Describe someone as Machiavellian and in that one word you describe him as devious, cunning, crafty, scheming – and above all, manipulative. By this we mean he achieves his ends by manoeuvring people in ways they do not quite understand, at least until it is too late. He does it by blandishments and flattery, or by tricks and sleight of hand; sometimes he does it by playing different interests off against each other, by pulling secret strings, by concealing his true aims with artifice and ruse, and always by misleading those whom he is getting to do what he wants. These were among the techniques that Niccolo Machiavelli advised a prince to adopt in ruling a populace.

That last point, about misleading people, is what makes manipulation so objectionable: it implies that the manipulator has acted against the will or the interests of those he battens upon. His victims feel, if they discover what he has done, that they have been subjects of a stratagem, which they would quite likely not have agreed to if they had realised what was happening. No one likes to be outwitted; still less does anyone like to be tricked. To describe a given act as involving manipulation implies that both these things have been done to someone.

In one way it might seem odd that manipulation should have such a pejorative connotation. After all, we often all try to persuade, influence and cajole others. And we are used to being subjected to persuasion and efforts at influence from the culture around us: advertisers are perpetually after our attention, salesmen after our money, and politicians after our votes, all of them employing as much inducement and enticement as they can muster. Neither they nor we are above employing whatever rhetorical arts we know, and even bribes of various kinds. Why is manipulation not regarded as just another version of this repertoire of activities, central as they all are to the continual negotiation and jockeying that is social life?

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Well: think of cases. Think of Iago cunningly manoeuvring Othello and Desdemona into tragedy. Think of contemporary politicians with a reputation for being the hidden hands, the puppet-masters, behind the arras: Lord Mandelson now, Dick Cheney during the two terms of George W Bush's presidency. In today's popular culture the person most identified as an arch-manipulator is Simon Cowell, magus of talent shows on British and American television. Their skill as operators might be admired, but not praised; manipulation is generally a dark and too often a dishonest matter, which explains its reputation.

The chief factor common to all manipulators is skill at penetrating the psychology of others. A needle-sharp awareness of the weakness and desires of those they practise upon is the manipulator's key weapon. Everyone has weaknesses, ranging from fears and insecurities to love for another person or an ambition so burning that it makes them vulnerable. Iago used hints and little tricks to awaken and then inflame Othello's jealousy; but most of the work was done by Othello himself. That is classic manipulation; a secret touch on the levers at just the right moments is enough.

Even hope can be a weakness that manipulators exploit. Stephen Jay Gould, better known for his biological insights, once astutely remarked that "when people learn no tools of judgment and merely follow their hopes, the seeds of political manipulation are sown".

Simone de Beauvoir said in her book The Second Sex, published in 1949, that women have a reputation for being manipulative because, in their oppressed and disempowered state, it is almost the only means they have of getting their way. There was nothing disempowered about Livia in ancient Rome or Lucrezia Borgia in more recent Florence, but no doubt both employed manipulation when not relying on poison. England's Elizabeth I did not need the poison.

The art of politics – some with justice call it a black art – almost always involves manipulation. Some of it is overt, as when party whips secure their own side's votes by direct threats to expose mistresses or concealed homosexual proclivities. But much of it is covert, a long game played by means of tweaking and pulling many threads. Politics is like herding cats, with so many conflicting urgencies and so many different interest groups on the warpath about their own special concerns, that the politician's life is very like being the conductor of an orchestra in a madhouse. Since rational discussion is not likely to get far in such a place, astute manipulation rises high on the list of practical options.

When a statesman is described as great because he was able to persuade his country, through oratory or example, to adopt a certain line of action, his guidance of affairs is not described as manipulation but as influence at least, and more likely as leadership. All successful manipulators could just as accurately be described as leaders, or as influencers and guides, because by definition they have led others along a path chosen by themselves. Just thus did Abraham Lincoln and Winston Churchill lead their countries at times of crisis. If it is said that part of how they achieved this was by activities behind closed doors, in whispered conversations, by rewarding some and excluding others, they are commended for their mastery of political skills.

But if it is Machiavelli or Cardinal Richelieu, Metternich or Lloyd George we describe as doing such things, the positive words applied to Lincoln and Churchill are replaced by their negative twins: Richelieu and Lloyd George did not lead or guide but instead managed by means of sly and wily plots: they manipulated.

The word "manipulate" has a fascinating etymology. It derives obviously enough from the Latin for hand (manus) and "to fill" (plere) and occurs in that ancient tongue as manipulus to mean, literally, a handful (and figuratively, a sheaf of wheat). In French manipule is a pharmacist's measure – a handful of medicinal powder, for example. Manipulation in that same language meant a certain method of mining ore, by pickaxe and sweat. Its first recorded use in English with the negative connotation of underhandedly manoeuvring others without their knowledge and against their will, is very recent: it dates only from the 1820s.

The name might be young, but the practice is old. In ancient Athens the Sophists were paid handsome fees to teach the art of rhetoric. They openly advertised their ability to teach anyone how to argue convincingly for either side of a case. Socrates despised the Sophists for being indifferent to truth, and interested only in winning points in arguments no matter whether they were on the right or the wrong side. But a public career in Athenian society required skills in oratory and advocacy, and therefore the Sophists taught all the tricks of argument a speaker could use to manipulate his audience's views and sentiments. One of the best more recent compendiums of such tricks is Arthur Schopenhauer's little classic, 38 Ways to Win An Argument.

In our own day the palm for manipulative skill goes to the Hollywood film industry. Any run-of-the-mill movie in any genre, whether romantic or "family", animated, horror or adventure, can make its audience laugh, jump or weep at the press of a hackneyed button. We all recognise the tropes that achieve this, and yet they still work. In this case we might be more than half-willing for them to work; we go to the cinema not to glower at the screen on guard against being manipulated, but precisely in order to be manipulated. It is a generally benign and often cathartic experience, and to be welcomed accordingly; but it is manipulation nevertheless, even if it is one of the very few cases where we are unlikely to think it disagreeable.

It is obvious why less benign forms of manipulation matter. They typically involve unfairness, and come too close for comfort to lying and cheating. They use people as pawns in the achievement of the manipulator's aims, in violation of the great ethical principle enunciated by Immanuel Kant, that other people should always be treated as ends in themselves, never as means to further ends.

Manipulation is par excellence the using of people as means. If we do not mind being persuaded, it is because we are aware of what is happening. Discussion, argument, even bribery, which changes our minds or re-routes our actions, is a far cry from a process in which we find ourselves doing something or taking a position that we did not realise we were being steered into by activities we did not fully understand.

The skills of psychological penetration that the manipulator relies on can be combated only by two things: having no weaknesses, which is a human impossibility though it was recommended by the Stoics of ancient times, or by being watchful and sceptical, which is far more achievable. Count your spoons when the snake-oil salesmen visit: that's the motto for the forefront of our minds when the advertisers, politicians, preachers – and talent-show judges – are at work among us.