Falls at height are among the major causes of fatal accidents at work, especially in the construction sector. Maintaining balance while performing a tool with both hands generates physical efforts and mental loading that needs to be managed for workers’ safety and health. The purpose of the study is to compare perceived (dis)comfort (overall and localized), the ergonomic risk and the perceived effort through the acquired postures that subjects assumed during the execution of simple and common tasks both on a ladder and on the ground. 26 subjects were asked to perform four tasks in both conditions: top screwing, frontal screwing, object picking from the bottom forward, and object picking from the bottom sideways. Subjective and objective data were gathered for assessing subjective experience (discomfort and effort, perceived) and ergonomic risk. Results highlighted few ergonomic risk differences among “on ladder” and “on ground” tasks, while subjective data reveal significant differences in different scenarios. Main results regard knees and neck areas as the most critical ones.