Organizational transformation for digitalization is a daily challenge for organizations. Successful change can be defined as the combined result of a number of factors, in which the attitude, trust and/or distrust of employees towards technology is of paramount importance. The aim of this study was to explore which factors most influence employees’ trust in technology and how the risk they pose can be mitigated. The quantitative research analyzed 473 respondents (Smart PLS3, using SEM model) and came to the following conclusions. Employees’ trust in technology depends primarily on the supportive role of management, and to a lesser extent on the digital readiness of the company and the training provided in the organization. The supportive role of management is a key element in the model, as it affects trust not only in a direct way, but also indirectly, through several pathways in the model. This means that the supportive role of leadership is clearly a decisive influence and its importance helps to assess the risk of trust or lack of trust.