The presumption is you're only allowed to give bad, unpleasant and controversial news in private. Andy You could even send an unflattering photo. Andy Card violated this on 9/11 when he publicly whispered into Bush's ear at that Florida school.

What about good or pleasant news? Do the same restrictions apply? I'd reckon the counselors would compete to be the one to deliver good news, as those counselors usually found favor.

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This reminds me of a line I saw in a recent Tetlock article about a giant "World in 2025" type forecast with lots of vaguely worded probability-terms, and how the writers may be legitimately reluctant to assign quantitative probabilities, since if they say a well-calibrated 75%, they'll be wrong 1 time in 4 and then the politicians will be all like, "You were WRONG!"

My immediate thought was that the writers ought to assign log-odds instead, i.e. say "+2 bits credibility" instead of "80% probability".  Since politicians can't do math, they would be unable to translate into probabilities, and the writers would be safe.

(The section explaining the "+2 bits" language should also say, "An event assigned +2 bits credibility should fail to occur around 1 time in 5" and always be phrased in terms of the exception rather than the rule.)

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All three of your points are guesses at his intent when he says exactly why, "He who does otherwise is either overthrown by flatterers, or is so often changed by varying opinions that he falls into contempt." The first part is the typical groupthink (or worse the straight up "yes, man" type) scenario that has shown to cause havoc in business, government, and other groups. The second part quickly describes a wishy-washy leader, the type no one would want to follow.He also sets the context to which his advice applies: "a wise prince," the kind that apparently holds courts, likely the fancy, royal kind.

As to whether this applies at all to your needs, you'll have to ask yourself if the context applies. Are you in a situation similar to that of a prince? And second, are the consequences those that could happen in your situation?

If you are responsible for a part of other people's lives that they perceive as important, then you could potentially be qualified as a prince.

Let's say that you are making an important decision that affects others based on prediction markets. Would you appear wishy-washy? Only if you announce conflicting decisions while the market is turbulent, switching your position every few days. If you wait until it is done or at least likely one way or the other, then you can take that information along with information from other sources,  and make one decision, wrong or right. You might be wrong, but your people are less likely to want someone else as a leader.

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On the one hand, you don't have to admit you use prediction markets in public.

On the other hand, Machiavelli didn't know about prediction markets anyway.

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We can make this simpler, in order to better understand it: What is power but the ability to set a course of action and induce others to follow it, either by their own free will or by compulsion?

The leader who allows the opinions of others to determine his own action hands to that other a portion of his power. Now it is not his will that is worked upon the world, but the advice-giver's, through him. He is merely the vessell. This is the fundamental truth that underlies all the reasons you posit --- that is why being seen to be swayed by advice could cause one to lose status, could prompt one's followers to spend all their time scheming to change your mind. If they can just talk you into it, they can get what they want.

Machiavelli, being what you might call fairly bright, of course realizes the flip side of this problem --- no human is omniscient. There's lots of times when seeking out outside information sources and perspectives can improve decision making. Thus his counsel is not to never listen to anybody, but to never be seen to be listening to anybody.

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"Telling the truth" is essentially a euphemism for expressing disagreement. As you've pointed out, disagreement is disrespect. Letting everyone tell the leader the truth is allowing public disrespect.

A prediction market is a collection of personal opinions, agreements and disagreements, and inviting and accepting their determinations would be tantamount to listening to the free expression of disrespect.

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I think your #1 is right.  

Villam Bur's point persuades me as well.  

I logged on to make the same point that Mjrharris made first.  Damn you, Mjrharris for thinking of it first.  

But he was so pithy, perhaps I can gain a tiny bit of status by expanding.  The general public doesn't know what it wants.  They can overhear the advice, realize that it serves the community's interests (or their own factional interests) and want it followed.  But the leader's interests are different from those of the community, and now he has to surpress/massacre/demonize that group to follow his own preferences, which he wouldn't need to do absent the public advice.  

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"...Outside of these, he should listen to no one, pursue the thing resolved on, and be steadfast in his resolutions. He who does otherwise is either overthrown by flatterers, or is so often changed by varying opinions that he falls into contempt."Here, it sounds like Machiavelli is concerned with the ruler being too persuadable—that is, unable to listen without being subject to irrational levels of influence, except perhaps by resolving not to be influenced at all. I'm not entirely sure what it means to be overthrown by flatterers, but there's no reason a rational listener would be "so often changed by varying opinions" as long as he got a broad sample before making up his mind the first time. If he's unable to defend against silver tongues, though, then this would be a serious risk.

