Issue Number 13: Leadership and Frank Sinatra

Ed Walters, who worked as a pit boss in Las Vegas tells a great story about Don Rickles, the famously warm-hearted insult comedian, and Frank Sinatra. It was fairly early in Rickles’ career and he was on stage in one of the smaller rooms at the Sahara Lounge when Frank Sinatra and his entourage came in. Sinatra had a reputation for either loving you or not wanting to have anything to do with you. As soon as Rickles spotted Sinatra he began insulting him. The audience grew quiet. Nobody was sure how Sinatra would react. The pit bosses moved to the back of the room in case there was trouble.

Rickles threw a few more jabs at Sinatra and then turned around to nervously ask his backup band: “Is he smiling?” Sinatra started laughing and everyone relaxed.

The kind of humor you allow in the workplace has a powerful effect on others. Since you are the leader, people will ask themselves the same question Don Rickles asked. If you are smiling or laughing, you send the message that you are enjoying it – and condoning it.

Through your behavior you determine what is acceptable and what is not acceptable. It is part of your responsibility as a leader to set the parameters and to provide guidance and consequences for those who do not abide by them.

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