A qualitative study using grounded theory methods was conducted to (a) examine what philosophy of technology assumptions are present in the thinking of K-12 technology leaders, (b) investigate how the assumptions may influence technology decision making, and (c) explore whether technological determinist assumptions are present. Subjects involved technology directors and instructional technology specialists from school districts, and data collection involved interviews and a written questionnaire. Three broad philosophy of technology views were widely held by participants, including an instrumental view of technology, technological optimism, and a technological determinist perspective that sees technological change as inevitable. Technology leaders were guided by two main approaches to technology decision making in cognitive dissonance with each other, represented by the categories "Educational goals and curriculum should drive technology," and "Keep up with Technology (or be left behind)." The researcher concluded that as leaders deal with their perceived experience of the inevitability of technological change, and their concern for preparing students for a technological future, the core category Keep up with technology (or be left behind) is given the greater weight in technology decision making. A risk is that this can on occasion mean a quickness to adopt technology for the sake of technology, without aligning the technology implementation with educational goals.