Most corporate transformations fail because they’re approached as fixed, top-down programs with predefined goals, timelines, and financial targets. But as the environment changes—because of technological disruption, for example, or new customer expectations—those assumptions quickly become obsolete. That’s why companies should treat transformation as a learning journey: an evolving process in which strategy, priorities, and even the destination are continually refined. Drawing on research into large-scale transformations and contrasting the experiences of DBS Bank and GE, the authors identify four types of transformation initiatives—pilots, options, established business improvements, and ventures—that together generate critical learning and sustain momentum. They also recommend three leadership practices to keep transformation efforts coherent over time.