This study aimed to develop a scenario-based questionnaire for evaluating medium-level leadership behaviors within the Greek National Healthcare System (NHS), drawing upon the principles of servant leadership theory. Data for this pilot study were collected in the first quarter of 2019, using a sample of 33 (22.9% of all medium-level managerial positions) medium-level managers from the Greek NHS hospital cluster located in North Attica. To assess managerial behaviors, an ordinal scale was employed, revealing non-normal data distributions. Consequently, our analysis involved presenting descriptive statistics, utilizing non-parametric tests to explore distinctions in managerial behaviors, and conducting thematic analysis of responses to open-ended questions, with frequencies and relative frequencies of each theme meticulously recorded. Overall, our findings indicate that, in most cases, managers exhibited positive behaviors toward their employees, regardless of whether the outcomes were positive, negative, or unknown. Positive behaviors towards the administration were comparatively rare. Significant differences were observed, highlighting that managers were more inclined to exhibit positive behaviors when the outcome was known, particularly in scenarios involving employee management. Within each scenario, behavioral patterns varied, with managers demonstrating a propensity to take credit for employee success in positive outcomes but distancing themselves from negative outcomes when reporting to the administration. Furthermore, the survey responses underscored the prevalence of positive attitudes regarding accountability and stewardship, with stewardship showing a positive correlation with scenario-based behaviors. Finally, our study brought to light several challenges in the management of the Greek NHS, including the absence of comprehensive managerial evaluation, the lack of meritocracy, regulatory deficiencies, and a shortage of leadership skills among current managers. These findings emphasize the importance of scenario-based assessments for Greek hospital managers, as they can help connect managerial behaviors to stewardship, accountability, and skills, ultimately contributing to the enhancement of leadership within the Greek NHS.