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Digital transformation increasingly becomes important in organizations’ strategic directions because digitally transforming a business promotes effectiveness, innovation, and competitiveness. However, many digital transformations fail because organizations are too focused on business benefits or advanced technologies’ potential. Thereby, organizations tend to overlook employee-related changes and employee-related effects. To understand why digital transformation approaches fail, which barriers arise, and how these barriers can be mitigated, we conducted a case study in the banking industry. Based on a quantitative survey completed by more than 7,000 respondents, we shed light on common barriers to digital transformation and derive recommendations for action. Thereby, we focus on both technological conditions as well as on employee-related changes. Our findings yield insightful implications on how to shape organizations’ digital transformation successfully.

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