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Prospect Meetings Falling Flat? Jon Bassford’s Curiosity Cure

Orchestraight Team

Orchestraight Team

March 5, 2026

2 min read

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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Orchestraight Team

Orchestraight Team

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