In June 2010, we reported to the United States Air Force Academy to teach in the Department of Electrical and Computer Engineering. Each of us brought different skill sets, different experiences, and different interests from different jobs in different locations. Yet, throughout our first year we simultaneously observed common stumbling blocks leading to some dilemmas and curiosities. This paper presents some of these common observations from three dissimilar instructors within a contextual framework promoting a learning-centered paradigm and balancing technical syllabus content with real-world "soft" skills. It is not our intention to define these observations as "Tricks of the Trade" or "Best Practices," although some recommendations are made. Rather, our intent is that these 10 observations will open dialogue in other institutions and departments to collectively address these issues.