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3 Leadership Keys from the World's #1 Caddie

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There are too many yes men in life. We don’t need another manager who will tell us what we want to hear. We need managers who will challenge our thinking, strategy, and direction. Steve Williams is not a yes man; he believes in speaking his mind and giving his opinion to you. This is done in the spirit of wanting the best for you.

In one interview, Steve was asked, “What was your biggest regret at caddying.” He told the story of caddying for Raymond Floyd, who wanted to become the oldest man to win the US Masters. Raymond had told Steve he was going to hit a fade into the 17th green. Steve had a thought, “but what if you pull it?” However, he never spoke it as he was overwhelmed a little by Raymond's reputation at that event.

Raymond did pull that shot and lost in the playoff. Steve regrets not speaking his mind on that occasion.

The best managers I have ever had challenged my thinking, plans, and goals—and that was a great thing as it made me a stronger person.

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