This study analyzed the conversational strategies used by Kim Kardashian and Kris Jenner at The New York Times conference. The writer aimed to identify their conversational strategies when talking about business topics while discovering the similarities and differences based on their age and status. Following Coates' (2013) theory on gender and conversational strategies, the study classified strategies into seven aspects: minimal responses, hedges, tag questions, questions, commands and directives, swearing and taboo languages, and compliments. Using a descriptive qualitative approach, the study found that Kim Kardashian employed five strategies: minimal responses, hedges, questions, swearing and taboo languages, and compliments. Meanwhile, Kris Jenner used six strategies: minimal responses, hedges, questions, commands and directives, swearing and taboo languages, and compliments. The study showed that there were more similarities in their conversational strategies compared to the differences which were not significant due to their shared status as businesswomen. The writer concluded that the conversational strategies of the two women might be influenced by the context, their status, and their age. More studies focusing on videos with longer duration including two generations with a bigger age gap are recommended for further research.