A system, method and computer program product for real-time observation assessment is provided. The invention, designed for educators, takes advantage of handheld computers, desktop/laptop computers and the increasing presence of Internet access in order to reduce the paperwork associated with conventional educational assessments. The invention includes an array of instructional assessment applications designed to run on handheld computers. The instructional assessment applications may be based on existing and widely-used paper methodologies. A common Web-based platform for assessment application distribution, selection, download, data management and reporting is also provided. Users can then periodically synchronize instructional data (assessments, diagnostic results, notes and/or schedules) to the Web site. At the Web site, browser-based reports and analysis can be viewed, administered and shared via electronic mail.