Scholars have emphasized that decisions about technology can be influenced by philosophy of technology assumptions, and have argued for research that critically questions technological determinist assumptions. Empirical studies of technology management in fields other than K-12 education provided evidence that philosophy of technology assumptions, including technological determinism, can influence the practice of technology leadership. A qualitative study 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. The research design aligned with Corbin and Strauss qualitative data analysis, and employed constant comparative analysis, theoretical sampling, and theoretical saturation of categories. Subjects involved 31 technology directors and instructional technology specialists from Virginia school districts, and data collection involved interviews following a semi-structured protocol, and a written questionnaire with open-ended questions. The study found that 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. The core category and central phenomenon that emerged was that technology leaders approach technology leadership through a practice of "Keep up with technology (or be left behind)." The core category had two main properties that are in conflict with each other, "pressure to keep up with technology," and the "resistance to technological change" they encounter in schools. The study found that technology leaders are guided by two main approaches to technology decision making, represented by the categories "Educational goals and curriculum should drive technology," and "Keep up with Technology (or be left behind)." 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. The researcher recommends that similar qualitative studies be conducted involving technology leaders outside Virginia, and with other types of educators. It is also recommended that data from this or other qualitative studies be used to help develop and validate a quantitative instrument to measure philosophy of technology assumptions, for use in quantitative studies. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]