(The top paragraph seems more concerned with status.)

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A Prince in Machiavelli's day had to demonstrate his superiority. Rather like Vladimir Putin or Mussolini, the leader has to be better than everybody at everything, or at least portray himself that way. So a Prince couldn't be seen to be listening to advisors because he's supposed to be wiser than they are. 

(But of course Machiavelli and Cosimo de Medici knew perfectly well that you need advice, so this is how to get it without seeming to.)

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Re #3:  "If people can influence you by telling you things...".

Then people might assume that you are already under the spell of powerful lobbies.  A large class of middle-powered class merchants and bureaucrats with no opportunity for such lobbying have better reason  to support you if they think you are serving the public good as you see it.

This logic applies in contemporary democracies too.

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The prince may want to conceal certain material facts or goals from the general public, which are relevant to a decision. Arguments for a course of action may appear strong based on publicly known facts. If the prince openly ignores this advice, the prince may appear foolish or be forced to implicitly reveal their true goal. For example, suppose the prince has a peace treaty with a neighboring state, but secretly plans to betray them soon. An advisor says, now that we are at peace, we should reduce the size of our army. Oops.

Decision markets similarly have the potential to expose hidden agendas when their recommendations are sometimes ignored.

The prince may want to train people not to question or argue with orders, to produce better compliance. Advice to the prince can also inform others that the prince's action is not in their interest, which will make them less cooperative.

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 Machiavelli was trying to persuade Lorenzo de Medici to think differently about taking advice or not. So he was smart enough to advise receive advice without going against a dogmatic truth of those times where a leader must do the opposite.

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Maybe this ties in with Robin's long-ago post on why CEO's pay so much for advice from outside consultants. The CEO can't afford to appear to be getting this advice from inside counselors, because he then has to share status with those counselors. The outside consultants come and go.

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I interpreted Machiavelli's suggestion very differently. It doesn't seem concerned specifically with [the 16th century equivalent of] prediction markets or even political decisions in general. I take it as a very broad statement that amounts to this: As their leader, people should respect you enough to hold their tongue—much in the same way a small boy would hold his tongue when addressing his father.

Think of a person who values brutal, uncensored, uncurved honesty. If she's rude, you should have the right to tell her. If she's offending you, you should have the right to tell her. If she's not doing enough of one thing or another, if she's not presenting herself appropriately, if she's not lenient enough or too lenient, or if she's getting angry over something she shouldn't be getting angry about—you should have the right to tell her. If you think those pants make her look fat, tell her. If you think she's too trusting, tell her. If you think she's too harsh, tell her. Etc.

A flatterer is someone who would... well... flatter you. The only way to guard against this is by telling people that flattery will get them nowhere—but instead speak the cold, hard truth. Flattery is thus useless, and the otherwise flatterer is free to speak his/her mind as he/she sees fit. After a while, especially from someone who doesn't have a very positive opinion of you, being able to consistently speak the "cold, hard truth" diminishes respect for the position of power itself.  

The solution to the dilemma of whether or not one should allow the public to speak freely their truths towards you or be constantly buttered up by flatterers is—get a close group of advisers who will speak the cold, hard truth. In this case, "the more freely he shall speak, the more he shall be preferred." 

King Lear's Jester, if you would.

I don't see this as being concerned with "advisers" and "advising" in the same way prediction markets are concerned with advising. 

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I think Machiavelli just correctly realized that in his time there was no public source of information anywhere near as good as prediction markets.  I'd wager "expert" predictions were of even lower quality than today (and fewer were available).

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A lot of advice is probabilistic.  A plan may succeed, or it may fail. Even if you accept only the 90% probability advice, and reject only the 10% probability advice, there will inevitably be cases where you were wrong. Your opponents will remember them selectively and use them against you. Especially accepting a wrong advice (a good probabilistic advice that randomly turned out wrong) will make you seem weak and easy to manipulate. For a ruler, such an image could be fatal, because other strong people would predict their fall, which can be a self-fulfilling prophecy.

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