Drilling is from Morrilton, Arkansas. He received a marketing degree from the University of Arkansas at Fayetteville, and a degree from the Advanced Management Program at Emory University. He began working for SBC Arkansas in 1979.
Drilling became president of the Arkansas branch of Southwestern Bell in July 2002. Drilling was 2005 board chairperson of the Greater Little Rock Regional Chamber of Commerce and 2008 president of Fifty for the Future. He is also a director of Simmons First National Corporation, Arkansas Children's Hospital, and the Little Rock Public Education Foundation. He is president of the Big Brothers and Big Sisters of Central Arkansas Foundation. He has served in a leadership position on Vision Little Rock, the Arkansas Children's Hospital Research Institute Board, the UAMS Foundation Board, the Arkansas State Chamber of Commerce Executive Committee, the Sam M. Walton College of Business Dean's Executive Advisory Board, the UAMS BioVentures Advisory Board, the Governor's Information Technology Oversight Committee, the University of Arkansas 2010 Commission, Little Rock Public School Foundation Board, Lyon College President's Council, and UALR College of Business Administration Advisory Board.
Drilling lives in Little Rock with his wife Cindee.