Due to resource constraints, today teaching of IT-based courses and software applications is posing greater challenges than before. Also the student body, being widely diverged and exposed to many electronic gadgets and technologies, requires a different teaching style. Indeed, there is a need for paradigm shift in teaching and assessment of learning. This paper addresses various issues in teaching introductory level business software in a teaching university. The students in the course come with different levels of ability, perception, learning habits, technical skills, and exposure to different types of technology. The course adopts the latest educational technologies MyITLab and Blackboard in delivering the course materials in face-to-face as well as purely online classes. The effectiveness of the course delivery, limitations and opportunities are studied through a well-designed questionnaire survey. A major finding is that students preferred self-directed study over rigid, teacher-directed class room-based delivery.