The leaders of almost every school face the same challenging situation: They must create schools that reflect the dominant role of digital IT in society and they must prepare students for that world; but the changing landscape of teaching, inadequate technical expertise, and limited resources are genuine barriers to this work. What we know, how we know it, and what we know about learning is advancing at a rate that fast outpaces teachers’ capacity to respond to it. Operating and maintaining the IT systems in schools requires expertise that is far beyond that of the “tech-savvy” teachers who managed the first IT systems installed in schools. IT professionals who are “imported” into education from other businesses and industries often find the practices, assumptions, and expectations that served them well in other settings do not transfer into education. Teachers and students are different from workers, and the IT (including the hardware, the software configurations, and the personnel) they rely on for their work must accommodate those differences. IT is also a capital-intensive aspect of operating schools. Devices and network upgrades can consume years’ worth of technology budgets in a short time, and the total cost of ownership of devices places on-going demands on budgets. Further, technology introduces new and rapidly evolving regulatory and policy issues into school management.