This article explores the use made of humour in three different private sector organizations. It draws on observations of managers working towards a management qualification and, from the jokes they exchange, it argues that studying humour may offer insights into sentiments not easily articulated in ‘serious’ conversation. Humour’s ambiguity enables contentious statements to be made without fear of recrimination. Equally, constructing jokes by juxtaposing two different frames of reference provides a glimpse of alternative (and shared) perceptions of ‘reality’. This sensitivity to complexity makes humour a particularly appropriate vehicle for conveying ambitions, subversions, triumphs and failures and this article considers some of the ‘serious’ messages underlying the jokes.