Research on the strategic Information Systems (IS) planning is typically concentrated on large firms. However, the outcomes of this research may not be sufficient to adequately apply to Small and Medium Enterprises (SMEs). Responding to the limited body of work in SMEs with respect to strategic IS planning, this research aims to fill the gap in the body of literature. Having limited resources available, financially and technically, strategic IS planning is getting more crucial for SMEs. Prior work suggests that a high level of internal competencies such as IT leadership by the owner or the top management of the firm are important for progressive IT development to take place in SMEs. Having said that IS is getting paramount for firm’s survival to optimize IS effectively, it is incumbent to investigate the factors influencing strategic IS planning amongst the SMEs. This study contributes to research and practice by providing indepth insights into the IS planning processes in SMEs with a particular focus on the roles of top management and users. Researchers can use these results, which are somewhat different from larger organizations, to revise IS planning phases.