Teacher has a new role in the digital age. Call him facilitator or mentor. He is expected to help learners learn at their own pace rather than push concepts and rules onto them. Though such roles have been around for years, e-learning is forcing them in letter and spirit and changing many a rules for the teacher and the taught. Profile and expectations of students have changed. They demand personalized education that matches their intellect, goals and constraints. In response to such changing needs, we observe many variants of technology based courses being adopted by educational institutes. But do these variants offer any thing different or are they old wine in new bottle? The key difference lies in the manner in which teaching and administrative processes and controls are managed while balancing student convenience with quality of learning. It needs a separate set of skills, culture and sensitivity. This article, based on study of literature and personal experience, brings forth some critical skills that teachers need to acquire to operate in the digital and particularly in the virtual space. Such skills are also analyzed in the light of convenience versus quality.