Sweden has experienced an increase in sickness absenteeism, stress related health problems and a deterioration of psychosocial working conditions. Several researchers have emphasized that leadership with a focus on developing human resource practices is a necessary component of a high organizational performance. The purpose of this article is to explore whether there are patterns in leadership values and methodologies associated with subordinates´ views of leadership, health outcomes and quality aspects. Four public and four private organizations in northern Sweden were studied. McGregor´s X and Y hypotheses, plus three other hypotheses, were used as a base for the analyses. Data was gathered through in-depth interviews with the leaders, questionnaires (completed by leaders and co-workers), and assessment of selected human resource accounting data (sickness absenteeism). The leader views were mirrored with the co-worker views through a comparison of qualitative and quantitative results in a stepwise analysis process. The study´s main findings were that leaders with more X hypotheses get lower results concerning employee judged leadership and quality aspects and, to some extent, lower results concerning health outcomes. The explanatory analyses concerning leadership and health are complex with many influencing factors.