Churchill’s probing questions

When civilian leaders oversee military personnel, the dynamic can prove challenging. Without trust and mutual respect, less sharing of information and more obfuscation can lead to tragically wrongheaded decisions.

Winston Churchill understood this. As Great Britain’s strategic position weakened in World War II, Churchill demanded more options from his military team and listened intently to their input. He liked to ask piercing questions that made military officers uncomfortable. “It is always right to probe,” he said.

Churchill tolerated—and often encouraged—generals to present opposing viewpoints from his own. He wanted to hear the best arguments from all sides before making a decision.

Churchill resisted issuing orders without considering the military staff’s wide-ranging perspectives. As a result, commanders felt that their voices were heard—even if Churchill ultimately reached a different conclusion.

Another civilian leader, David Ben-Gurion, was Israel’s prime minister during its War of Independence. Leading up to that war, Ben-Gurion conducted “the seminar”—a two-month process in which he suspended his normal duties so that he could interview his military personnel. He inquired about many areas from training and equipment to the command structure to quality of intelligence gathering, using their responses to distinguish between strong leaders and the less competent.

— Adapted from Supreme Command, Eliot A. Cohen, Anchor.