When Praise Becomes a Problem: Spotting Manipulative Insincerity in People and AI
I once gave a pitch to a venture capitalist — let’s call him Billy — that went horribly wrong. I only got through about half of my presentation because Billy asked about a competitor I’d never even heard of. I got so flustered that I became totally incoherent for most of the rest of the meeting.
The next day, Billy called me up and said how much he’d enjoyed the meeting.
“Really?” I blurted out. “I thought it was the worst pitch I ever gave!”
“Oh, you’re much too hard on yourself!” he said, and then proceeded to tell me how impressed he was. He dismissed my ignorance of a major new competitor as totally unimportant.
I was completely confused. Was my understanding of what made a good pitch totally off? Was I just having an irrational crisis of confidence? Had I actually done as well as he said?
Then he pivoted. He told me how impressed he was by my background and mentioned a company where I used to work. “Did you happen to know X there?” he asked. “Would you mind introducing me to him?”
Suddenly, it all made sense. Billy didn’t actually think my pitch went well at all. He was just using false praise to manipulate me into making an introduction he wanted. This was a perfect example of Manipulative Insincerity — praise given not because it’s genuine, but to accomplish a hidden agenda. His praise lacked both care for me as a person and a challenge to do better. It wasn’t about me at all.
That experience taught me just how disorienting and confusing false flattery can be. It made me question my own judgment and created unnecessary self-doubt, all while serving someone else’s ulterior motives.
False flattery and telling people only what they want to hear is one of the most dangerous communication styles in the workplace. Unfortunately, this kind of communication is more common than we’d like to admit — and its consequences are far-reaching.
The Problem with “Yes People”
In teams where people only say what they think the boss wants to hear, real problems quickly take root. Rather than surfacing concerns or offering helpful feedback, people resort to insincere flattery. I’ve seen this behavior — political, passive-aggressive, and often gossipy — create toxic environments where relationships and work suffer. It might make for entertaining stories later, but it’s a recipe for dysfunction.
Leaders in these environments lose sight of reality. When surrounded by agreement, they overlook crucial information and develop dangerous oversights regarding their decisions, strategies, and behaviors. It’s the classic “emperor has no clothes” scenario — where everyone sees the problem except the person in charge.
The outward harmony can be misleading, too. When people are afraid to voice real concerns, the culture might look friendly, but it’s actually one of Ruinous Empathy.
It also kills innovation. When teams don’t feel safe to challenge ideas or suggest alternatives, progress stalls. The best solutions often come from disagreement and debate — not blind consensus.
People with good BS detectors notice this dynamic quickly. They want honest feedback and recognition based on merit. When everyone gets the same vague compliments, regardless of performance, trust erodes. People begin to feel that their contributions don’t matter — and they leave.
And they really do leave. According to MIT Sloan Management Review, toxic culture — not pay — is the top predictor of attrition. When people don’t feel heard, when honesty is missing, they disengage and move on.
Insincere Praise Creates Real Harm
Praise that isn’t genuine can be just as damaging. It reinforces inflated self-perception, especially in people who already have an elevated view of their own abilities. Instead of helping someone grow, you end up encouraging the very behaviors that need to be challenged.
It also puts your own credibility at risk. I learned this the hard way when I tried to smooth over a disagreement at Google with Larry Page by offering praise I didn’t mean. He had an excellent BS meter and saw right through it. That moment drove home a core lesson: it’s arrogant to think people don’t sense what you really think.
False praise also creates confusion about what success looks like. Think of former U.S. President George W. Bush’s infamous “Heck of a job, Brownie!” comment during Hurricane Katrina. The praise was meant to reassure, but instead it highlighted the failure — and made things worse. We do the same thing in the workplace when we praise someone who clearly hasn’t delivered.
And when praise becomes a pattern of avoidance, it gets harder to offer real feedback later. The longer we avoid the truth, the more difficult it becomes to deliver it when it’s needed most.
This is why specificity matters so much. Instead of offering vague praise like “You’re brilliant,” say something like, “I really liked how you handled that client objection — you acknowledged their concern and offered clear data to respond.” That kind of feedback is useful, credible, and grounded in reality. (If you need more practice, this month’s Radical Candor Community course is all about giving feedback. Join now for free and get 24/7 access to our Radical Candor AI — no flattery or fluff, just care, challenge and actionable advice.)
