Workplace coaching is increasingly popular as a global learning and development tool for enhancing employees’ professional capabilities. However, little is known about the role of cross-cultural factors in coaching and the relationships between cross-cultural factors and both coaching approach and motivation factors. Accordingly, by drawing on and integrating theories from the research areas of cross-cultural psychology, regulatory focus, and training, we propose a theoretical framework that unravels the effectiveness of different coaching approaches in different cultural and coaching contexts. We propose that chronic regulatory focus is an underlying mechanism that predicts the effectiveness of a chosen coaching approach in specific contexts of societal uncertainty avoidance (i.e., low vs. high uncertainty avoidance). Furthermore, we propose that coaching context elicits coachee situational regulatory focus, and that compatibility between coachee chronic and situational regulatory focus has a significant impact on coachee pre-coaching motivation. We conclude by discussing implications for future research and practice.