This mix-method study aimed to investigate the conception of leadership effectiveness at secondary school level in Sindh Pakistan. The Leadership Challenges, the Impact of existing System Support and Leadership Coping Approaches were thoroughly explored. The population of this study was based on 448 (both male and female from rural and urban areas) heads of secondary schools of 9 districts of Hyderabad directorate of schools. Data were collected through in-depth individual interviews, and then focus group discussions. Thus, box-oriented Sindh Leadership Challenges Survey Questionnaire [SLCSQ-2013] and Impact of System Support and Leadership Coping Approaches Survey Questionnaire [ISSLCASQ-2013) were developed on the basis of initially collected qualitative data. These Questionnaires were then administered to a wide randomly selected stratified sample of 90 subjects of same population to justify the qualitative data. Major findings of this study reveal that school heads are experiencing serious challenges in many areas of their administration: authority and power, district school relationship, instructional leadership practice, financial management, conduct of annual exams, staff union relationship and community relationship. They are highly challenged by bureaucratic and political forces in performing different leadership roles. They face lack of existing system support in face of such challenges. This study also revealed that heads of schools use various Leadership Coping Approaches: documenting, performing teaching role, dealing according to the professional level of the staff, adopting flexibility in authority and power and reconciliatory approach etc to deal with challenges. xiii Keywords: Leadership Challenges, School leaders, Context, System Supporting Strategies, Leadership Coping Approaches (Strategies and Styles)