Most of us engage in cross cultural communication in a variety of ways, often times without even realizing we are doing so. These cultural interactions can occur when we dine at our favorite ethnic restaurant or even when we visit another portion of the very country we live in. In most of these situations, a lack of cultural awareness resulting in a misstep or insensitivity can be harmless, though possibly embarrassing. In other situations, however, cultural awareness and the ability to communicate across boundaries can be crucial. Such is the case for military members who are increasingly being called upon to travel the world, establish relationship with the people they meet, and engage in mentoring and training activities. Unfortunately, many of these mentors have had very little exposure to the cultures that they now find themselves operating in. Missteps or insensitivity can result in misperceptions that can become a threat to the entire mission. This paper focuses on how awareness of a few basic cultural characteristics could have assisted mentors to the Afghan Air Corps in understanding the Afghan position in a particular dispute. Advanced knowledge concerning the cultural implications of individualist and communitarian mentalities, time orientations, and views regarding free-will could have quickly allowed both American mentors and their Afghan counterparts to understand the positions taken by each.