Given the inordinate effect on their lives and livelihoods, managers, developers, and students are eager to learn about the many pertinent ethical issues one may find in the midst of a technological disruption brought about by widespread automation and use of artificial intelligence (AI). That is, until you call into question some of their tacit assumptions about innovation, technology, the good life, and themselves. In this chapter, two educators reflect on their respective experiences teaching AI ethics and adjacent topics in Canada, Germany, Ireland, Switzerland, and the United States. We relay our interdisciplinary teaching experiences at the undergraduate, graduate, and executive education levels in schools of communication, universities of technology, and business schools. Our perspective focuses on critical self-reflection and the opportunities and challenges of teaching AI ethics in these contexts. We provide a brief overview and reflect upon strategies that worked well for us, strategies that did not, and recommendations in order to bridge the chasm between the two.