Prospect Meetings Falling Flat? Jon Bassford’s Curiosity Cure episode artwork

EPISODE · Mar 5, 2026 · 33 MIN

Prospect Meetings Falling Flat? Jon Bassford’s Curiosity Cure

from Own The Room: How to Control Perception, Read the Room, and Win High Stakes Conversations

Your prospect meetings fall flat because you're asking terrible questions, and you don't even know it. Jon Bassford, bestselling author of The Curious Leader, reveals how the way you word a question completely dictates the answer you get. He breaks down a genius hack: load your last few sales calls into ChatGPT and ask "where could I have gone deeper?" to instantly level up your questioning game. Stop leading with your opinions in meetings and let others speak first... you'll unlock perspectives you never would've generated yourself. Ego kills curiosity, and curiosity is what closes deals.Here's the kicker: you don't need massive changes to see results. Jon transformed an entire organization's revenue by 20% without spending a dollar... just by pulling one buried document out of a manual and making it accessible. Key insights:1:07 - Curiosity as a natural vs. learned skill3:21 - Tap into your team's curiosity6:11 - Use AI (ChatGPT) to improve your questions12:04 - Overcoming fear of change14:06 - Small changes, huge impact21:37 - Handling the 2AM entrepreneur fear27:12 - The "I'm not ready yet" mythFollow Jake:LinkedIn: https://www.linkedin.com/in/jakestahl/TikTok: @JakeTheMindMechanicPodcast: https://thejakestahl.com/podcast/Book: Own the Room: https://thejakestahl.com/books/Connect with Jon Bassford:LinkedIn: https://www.linkedin.com/in/jonbassford/Company: https://think-lateral.com/about-us/Book: https://www.amazon.com/Curious-Leader-Unlocking-Innovation-Empowering/dp/1962280780This episode is brought to you by Orchestraight. Start your free 7-day trial at orchestraight.com.Orchestraight. The straightest path to success.

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Prospect Meetings Falling Flat? Jon Bassford’s Curiosity Cure

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This episode is 33 minutes long.

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This episode was published on March 5, 2026.

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Your prospect meetings fall flat because you're asking terrible questions, and you don't even know it. Jon Bassford, bestselling author of The Curious Leader, reveals how the way you word a question completely dictates the answer you get. He breaks...

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