Management interviews: the most underdeveloped skill in investing | Ross O'Toole

Effective management interviews require a structured approach to bypass the polished sales narratives often presented by executives. Ross O'Toole, author of *Breaking the Script*, argues that investors must move beyond standard inquiries by utilizing specific tactics, such as framing questions with "what" rather than "why" to minimize defensiveness. Poking—the use of provocative, follow-up questions—helps break through rehearsed responses, while requesting negative examples provides a necessary counterweight to management's inherent optimism. Because management teams are skilled at storytelling, longitudinal tracking across multiple quarters is essential for establishing a credible baseline. While AI tools can assist with preparation and data synthesis, human judgment remains the critical component in evaluating leadership quality and strategic vision, particularly when navigating contentious situations like activist campaigns or post-earnings volatility.