Nowadays effective leadership skills integrate traditional school leadership roles including teacher supervision, maintenance of facilities and evaluation with specific aspects of learning and teaching. Instructional leaders also look into the instructional and curricular matters that affect school performance in a world where technology has become a vital tool in the education sector. However, instructional leaders and supervisors need to liaise with other stakeholders and perform evaluation on a regular basis. This paper will look into challenges, benefits of collaboration, key issues in developmental leadership, issues in evaluating teachers, summative, formative evaluations and propose a mentoring instrument in line with evaluation. Collaboration is a time consuming venture that requires effective communication to all stakeholders. Thus, collaboration also requires a lot of negotiation to avoid conflicts between supervisors and teachers, the results of the process are not instant and supervisors have to accommodate different personalities and teaching styles. In addition, the evaluation may be unable to highlight on individual weakness and strengths when carried out on a group.