How to Be Cunning

Being Perceptive

Always seek more information. Cunning people perceive things that others miss. They see life’s hidden machinery - the real motives that drive interactions, rather than the stated motives. The first, most important step to seeing things as they actually are is to always get as much information as possible before making your decisions. This can be as simple as taking the time to look around before dropping an anonymous love note into someone’s locker so that you don’t get spotted or as complex and involved as doing hours of research on the person you’re about to interview so that you can surprise him with particularly biting questions. When approaching all major decisions, keep your eyes peeled and have a voracious thirst for more information. You can never be too well-informed. In order to see the whole picture, first the speed has to slow down. You want to have a wide range of understanding about your circumstances or your surroundings before acting. Usually, the people who are not very perceptive are the one who cannot have perspective on both sides, and they sometimes tend to get into this bias, protective bias.

Question others’ motives. Cunning people are renowned for their ability to see through others’ facades. Almost everyone tells white lies on a daily basis - it’s perfectly natural. A cunning person sees a person’s true intentions - he does this because he’s able to “read” people and also because he’s done his homework (see above.) Never assume someone’s telling you the truth until you have supporting evidence. However, it's also not wise to instantly assume everyone is lying. Use the information available to you to make your best guess at someone’s true motivation. Try to build your ability to read others’ faces. Most people are good liars, but not great ones. With practice, you may find that you’re able to notice when the emotion on a person’s face doesn’t match with what he or she is saying.Be Cunning Step 2Bullet1.jpg

Look for small details. Cunning people never balk at the prospect of closely scrutinizing people and things for small details that may be manipulated for their benefit. Try to be a stickler for details, within reason. For instance, read every line of your contract rather than glossing over the entire thing. If you pay attention to life’s details, you’ll find yourself better-equipped to exploit opportunities when they present themselves. Paying attention to details isn’t only useful for grim, serious purposes. If you’re in a prank war with friends, for example, pay attention to your surroundings when you enter your room - if you see any small detail that’s out of the ordinary, you have reason to be suspicious.Be Cunning Step 3Bullet1.jpg

Be alert. A person can’t be cunning if she is too tired, unfocused, or distracted to notice what’s going on. An important part of being cunning is being active and alert when it’s most important. Much of this a matter of fulfilling some of your basic biological needs - try, for example, to get a good night’s rest before important events and to rid yourself of distractions like hunger, restlessness from lack of exercise, etc. If you’re running on fumes, you may want to use a moderate amount of caffeine in the form of coffee, tea, or an energy drink to perk yourself up. However, use caution - some people find it harder to focus on a caffeine high. Also, be sure to control your level of use, as becoming a caffeine addict will eventually rob your caffeine source of most of its alertness-boosting benefits.Be Cunning Step 4Bullet1.jpg

Take an objective point of view. Cunning people try not to let their perception and decision-making be clouded by emotion or prejudice. Instead, they prefer objective, factual truths. It’s easy to tell yourself to take an objective point of view, but it’s a much harder matter to set about doing it. Try to detach yourself from, or, at the very least, control, your emotions when you're faced with difficult decisions. No one has ever made a better decision because he was angry.

Make note of others’ strengths and weaknesses. This step is crucial. Cunning people better themselves by fooling, tricking, or otherwise deceiving other people. A given person is much easier for a cunning person to trick when his strengths and weaknesses are known, rather than unknown. Knowing a person’s weaknesses is especially useful - these can be used to sway a person into making rash decisions or doing things that benefit you. Similarly, a person’s strengths are to be avoided when possible - a cunning person won’t try to outfox someone in an area that he excels in. Let’s use an example. Say that you’re trying to convince a reluctant friend to buy a ticket to a fundraiser you’re throwing. You know your friend is normally pretty stubborn, but you also know he’s got a tremendous sweet tooth and that he also likes to be thought of as a gracious guest. You might casually invite him over to hang out, making sure there’s a tray of warm cookies on the counter as he walks in. Let him eat as many as he wants, then ask him to buy a ticket. He’s just enjoyed your hospitality and he doesn’t want to appear rude, so he’s much more likely to agree.Be Cunning Step 6Bullet1.jpg

Building Your Intelligence

Practice, practice, practice. If you were born perfectly cunning and ruthless, you may be a psychopath. Like any other skill, cunning is something that most people have to work at. Some people are naturally more cunning than others, while others are more gullible. Regardless of your starting point, know that you can always improve your ability to be cunning through practice. Try to find low-stakes opportunities for practice so that you’re well-prepared when the time comes to be cunning in a serious situation. Performing good-natured pranks and practical jokes are a good way to build many of the skills you’ll need to be cunning without exposing yourself to much risk. For example, many pranks require you to act, lie, suppress your emotions, and ascertain others’ true motives if you want the prank to go off without a hitch.Be Cunning Step 7Bullet1.jpg

Never take anything at face value. Cunning people are skeptics at heart. Never accept the information you’re supplied with or the impression someone gives you without thinking about it first. Constantly ask yourself whether the people you interact with seem genuine. Look for ways that these people may be distorting the truth or outright lying in order to advance their agenda. Investigative journalists routinely cut through mountains of lies and pretense to get to the truth. If you’re looking to sharpen your skeptic’s eye, you probably don’t need to go to journalism school, but you may benefit from researching and watching how journalists coax facts from their subjects in one-on-one interviews.Be Cunning Step 8Bullet1.jpg

Consider all possible outcomes. The great British Prime Minister Winston Churchill was noted for his cunning wit, among many other things. He had a reputation for crafting clever, biting quips and one-liners out of thin air. In fact, because of a speech impediment, he actually crafted most of his witty responses beforehand by trying to consider every possible objection he might face. Take Churchill’s success to heart. Before important situations, take time to imagine every possible way the situation may play out and have your responses planned. The worst case scenario with this approach is that things will turn out in a way you didn’t anticipate. However, in the rare occasion that this happens, you won’t be any worse off than if you hadn’t considered any outcomes at all.

