A growing of health-care organizations are in the process of modifying their clinical information systems (CIS) to support browser-based access. Consequently, care-providers are expected to modify their workflow to take advantage of the new technology. Intuitive interfaces, fast response and new functionality are few of the features used to promote endorsement of the change. In parallel, administrators are required to constantly assess user compliance and intervene where necessary to prevent rejection. Such monitoring translates to frequent surveys, analysis of logs and prudent utilization of user-groups. These methods tend to further burden users, suffer from "post-hoc" temporality and are difficult to maintain. In this paper we suggest an alternative approach to such data acquisition. "CareQuest" is an interactive Web-based service that can be woven into clinical applications without coding. It acquires information from the clinician at the relevant point in her workflow. It allows extensive interaction customization, data-driven response, real-time Web-based data-analysis, and full Web-based administration.