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Hiring Season

Heads of School know that January/February is the absolute pinnacle of the high paced reality of running a school. So many things come together at once: admission decisions, contracts for employees, snow days, and hiring jump to mind. I have always felt that bringing new talent to campus is likely the most important role of a Head of School. Without question finding people with the right skill set and temperament to make classrooms come alive is essential to the future of the school and the experience of your children.

Yet we also know hiring is an imperfect science. It is a blend of art and science when one tries to understand not just skills but ultimately the nebulous notion of “match” with the institution. It is one of the most enrapturing parts of my job – trying to formulate questions that will somehow unravel the mystery of hiring one candidate at a time. At the end of it all, there is always a blend of personal emotional intelligence (e.g. relationship-building) that seems most essential, but a depth of background and content knowledge that is almost equally important. Trying to assess attitude, work ethic, and resilience are all part of the puzzle as well.


While it is clearly one of my favorite aspects of my work, it can be the most challenging. The Head of School Office seemingly grinds to a halt this time of year as we turn our attention to finding the best educators in the country. However, after eight years in this seat I have found hiring can also be the most humbling. There is no reference, background check, or question that can fully predict success in a new environment. There is always a leap of faith on both sides in the end, and this is part of what makes it so fascinating. Given we are deep into this world as of this writing, I wait to see who might be new to the Hilltop next year.

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