You’ve probably felt it. That prickle on the back of your neck when a coworker "accidentally" forgets to include you on a crucial email thread, only to apologize with a smile that doesn't reach their eyes. Or maybe it's the friend who subtly nudges you toward a bad decision while pretending to be your biggest cheerleader. That is the essence of what it means to be conniving.
It isn’t just about being a jerk. It’s deeper. It’s quieter.
While a bully will shove you in broad daylight, a conniving person is already halfway through a three-month plan to make sure you aren't in the room when the promotions are handed out. They work in shadows. Honestly, the word itself sounds like a snake slithering through tall grass—smooth, quiet, and intentional.
What Does Conniving Actually Mean?
At its core, conniving refers to someone who is involved in conspiring or "feigning ignorance" of a wrongdoing. The Latin root is connivere, which means "to wink." Think about that for a second. It literally implies someone seeing something wrong, winking at it, and letting it happen because it serves their agenda.
Nowadays, we use it to describe people who are manipulative and calculating. They aren't impulsive. If someone screams at you in traffic, they’re just angry. If someone spends two weeks befriending your assistant to find out your schedule so they can "coincidentally" bump into your boss at the gym? That’s conniving.
It requires a high level of Machiavellian intelligence. You have to be able to model someone else’s thoughts in your head to stay two steps ahead.
The Psychological Profile: Why People Do It
Psychologists often link this behavior to the "Dark Triad"—narcissism, Machiavellianism, and psychopathy. But let's be real: not every conniving person is a clinical psychopath. Most are just incredibly insecure or hyper-competitive.
Dr. Harriet Braiker, in her book Who’s Pulling Your Strings?, highlights how manipulators use a "controlled" persona to gain power. A conniving person doesn't want to look like the villain. They want to look like the victim or the hero.
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They use tactics like:
- Selective Disclosure: Giving you 90% of the truth but withholding the 10% that would change your entire perspective.
- Triangulation: Telling Person A something bad about Person B, then telling Person B that Person A is worried about them. Now they control the flow of information between both parties.
- Gaslighting: Making you doubt your own memory of an event so they can rewrite the narrative to suit their goals.
It’s exhausting. Imagine the mental energy required to keep all those lies straight. Most of us just want to eat lunch and watch Netflix, but the conniving mind is always "on."
Conniving vs. Ambitious: Where Is the Line?
This is where it gets tricky. In business, we often reward "strategic thinking." Is a CEO conniving, or are they just good at their job?
The difference is transparency and intent.
Ambitious people want to win. They might be aggressive, but you usually see them coming. They want the trophy, the bonus, the title. Conniving people don't just want to win; they often want to ensure someone else loses, and they want to do it without getting their hands dirty.
If you're strategic, you’re playing the board. If you're conniving, you’re trying to tip the table when the referee isn't looking.
Spotting the Red Flags in the Wild
You can't always see it immediately. That's the point. But patterns eventually emerge.
One big sign? The "Secret Sharer." This is the person who comes to you on day two of a new job and tells you "the real deal" about everyone else. They’re building a false sense of intimacy. By sharing "secrets," they make you feel like an insider. In reality, they’re just checking to see if you’re gullible enough to repeat what they told you so they can use it against you later.
Watch out for the "Praise Sandwich" that feels a bit too sour. "You did such a great job on that presentation! It's amazing how you managed to pull it off even though you were so behind on the research." See what they did there? They complimented you while simultaneously planting the idea that you’re disorganized.
The Cost of Living This Way
It’s a lonely road. People who are consistently conniving eventually run out of allies. Once the mask slips, trust is gone forever. In social circles, this leads to being "iced out." In professional settings, it leads to a reputation that follows you through LinkedIn like a bad smell.
There's a famous study in game theory called the "Prisoner's Dilemma." The most successful long-term strategy is almost always "Tit-for-Tat" with forgiveness—basically, being cooperative until someone burns you. Conniving people play a "Defect" strategy. It works once or twice, but then the system shuts them out.
How to Protect Yourself
If you realize you’re dealing with someone conniving, your best move is "Gray Rocking."
Basically, you become as boring as a gray rock. Don't give them emotional reactions. Don't share personal stories. Keep all communication professional and, most importantly, in writing.
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If they tell you something verbally, follow up with an email: "Just to confirm our conversation, we agreed on X, Y, and Z." This kills their ability to gaslight you later. They hate a paper trail. It’s the sunlight that kills their shadow work.
Actionable Steps for Dealing with Manipulation
If you suspect someone in your life is being conniving, don't panic or start a confrontation without evidence. Use these steps to regain control:
- Document Everything: Start a "memos to self" folder. Note dates, times, and specific phrases used. You aren't being paranoid; you're being precise.
- Verify Information: If they tell you "everyone is saying" something, go to the source. Usually, "everyone" is just them.
- Set Hard Boundaries: If they try to pull you into a gossip session or a "hush-hush" plan, shut it down immediately. "I'm not comfortable discussing that without [Name] present" is a power move.
- Trust Your Gut: If a situation feels overly complicated or someone’s "kindness" feels like a transaction, listen to that instinct.
- Distance Yourself: You cannot change a conniving person. You can only change your proximity to them. Whether it’s a job transfer or a friendship breakup, peace of mind is worth the cost of the exit.