Many conversations involve sending or receiving "bad news." These conversations are often dreaded, poorly executed, or avoided altogether. Ways need to be found to make them less difficult and more productive. We explored these issues through three methodologically diverse studies. Study 1 comprised in-depth interviews with 24 nurse managers. Interviews shed light on the characteristics of difficult conversations and strategies for making them less awkward and more successful. Study 2 was a survey investigating relationships between six dimensions of supportive communication and participant satisfaction with a difficult superior-subordinate conversation. Study 3 experimentally manipulated two supportive communication behaviors, plus a third variable, face-work. Together, these studies show that successful outcomes from difficult workplace conversations require the parties to balance task and relational goals, with the latter particularly dependent on acts of empathy and face-giving.