Upon graduation, engineering (and science) undergraduate and graduate students are typically well-prepared for success in technical problem solving. However, they have had little exposure to the vagaries associated with the interplay of "people" and technical problems (sometimes referred to as sociotechnical efforts), especially as related to service as the leader of small or large groups. They also have had limited, if any, opportunity to integrate communication skills and ethical behavior with decision making, risk taking, and running meetings. Since well-defined rubrics to address such issues are not available, and "correct" solutions are evasive at best, students and early- to mid-career engineers frequently display frustration and anxiety when initially placed in such positions. Courses and workshops can offer background on technical leadership and build awareness of and approaches to typical problems encountered on teams. Interactive discussion of possible underlying causes for the emergence of these complex multi-faceted issues, along with consequences (good and bad) that ensue from the specific decisions made, assists development of the skill set needed to deal effectively with uncertainty and problems created by personalities, beliefs, biases, and emotions.