How AI can sharpen asking and listening

Jeff shows AI as a brainstorming partner for questions and a tool to analyze transcripts.

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#672: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E.

Today's letter I stands for Increasing Your Income. This episode originally aired in August 2024, but the strategies are more essential than ever.

Jeff Wetzler, Ed.D., reveals why the people around us withhold crucial information — and how asking better questions can transform your negotiations and net worth.

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You've mastered the art of asking for what you want — or have you?

Jeff Wetzler, Ed.D., a former education executive, joins us to reveal why most of us fail to extract crucial information from the people around us.

Think about it: when was the last time someone told you what they really thought about your work? Or shared that game-changing idea they'd been sitting on?

Wetzler discovered four categories of information people routinely withhold — and the cost runs deeper than you might expect.

We explore why people stay silent about their struggles, unpopular opinions, observations about us, and innovative ideas.

The reasons range from fear to simple exhaustion, but one stands out: they don't think we want to know.

Here's a startling example from Harvard Business School research: investigators planted smudges on their faces and surveyed people. Less than three percent told them about the mark that they could wipe off in one second. But when asked later, 100 percent had noticed it.

If people won't share something that simple, what else are they keeping from us?

Wetzler shares his Ask Approach — five steps that unlock hidden information in any negotiation or relationship. We walk through real scenarios, from salary negotiations to buying cars, showing how curiosity beats strategy every time.

One mechanic story drives this home. Facing a $2,000 air conditioning repair, Wetzler asked one question: "Do you have any other creative ideas?" The mechanic paused, then offered a $75 solution that worked perfectly. That five-second question saved $1,925.

We discuss practical listening techniques, including the "doorknob moment" — why therapists know the most important information comes at minute 49 of a 50-minute session. Wetzler explains why our minds process 900 words per minute while our mouths manage only 125, creating a massive information gap.

The conversation includes AI's surprising role in sharpening these skills, helping us frame conversations into content, emotion, and action.

Wetzler demonstrates how technology can enhance rather than replace our uniquely human ability to connect and learn from each other.

Timestamps:

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(00:00) What's at stake in asking better questions

(02:33) Four categories of information people withhold

(06:33) The smudge experiment reveals our silence

(09:13) Why people don't tell us what they think

(12:53) The Ask Approach begins with curiosity

(14:48) Making it safe for truth-telling

(18:53) CEOs share how to get honest feedback

(22:13) Posing quality questions vs crummy questions

(30:58) Listening across three channels

(34:28) The doorknob moment phenomenon

(37:43) How to listen better in negotiations

(42:13) Reflect and reconnect strategies