After his playing career Hill returned to Princeton to complete his baccalaureate degree, earning a B.A. in psychology in 1985. He then became an assistant coach at Lawrenceville School in Lawrenceville, New Jersey. Three years later he was promoted as head coach. Hill won two Coach of the Year Awards and in 1990, led Lawrenceville to the New Jersey State Prep School Championship.
In 1991, Hill entered the collegiate level by returning to his alma mater Princeton as an assistant coach under Pete Carril. In 1995, he succeeded Jack Rohan as head coach at Columbia University. In eight seasons as head coach of the Lions, Hill was unable to lead the team to a winning campaign and compiled a 72–141 record. On March 10, 2003, two days after Columbia finished with a 2–25 record (0–14 in Ivy League play), the worst season in the school's 103-year basketball history, Hill was fired.
During the 2003–04 NBA season, Hill became an assistant coach to Terry Stotts in Atlanta. After one season, he was hired by the Boston Celtics to aid Doc Rivers as assistant coach. When Rivers became the head coach of the Los Angeles Clippers, he retained Hill as an assistant.[2] On November 16, 2020, the Clippers announced that Hill would not be retained as assistant coach.[3]
On June 9, 2021, Hill was named Director of Basketball Administration for men's basketball at Indiana University. He and Indiana head coach Mike Woodson coached together with the Clippers from 2014 to 2018.[1]
