Generation XP was one of the four Digital Opportunities pilot projects carried out in partnership between the New Zealand government, schools, businesses and Maori organizations between 2001 and 2003. One aim of the projects was ‘to help bridge the digital divide’ between students from low-income families and of varied ethnicities, and other students. Other aims were to trial the concept of public-private partnership in ICT education and to learn lessons which might be useful in the design of new initiatives. The present paper describes the author’s experience in the application of Soft Systems Methodology in evaluating the Generation XP project.