This article investigates how planning is influenced by five categories of questions (what, who, when/where, how and why) and the interactions between them. Planning theories differ in their answers to these questions, but all of them are primarily built around an assumed connection between the questions of ‘what’ and ‘how’. This orthodox assumption of a ‘what–how’ connection is shown to be responsible for the failure of planning theories in practice and their inability to address issues of power. The article illustrates that both ends and means (‘what’ and ‘how’) are predefined by answers to three fundamental questions (‘who’, ‘when/where’ and ‘why’) and that there is no direct connection between ‘what’ and ‘how’ in practice.