This article investigates the perceptions of English headteachers to questions addressing the setting of goals and the effects of external pressure on headteachers. The research utilizes semi-structured interviews with headteachers from a variety of contexts. These interviews were used to write individual headteacher "portraits", which were then re-examined to answer the questions generated. The findings suggest that: (1) contrary to current literature, it is not sensible to suggest either that headteachers have considerable flexibility in how they approach their work, nor that they are so ground down by legislative imperatives that they can do little more than be agents of implementation; (2) appropriate CPD should be individually tailored to the contexts and personalities of the individuals involved; (3) English headteachers may be so focussed on the local that they may fail to have a sufficient grasp of the global and national changes around them to fully lead the profession in responding appropriately to these.