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Schools have become places filled with digital tools. Despite this fact, school leaders find technology planning to be an area of relative weakness. This chapter describes the experience of four school leaders who adopted an unfamiliar strategy for making technology decisions. The leader participated in a series of semi-structured interviews. Two leaders displayed characteristics of early adopters of the innovative planning strategy and two displayed characteristics of early majority user of the strategy. Profiles of the two types of leaders are presented. The aspects of the planning strategy that differentiated it from more familiar planning strategies for these leaders are discussed.