Questions I Ask Successful Men

Over the years I’ve had the good fortune to spend time with successful men. Football coaches, best-selling authors, successful businessmen, professional athletes, and others. Sometimes I was interviewing them for The Modern Southern Gentleman Podcast (click here to listen and subscribe). While other times were surprise encounters at a ball game or party. I decided I never wanted to waste one of these opportunities so I developed several questions to ask every successful man I met:

  • What were the greatest successes in your life and what were the causes?

  • What were the greatest failures in your life and what were the causes?

  • What would you do differently if you were starting over?

  • What kind of books do you read?

  • How do you manage your time?

  • How do you manage your money?

  • What have been the greatest lessons you’ve learned?

  • What have been the greatest surprises in your life?



I keep this list of questions on my phone so I’m always ready to learn.