From 1959 until 1965, Keady was the head coach at Beloit. Keady recognized the importance of education and never stopped studying, even when coaching. He received his master's degree in teaching from Kansas State in 1964. He has a record of 142 wins to 47 losses while coaching high school basketball (.751). He began his career at Beloit in 1959, just two years after graduating from college. In three seasons, he had a record of 30-12. In 1962-63, he led the Wildcats to their first undefeated regular season (21-0) and first playoff appearance. The team was eliminated by eventual state champion Janesville High School. In 1963-64, Beloit went 20-1 and won its second consecutive state title. The team was made up of players from Wisconsin and Illinois - many of them new to the area - which helped it win over opponents. For this reason, some say Beloit was ahead of its time with its successful recruiting program. After the 1963-64 season, Keady left Beloit for an assistant coaching position at Northwestern University. He stayed there for one year before returning home to take over the head coaching job at Greenfield High School in 1965. During his second stint at Greenfield, he had a record of 44-13 and led the Knights to the state semifinals in 1971.