There Are Many Paths to Leadership

 Amy Jolly is the Head of Applewild School, an independent school an hour outside Boston. Previously, Amy served as Head of the Maine Girls’ Academy, which you can learn more about in this episode of The Enrollment Spectrum Podcast.

She honed her skill set with years of work in admissions and financial aid. In her current role, Amy’s leveraging her enrollment expertise to launch a new boarding program for international students. In our Q&A, learn more about her leadership journey and how it prepared Amy to lead a school. 

Who do you look up to as an inspiring leader from the world outside schools?

I have been a big fan of Jim Collins (author of Good to Great) for my entire career. His thoughts on how to build a team and manage an organization are timeless. His ideas around getting the right people on the proverbial bus is a guiding principle. Schools are very human-centered enterprises, so having the right people in the right positions is the only way to achieve excellence.  

On your pathway to leadership, who has been a valuable mentor for you and how did they help you?

I am lucky to have friends who encouraged me to take the plunge and apply for headships. I'm embarrassed to admit, but they saw my potential before I did. I've often reflected on why it was like that. I think, if you are successful in admissions, no one is eager for you to move on! 

What advice would you offer an enrollment professional who wants to grow their own leadership capacity?  

I encourage enrollment people to fearlessly engage in the broader life of the school. Volunteering for task forces, participating in committee work, observing classes, and developing ideas for new programs are all ways to show an interest and competency in working at an institutional level. Get out there and share your expertise by speaking at regional and national conferences and mentor others!  Read about educational trends and topics to become current and fluent in the present educational vernacular.

It is my experience that enrollment management experience is excellent preparation for leadership. There is no other role in a school that allows one to think strategically, be accountable for finite goals, to see every teacher in action, to hear directly from the marketplace about the institution's strengths and weaknesses, and to practice addressing difficult interpersonal conflicts (every denial we issue is an opportunity for this!).  Schools need more heads with the skills learned in enrollment management. Enrollment management professionals bring entrepreneurial and results-focused leadership!


Amy Jolly - Applewild SchoolAmy Jolly, Head of School — Applewild School (MA)


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