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The current workforce in the United States is rapidly changing and is increasingly inclusive of individuals from a broad range of ages, ethnicities, and cultural backgrounds. Engaging and leading a diverse workforce creates great opportunities for innovation and adaptation in our evolving medical economic and clinical care delivery environment. For optimal engagement of employees and partners, orthopaedic surgeons must develop the necessary skills for executing change inside complex organizations and across teams composed of a variety of providers and skilled workers. Important skills include leadership, effective communication, and negotiation within an ever-changing employee milieu. Understanding generalizable differences between age-based generations can increase the effectiveness of one’s strategies to execute change and increase organizational performance. One of the greatest impediments to effective communication and negotiations that all leaders face is unconscious bias. For leaders, even the tiniest unconscious biases have an outsized impact. Common domains that harbor unconscious bias include sex, race, and ethnicity. Addressing unconscious bias begins with developing awareness and then deploying various tactics that might include equity in compensation, promotion, and “being heard.” Effective negotiation skills also are essential to lead a diverse workforce and develop a successful organization. The most basic goal in any negotiation should be to establish a relationship (or deepen an existing relationship) while seeking an agreement that provides win-win opportunities for all parties. To effectively achieve a win-win scenario, leaders must recognize and address their tendency to interpret others’ behaviors, values, and beliefs through the lens of their own beliefs and experiences. Finally, and fortunately, there is a set of leader attributes that transcends the generational differences and diversity that is encountered in the workplace. These attributes include integrity, credibility, effective listening, having a vision of your destination, fairness, humility, and caring.