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Question Master

Anytime I meet someone who is doing something really positive with their lives, I try to ask them quality questions to get a better understanding of what they do and how they got there. Every once in a while I meet someone who is extremely successful financially, but so miserable internally. I always want to know why.

It was Saturday night in Mexico for my girlfriend’s bachelorette party. We were invited by this man to come join him in his “I’ve got the biggest table in the whole club, you’ll love it” kind of booth. All of our girls drank his expensive alcohol and enjoyed anything he paid for, really. He told the girls about his $40,000 private jet ride he took to get there, about his couple thousand dollar booth we were in, about the mansion he was staying in down the street…

I observed him for a minute. I looked at his demeanor and how he talked to all of the women in his booth. He seemed nice, but something was off.

After a while or so, I looked around and thought “this man has to be putting in some serious work to have all of this,” so I walked over to start a conversation. I wanted to ask him how he got to be where he is now. Truthfully, I didn’t care so much about where he works or how much he makes, I wanted to know why he seemed so unfulfilled.

It took a few minutes for him to take me seriously - a nightclub may not the best place to have a serious business/life talk. He told me about his story of growing up very very poor. His family didn’t have much money and he was living in his car, completely broke, in his mid 20’s. He said he wanted to make a life for himself and he wanted to have a lot of money. He works 70 hours a week and on vacation he responds to emails for 3 hours each day. I congratulated him, gave him a high five and a “You deserve it. Good for you.”

After taking the time to ask him about his story and to thank him for sharing things he works hard for, you would not believe how much his attitude changed. I think he felt appreciated and listened to. It was only a matter of minutes until he went back to being the way he was, a little obnoxious, standing on the table pouring champagne over people.

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Olivia Reed