Prospect Meetings Falling Flat? Jon Bassford’s Curiosity Cure

Orchestraight Team
March 5, 2026
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 skill
3:21 - Tap into your team's curiosity
6:11 - Use AI (ChatGPT) to improve your questions
12:04 - Overcoming fear of change
14:06 - Small changes, huge impact
21:37 - Handling the 2AM entrepreneur fear
27:12 - The "I'm not ready yet" myth
Follow Jake:
LinkedIn: https://www.linkedin.com/in/jakestahl/
TikTok: @JakeTheMindMechanic
Podcast: 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/1962280780
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About the Author

Orchestraight Team
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