The high-school-to-college transition can be difficult as students are adapting to a multitude of academic and social changes simultaneously. The University of Wyoming has created a first-semester program targeted at development of student skills for at-risk students using paired first-year seminar classes. Using student survey data from both pre- and post-course series, students were asked how important they thought academic and non-academic skills were as well as how much preparation time they were spending outside of class. Results from this work show large changes in the importance of skills and time spent studying during the transition from high school to college. This highlights the need to focus specifically on teaching skills to help students through the transition and suggests that not all skills are equal and data shows that students take longer than one semester to match their expected and actual amounts of time they spend outside of class studying.