I learned something about flattery the hard way – from a conversation that sounded “nice” and also out of place.
A client of mine called me and came in with heavy praise. It was nonstop flattery. He told me my business was incredible, “exactly what people need.” Then he offered to “help promote it” and “open doors” for me.
It was strange, but I didn’t see through it initially. I was tired that week and a little too open. So instead of slowing down, I started talking. I shared pieces of my growth plan, how I explain what I do, and what I’d learned the hard way.
The next day, the compliments came again … and so did the ask. This time it wasn’t about promotion. He wanted help with “sensitive legal issues.” He was curious about the business paperwork I’d already paid an attorney to draft. He didn’t say, “Can you introduce me to your lawyer?” He spoke casually, “Can you send me what you have?”
That was the moment the warmth drained out of the phone. I could feel the shift from “You’re amazing” to “Give me access.”
Thankfully, I didn’t hand him what he wanted. I made an excuse, slowed the conversation down, and kept my documents to myself. Two weeks later, I noticed he’d opened a copycat business. It wasn’t well executed, but the point landed like an arrow to my gut: he hadn’t been trying to help me at all. The praise wasn’t generosity. It was a tactic – meant to lower my guard so I’d hand over information that didn’t belong to him.
I can’t prove what was in his heart, but I can recognize the pattern: big, vague praise … followed by pressure … followed by a request that crosses a line.
To be clear, most compliments are harmless. Some are life-giving. A good word at the right time can keep a person going. But flattery is different. Flattery often isn’t about building you up; it’s about moving you – toward a yes, a secret, a shortcut, a favor.
Centuries ago, Machiavelli watched powerful people get surrounded by yes-men. In “The Prince,” he warned that leaders who only hear sweet words are easy to steer. When nobody dares to tell you the truth, you don’t just get praised – you get guided.
We’ve been telling stories about this trap for a long time, too. In one of Aesop’s fables, a crow holds a piece of cheese while a fox praises its “magnificent voice.” The crow sings. The cheese drops. The fox eats. It’s simple, but it sticks: a little praise, and we loosen our grip.
In “King Lear,” the tragedy begins with a risky demand: Lear asks his daughters to publicly declare how much they love him, turning love into a performance. One daughter lays it on thick – so thick she even claims her love is too great for words while delivering a long, polished speech –and everyone watching can sense it’s not honest, it’s calculated. Lear, hungry to be reassured, can’t tell the difference, and that single mistake lights the fuse for what follows: the people who flatter him get rewarded, the one who won’t perform gets punished, and the kingdom pays for it.
That’s the cost when we mistake flattery for truth: we trade our judgment for a quick hit of comfort.
So what do we do with that, without turning into suspicious, hard-edged people? We do something small: we pause.
When praise is specific, it usually feels steady. “You handled that conversation well.” “You showed up when it mattered.” You can rest in that kind of compliment.
But when praise is oversized, urgent, and followed by a request – especially a request for access – take one step back. Ask yourself: What exactly is this person praising? What do they want next? If you can’t answer the first question, don’t rush to answer the second.
You can still be kind. You can still say thank you. You just don’t have to hand over the keys.
Because the goal isn’t to stop trusting everyone. The goal is to trust with your eyes open.
That moment might protect more than your pride. It might protect your peace, your work and the things you’ve built the slow, honest way.
• Toby Moore is a Shaw Local News Network columnist, star of the Emmy-nominated film “A Separate Peace” and CEO of CubeStream Inc. He can be reached at feedback@shawmedia.com.