Lesson 3.5: The Art of Caddy Conversation
“The golf course is one of the last places in the world where a young person and a CEO stand on equal ground.”
Most people think of caddying as a way to earn money. And it is. But for a motivated young person who pays attention, caddying is something far more valuable than a paycheck — it’s access to successful, accomplished, influential people in a setting where they are relaxed, present, and willing to talk.
On any given Saturday morning at a private club, you might be walking alongside a business owner, a surgeon, an attorney, a college administrator, or a startup founder. These are people who are otherwise very difficult to reach. On the golf course, you have four hours with them.
The right way to make the most of it:
The key is genuine curiosity, delivered at the right moment, in a completely natural tone. You are not networking. You are not conducting an informational interview. You are a young person who is genuinely interested in people — and you happen to be in a position where interesting people are right beside you for four hours.
One good question is worth more than ten awkward ones. Ask something real, listen fully, and follow the conversation where it goes. That’s it. The opportunities that come from genuine connection — mentorship, references, introductions, job opportunities — cannot be forced. They emerge naturally when the relationship is real.
Conversation starters that feel natural (not nosy):
About their work — without asking directly:
- “Did you always know what you wanted to do, or did you figure it out as you went?”
- “What’s the most surprising thing about the work you do — something most people wouldn’t expect?”
- “What did you think you were going to do when you were my age?”
About their journey and lessons learned:
- “What’s the best piece of advice someone gave you early on that actually turned out to be true?”
- “If you could go back and tell your younger self one thing, what would it be?”
- “Is there a person who really changed the direction of things for you — a mentor or someone who took a chance on you?”
About golf — always a safe entry point:
- “How long have you been playing? Did someone get you into it?”
- “Do you have a favorite course you’ve ever played?”
- “Is there somewhere you’ve always wanted to play that you haven’t gotten to yet?”
What NOT to ask — ever:
❌ “How much money do you make?”
❌ “Can you get me a job?”
❌ “Do you know anyone who could help me with…?”
❌ Anything about politics or religion
❌ Multiple questions back-to-back
✓ Ask one genuine question
✓ Listen fully — really listen
✓ Follow up on what they say
✓ Remember answers and circle back
✓ Let relationships develop naturally
The best caddies don’t just ask questions — they remember the answers. If a player mentions their business early in the round, circle back to it naturally on the back nine. “You mentioned you started the company right out of college — did you always have that plan?” This signals something powerful that most adults don’t experience even from other adults: you were actually listening.
Conversation preparation exercise: choose three conversation starters from this lesson that feel most natural for you personally. Practice saying each one out loud — to a mirror, to a parent, to a friend — until they feel completely natural rather than rehearsed. The goal is to be able to ask these questions in a genuine, easy tone without sounding like you’re reading from a list. Then, during your next social interaction with an adult you don’t know well (a neighbor, a family friend, a coach), practice asking one thoughtful question and listening fully to the answer. Write down what you learned from the conversation.