Hale played minor league baseball from 1983 to 1988 in the Boston Red Sox and Oakland Athletics organizations.

Hale started his managerial career in 1993 in the Boston farm system with High-A Fort Lauderdale Red Sox in the Florida State League.

That season, he also coached United States team in the All-Star Futures Game at Fenway Park, and was honored as Minor League Manager of the Year by Baseball America, The Sporting News and USA Today Baseball Weekly, as well as winning Eastern League honor.

Following the 2012 season, on November 24, 2012, Hale was named as the new bench coach for the Toronto Blue Jays, replacing Don Wakamatsu.

He was named to the major league coaching staff in July 2020, as Eric Young opted not to travel with the team during the 2020 season, shortened as a result of the COVID-19 pandemic.