Working on a small campus has many advantages: Familiarity with the majority of faculty and staff, in-depth knowledge of how systems interact, adding the personal touch to each interaction with the users. However, this can also be a challenge, as knowing the personal history of some users leads us to make assumptions and generalizations with their problems. This talk will cover how we at Grinnell College deal with a very heterogeneous user base, and what we have learned through training and experience about what to do, and what not to do, with those “difficult” situations. Categories and Subject Descriptors K.7.0 [The Computing Profession]: General. General Terms: Management, Human Factors.