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On Leadership

3/22/14 by SkyeWintrest
Updated 5/1/14

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Damnit. I had something like three pages here and it was deleted because I accidentally refreshed. OH WELL, NOW IT'S TEN PAGES. Anyway, I took the last two days to read "The Prince" by the recommendation of someone who knows quite a bit more about leadership than I do (you can read it here). They stated that it was one of the bases of leadership, and I can't exactly agree. So, heads-up, this is going to be a massively long post about the book and my ramblings on what I think about it. I could be wrong about things due to being an idealistic teenager (and possibly not having enough experience with people and the world), and I'd like to know if you think I am. I will gladly have a nice reasonably and polite debate about things, as I'd rather clear things up.



The Prince is a valuable book, and I have no intention of pretending that it isn't. It demonstrates an effective way to rule and keep power, and provides many good suggestions for courses of action, with examples to support them. However, while it has good points, it also has two major flaws. I will state some good suggestions that I agree with, and then get into the flaws and multitude of examples which I disagree with.


Things I agree with:

1. Descriptions of "principalities" and the ways which people come to them are accurate as far as I can see.

2. If a principality is highly organized based on a ruling figure, then taking the place of that figure after removing them is easy, though removing the figure is difficult.

3. The ways people come to ruling principalities drastically change their initial powers in that principality. The more involved the person was in creating their own power, the more power they will have.

4. Rulers are given power by the people, and if the people hate them, they have far less power and will be incapable of ruling or likely even keeping their position.

5. Analysis of three main categories of armed forces are good, though it doesn't account for possible autonomous robot armies (understandably. Not really an issue either, since that's not going to happen for a bit if it will at all).

6. A ruler should be capable of doing something which is percieved as "mean" in order to avoid larger problems.

7. Internal conspiracies aren't very problematic when you are held in esteem and the people love you.

8. While the book separates "people" and "soldiers" specifically, it is true that there are divides between groups of subjects, and they can't all be pleased at once - just like not all the varied dieties in religions can all be true simultaneously.

9. Benefits and drawbacks of fortresses.

10. There are many good ways to placate the common uneducated people.

11. The people that surround you as allies play a strong role in determining how people see you.

12. Flattery is not something to be listened to.

13. Allies need to be kept close and not alienated - dependent allies even more so.

14. Solidifying and creating a solid power foundation is extremely importont for any leader.

This is by no means an exhaustive list. There is a lot of value in tshihe book, and as I said - I have no intention of pretending otherwise.


Things I disagree with:

Before I continue, I need to differentiate between two highly related but distinct things: Good leadership, and the obtaining/keeping of a position of leadership. Good leadership needs a position of leadership (quite possibly increasing) to be fully effective, and in order to keep a position of leadership, the leader must have some capability of leading well. Here is the difference between the two as I see it.

Obtaining/keeping a position of leadership is exactly what it says, and you need a semblance of good leadership to do this, otherwise your would-be subjects will refuse or remove you. This can also be called skilled, or powerful leadership. If you do not have the control necessary for this, you are a weak leader.

Good leadership is more difficult to grasp: It is taking people and guiding them do to more than they would otherwise, something larger than the leader or any group of people alone. It is also bringing them to a better situation than they would otherwise be in. Good leaders understand that they lead for the people rather than themselves, and the best of leaders will benefit people beyond their followers, though they will of course favor their current followers. It should also be noted that a good leader will also know when it is time for them to step down - if there is someone else who would be able to lead more efficiently and effectively, along with keeping the ideals of the people in mind.

1. With this in mind, the first issue with The Prince will likely become very clear. It is focused on siezing and holding the position of 'leader' more than good leadership. There are aspects of good leadership by necessity, but it does not look as if they are there for more purpose than the primary goal - siezing and holding power. This is a problem with this being a basis for leadership, as it promotes the individual over the group, and holding power over doing the best thing for people in general.

2. The second problem is that it is outdated in several respects. Much of it would fail in light of the rapid communication allowing news to spread rapidly along with the easy access of uneducated people to the correct perceptions of the more educated - knowledge of things such as common failings of the brain along with knowledge of logical fallacies and critical thinking make it more difficult to fool people with the deciet recommended in The Prince. Furthermore, the recommendations for military matters are undermined by first-world countries not participating in wars with each other, and interrupting in the wars of third-world countries far beneath them, which are raised up due to resources. In The Prince, interpretation of the suggestions indicate that rapid and powerful conquering of these countries is the best course of action - but this would be an extremely poor move due to the other countries that also want the resources.


