Communication between patient and healthcare provider is an essential part of care planning. A patient’s personal health record (PHR) contains medical information that can be easily accessed, updated, and used via the Internet to facilitate and improve treatment plans. However, PHRs are not widely adopted. The goal of this study was to explore the challenges and design a roadmap to adoption. Data were collected via semistructured face-to-face interviews and analyzed with a qualitative approach. This study included 35 subjects selected from a sample of CEOs, chief information officers (CIOs), and health informatics project managers (HIPMs); the sample included key executives and project managers in the health information technology business. This study revealed that executives see the PHR as a tool to improve communication and patient care and reduce cost. However, a lack of electronic health record (EHR) systems, poor PHR integration with EHR systems, lack of user experience, and computer and health illiteracy were identified as barriers to PHR adoption. Therefore, adoption was not found to be a top priority for executives. Nevertheless, the PHR ought to be part of the information technology strategy in every hospital. Effective staff training, better patient orientation, and dedicated health informaticians can ensure a smooth and safe journey toward a useful PHR.