Ragland grew up in Wylam. He graduated from Ensley High School, being among the first African American students to integrate there. Upon graduation in 1974, Ragland enrolled in the University of Alabama at Birmingham (UAB), eventually settling on a major in elementary education.
In 1978, Ragland got his first full-time teaching job at Center Street Elementary School, and was transferred to Huffman Middle School after three years. In 1989 he returned to Center Street Elementary as assistant principal, then in 1990, left the Birmingham area to become principal of Western Height Elementary School in Eufaula.
In 1998, after he was named Alabama National Distinguished Principal, he returned to serve as early childhood/elementary personnel coordinator for Birmingham City Schools central office. In 2003 he became a hearing officer for the system. In 2004, he left Birmingham again to become superintendent of Greene County, Alabama schools until 2007.
After Donnie Breaseale announced he was retiring effective on August 1, 2007, Ragland was selected from a field of five candidates for Midfield's superintendent position, marking yet another return to the Birmingham area for him. In 2010, Ragland informed the board that he would rather not extend his contract, retiring on September 1 of that year..
- Plott, Bill (July 27, 2007) "Midfield chooses Ragland as new superintendent." The Birmingham News
- Plott, Bill (July 31, 2007) "Superintendent touts healthy dose of academic competition." The Birmingham News
- Norris, Toraine (April 5, 2010) "Midfield school superintendent won't try to extend contract." The Birmingham News