Stop Asking “What’s Your Biggest Challenge?" on Cold Calls

No One Wants a Cold Call Quiz

Bad cold calls feel like an interrogation.

🔍 “What’s your biggest challenge?”

🔍 “What’s keeping you up at night?”

🔍 “What are your top priorities this year?”

When prospects feel grilled, they shut down. But great cold calls? They feel like conversations.

So let’s dive into the 3 simple shifts that can turn cold calls into real conversations - and avoid the dreaded interrogation energy!

Pssst: Want to make your calls more relevant without spending hours researching?
(I’ll be tuning in to hear more on how to use buyer intent to make cold calls more relevant and better timed 👀)

1. Give Cold Calls Structure

Asking a prospect to share their biggest challenge out of the blue is like putting them on the spot for a pop quiz.

Instead, give them two real challenges to react to

Cold Call Challenge Framing Template

“Not sure about you, but most [job titles] I speak with are either

[Challenge A], or

[Challenge B].

Which one feels more real in your world?”

Example for VP Sales

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