Described is a technology for analyzing usage of a software program's features. Software instrumentation data is collected during actual user program usage sessions. The collected data is then processed to determine various feature usage counts and other information, cross-feature usage (e.g., among users who use a feature, how many use another feature or program), and characteristics of feature users, e.g., how long, how much, how often and how extensive feature users use a program. Session analysis may be performed to provide information about the number of sessions in which a set of features occur. Feature usage trends over time may also be determined via analysis. A user interface is described for facilitating selection of one or more features to analyze, for facilitating selection of a group of users, and/or for outputting results corresponding to the analysis.