A Lesson in Sales from an Unexpected Encounter

One morning, on my way home from the gym, I had an unusual encounter that left me thinking about sales, storytelling, and the power of curiosity.

I was walking down the street, headphones on, minding my own business, when a stranger who looked strikingly like Jerry Lewis stopped me with a friendly “Hello.” He asked, “Can I ask what you’re listening to?”

I was caught off guard. I’m used to people chatting casually, but this felt different. His curiosity was contagious—I started to wonder, Why does he want to know what I’m listening to? I replied, “No, not music.” This made him lean in even further.

“So what is it that you’re listening to?” he asked again, with genuine curiosity.

I answered, “It’s a talk.”

“Oh, you’re giving a talk?” he asked, still curious.

“No, no,” I laughed. “I’m listening to a lecture. Someone else is speaking.”

His curiosity only grew. “What’s the lecture about?”

I could tell he wasn’t just making small talk. There was a direction to his questions, so I indulged him. “It’s a religious lecture,” I explained, thinking this might satisfy him.

But he wasn’t finished. “Yeah, but what specifically is it about?” he probed again, wanting more.

At this point, I couldn’t help but admire his approach. He wasn’t demanding anything outright, yet here I was, willingly engaged, curious to see where this would go. After a few minutes of our back-and-forth, he finally got to his point:

“Do you have 50p?”

Now, I typically don’t carry cash after the gym. I told him I only had my card, but the exchange lingered with me long after I walked away.

This wasn’t your typical street pitch. He had engaged me by tapping into my curiosity, slowly revealing his purpose, and building rapport. In those few minutes, he demonstrated an approach that’s incredibly relevant in sales. Often, the best way to engage someone isn’t with a hard sell but by creating curiosity, building a story, and drawing them in until they’re genuinely interested in the outcome.

This encounter reminded me that, just like in sales, the key is to engage first and ask second. This man’s approach showed me a masterclass in storytelling—and gave me a new perspective on how to start conversations that could lead anywhere. Sometimes, the most valuable sales lessons come from the most unexpected sources.

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