Previous studies have contextualized student-led, asynchronous online discussions as collaborative learning experiences that positively impact students’ learning and foster higher order cognitive skills. From a leadership education perspective, student-led discussions have come to the fore as a helpful resource for deepening learning because of their focus on collaboration and shared leadership. While literature on student-led online discussions, leadership learning, and cognitive skill is plentiful, there is no single study that explores all these elements together or fully points to how practicing meaning-making in online, asynchronous leadership courses can inform larger cognitive processes. Thus, the purpose of this conceptual content analysis-based study was to examine 35 undergraduate students’ collaborative discussion board posts at the beginning, middle, and end of an online, asynchronous Ethics and Leadership class to assess not only if and to what extent students expressed cognitive skills, in general, but also if and to what extent they understood ethical leadership via these types of discussions. Further, from an exploratory lens, this study examined if there was a relationship between expression of higher order cognitive skills and more complex ethical leadership understanding. Results indicate that, while students achieved higher order cognitive skills and more holistic ethical leadership understanding overall, robustness of student engagement could be situational in nature and expressions of cognitive skills and ethical leadership understanding tapered as the course progressed. Additional findings and implications are discussed.