Research has argued that one reason for IT project failure is the lack of top management support. However, obtaining top management support is often considered outside the IT project team’s locus of control. Our research demonstrates that top management support can be obtained through continuous engagement. Also, a failure to engage can decrease top management support. We reveal an engagement strategy that starts with small favor requests followed by increasingly onerous favors rewarded by small concessions. This is demonstrated through a case study of the support of three division heads and their corresponding divisions in the implementation of an enterprise system. In case 1, an indifferent division head withdrew support after a lack of IT engagement. In case 2, a hostile division head became an advocate of the system after continuous IT engagement. Finally, in case 3, a supportive division head became more supportive as a result of continuous engagement by IT.