Healthcare information technology is a key factor in improving quality and reducing cost in healthcare, and yet, the successful implementation of health IT varies greatly among healthcare systems. A review of the health IT literature supplemented by an analysis of the experience of successful IT implementation in Maccabi Healthcare Services, reveals that, despite differences among countries, common barriers to implementation of health IT and common critical success factors can be identified. Barriers include lack of clear benefits, sufficient incentives and adequate support for clinicians as well as payer–provider relationships, marketplace competition and privacy legislation. Critical success factors are innovative leadership, integrated management and collaboration with the doctors based on concrete needs, benefits, incentives and support. Dilemmas for managers include proof of return on investment for health IT versus leadership and tough management decisions; the optimal balance in the tradeoff between market dynamics, competition and choice, and the value of an integrated system that can generate significant benefit to clinicians, patients and payers; and the appropriate balance between privacy and improved quality of care, including the reduction of clinical error.