The aim was to test some psychometric properties of a questionnaire designed to measure leaders’ tendency to over- and underestimate themselves and their organizations when they are facing problems. Data were obtained from 63 Swedish managers who had attended leadership courses. As predicted, the findings show that leaders who overestimate their capacity to handle problems also overestimate their organization’s capacity to handle the demands, and vice versa. Contrary to prediction, positive correlations were found between the over- and underestimation scales. It was suggested that these last-mentioned finding reflects a general, cognitive ability and personality-based tendency to appraise situations more or less realistically. Similar patterns have been found in studies on destructive leadership and stress research focusing on daily hassles and uplifts. A combined estimation index was computed (Cronbach alpha = .72) and preliminary scale limits to be used by leadership training facilitators and coaches are presented.