This qualitative case study explores considerations for leading instructional initiatives in high-performing high schools by examining a pilot one-to-one laptop initiative in a Catholic high school. As participant-observer, Cameron collected data through open-ended electronic surveys and the left- and right-hand column case method and reviewed documents to compare responses from those involved in the initiative and their department chairs (i.e., immediate supervisors to the teachers involved in the pilot). Findings and discussion reveal how two participant groups made different sense of the pilot laptop initiative. We advocate that an awareness of sensemaking and sensegiving are necessary leadership considerations when leading instructional initiatives, particularly if the new instructional approach differs significantly from the status quo.