Techniques for real-time observation assessment are provided. The techniques, which are designed for educators, take advantage of handheld computers, desktop/laptop computers and Internet access in order to reduce the paperwork associated with conventional educational assessments. An array of instructional assessment applications are 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.