According to research, dual enrollment (DE) participation is associated with a range of positive college outcomes (such as GPA, credit accumulation, and persistence) for mainstream students, as well as those in career-technical education pathways and programs. In addition, lower achieving, lower income students may experience greater gains from dual enrollment than higher achieving, more advantaged students. This paper presents a list of guiding questions that should be asked at various stages of implementing a dual enrollment program, starting from what to ask when seeking to establish a partnership, to the what should be asked when evaluating the success of the program. (Contains 2 footnotes.) [For related reports, see "What We Know about Dual Enrollment. Research Overview" (ED530528) and "City College of San Francisco Academy and Pathway Dual Enrollment Program. Case Study" (ED530529).]