Alison Squire is a native of the Washington area. She graduated with honors from Amherst College in 2004 with a bachelor's degree in American studies. As part of the District of Columbia Teaching Fellowship, Alison completed her master's degree in the art of teaching at Trinity University. Previously, Alison taught students with special needs for two years in Clark Elementary School in District of Columbia Public Schools (DCPS). She taught seventh grade language arts and social studies at City Collegiate.
After attending the Paul Klee Summer Teaching Institute in summer 2006, Alison and her colleague Georgia Stockdale were selected to become Paul Klee mentor teachers. While attending the institute, she and Georgia formulated an integrated teaching unit based on what they had learned about Paul Klee, designed to connect the artist's work to their students' sense of identity during adolescence. In Alison's language arts class, students wrote reflective journal responses about Paul Klee's work, then wrote about their self image, the image they present to the community, and changes they have seen in themselves.