Learning to Read People with Wisdom and Discernment
In his book Talking to Strangers, Malcolm Gladwell explores why so many of our interactions with strangers go wrong. For example, how did Fidel Castro fool the CIA for an entire generation? Why did Prime Minister of England Neville Chamberlain think he could trust Adolf Hitler after meeting him, but Winston Churchill – who never met him – never trusted him?
Gladwell notes that the people who were right about Hitler were those who knew the least about him personally, and the ones who were wrong about him were the ones who had talked with him for hours.
But this plays itself out over and over again.
Why did so many trust Bernie Madoff with their money?
Why did so many parents trust Jerry Sandusky with their children?
In other words, why can’t we tell when the stranger in front of us is lying to our face, and how is it that meeting a stranger can sometimes make us worse at making sense of that person than not meeting them?
Gladwell’s thesis is that something is wrong with the tools and strategies we use to make sense of people we don’t know. And because we don’t know how to talk to strangers, we invite conflict and misunderstanding into our lives and into our world.
It’s a fascinating read.
It caused me to reflect upon how I read people—and I do read people. We all do. But I read people better now than I did when I was younger, mostly due to a litany of lessons learned the hard way.
Here are a few lessons I’ve learned:
Keep an eye on their ego. For example, if someone is a singer and is not asked to sing, how do they react? If they demand to know why or are offended that they aren’t asked, take note.
Pay attention to what they tell you. If they gossip to you, they will gossip about you. They are simply gossipers.
Add up pink flags. We all know the phrase “That’s a red flag”—meaning something to take note of. But I’ve learned to talk about “pink flags”—meaning something of notice, but not quite certain. If enough pink flags present themselves, add them up to a full-blooded red.
Observe their reaction to sin. Sin is real and is present in every human life. How do they react to it when they see it? Some lean toward grace, others toward truth. Look for those who keep it in balance.
Gauge their sensitivity meter. If someone is quick to take offense, has their feelings easily hurt, and always seems to take things the wrong way, you realize they are highly sensitive people. Translation: they are often relationally unsafe.
And last but not least, take a lesson from Gladwell’s research and pick up the phone. This is critical for anyone engaged in hiring staff or recruiting volunteers. I’ve written about what this entails in What They Didn’t Teach You in Seminary. I’ve been told this chapter alone is worth the price of the book.
All I know is I wish someone had told me about it.
James Emery White
Editor’s Note
This blog was originally published in 2019 and the Church & Culture Team thought that you would enjoy reading it again.
Sources
Malcolm Gladwell, Talking to Strangers.
James Emery White, What They Didn’t Teach You in Seminary, order from Amazon.
Photo Courtesy:©GettyImages/PeopleImages
Published Date: July 24, 2025
James Emery White is the founding and senior pastor of Mecklenburg Community Church in Charlotte, NC, and a former professor of theology and culture at Gordon-Conwell Theological Seminary, where he also served as their fourth president. His latest book, Hybrid Church: Rethinking the Church for a Post-Christian Digital Age, is now available on Amazon or from your favorite bookseller. To enjoy a free subscription to the Church & Culture blog, visit churchandculture.org where you can view past blogs in our archive, read the latest church and culture news from around the world, and listen to the Church & Culture Podcast. Follow Dr. White on X, Facebook, and Instagram at @JamesEmeryWhite.
Originally published July 24, 2025.
