Confidently You: Women in Leadership · Rebecca Malotke-Meslin & Lynne Macziewski

Headspace: Polly Fredlund

·52 min·3 clips

"Admissions officers, you are the chief revenue officers."

1. Confidently You: Women in Leadership features Polly Fredlund, head of school at Westover in Middlebury, Connecticut, as the episode's guest. 2. Rebecca Malotke-Messlin and Lynn Macheskey interview Polly, drawing on Rebecca's coaching background and Lynn's role as head of the Baldwin School. 3. The episode asks how Polly moved from admissions and communications into headship while staying authentic as a woman leader. 4. Polly says she has been "in school since pre-K," starting as a student before becoming a lacrosse coach, outdoor leader, English teacher, and dean of students at Forest Ridge School in Bellevue, Washington. 5. She explains that comparative literary studies did not map to a direct job, so education became the place where she could enter schools and build a career. 6. Polly describes returning to her alma mater, Hathaway Brown, in Cleveland, where Sarah Leota Johnston mentored her in the admissions office. 7. She says admissions helped her work toward more diverse school communities because Hathaway Brown in the 1980s was predominantly affluent and white. 8. Polly details her 10 years at the Bush School, where she moved into senior leadership, became director of admissions and financial aid, and later took on communications, marketing, summer programs, and a house program. 9. She describes a Washington, D.C., move that did not work, strained her marriage, and ended with a call to Frank Magasin asking whether she could return to Bush. 10. Polly says she answered three questions honestly, kept a relationship intact, and returned to Seattle for another long stretch of work. 11. She calls her current headship at Westover "an earned position" and says she is "120% ready" after years of preparation and family tradeoffs. 12. Polly says the biggest personal hurdle was asking her children to sacrifice for her career, especially when her daughter was entering 11th grade. 13. She also links headship to financial independence, saying the salary matters because independent-school educators often struggle with bills in coastal cities like Seattle. 14. Polly argues that admissions is the same intersection as headship because it connects internal school life with external perceptions from alums, families, and the marketplace. 15. She says admissions work teaches relationship-building, delivering bad news, finance committee work, and board exposure, all of which translate directly to headship. 16. Polly describes being told she was a "real sweetheart" after a headship interview and says women in leadership can be friendly, relational, and still make hard decisions. 17. She says a strengths assessment confirmed her love of learning, which shows up in chapel programming, Lumina events, and a bridge-building conversation on Israel and Gaza with a monsignor, a rabbi, and a local mom. 18. Polly's tone shifts between practical leadership advice, candid family stories, and reflective discussion, while Rebecca and Lynn respond with their own examples and agreement. 19. Listeners interested in women's leadership in independent schools will get the most from this conversation. 20. Listeners looking for a celebrity-style or highly scripted interview probably will not.

As heard by us

Admissions and enrollment are framed as direct preparation for headship.

Polly Fredlund's conversation treats admissions and enrollment work as real preparation for headship, not a side route around it. The strongest stretch comes when it draws a clean line between the job schools say they want and the job enrollment leaders actually do: shaping the…

Read the full review in PlayNext →

Why you'd press play

You want a candid look at how admissions work can prepare you for headship.

Read the full recommendation in PlayNext →

Listen to the show on

Apple Podcasts Spotify

Play clips from this episode More from Confidently You: Women in Leadership