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Recent research has emerged suggesting there are many diverse contemporary school systems that have begun redesigning core organizational structures in pursuit of the broad policy goals of educational excellence and equity (e.g., Peurach et al., 2019). One of the most notable of these changes has been the emergence of what Bulkley, Marsh et al. (2021) refer to as “portfolio-managed models.” (or PMMs) In this paper, we set out to investigate superintendent perceptions of organizational conditions in regional, Catholic (arch)diocesan systems of schools that have long had decentralized, portfolio-style approaches to system organization. The paper's findings center on the embrace of limited role of superintendent leadership, constraints afforded by organizational structures, and minimal attempts to disrupt these patterns of system functioning.