The research reported in this paper outlines the impact of confidence, competition, and failure in relation to adolescent girls and leadership behaviour. Focus groups were used as the method of data collection. These focus groups were facilitated electronically using Skype Instant Messaging. Participants were girls from single-sex schools; all were in their final year of schooling and currently held a leadership position. Students were located in schools across Australia, with one school located in South Africa. It was made apparent by this study that girls, at times, lacked confidence in themselves and their ability to enact leadership. Whilst it was acknowledged that girls had a highly competitive nature, especially in the academic and sporting domains, the word 'doubt' continuously resonated throughout student responses. Continued research into this domain will be important in ensuring that girls overcome this 'doubt' and have confidence in their capacity as leaders both within the school context and beyond.