We focus, in the context of difficult or challenging communication, on the integration of individual, inner practice and skillful speaking. After a review of eight general guidelines for skillful speech and how we do inner practice related to, but separate from, such challenging communication, we look at ways to bring inner practice in speaking and relating. We also focus on several more "outer" skillful ways of speaking to bring about mutual understanding, including using relatively neutral observations free of interpretations, and cultivating the practice of empathy. We then look at how to integrate more inner and more outer dimensions of practice in the context of several challenging situations.