In November 2008, Secondary Futures invited a group of business and community leaders to discuss with some of the Guardians of the Secondary Futures project Bernice Mene and Gillian Heald, and Tony Mackay representing the OECD their ideas about future ramifications of the project. Nicola Meek, Chief Executive, Secondary Futures and Stephanie Pride, Chief Adviser of Secondary Futures hosted the session. Secondary Future conversations about the need for an education system that produces the citizens, the workforce and the leaders that we will need in 2028 highlighted the fact that all sectors of the New Zealand society need partake in this effort. Discussions so far have identified the changes needed to create a successful learning environment for New Zealand’s future, including deeper learning connections between the education sector, workplaces and the community. Some of these are already underway. The changes in learning culture that are necessary to New Zealand’s future will continue to gain momentum. These interview excerpts summarise the Tacit Knowledge of leaders who have successfully commercialized innovation from New Zealand and their thoughts about success, leadership and education. This is the type of stories that need to be told, shared and learnt and exemplify how we might continue to build the collective capability to evolve our systems to address new needs as they emerge.