Irony and humor play an important role in both organizing and organizations, because they both help to collide and contrast ideas as well as mitigate and moderate criticism. Our empirical observations of a senior management team suggest participants frequently use verbal irony and aggressive conversational humor through ‘ironic personae’ – a cast of characters, real or imaginary – as a vehicle for pragmatically making sense of complicated topics. We show how ironic personae perform three functions: (i) testing new positions on topics in a non-committal way; (ii) stretching the frame of comparison of a group; and (iii) aligning shared understanding and commitment. Thus, our analysis sheds light on an underexplored and undertheorised pragmatic vehicle for the expression of humorous verbal irony and aggressive conversational humor.