[5][6] Her father served as an Indiana deputy attorney general from 1930 to 1932 and was a prominent civil rights lawyer in the state and involved in the early efforts of the National Association for the Advancement of Colored People.
[4][9] In February 1965, Conn joined Marie T. Lauck and Jane Hunt Davis to form a private law practice in Indianapolis.
[10] Later that year Conn began serving as a Marion County, Indiana, deputy prosecuting attorney in the Nineteenth Judicial Circuit.
[9][11] A Republican, Conn twice won elections as state representative from Marion County (in the multi-member 26th district) to the Indiana General Assembly.
[7][9][10] In 1968, while still serving as a state representative, Conn became an assistant city attorney for Indianapolis under Richard Lugar's mayoral administration and remained in that position until 1970.
[5][9] Conn also made a bid for Marion County municipal court judge in 1974, but she was defeated in the primary and remained a public defender until her death in 1981.
Conn also remained active in the Talladega College Alumni Association, as a member of the advisory board at Vincennes University, and the Chi chapter of Delta Sigma Theta in Indianapolis, where she served as its president in 1963.
The Indiana Senate adopted a resolution memorializing her service and President Ronald Reagan signed a condolence note sent to Bailey's daughter, Matinel Brandon Conn.[6] She is buried at Crown Hill Cemetery in Indianapolis.