The recruitment of sufficient numbers of suitably qualified teachers into headship is an international issue and to address this in Scotland alternative headship preparation programmes were trialled to provide greater flexibility in order to better match the individual development needs and circumstances of the aspirant head teachers. Drawing from the evaluation data of one of these programmes, the National Flexible Routes to Headship, the article analyses the key learning processes critical for the design of individualised leadership development programmes. The article begins with the policy context from which the proposal for the alternative headship preparation programmes emerged.