Engineering communication is a highly desirable competence in industry. However, to become efficient communicators, engineers must consider cross-generational styles in the process. In this exploratory case study, engineering leaders from four industrial segments (High-Tech, Automotive, Aerospace, and Manufacturing) who have had a history of communicating throughout different contexts and projects were studied. Interviews and memos were primary data sources used in this study. Key findings included the need for younger generations of engineers to communicate thoughtfully and with humility. Also, older engineers expressed the need to adjust their communication styles with younger engineers by adapting their communication to include varying modalities (e.g., in person, in writing, with technology). The findings from this exploratory study can help engineering educators consider how to teach communication skills to students while increasing their awareness for cross-generational interactions upon graduation.