Chad SilversteinBuilt To Lead · Entrepreneur , Advisor, & Thought Leader

The Power of Curious Questions

Name: The Power of Curious Questions
Uploaded: 2025-11-12T17:40:31+00:00
Duration: 1 min 51 s
Channel: Chad Silverstein
Description: In this solo talk, Chad Silverstein emphasizes that great leaders gain a decisive edge by asking thoughtful, curious questions. He argues that most…

12 Nov 2025 · 2 min

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In this solo talk, Chad Silverstein emphasizes that great leaders gain a decisive edge by asking thoughtful, curious questions. He argues that most people default to talking about themselves, but leaders should act like “Curious George,” probing deeper and then questioning the initial answers, which are often superficial. Silverstein illustrates the practice used in the Built to Lead program: after a speaker shares an idea, listeners ask them to repeat it multiple times, each iteration sharpening clarity and conciseness. He explains that this iterative questioning reveals more insight than resumes, background checks, or references. The same principle applies when vetting vendors, hiring attorneys or accountants, and especially when managing underperforming teammates—leaders must tune into signs of disengagement, ask hard, specific questions, and not shy away from uncomfortable inquiries.

Chapters

The power behind asking good, curious questions. It's unbelievable. The best leaders ask the best questions. And if you think about the scenarios that you come across as a leader, whether you're interviewing people, whether you're trying to figure out if someone's a good business to do business with, you're trying to vet certain vendors, you're trying to hire an attorney, you want your accountants, whatever the case, you know, most people are just talking about themselves. They just want to be known for whatever it is that they're known for, and they're not doing their due diligence to not interrogate GATE, but to be Curious George and to just ask the right questions and then question those answers, because usually the first answer is not so good. This is why in Built to Lead practice, if you've ever been in one, we ask someone to speak, and then when they share whatever there is they're thinking, usually you'll hear one of the builders say, say it again, you know. And usually after the second time, gets a little bit better. And you know what, say it one more time. Usually then the person just CCD, clear, concise, direct. They pop it out and you could see the difference. They just say it with such clarity, such pop. But typically what happens when people answer their first time, they're not thinking. They just respond to whatever it is. They're reacting to whatever it is you ask them. Asking the best questions, being very, very thoughtful into why you're asking certain things and what you're trying to gain from their answers, and then questioning those answers Tells you so much more than a resume, a background check, a reference check. And same goes with your teammates. When people are underperforming and when you know something's going wrong in their life because they've gone dark, tune into that, ask good questions, and don't go easy on your questions. Sometimes you got to ask the hard questions.