Leadership is crucial to all organizations, whether we speak about commercial, governmental and even non-governmental institutions. Quite often the most recognized leaders are connected with a success story being its remarkable victory in sport or business achievement. In prisons, however, leaders face many complex challenges, not excluding those related to the financial condition, ability to motivate staff or flexibility to adapt to new technologies. Social responsibility and sensitivity of public on prisons´ clients (in a positive and negative way) are just two among many complex variables that increase demands on the profile of Prison leaders. Without underestimating many demanding positions, running a prison is one of the most difficult jobs. Therefore, leadership development programs in prisons should be focused, supported and encouraged by any possible means.