Globalisation and rapid environmental change have created many challenges for public and private organisations across Iraq as a developing country, particularly in the higher education sector. This includes, for example, decreases in government funding; increased demand for higher education; a need for economic transformation, and related competitiveness of organizations. Such challenges require exceptional leaders and strategic planning in order to take action to improve. In Iraq, the higher education sector is still one of the main foundations in progressing the knowledge economy. Studies into leadership style, strategic planning processes, and the importance of leadership and organisational culture to an organisation’s success have been used to assist both public and private Iraqi colleges in responding to the challenges they face. Although, some studies have examined the interaction between leadership and strategic planning, and leadership and organisational success, there has been no empirical study that has investigated how these three variables interact together. Thus, this study aimed, firstly, to identify the current leadership styles and strategic planning processes in the colleges and the challenges they faced, and to gain an understanding from the perspective of the senior leaders themselves as to how they might best respond to the current situation. Secondly, based on the participants’ experiences, knowledge and perceptions, the study aimed to identify implications for both practice and policy to help improve the colleges’ outcomes. The study involved a mixed-methods approach and was conducted in two stages. During the first stage, the researcher gathered quantitative data by administering a survey package to 129 leaders (deans, associate deans, and heads of departments) across both public and private colleges in the capital city of Baghdad. During the second stage, the researcher gathered qualitative data to more deeply explore the survey results by conducting individual interviews with a sub-sample of 21 leaders from both college types (ten public and 11 private). In the data analyses stages, both descriptive statistics and inferential statistics were applied to compiling tables and charts, and to test hypotheses, by employing the Statistical Package for Social Sciences (SPSS), Microsoft Excel, and NVivo. The results of study showed that both transformational and transactional leadership styles played a varied and vital role in the colleges’ strategic planning processes, and in turn their success. The fact that private colleges were ‘for profit’ and public colleges were ‘not for profit’, as well as their contrasting funding models, highlighted key differences between the two college types’ leadership and general modus operandi. While it was found that both transformative leadership and transactional leadership styles were necessary to address the challenges colleges faced in the Iraqi educational context, the impetus for change extended far beyond the need for professional development of leaders. The embracing of information communication technologies, and reliable Internet was seen as necessary in all aspects of the colleges’ work and provision for teaching and learning, and students’ success. This applied to both college types along with the need for closer adherence to government regulations and more focused government coordination of colleges’ administrative functions. Furthermore, implications for making successful improvements to practice also identified the need to manage the challenge of sociocultural influences on the appointments and promotions of leaders. It was concluded that a greater emphasis on teamwork and provision of incentives for staff, along with a ‘boost’ to pedagogy and practice, which could be provided through the adoption of information communication technologies and appropriate professional development strategies, would enhance the colleges’ ranks and the status of their qualifications. Also, theoretically, the study offers a value-add to leadership, strategic planning process, and organisational success literature in the form of a conceptual model that links these variables in the context of Iraqi higher education sector.