This research aimed to better understand how engineering graduate students entering industry or government careers feel prepared from a skills development perspective. We sought to understand this alignment between graduate education and industry or government positions from two perspectives: 1) experienced engineering professionals who hire new engineering graduate degree holders, and 2) new engineering graduate degree holders in their new roles within the past few years. Our paper reports on findings from five interviews conducted with experienced structural engineering professionals with over 20 years of experience as well as eight interviews with recent alumni of graduate programs who reflected on how their educational experiences prepared them to enter the workforce. Results from the executives’ interviews revealed that a structural engineering candidate with a thesis-based master’s was preferable at some companies compared to a non-thesis master’s candidate because writing a thesis helps graduate students develop critical thinking and communication skills. Structural engineering employers were more skeptical of recent doctorate applicants as compared to recent master’s applicants based on the assumption that PhDs may be overqualified or have too specific expertise that could not be translated easily into industry. From the interviews conducted with recent alumni, our study found that all participants experienced some gap with respect to preparedness for the workforce when transitioning from academia to industry or government. In particular, recent alumni emphasized an opportunity for graduate programs to enhance how they help graduate students develop professional skills such as collaboration and communication.