Most will agree that the use of Internet to support teaching and learning has become a mainstay of management education with the widespread use of online content, discussion boards, document sharing, email, virtual classrooms, etc. But, whether it is effective or not is debatable. Sometimes learners and instructors report very positive experiences. Other times the results are less than ideal. Considering the sizeable time, effort, and expense involved in designing and implementing web-based courses, this can be particularly disappointing for everyone involved. Our experience sheds new light on this issue. We have discovered that developing management soft skills (e.g., critical thinking) online requires a fundamentally different approach from that of technical hard skills (e.g., book keeping). Technologies that promote one skill set generally get in the way of the other. The mismatch between the required pedagogy and use of technology, we argue, lies at the heart of the disappointment. This article alerts educators to the problems and the questions that need to be asked, and provides a case study illustrating the importance of aligning pedagogy and technology. (Contains 13 notes, 3 tables, and 3 figures.)