Katherine Graham, Confidence

She came late in life to leading The Post.  She hired bold editors who she had little control over, and she backed them up on key decisions.  It's not easy to hire someone you know has a stronger personality than you, or who is more capable than you. She made bold decisions and stuck with them, although she was personally socially awkward and lacked confidence.

From The Washington Post obituary:

Mrs. Graham's imprint was the product both of her values, which suffused the paper, and of the crucial decisions she made about its leadership and direction. At The Post and Newsweek, she chose great editors, such as The Post's Benjamin Bradlee, and then gave them the independence and resources they needed to produce strong journalism. She also supported them at crucial moments, when their work was doubted or under attack by powerful forces in and outside of government. Two of those cases helped define her career, and The Post: her refusal to bow to the government's efforts to block publication of the Pentagon Papers and her backing of the paper's coverage of the Watergate scandal.

Her decision in 1971 to publish the Pentagon's secret history of the Vietnam War, after a federal court already had blocked the New York Times from doing so, was even harder than it appears in retrospect. There was nothing harmful to national security in the papers, but the Nixon administration claimed otherwise, and its henchmen were not above threatening The Washington Post Co.'s television licenses. Mrs. Graham's lawyers advised against publication; they said the entire business could be ruined. But after listening to the arguments on both sides, Mrs. Graham said, "Let's go. Let's publish." In those circumstances, she didn't believe that the government ought to be telling a newspaper what it could not print.