[1] During her childhood, Stiff played basketball for Catholic Youth Organization and cites her coach, Sister Mary Cleary, as a major influence on her athletic career.
[2] Following graduation, Stiff was recruited to play collegiate basketball at Southern Connecticut State University by a coach who left before she began her freshman year.
[1] With her Bachelor of Science degree, Stiff began her coaching career with the Western Connecticut State University's field hockey team from 1983 until 1985.
From there, she transferred to the Rensselaer Polytechnic Institute where she served as head coach for the women's basketball team and a physical education instructor for three years.
After being rejected by North Carolina's head coach Sylvia Hatchell, she approached Tennessee's Pat Summitt who accepted after convincing from Stiff that it was "for the good of the game."
[7] In 2008, Stiff was named the top advocate for women's basketball by The Tampa Tribune, who recognized her efforts to raise exposure for the sport through ESPN.