Technology in the 21st century is dominating the way we live our lives. Computers, Internet, cell phones, global positioning systems, and video game programs all shape the way we view the world. As technology advances, expectations for the use of technology and the data that technology provides advance. Technology is making it easier for our society to become data driven. Many, if not all, decisions made by businesses, school districts, and major corporations are based on collected data. The idea of collecting data about the strengths and weaknesses of a physical education program in an efficient manner left the author with an interesting question: How can one incorporate technology into physical education in a way that would collect assessment information that can be converted into meaningful data for students, staff, and administrators? The answer that the author came up with was to use personal digital assistants (PDAs).