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Assistant to the Head of School and Administrative Leadership Team

February 25, 2026

Position OverviewThe Assistant to the Head of School and Administrative Leadership Team provides administrative support to the Head of School and other senior school leaders, thereby facilitating the smooth and collaborative functioning of the school. In so doing, they maximize the efficiency of the leadership team’s work, both individually and collectively, and ensure that Kents Hill’s leaders maintain a consistent level of professionalism and polish across their work. Responsibilities<ul><li>Assist in maintaining calendars for the Head of School and Assistant Head of School, handling correspondence related to the offices and calendars of the Head of School and Assistant Head of School with timeliness, accuracy, and professionalism. </li><li>Serve as a professional, friendly, and responsive face to the organization, guiding inquiries to the proper person on the school’s administrative leadership team.</li><li>Provide logistical and administrative support for Board Meetings, both in person and online.</li><li>Manage budgets and reimbursements for members of the school’s administrative leadership team, as needed. </li><li>Manage work-related travel details for members of the school’s administrative leadership team, as needed.</li><li>Coordinate visitor schedules for members of the school’s administrative leadership team, as needed.</li><li>Provide logistical support to the school leadership team, including the creation and updating of agendas, calendars, and collaborative work spaces. </li><li>Maintain the school’s “Master Calendar” of events, including the coordination of monthly meetings to prevent calendaring conflicts across the busy life of the school. </li><li>Provide logistical support for school events sponsored by the Head of School and/or in the Head of School residence.</li><li>Provide administrative support for Kents Hill’s relationship with the surrounding community. </li><li>Maintain confidentiality of conversations and materials within the offices of members of the school’s administrative leadership team. </li><li>Work independently and with initiative to anticipate and resolve challenges in the effective running of the school. </li><li>Demonstrate creativity and flexibility in responding to the busy life of the school, including through the adaptive use of technology.</li><li>Remain professional under pressure, including in responding to school emergencies, as directed by the school leadership team.</li><li>Other duties as assigned by the Head of School, Assistant Head of School, and Chief of Staff.</li></ul>How To Apply<ul><li>Please send a letter of interest and resume to HR@kentshill.org with the subject line "Assistant to the Head of School."</li></ul>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

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Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

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Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

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Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

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This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...