Is it possible for a leader to be both humble and confident? At what point does confidence become arrogance, and perhaps dangerous? In a very unique conversation, this episode is the result of a very thoughtful email Russ received from an avid listener, David Deppner. A veteran leader himself, Deppner inspired some self-examination on Russ’s part, and the two explored the dichotomies of leadership in trying to maintain intellectual humility and still convey the confidence people need.


1- What did you learn about Churchill’s leadership style from last week’s episode? Would you now dub him a good leader? Why or why not? When does a leader need confidence? Arrogance?


2- How does good leadership compare across different sectors, such as business, medicine, and politics? To what extent should we admire people who aspire to leadership?


3- Roberts and Deppner spend a good bit of time talking about lying. When is it appropriate for a doctor to lie to a patient?  How much lying is prompted by malpractice? Should a doctor or surgeon ever say they’re sorry for a bad outcome?


4- What does Roberts mean when he says, “a rule of thumb can be incredibly unjust and still be the right rule?” What examples does he use in the context of this claim, and how convincing did you find them? Can you provide any other examples either in support of or in opposition to Roberts’s statement?


5- Russ references his previous conversation with Charlan Nemeth on troublemakers in history. Are such ‘toublemakers’ necessarily confident? Humble?


Bonus Question: Should Russ speak out more on policy issues? Why or why not?