The COVID-19 pandemic has caused a rapid transformation in the healthcare industry. Telemedicine, mHealth, and artificial intelligence technologies have become integral components of healthcare delivery, enabling remote consultations, symptom tracking, medication reminders, diagnosis, and treatment. However, the adoption of these technologies in healthcare organisations is often met with resistance from shareholders. The most frequent reasons are fear of technology, uncertainty about the impact of technology solutions on patient care, ethical and regulatory concerns, skepticism about the effectiveness of remote medical consultations, concerns about data privacy and security, reluctance to change workflows, risk of job losses due to automation of certain processes, and possible conflicts of interest. This article explores the complex landscape of shareholder resistance during software implementation projects, the origins of this problem, its manifestations, advantages, disadvantages, and consequences. The article also examines this issue through the prism of the Lewin’s Change Model and the Transtheoretical Model of Change, and demonstrates it on the examples of Information Technology Company and Microsoft. The article offers strategic recommendations for healthcare organisations to effectively manage and mitigate these challenges, facilitating a successful transition to the healthcare technology landscape. Among the main problems, the article discusses the following things: creating open and transparent communication channels for shareholders; joint problem-solving sessions with all stakeholders; an iterative approach to implementing IT projects in healthcare facilities, which allows reviewing, adjusting, and agreeing on solutions at each iteration; involving shareholders in decision-making at the early stages of the software implementation process; comprehensive programs to improve shareholder competencies; targeting opinion leaders who are supporters of changes in the organisation; maintaining continuous feedback, etc.