Technology expenditures and usage in schools have risen by nearly 300 percent during the last three decades. Few principals claim to be technology experts, but most aspire to design a map that leads their schools to success with educational technology. The key to success on the journey is not to know everything, but to ask the right questions. This article presents ten questions that will help principals lead others to technology success: (1) What are the technology trends I need to know about?; (2) What does the research say about schools and technology?; (3) What do I need to know about technology to move my school forward?; (4) Are there guidelines to help me?; (5) How do I construct a safety net for technology in the school?; (6) How do I know I have created effective policies and plans?; (7) How do I promote the integration of technology in the classroom?; (8) How much will all of this cost and where do I get the funds?; (9) How do I work with technology experts?; and (10) How will I measure success?