The Rosebank Business Precinct is one of Auckland’s most highly developed Business Improvement Districts. This descriptive study, undertaken for Auckland City Council, examines the gaps between what Rosebank businesses actually want and what the workforce presently provides. It goes on to investigate the potential for cluster development in Rosebank. The findings show that the top training needs of Rosebank businesses were management, applied technology & trades, computing & information technology, and accounting. “Developing a Green Business” was the fifth most mentioned training need. Many owner/managers held unsupportive attitudes toward training and education. The paper makes recommendations in the fields of labour force development; agglomeration economics; and community entrepreneurship.