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This paper investigates middle managers’ resistance to digital transformation initiatives and suggests strategies for overcoming such resistance using the example of a major Russian transportation company. This study employed a mixed-methods approach to assess middle managers’ values and to identify patterns of resistance behavior. The case studies further illustrate the resistance of middle managers and how the company under study responded to these incidents. The findings reveal a significant relationship between employees’ attitudes toward routine and their resistance to digital transformation. Managers with high scores in tradition, conformity, security, and power values, as well as a strong positive attitude toward routine, were more resistant to change. Conversely, those with high scores in universalism, self-direction, and stimulation values were more open to change. By addressing the values and concerns driving middle managers’ attitudes, organizations can better support them in overcoming resistance to digital transformation. The study also offers practical strategies for aligning digital transformation efforts with middle managers’ values, thereby fostering a more positive attitude toward change and facilitating successful implementation.
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