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March 30, 2026 · Louie Bernstein

The weirdest sales interview question

hiring
Here's the weirdest question I ask in a sales interview (and why it works).
Most founders ask standard questions.
"Sell me this pen."
"Walk me through your resume."

I ask this instead:
"On a scale of 1 to 10, with 10 being the luckiest, how lucky are you?"

If they say 1 or 2? I pass.
I want to hear an 8, 9, or 10.

Here is why:
- People who think they are lucky are optimistic.
- Optimistic salespeople sell more. Period.

Don't fall for the "I don't believe in luck, I make my own luck" line.
That sounds tough, but often it masks a cynic.

You want someone who sees opportunity in the world, not just obstacles.

You can teach product knowledge.
You cannot teach a positive outlook.
Hire for optimism.

Save this post for your next interview and see if I'm right.
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P.S. I have two new Resilience Frameworks for Founders and Entrepreneurs coming out March 16th. They're built from my 50 years of experience and applied to the challenges today's founders face.