The development of a learning city requires city leaders to build a complex partnership with a potentially large number of stakeholders in city institutions, business and civic society. Of the wide variety of measurement tools available to cities to gain some understanding of their strategy needs and performance, the paper argues that a benchmarking approach, using a mixture of qualitative self-assessment supported by some qualitative data offers the most fruitful approach to assess the strengths and weaknesses of policy and practice, and offers a guide to prioritising actions.