We often think of cunning as a type of sly or crooked intelligence, but there’s a clear difference between being cunning and being truly wise. The difference isn’t just about being honest—it’s also about skill. Some people are like card players who can shuffle the deck expertly but don’t actually know how to play the game. In the same way, some people are great at plotting and manipulating others but lack real mental strength.
It’s also one thing to understand people and another to understand how to handle real issues. Many are experts in reading others’ moods but struggle with the actual substance of business or decision-making. These are the kinds of people who study others more than they study facts or principles. They’re better suited for hands-on work rather than offering sound advice and tend to only thrive in environments they’re familiar with. If you introduce them to new people or situations, they often lose their way. This aligns with the old rule for identifying fools and wise men: “Send them both naked among strangers, and you’ll see.” A person’s true character and abilities are revealed when they are stripped of their status, possessions, and familiar surroundings. But even this doesn’t quite apply to the cunning. They’re like vendors at a market stall; it’s worth looking at what they sell, but they’re not managing the entire marketplace.
A cunning person often relies on small tricks, such as maintaining intense eye contact while speaking—something Jesuits used to teach. However, this should be done carefully, with an occasional humble glance away, as the Jesuits also advised. This creates an impression of focus without appearing aggressive.
Another trick is to distract someone with unrelated conversation when you need something done quickly. I once knew an advisor to Queen Elizabeth who always began by discussing matters of state before presenting documents for her to sign. This way, her focus was diverted, and she was less likely to scrutinize the papers too closely. A similar tactic works when someone is in a rush. If you bring up a request at the last minute, they’re often too hurried to think it through properly.
If you want to sabotage a plan that someone else is likely to propose effectively, pretend to support it and bring it up yourself in a clumsy or half-hearted way. This makes the plan seem weak or poorly thought out, increasing the chances that it will fail or be dismissed.
Interrupting yourself mid-sentence, as though you’ve caught yourself from saying too much, can pique someone’s curiosity. People often want to know more when they feel something is being withheld. Similarly, it’s more effective to let others draw information out of you than to offer it freely. You can prompt questions by behaving unusually, as Nehemiah did when he appeared sad before the king, leading the king to ask what troubled him.
In delicate matters, it’s wise to let someone less important introduce the topic, saving your words for later when they carry more weight. For instance, Narcissus handled the awkward announcement of Messalina’s scandal by letting someone else broach the subject, only stepping in afterward as if by coincidence.
If you don’t want your involvement to be obvious, it helps to attribute your actions to public opinion, saying, “People are saying…” or “There’s a rumor going around…” This deflects attention from yourself.
I once knew a man who would always add the most important points in the postscript of his letters, as though they were an afterthought. Another person I knew would casually mention crucial matters only after talking about other things, pretending he’d almost forgotten. These tactics make the message seem less calculated.
Sometimes people stage situations to create opportunities to reveal what they want others to know. They might “accidentally” be found holding a letter or doing something unusual, prompting someone to ask about it. This allows them to share their message without appearing to do so intentionally.
Another strategy is to express an idea yourself and hope others will repeat it. I recall two men vying for the same position under Queen Elizabeth. One of them remarked that taking on such a role during a declining monarchy was risky. The second man repeated this to others, and eventually, the comment reached the queen. She was so displeased by the idea of a “declining monarchy” that she refused to consider the second man for the position.
There’s also the trick we call “turning the cat in the pan,” where someone attributes their own words or ideas to someone else. This makes it hard to tell who first introduced the idea, creating ambiguity and room for manipulation.
Some justify themselves by criticizing others indirectly, using phrases like “I’m not the type to do that.” For instance, Tigellinus excused himself by claiming he wasn’t pursuing power but was simply loyal to the emperor.
Storytelling is another weapon of the cunning. Wrapping advice or criticism in an anecdote can make it more digestible while protecting the speaker. It also keeps the listener entertained, which makes them less defensive.
When you want a specific answer, phrasing your question to lead the other person toward your desired response can be very effective. People are less resistant when they feel they’re agreeing with their own conclusions rather than yours.
Some will wait patiently for the perfect moment to say what they’ve been holding back. They’ll circle around the topic, bringing up unrelated matters until they can slip in their real point. It’s a strategy requiring great patience but can be highly effective.
Unexpected, bold questions can catch people off guard and reveal their true intentions. It’s like calling someone by a name they’re trying to hide; their reaction betrays them.
All these minor strategies—the “small wares” of cunning—are endless. It would be helpful to list them, as they often cause more harm than good when mistaken for true wisdom.
Some people are skilled at navigating the superficial aspects of business—like finding loopholes or taking advantage of others—but they lack the ability to grasp the bigger picture. They’re like houses with well-designed staircases but no grand rooms. You’ll often see these people spot small weaknesses or flaws in a situation and exploit them to their advantage, but they’re unable to properly analyze or debate serious issues. Despite this, they often pretend to be experts and try to appear skilled at leading or giving advice. Some people rely more on taking advantage of others or tricking them, rather than focusing on solid, honest work. As Solomon wisely said, “The prudent man pays attention to his steps, but the fool is distracted by deceit.”
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