One of the difficulties of explaining pragmatism and continental philosophy to a person versed only in the analytic tradition, and vice-versa I presume, is grasping the pervasive concepts that a tradition takes for granted. In fact, it is difficult to realize that a tradition has such concepts and what they are unless one studies multiple traditions or divergent subfields within a tradition. For instance, one must comprehend how modern formal logic structures how mainstream analytic philosophy argues in order to grasp many subtleties. Likewise, a person studying recent continental philosophy will be at a severe disadvantage without a solid grasp of phenomenology, hermeneutics, historical-thinking and the concepts of subjectivity, discourse, embodied, etc.
What about pragmatism? Recently, I presented a number of posts on process metaphysics, especially a book Beyond Mechanism, that reminded me of common barrier for understanding the subtleties of pragmatism. Much of classical and contemporary (neoclassical) pragmatism integrates processive and temporalist metaphysics in its thought, whereas analytic philosophy is over-whelmingly mechanistic. In large part, early pragmatism was a response to mechanistic metaphysics and the battle between mechanism and organicism (usually a proxy for idealism).
Trying to explain seemingly unrelated ethical concepts to a person not familiar with an event ontology, phenomenology, or habit psychology challenges both. But the think the biggest problem, at least in my experience, is that when a person points out differences in tradition that are not merely superficial, most audiences react by presuming that the other person is doing something illegitimate or evasive. The odd thing is, the more alien the tradition, the more the person gets a pass: few philosophers in the U.S. complain about incomprehension of a Buddhist answer, yet they will complain about an analytic, continental, or Americanist answer. The presumption of familiarity seems to be a barrier to understanding.