In this conversation, Jeff Stocker discusses his background, his role in healthcare IT, and his perspective on sales. He emphasizes the importance of authenticity and genuine connection in sales, and how it is not mutually exclusive from making a living. Jeff also highlights the value of structured training in sales and the impact it had on his career. He shares two milestones that catapulted him to the next level: the opportunity to pursue domestic government sales and the success he achieved in government contracts. These experiences instilled confidence in himself and his belief in the value of the work he was doing. In this conversation, Jeff discusses his transition from being an individual contributor to managing people and the challenges that come with it. He emphasizes the importance of being a therapist as a leader and manager, listening to and understanding the grievances of team members while remaining focused on the mission. Jeff also talks about the dynamics of managing people of different ages and experience levels. The conversation then shifts to the dichotomy between management and leadership and the need to balance listening and empathy with making tough decisions. They discuss the unrealistic expectations set by higher-ups and the choices leaders have to make in navigating those expectations. They also explore the growth potential in healthcare information technology and the importance of understanding the industry and staying informed. Jeff shares his habits of remaining a student of healthcare and practicing mindfulness to stay focused and motivated.