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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.
======
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.
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.
======
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.