You know the type. They’re the ones who seem helpful while quietly steering the conversation toward a result that only benefits them. It’s a specific kind of manipulation that feels oily. When we look for another word for conniving, we aren't just looking for a synonym; we’re looking for a way to describe that exact moment when someone’s secret agenda clashes with your trust.
Language is weirdly specific about being sneaky. Honestly, a "conniver" is different from a "liar." A liar just says things that aren't true. A conniver builds a whole architecture of deception. They plan. They plot. They collaborate in shadows. If you've ever felt like you were being played like a pawn in a game you didn't even know was happening, you've met a conniver.
The Subtle Art of Being Scheming
If you want a more common way to say it, "scheming" is your best bet. It’s the bread and butter of corporate backstabbing and reality TV drama. But "scheming" feels a bit loud, doesn't it? It implies someone sitting over a blueprint with a mustache to twirl.
Real-world conniving is usually quieter. It’s "calculating." A calculating person doesn't necessarily want to hurt you, but they definitely don't care if you get hurt in the process of them getting what they want. They treat people like variables in an equation. In psychology, this often tracks with what experts call the "Dark Triad"—specifically Machiavellianism. Named after Niccolò Machiavelli, who wrote The Prince, it describes a personality trait centered on interpersonal manipulation and a cold, cynical disregard for morality.
Think about the office environment. Someone might be devious. That’s a great word because it literally comes from the Latin devius, meaning "out of the way." They aren't taking the straight path. They’re taking the long, winding road behind the bushes to get to the promotion before you do.
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When "Crafty" Isn't a Compliment
Sometimes people use "crafty" or "wily" as if they’re positive traits. We talk about a "wily veteran" in sports or a "crafty" negotiator. But there is a razor-thin line here.
When "crafty" turns into conniving, the intent changes. It’s no longer about skill; it’s about exploitation. It’s the difference between a magician doing a trick and a con artist stealing your wallet. One is for entertainment; the other is predatory. Words like underhanded or shrewd (in its worst sense) fit here.
The Difference Between Collaboration and Collusion
This is where it gets interesting. "Conniving" actually comes from the Latin connivere, which means "to wink." It’s the idea of two people looking at each other and winking as they agree to ignore a crime or pull off a scam. It’s a social act. You rarely connive alone.
If you're looking for a word that hits that "secret team-up" vibe, try collusive.
In business, collusion is a literal crime. It’s when companies secretly agree to keep prices high. It’s the corporate version of a secret handshake. It’s "cabalistic." While "cabal" usually refers to political groups, it captures that feeling of a small, secret group of people working against the interests of the majority.
Machiavellianism: The Professional Grade Version
If you’re talking about someone truly high-level, "Machiavellian" is the gold standard.
Back in the 1970s, psychologists Richard Christie and Florence Geis developed the "Mach-IV" test to measure this. People who score high on the Mach scale are basically professional-grade connivers. They believe that "the ends justify the means." They are the masters of insidious behavior.
"Insidious" is a terrifyingly good word. It describes something that spreads gradually and secretly, but with very harmful effects. Think of it like a slow-acting poison or a rumor that slowly ruins someone’s reputation without them ever knowing where it started.
Don't Mistake Ambition for Being Designing
We’ve all met the person who is designing. It sounds like they should be making clothes, but in a social context, a "designing person" is someone who is always setting traps. They’re always "on." Every dinner invitation has a hidden price tag. Every compliment is a setup for a future favor.
Is it just ambition? Usually, no.
The Harvard Business Review has published several pieces on "political skill" in the workplace. There’s a massive difference between someone who is politically savvy—meaning they know how to navigate social structures—and someone who is duplicitous. Duplicity is "two-faced-ness." It’s the hallmark of the conniver. They have the face they show you and the face they show the person they’re actually working with.
How to Describe the "Vibe" of a Conniver
Sometimes you don't need a clinical word. You need a word that describes the feeling in your gut.
- Shifty: This is the physical manifestation. They can't look you in the eye.
- Slippery: Try to pin them down on a promise? They slide right out of it.
- Sneaky: Simple, classic, effective.
- Furtive: They’re doing things in a way that suggests they’re trying to avoid notice, usually because of guilt.
If you’re writing a story or a character study, you might want something more literary. Guileful is a beautiful, old-school word. "Guile" is that clever, usually dishonest, intelligence. It’s the fox in the hen house.
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The Social Cost of Being Calculated
Why does this matter? Because labeling it correctly helps you set boundaries. If you call someone "mean," you’re talking about their temperament. If you call them conniving, you’re talking about their strategy.
A mean person might just yell at you. A plotting person will wait until you’re at your most vulnerable to make their move. This is why "trenchant" or "incisive" (which are usually good) can sometimes veer into the territory of someone who uses their intellect to dissect others for sport.
People who are habitually artful in their deception eventually hit a wall. Trust is a finite resource. Once you’re labeled as "double-dealing," that’s a hard tag to shake.
Spotting the Red Flags
You can usually spot a conniver by their "asymmetric information" style. They know everything about everyone, but no one knows anything about them. They "triangulate"—they talk to Person A about Person B, and Person B about Person A, ensuring the two never actually talk to each other.
It’s surreptitious. It’s done under the radar.
If you find yourself in a situation where someone is being obsequious (excessively fawning or suck-up-ish), watch out. Often, the biggest connivers start as the biggest flatterers. They use "ingratiation" as a smoke screen.
Actionable Steps for Dealing with the "Designing" Person
You’ve identified the behavior. You’ve found the right word for it. Now what? You can’t always just walk away, especially if this person is your boss or your mother-in-law.
1. Force Transparency
The conniver’s greatest weapon is the "secret." If they tell you something "in confidence" that feels like a plot, bring it into the light. Copy people on emails. Summarize "private" conversations in public threads. "Just so we’re all on the same page" is the ultimate kryptonite for a schemer.
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2. Watch the "Information Economy"
Notice if they’re trading secrets like currency. If they’re giving you "dirt" on someone else, they are almost certainly giving your dirt to someone else. Stop feeding the machine. Become a "black hole" for gossip.
3. Label the Behavior, Not the Person
If you have to confront them, don't say "You’re a conniver." They’ll just manipulate their way out of that. Instead, say, "This plan seems a bit underhanded to me," or "I'm uncomfortable with how calculating this approach feels." It’s much harder to defend a specific action than a personality trait.
4. Document Everything
This isn't just for HR. It's for your own sanity. People who are deceitful thrive on "gaslighting"—making you doubt your own memory of events. Having a paper trail (or even just a private journal) keeps your reality grounded.
5. Trust Your Gut "Ick" Factor
We have evolved to detect social threats. If someone feels predatory or disingenuous, they probably are. Don't wait for "proof" to distance yourself emotionally.
Language gives us power. When you move past the basic "he’s a liar" and realize "he is colluding to undermine my project," you can react with precision. Whether you call it being vulpine (fox-like) or just plain crooked, knowing the nuances of these words helps you navigate a world that isn't always as straightforward as we’d like it to be.
Focus on clarity. The next time you see that "wink" across the room, you’ll know exactly what it’s called.