We test the hypothesis that work practices complement IT investment, in part, by accelerating how rapidly employees acquire the skills needed to use new IT systems. We combine support request data from an EMR vendor with survey responses on work practices from 962 employees from 15 client nursing homes. Nursing homes using work practices that prior studies have shown to complement IT investment—those promoting discretion, teamwork, training, high staffing levels, and communication—experienced more rapid declines in requests for technical support. We then show that these benefits are due, in part, because the use of these work practices facilitates learning for workers in frontline occupations who otherwise may not have the freedom to experiment with and adapt the new technology systems. For many frontline workers, discretion was more important than training in explaining IT learning. Implications for the healthcare industry are discussed.