Cameron HeroldFounder of the COO Alliance & Invest In Your Leaders Training

How to Build Trust in Unfamiliar Rooms | Sheldon Cummings

28 Apr 2026 · 1 min

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1:08

Sheldon Cummings credits his private-school upbringing with teaching him to build trust quickly in unfamiliar settings. That habit of connecting with strangers paid off later when he encountered former classmates during job interviews. He argues that deliberately seeking uncomfortable environments builds the self-reliance and networking skills that matter most in a career.

Chapters

Did something happen with you at the private school? Did you see anything and learn anything from that that you still carry with you today? When you first get out of school, whether that be high school, whether that be undergrad, for me, it wasn't an immediate impact of the network. As you progress through your career, then you find connection points. As you are potentially interviewing with a company and now it's the, oh, so-and-so that I used to work with is also at that organization. And then you're building that connection where you can learn more about it and what really is happening at that organization. The benefit that is immediate when you're going through the private school and the college, etc., is this notion of resiliency, this notion of putting yourself into environments where you're not comfortable and sort of relying on yourself and quickly building a network and quickly building trust. Didn't know what that high school, you know, was. Never heard of prep school. Never lived outside, you know, overseas before in the US. And when people hear about my background, they would think about me being born in a military family. But the reality is, is, you know, my parents still in the same hole that I was in, you know, when I was a kid.