Bolek got his start in coaching with Cuyahoga Community College in 1979 and 1980. During his tenure there, they were OhioJunior College champions. At Mississippi State University in 1981, Bolek was a graduate assistant for the team as they made it to the College World Series. He then managed at the professional level (see chart below) and spent two years as a coach for the Cleveland Indians (1992–93). Bolek became the Director of Baseball at IMG Academy in 1995.