When AI Starts Acting Like a “Yes Person”
The dangers of Manipulative Insincerity aren’t limited to human interactions — they’re also starting to show up in how we design and use AI. A sycophantic AI, one that only tells you what you want to hear, creates problems that are remarkably similar to those caused by yes people in the workplace.
It can trap you in an information bubble, reinforcing your existing beliefs and shielding you from different perspectives. Just like well-meaning team members who never speak up, AI that avoids disagreement leads to bias and poor decision-making.
It also emphasizes short-term comfort over long-term growth. Sure, it might feel good when your AI assistant tells you all your ideas are great — but that doesn’t help you improve. Just like a colleague who avoids hard truths to be liked or gain political favor, a flattering AI undermines trust and results.
Over time, this false sense of validation creates a sense of progress or competence that isn’t real. When feedback is always positive, it becomes harder to know where you actually stand — and easier to make poor choices as a result.
And the stakes can be high. If an AI doesn’t warn you about flawed thinking or risks, you may move ahead with plans that ultimately fail. In the same way people suffer in companies where no one challenges bad ideas; users suffer when their tools won’t speak up.
How to Identify False Flattery IRL and in AI
Distinguishing between false flattery and genuine praise — whether from humans or AI — comes down to a few key indicators that are remarkably consistent across both contexts.
One of the clearest signals of sincerity is specificity. Genuine praise is detailed and precise. The more vague your praise is, the less genuine it feels. When someone (or an AI) tells you exactly what they admired about your work and why it mattered, their sincerity typically shines through. In contrast, vague compliments like “Great job!” or “You’re amazing!” without any supporting detail often signal flattery rather than real appreciation.
Timing and context also offer important clues. Praise that follows closely on the heels of strong performance tends to be more credible. When you see something great, the key is to point it out right away. Immediate feedback usually feels more authentic. On the other hand, be cautious when praise shows up at suspiciously convenient moments — like when someone wants a favor or is trying to soften upcoming criticism with a “feedback sandwich.”
Another red flag is when praise becomes personal rather than action-oriented. Telling someone “you are a genius” is just as unhelpful as calling them “a dumbass.” Both shift focus from what the person did to who they are. Genuine praise highlights the action or behavior that made a difference: “I liked how you led that meeting — it kept the team focused on our goals and energized to start the next project.”
When it comes to AI, a major warning sign is excessive agreement or shallow validation. If an AI constantly reinforces your ideas without offering helpful feedback or asking probing questions, that’s not praise — it’s a performance. Truly useful AI will sometimes challenge your assumptions or suggest improvements, even while highlighting what’s working well.
The Path Forward: Radical Candor
Whether we’re leading teams, mentoring others, or designing technology, the secret sauce for success is the same: Radical Candor. That means caring personally and challenging directly to give feedback that is kind, clear, specific, and sincere. It helps you grow, reinforces behaviors worth repeating, and builds trust — none of which can be achieved through flattery alone.
In the workplace, it’s about building cultures where people feel safe speaking honestly, and where feedback is viewed as a gift, not a threat. With AI, it’s about developing systems that don’t just flatter us, but help us get better.
TL;DR: Radical Candor without caring personally and challenging directly can quickly devolve into cruelty. Radical Candor is not a license to say whatever you want — it’s a responsibility to say what will help, in a way that cares.
In a world full of manipulation and disinformation, honest, caring conversations are radical acts of leadership. Radical Candor isn’t about being the loudest voice in the room. It’s about building trust, creating clarity, and helping people grow .
Want to lead better, listen better, and make work feel more human again? Don’t miss our next public workshop with TEDx speaker and Radical Candor Principal Coach and Podcast Host Amy Sandler. Sign up here, or check our events page for additional dates.
Radical Respect is a weekly newsletter I am publishing on LinkedIn to highlight some of the things that get in the way of creating a collaborative, respectful working environment. A healthy organization is not merely an absence of unpleasant symptoms. Creating a just working environment is about eliminating bad behavior and reinforcing collaborative, respectful behavior. Each week I’ll offer tips on how to do that so you can create a workplace where everyone feels supported and respected. Learn more in my new book Radical Respect, available wherever books are sold! You can also follow Radical Candor® and the Radical Candor Podcast more tips about building better relationships at work.
