This study proposed a in-depth look at the influences of personal traits and the attitudes of the main players involved in generational transition: Senior and Juniors. The instrument used is the Test di Attitudine Imprenditoriale (T.A.I. ), [“Entrepreneurial Attitude Test”], which describes entrepreneurial potential with regards to eight factors: A. Tendencies toward creativity and innovation, degree of determination in reaching goals, and personal perception as to overall handling of work situations. B. Attitudes toward management and leadership; C. Ability to perceive environmental change and adaptability; D. The desire for fame, success and social affirmation and respect of others; E. The desire to realize oneself through one’s job, which must be pleasant, satisfying and interesting, apart from any economic goals. F. Curiosity for the new; G. Tendency to reorient one’s goals according to external situation; H. Necessity of having one’s own independent space to make decisions and choices