Incompetent Sycophants vs. Smart Employees Who Speak Up

Employees who deal with their bosses usually fall into two broad types. There are the ones who look incompetent at a glance, yet somehow get promoted faster than anyone else and earn more money. And then there are the smart, capable, clear-headed employees who actually do the work well, but somehow never get treated well.

Which one are you? It’s really a matter of temperament you don’t get to choose, but unfortunately, that one trait shapes nearly everything about your life at work. The way your boss treats you, your salary, and even your promotions.

I used to think the same thing all the time, both as an individual employee and later as an HR manager: an employee who works well and speaks honestly, even if they’re a bit sharp, is better than one who flatters their way through everything without real skill. But after going through years and working in different organizations, what I came to feel was something else entirely. I thought a company was an organization, a system. In reality, though, you end up existing as one individual boss’s subordinate.

There was one moment when I understood that most clearly.

"Everything she said was right, but she’s annoying."

I heard that directly. The situation could have caused financial damage and legal liability for the company, so during the report, I added my opinion to correct the course. Since it went against the direction my boss was pushing, the irritation came right out. An employee who speaks the truth may be a great asset to a company, but from an individual boss’s point of view, that person can be terribly awkward and uncomfortable to deal with. They make the boss feel incompetent, and even create the threat that, "If this kid gets a little more confident, they won’t listen to me anymore." It would be nice if department heads or CEOs carefully watched for these blind spots in an organization, but they, too, are just people trying to get through a suffocating day while making heavy decisions, so they don’t always have the room to look into every small detail.

On the other hand, what about the employee who flatters? They always make the boss feel good and puffed up. Especially for a boss full of narcissism, they’re the best kind of subordinate. Even if the work is sloppy, praise them as the best and they’ll be smiling all day. The team atmosphere gets lighter too, and honestly, sometimes that warm, easygoing mood is enviable. From an organizational perspective, it’s a problem that should be corrected, but even the person making that decision is an individual with feelings. One thing I want to make clear is that this isn’t about saying flattering employees are bad. That, too, is a real workplace skill, and as I always say, this is not about whether an individual is morally right or wrong. It’s a matter for the organization to set direction and manage.

So what are we supposed to do? Honestly, this is something I’ve worried about every day, and I still do. I’ve tried this and that, but I don’t have a perfect answer. If I had to suggest one thing, it would be a "half spicy, half fried" strategy.

Speak up only when it really matters. If the company’s fate is on the line, or if it affects your team’s performance, then it’s worth trying once or twice. But never use the tone of "I’m right!" Instead, approach it like this: "I’m worried this might end up reflecting badly on you too, sir. What if we try it this way? At the very least, if there’s a problem, we may be able to avoid taking the blame." Casually mention that you yourself could be affected. There are more bosses than you’d think who only take a closer look when they hear their own reputation or position could be at risk.

For everything else, flatter. Even if it sticks in your throat, force out a few words now and then. But don’t think, "I’m flattering them right now." Think instead, "Let me make the person I work with in this space feel good," and "You smile, I smile." In other words, try to see them, even briefly, not as an annoying boss, but as a coworker and a person. In fact, a blunt little comment said calmly here and there often works better than cringey flattery that’s obviously transparent. "It really does work out when we follow what you said." That’s the most efficient line: not too heavy, but enough to satisfy a boss’s narcissism.