We detail some lessons learned while designing and testing a decision-theoretic advising support tool for undergraduates at a large state university. Between 2009 and 2011 we conducted two surveys of over 500 students in multiple majors and colleges. These surveys asked students detailed questions about their preferences concerning course selection, advising, and career paths. We present data from this study which may be helpful for faculty and staff who advise undergraduate students. We find that advising support software tools can augment the student-advisor relationship, particularly in terms of course planning, but cannot and should not replace in-person advising.