This paper presents data gathered as part of an evaluation study of a grant-making initiative undertaken by a national organization involved with Jewish day schooling. The initiative disbursed grants to 30 established Jewish day schools for use during the 2002-2003 school year. The goal of the initiative was to encourage and support day schools to effectively utilize expert assistance in order to facilitate growth and improvement in three key areas: (1) Judaic studies; (2) the educational program in general; and (3) management/organizational development. The goals of the evaluation study were to inform the funding organization about the grantees' experiences working with the funder; to elicit and report learning from the schools; to assess the early impact of their investment; and to gain a better understanding of what it takes to effect change and improvement in Jewish day schools. The data collected in this study consist primarily of the perceptions and reflections of school informants--primarily heads of school--and the consultants that worked with schools. The study focuses on the key areas of school or organizational functioning that have been identified as significant by the literature on change. This paper documents those barriers and challenges to change processes that appear to have been experienced in those key areas by the schools in the study. (Contains 2 footnotes and 2 tables.)