This study utilizes a mixed method approach to examine the relationship between IS/Business alignment practices and organizational choice of IS/business alignment strategy. To this end, the significance of six maturity factors of IS/Business alignment – governance, partnership, scope and architecture, communication, value, and skills – from the Strategic Alignment Maturity model are examined against three alignment strategies (independent, sequential, and synchronous) adopted by different organizations. Governance and partnership were found to be the most significant factors towards the evolutive process of IS/business alignment regardless of the alignment strategy. Moreover, our data shows that organizations that are most mature in partnership have a higher tendency to implement sequential integration strategy (IS strategy formulation follows and supports business strategy formulation) and not synchronous – where IS strategy formulation and business strategy formulation are done simultaneously. Follow-up group discussions with senior managers were also conducted in an attempt to identify the top management practices that advance the IS/business alignment process. The discussions revealed three management practices that considerably contribute to the process of aligning IS and business strategies: (1) the formalization of a program management process, (2) the improvement of support for hierarchies of authority, and (3) the integration of collaboration values. Those findings are discussed and future avenues of research are offered.