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Cyclical program reviews (CPRs), also called periodic or academic reviews at institutions of higher education, are undertaken to ensure that academic programs meet a variety of objectives related to teaching and learning, as well as professional credentialing, quality assurance, and institutional requirements. Preparing, reviewing, and implementing a CPR requires significant time and effort for those assigned to this task, especially if the program has never previously been through a CPR. Much has been written on how to undertake a CPR (Bresciani, 2006), what measures are useful in assessing programs (Jayachandran et al., 2019), and some of the problems that external reviewers encounter with CPRs (Halonen & Dunn, 2017). This article, however, provides new insights concerning important considerations that should be addressed when preparing to undertake a CPR—from the perspectives of both administrators and faculty at smaller institutions where the number of faculty may be small and resources for the CPR process are often limited. Drawing on a case study of CPRs in several social sciences programs and a broader survey of those involved in CPRs from 2015-2020 at a small Western Canadian university, the authors identify key issues in preparing a CPR, such as the timing of the review, the advantages and disadvantages of an individual approach versus a team approach in preparing the CPR, the role of administrators in the CPR process, the importance of institutional templates in preparing the CPR, and the need for clearly identified program learning outcomes to guide the CPR process. This article also examines how a pandemic can impact the CPR process.