I was in San Diego years ago for an early Dscoop, traveling with my daughter Emma. Emma and I share similar personalities, complete with a near-useless mental library of Monty Python quotes.
We also like to have harmless fun.
At a restaurant for lunch one day, we decided to hold an entire conversation in the form of a question. That is, all sentences need to be a question. We even took it too far (“You can never take it too far.” Ferris Bueller) by insisting the waitress participate whilst taking our order.
She played along, did great, and was well tipped as a result.
Asking questions is a core sales skill. The answers uncover solvable problems, root out issues, and allow reps to learn (provided they shut their traps and listen).
Most sales conversations stay surface-level:
- “How’s business?”
- “What are you working on?”
These are good starters. But they don’t go far enough.
And when you stop there, you get surface-level answers:
“Things are good.”
“We’re busy.”
“All set for now.”
End of opportunity.
The real value comes from what happens next.
Follow-up questions like:
- “What’s been the biggest challenge with that?”
- “How long has that been going on?”
- “What happens if that doesn’t get fixed?”
This is what people are really searching for when they look up how to uncover customer pain points in sales conversations.
Because until you understand the impact of a problem, there’s no urgency to solve it.
And without urgency, there’s no sale.
The difference between average and effective sales conversations isn’t confidence.
It’s curiosity.
Not just asking questions.
But asking better ones—and staying with them longer.
