The objective of the paper is to evaluate the quality of systemic change management (CHM) and readiness for change in five Central European countries. The secondary goal is to identify trends and upcoming changes in the field of digital innovations in healthcare. The results show that all compared countries (regardless of their historical context) deal with similar CHM challenges with a rather similar degree of success. A questionnaire distributed to hospitals clearly showed that there is still considerable room for improvement in terms of the use of specific CHM tools. A review focused on digital innovations based on the PRISMA statement showed that there are five main directions, namely, data collection and integration, telemedicine, artificial intelligence, electronic medical records, and M-Health. In the hospital environment, there are considerable reservations in applying change management principles, as well as the absence of a systemic approach. The main factors that must be monitored for a successful and sustainable CHM include a clearly defined and widely communicated vision, early engagement of all stakeholders, precisely set rules, adaptation to the local context and culture, provision of a technical base, and a step-by-step implementation with strong feedback.