CEO succession represents a challenge for many companies. The leadership style of the new CEO impacts employees’ attitudes which, in turn, might be biased by the comparison employees make with their previous CEO. Cristina Pratelli investigates how and why leadership style (dis)similarity between the predecessor and the successor develops and affects successor leadership effectiveness. After a literature review and a theoretical model, she presents results from a quantitative study with SMEs in Switzerland as well as a qualitative multiple-case study with family businesses based in Germany, Italy, and Switzerland. This work offers new insights into CEO selection, leadership development, and the effectiveness of organizations.