To Italian-Americans close to him, Sinatra became one of those guys known in Sicily as uomini rispettati, or men of respect. Such leaders were both majestic and humble. They would go out of their way to right a wrong. They’d see to things personally. Villagers would kiss their hands.
Sinatra did things personally. At Christmas, he’d pick dozens of presents himself, remembering clothing sizes and items his family and friends liked. When a California mudslide killed a friend’s wife and destroyed their home, Sinatra showed up in person to find the man a new house, oversee its furnishing and pay any uninsured hospital costs.
On the flip side, Sinatra could explode in a towering rage. He would throw things. He once permanently banished his loyal valet. His people couldn’t anticipate his reaction to anything because he was unpredictable.
This old-school style has its advantages, for sure. Sinatra’s crowd was loyal and compliant. They didn’t talk back.
The disadvantages? Aside from the self-induced blindness of being surrounded by “Yes” men, old-school bosses also trigger overreactions to their wishes.
For example, when Sinatra mentioned once that his Jeep in Palm Springs could use a fresh coat of paint, the word passed quickly down the ranks, growing more urgent until it turned into a command that had to be obeyed immediately.
That would require a special crew of painters working all night at overtime pay. That, in turn, required special approval, so the order had to be kicked back upstairs. When it reached Sinatra, he didn’t know what his people were talking about. After puzzling it out, he wearily told them he didn’t care when they painted the Jeep.
Lesson: Old school as it sounds, this scenario still plays out regularly in organizations, especially big ones. If you don’t want people kissing your hand, don’t be a boss. Be a leader.
— Adapted from “Frank Sinatra Has a Cold,” Gay Talese, Esquire.