Attaining reliable estimates of observational measures can be challenging in school and classroom settings, as behavior can be influenced by multiple contextual factors. Generalizability (G) studies can enable researchers to estimate the reliability of observational data, and decision (D) studies can inform how many observation sessions are necessary to achieve a criterion level of reliability. We conducted G and D studies using observational data from a randomized control trial focusing on social and academic participation of students with severe disabilities in inclusive secondary classrooms. Results highlight the importance of anchoring observational decisions to reliability estimates from existing or pilot data sets. We outline steps for conducting G and D studies and address options when reliability estimates are lower than desired.