Effective CIOs must demonstrate both operational and strategic leadership. Although it is unclear how and when CIOs make the transition from operational to strategic leadership, we argue that the transition depends on the accumulation of transitional capital. Timing and sequencing of CIO actions are critical to the accumulation of this transitional capital. Thus, strategic CIO leadership is earned and is contingent upon actions of the CIO in building operational excellence and social capital, sequencing and kairotic timing of these actions to accumulate transitional capital, and achieving acceptance by the top management team.