Living a sedentary lifestyle is one of the major causes of numerous health problems. To encourage employees to lead a less sedentary life, the Hanze University started a health promotion program. One of the interventions in the program was the use of an activity tracker to record participants’ daily step count. The daily step count served as input for a fortnightly coaching session. In this paper, we investigate the possibility of automating part of the coaching procedure on physical activity by providing personalized feedback throughout the day on a participant’s progress in achieving a personal step goal. The gathered step count data was used to train eight different machine learning algorithms to make hourly estimations of the probability of achieving a personalized, daily steps threshold. In 80% of the individual cases, the Random Forest algorithm was the best performing algorithm (mean accuracy = 0.93, range = 0.88–0.99, and mean F1-score = 0.90, range = 0.87–0.94). To demonstrate the practical usefulness of these models, we developed a proof-of-concept Web application that provides personalized feedback about whether a participant is expected to reach his or her daily threshold. We argue that the use of machine learning could become an invaluable asset in the process of automated personalized coaching. The individualized algorithms allow for predicting physical activity during the day and provides the possibility to intervene in time.