouses.

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