Information system (IS) projects have been seen to be failing at an alarmingly high rate. The prevailing explanations of IS failure have had only a limited success. Thus, the time may be right to look at the reasons for IS failure through an alternative perspective. This paper proposes that IS success should be explained in terms of managerial leadership intervention, from the sensemaking perspective. Managers are responsible for workplace outcomes; thus, it may be appropriate to explain their role in IS success as well. The sensemaking perspective can explain IS success through holistic user involvement, a concept which critiques of existing explanations have stated to be a requirement for explaining IS failure. This paper proposes a framework combining the theory of enactment and leadership enactment to theorize managerial leadership intervention for “IS success.” The proposed explanation postulates that the managerial leader’s envisioning of the future transaction set influences the liberation of the follower and cast enactment, while liberating followers and cast enactment constitute manager sensegiving. The managerial leader’s sense-giving influences follower sensemaking. Follower sensemaking, under the influence of managerial sensegiving, will lead to followers’ IS acceptance, and that constitutes IS success at the individual level. Further, collective level IS acceptance constitutes IS adaption/success, and this will influence the leader’s sensegiving, for the next round of sensemaking.