Few principals claim to be technology experts. Most aspire to design a map that leads their schools to success with educational technology. However, the key to success on the journey is not knowing everything or becoming a technology expert. It is about asking the right questions, exploring the answers to those questions, and creating a road map for the effective use of technology by the students and teachers in the school. This article discusses 10 questions for principals to answer that will help lead to technology success. These are: (1) What are the technology trends we need to know about?; (2) What does the research say about schools and technology?; (3) What do we need to know about technology to move our school forward?; (4) Are there guidelines to help?; (5) How do we construct a safety net for technology in the school?; (6) How do we know we have created effective policies and plans?; (7) How do we promote the integration of technology in the classroom?; (8) How much will all of this cost and where do we get the funds?; (9) How do we work with technology experts?; and (10) How will we measure success?