While central to any change process, emotions are often underdiscussed. This chapter delves into the emotional work inherent to coaching when facing and managing the emotions of the coachee, as well as one’s own. If left unattended, they can lead to cognitive bias and impact the coach’s decision-making process and actions. By examining two cases, this chapter highlights the importance of reflection, self-observation, and open and honest communication in order to identify and manage one’s own emotions, as well as the coachee’s.