Skipper has long been active in diversity initiatives and recruiting efforts on a local and national level. He has worked with the chief judge and other court leaders of the U.S. District Court for the Eastern District of Pennsylvania on committee projects to expand diverse jury pools as well as designing mentee training programs and recruiting efforts for diverse attorneys seeking appointment to the Criminal Justice Act Panel.

Skipper has also participated in recruiting and outreach efforts for diverse candidates at Duane Morris. Additionally, with the launching of the Federal Defender Diversity Fellowship Program, Skipper served as the co chair of the strategic planning committee where he was instrumental in the design and structure of the interviewing, training and selection committees which sought to match recent diverse law school graduates with Federal Defender Offices throughout the country. He has advocated for increased diversity throughout the legal profession.