Personality is one of the most crucial aspects of human life, since it influences all human behaviours in both personal and social life, and might also trigger important conflicts with a person’s surroundings in the setting of incompatible traits and characteristics. It is true that ‘one must be born’ for a certain medical specialty, but several components of personality might be educated with proper training. Increased levels of Conscientiousness, Agreeableness, and Openness associated with lower levels of Neuroticism might represent the key combination for achieving professional satisfaction in the medical profession. Medical students should receive proper interprofessional education, since effective interprofessional relationships among healthcare providers definitely improve patients’ safety. Empathy contributes to effective patient–physician communication, improving patient trust, compliance, and satisfaction, being positively correlated with Openness, Agreeableness, Conscientiousness and Extraversion. Emotional intelligence—the capacity to respond to one’s own and others’ emotions—was proven to contribute, in a synergistic way with empathy, to increasing empathic ability. Clinical communication skills represent a key component in medical students in order to achieve the best patient care, and they are certainly related and/or influenced by empathy, interprofessional collaboration skills, emotional intelligence and, especially, personality traits. Taking into account the complex interactions mentioned above, the implementation of effective courses based on these concepts in medical students, intending to promote the development of clinical communication skills, represents a real emergency, since it might result in a reduction in medical errors and subsequent related deaths. A thorough understanding of students’ personality is mandatory before designing these courses in order to provide a training tailored to their personality styles.