This paper explores the tension between voters' preferences for the personality traits of political leaders and their actual ability to discern those traits from text alone (whether written or spoken). While research consistently demonstrates that language use contains linguistic signatures indicative of personality traits, and voters in many countries--including the U.S.--prioritize certain traits in leaders, we show people are surprisingly poor at accurately interpreting personality traits from language alone. Specifically, using a range of methodologies and novel datasets, both experimental and observational, we show voters' perceptions of personality are often unreliable. These findings challenge assumptions about how personality plays into campaign communication and suggest that voters may be easily misled or unable to accurately judge leaders' personalities through speech or text. This has important implications for political campaigns, democratic representation, and the overall functioning of democratic governance.