Teeing it up with the boss is hard enough, but Greg McLaughlin’s rounds are tougher then most, since his boss is also the best player in the world.

“It’s more than a little intimidating,” says McLaughlin, a 10-handicap and president of the Tiger Woods Foundation. “I played with Tiger recently at Isleworth. It was a 2-handicapper, a 6 and me—our best ball against his. And we got to play any tees we wanted. So we played at about 5,800 yards while Tiger played from the tips.

“He just pounded us. He never came close to missing a shot and even holed out from a fairway bunker. We eventually just stopped pressing; we were totally defeated.”

McLaughlin’s game is a bit rusty because he’s been busy, commuting to Washington D.C. from Orange County, California, to organize the inaugural AT&T National, July 5–8, a difficult task since the deal only came together in early March.

Fortunately, tournament administration is nothing new for McLaughlin, 47, who was responsible for giving the then 16-year-old Woods his first PGA Tour exemption at the 1992 L.A. Open. Woods has returned the gesture many times since, playing in McLaughlin-run events like the Western Open and eventually, offering him a job.

In late 1999 Earl Woods asked McLaughlin to help run Woods’ post-season event at Sherwood Country Club. “Earl was starting to slow down just a little, and was looking for someone to help him grow their foundation,” he says.

In addition to monitoring millions of dollars in grants, McLaughlin oversees the Tiger Woods Learning Center in Anaheim and puts together fundraisers like Tiger Jam in Las Vegas—all the while reporting to a demanding, high-profile boss.

“In many ways, Tiger approaches the foundation like he does his golf game,” says McLaughlin. “He’s very committed, passionate and methodical. He listens and is very content to have the staff run the programs, but he has distinct opinions on where our efforts should be focused.”