Learn from your mistakes. Even the most experienced swindlers get caught every once in a while. If you’re looking to become confident, you’re bound to make eventual mistakes. Your schemes will be uncovered, you’ll be embarrassed, and you may have to apologize. Use your failures as learning experiences. Make note of exactly when and how your plans went wrong, then try never to make that mistake again.

Know yourself. The French theologian Pierre Charron once famously said, “the easiest way to be cheated is to believe yourself to be more cunning than others.” A cunning person should certainly be able to find others' strengths and weakness, but it's almost as important that she also be able to find her own. Give yourself a brutally frank evaluation. What are you good at? What are you bad at? What makes you nervous? When are you most confident? Be honest with yourself about your abilities. If you are, you'll know which of your strengths you should play to and which of your weaknesses you need to work on.

Deceiving Others

Perfect your poker face. Just as cunning people need to be able to read others’ faces, they must be able to keep others from reading their own. Pulling a trick on someone can naturally make you feel excited or antsy. It’s important to make sure your face doesn’t betray this information. Obviously, try not to grin or giggle when you’re deceiving someone. Instead, relax. Take deep breaths. Picture yourself doing something calming that you love. Do anything you can to stay (externally) cool as a cucumber. Appropriately, the actual game of poker is a great place to practice your poker face. In poker, if you want to win, you’ll need to keep your external façade completely calm when you have winning hands. You’ll also need to appear confident when you have awful hands. Practicing both of these skills will help you hone your cunning.Be Cunning Step 12Bullet1.jpg

Be confident and decisive. People are more likely to believe others who appear confident in their decision making. If you’re cunning, you should be ready to exploit this. Make your moves with firm confidence. Never second guess yourself. Try to view the trick you’re playing on someone as “no big deal” or as something you’ll be able to do perfectly without too much effort, even if this might not be 100% true. If you believe that you can do something, most other people will too, and you’ll be able to use this to deceive them. Basic confidence-building tips include: Pay attention to your physical appearance - dress well and groom yourself Have friendly body language - stand up straight, smile, and look people in the eye Feed your interests - pick hobbies you’re good at and excel at them Be gracious - strive for politeness and friendliness, but never pretend to agree with someone just to appease him or her.

Learn to lie. Lies are the cunning person’s best friend. Good lies are plausible, or at least hard to disprove. Lying well requires a great deal of intelligence and emotional control - not only must the liar tell lies that make logical sense, but she must also sell them through her voice and body language and keep her lies straight after she’s made them. As with many of the skills a cunning person uses, lying can be improved with plenty of practice and smart planning. Not only can a cunning person lie to other people - she can also lie to herself. This may seem minor, but it’s an important ability for a cunning person to have at her disposal, as it allows her to mentally convince herself that she’s confident, that she’s not likely to be caught, etc., which in turn makes her appear externally calm and relaxed.Be Cunning Step 14Bullet1.jpg

Set (metaphorical) traps. An old saying describes cunning as “finding the path that your enemy has chosen, then digging holes along that path.” Though it’s highly unlikely that you’ll ever have to set real traps for anyone, take the metaphor to heart. By judging another's strengths, weaknesses, and motivations, you can ascertain the “path” they are on and sabotage it for your personal benefit. Look for ways to exploit your enemy’s weaknesses while rendering their strengths useless. Try to put your enemies in situations where they’re likely to mess up. Let’s say you’re competing with a coworker you hate for a promotion. If, for instance, you know that this person is bad at giving presentations, you might try to volunteer to give an important joint presentation with him so that he’ll look bad in comparison to you.

Stay out of the spotlight. A cunning person never draws more attention to himself than is necessary. If you’re deceiving someone, interact with the person just as much as you normally would - no more, no less - or you may creep your subject out or clue him in to the fact that something is out of the ordinary. When you see someone begin to fall for your plan, don’t push too hard or he may realize he’s been duped. Instead, give your mark just enough rope to hang himself, then simply stand back until it’s all over. Though it can be tempting to gloat after you’ve successfully deceived someone, don’t. You gain nothing other than a momentary feeling of superiority and you risk starting a long-term grudge with the person you lord your victory over.Be Cunning Step 16Bullet1.jpg

Have an “out.” Cunning people consider all the possible outcomes for their schemes - even the outcomes that aren’t favorable. Always account for the possibility that your sense of cunning, however sharp, may fail you. Have a backup plan in place if things don’t go according to plan. Know what you’ll do to recover from a failure ahead of time. Have a story worked out in your head that allows you to plausibly deny any wrongdoing. Let’s say you’re sneaking around backstage at a concert without backstage passes when a security guard stops you and asks what you’re doing. To avoid trouble, you've planned beforehand to play dumb. Pretend that you’re lost and that you’re looking for the bathroom, or that your friend told you that the best place to watch the show was from back here. Pretend to be surprised at the news that you’ve broken a rule - you probably won’t get in any serious trouble if it seems like you stumbled backstage by accident.