Objectives: The aim was to investigate which factors influence the situational motivation of medical specialists and how situational and contextual motivation affect one another. Methods: A qualitative design was used, and a constructivist approach was adopted with the Self-Determination Theory of motivation as a framework. Twenty-two medical specialists from three medical centers in the Netherlands were recruited through convenience, snowball and purposive sampling and observed for two days each. At the end of the second observation day, a semi-structured interview was conducted. Data were transcribed and coded in an open manner. Themes were finalized through discussion and consensus. Results: Two-hundred and fifty hours of observation data together with the interview data identified that medical specialists experience six main themes influencing their situational motivation during a workday. Technical issues are influencing motivation negatively factors. Working with colleagues can be both a motivating factor and influence motivation negatively, e.g., filling in for each other through feelings of relatedness was motivating. Being in control of one's own planning through feelings of autonomy was motivating. Patient care, especially in combination with teaching, stimulated specialists' motivation. Conclusions: The results indicate that factors influencing motivation negatively are mainly tasks and organizational processes that distract from patient care or that compromise the quality of care. When optimizing the work environment of medical specialists, autonomous motivation and continuing professional development are stimulated. These, in turn, can improve the quality of patient care and wellbeing of specialists.