Skilling began his broadcasting profession at age 14, while still attending school at West Aurora High School, working for WKKD-AM & FM. He then worked in Aurora, Illinois, at WLXT-TV (Ch. 60).
Skilling attended the University of Wisconsin–Madison to study meteorology and journalism and while there, he worked at WKOW-TV and WTSO AM in Madison, Wisconsin. He also served as a meteorologist at WITI in Milwaukee, Wisconsin, from 1975 until 1978.
Skilling is famed for his elaborate weather presentations which involve the use of advanced tools and technology. He is also widely accepted and respected for his pinpoint accuracy in weather forecasting.
