Urban leaders make choices, but within contextual environments. This paper aims to highlight aspects of political leadership in European cities referring both to institutional settings within which the mayors operate and to behaviour, personal traits and perceptions of leaders. The paper will exploit empirical data gathered through a survey conducted for the second time ((the first time was in 2002-4) in several European countries, between 2014 and 2015. Respondents were mayors of cities with more than 10.000 inhabitants. In the paper, leadership styles will first be distinguished, based on the typology developed by John and Cole (1999), i.e. the leader's political values, task perceptions, role behaviour and attitude to the exercise of power. Then it will be tested if leadership styles (a) depend on local government types and national contexts as well as on city size, partisanship, gender and age of the mayor and (b) have an impact on time management (as a dependent variable). Furthermore (c), it will be checked if there are relations between electoral support, perceptions of influence and leadership styles.