There is a general sense of urgency that major technological transitions are required for sustainable development. Such transitions are best perceived as involving multiple transition steps along a transition path. Due to the path dependent and irreversible nature of innovation in complex technologies, an initial transition step along some preferred path may cut off paths that later may turn out to be more desirable. For these reasons, initial transition steps should allow for future flexibility, where we define flexibility as robustness regarding changing evidence and changing preferences. We propose a technology assessment methodology based on rugged fitness landscapes, which identifies the flexibility of initial transition steps in complex technologies. We illustrate our methodology by an empirical application to 2,646 possible future car systems.