Although enterprise systems (ES) are ubiquitous, many firms report less than stellar payoffs from these costly investments, with underutilization often attributed to failures in the implementation process. Unfortunately, research has not provided sufficient insights into these failures, in part because it has focused on actual usage, as opposed to proficient usage, as the benchmark for successful implementation. Moreover, research has not generally examined how the adoption process unfolds over time, thus overlooking potential underlying mechanisms that may help explain how adopters achieve proficiency. To begin addressing these shortcomings, we study how adopters' pre-adoption expectations, enacted over time, can influence their post-adoption proficiency, by shaping how and why they spend time using the system during the adoption period. We analyzed time-lagged survey data from 153 financial analysts, required to adopt new ES-based software, at a multinational bank. We found that adopters who hold pre-adoption expectations reflecting greater internal and external motives to adopt the system as well as systematically integrate it into their work routines are more apt to use the system in ways that enhance their cumulative knowledge of it, and subsequently develop higher levels of proficiency post-adoption. Moreover, greater organizational support enhanced the impact of adopters' expectations on proficiency, except when their actual use is low in which case organizational support had an adverse effect.