Examples of problems in The Prince's suggested leadership:

A prince does not spend much on colonies, for with little or no expense he can send them out and keep them there, and he offends a minority only of the citizens from whom he takes lands and houses to give them to the new inhabitants; and those whom he offends, remaining poor and scattered, are never able to injure him; whilst the rest being uninjured are easily kept quiet, and at the same time are anxious not to err for fear it should happen to them as it has to those who have been despoiled. In conclusion, I say that these colonies are not costly, they are more faithful, they injure less, and the injured, as has been said, being poor and scattered, cannot hurt. Upon this, one has to remark that men ought either to be well treated or crushed, because they can avenge themselves of lighter injuries, of more serious ones they cannot; therefore the injury that is to be done to a man ought to be of such a kind that one does not stand in fear of revenge.

  • This is a cruel way of destroying the native people of the land, and crushing them down in an attempt to keep them from rising against you. However, there are several significant issues. First of all, with the advent of communication, this would become common knowledge very rapidly, and global power would lessen. Second, this has the potential of making the people whose belongings you stole enemies for a long time, with a grudge against your bloodline and your followers. If such a grudge occurs, and they regain power, there will be trouble - as a result, they must be kept crushed permanently, a drain on resources. If the general population is more intelligent, they could also be worried and lose trust in you unless those whose belongings you stole are horrible and cruel with their money themselves.

When the duke occupied the Romagna he found it under the rule of weak masters, who rather plundered their subjects than ruled them, and gave them more cause for disunion than for union, so that the country was full of robbery, quarrels, and every kind of violence; and so, wishing to bring back peace and obedience to authority, he considered it necessary to give it a good governor. Thereupon he promoted Messer Ramiro d'Orco,(*) a swift and cruel man, to whom he gave the fullest power. This man in a short time restored peace and unity with the greatest success. Afterwards the duke considered that it was not advisable to confer such excessive authority, for he had no doubt but that he would become odious, so he set up a court of judgment in the country, under a most excellent president, wherein all cities had their advocates. And because he knew that the past severity had caused some hatred against himself, so, to clear himself in the minds of the people, and gain them entirely to himself, he desired to show that, if any cruelty had been practised, it had not originated with him, but in the natural sternness of the minister. Under this pretence he took Ramiro, and one morning caused him to be executed and left on the piazza at Cesena with the block and a bloody knife at his side. The barbarity of this spectacle caused the people to be at once satisfied and dismayed.

  • This is not an easy situation to deal with, but this being used as a good example is a poor idea. First, the initual situation is problematic - using a kinder person could easily have resulted in worse problems than what was done - bringing in "a swift and cruel man". Even assuming that obedience to authority is necessarily good (more in musings at the end), this was dealt with improperly. Bringing in Ramiro was not a bad choice, but the way he was dealt with was horribly done as an example of what should be done now, and still poorly done back then. First of all, attempting to show that "if any cruelty had been practised, it had not originated with him" - in modern times, this would have been ripped to shreds by the avenues of communication and critique. The only two options are that the duke is so foolish that he did not see what kind of man he was putting into "the fullest power", or that he knew precisely what he was doing, and therefore some of the cruelty originated with him. In addition, executing Ramiro was a foolish move. Any who the duke attempts to raise up to be another governor or similar, if they are intelligent enough to be even a decent governor, would likely be very wary about this situation, as Ramiro was executed for following the wishes of the duke in the way the duke expected him to (or should have, seeing as the duke knew his character).

Such was [the duke's] line of action as to present affairs. But as to the future he had to fear, in the first place, that a new successor to the Church might not be friendly to him and might seek to take from him that which Alexander had given him, so he decided to act in four ways. Firstly, by exterminating the families of those lords whom he had despoiled, so as to take away that pretext from the Pope.

  • Continuing with the duke, the first way he decided to act is the only one I mention here, as it is the problem case. In this case, it is assumed that exterminating a family is a better choice than leaving them alive after taking their valuables in order to keep the Pope from using it as an excuse to take the duke's possessions from Alexander.

A prince ought to have no other aim or thought, nor select anything else for his study, than war and its rules and discipline; for this is the sole art that belongs to him who rules, and it is of such force that it not only upholds those who are born princes, but it often enables men to rise from a private station to that rank. And, on the contrary, it is seen that when princes have thought more of ease than of arms they have lost their states.

  • This is simply incorrect. War should be relevant, and it should be practiced, but it shouldn't be on the mind all the time. Furthermore, while thinking more of ease than arms, this might happen, but in today's society there is far more than war to consider - and a leader which prioritizes things other than war can still do well, without "losing their states", as stated in this quote.

a question arises: whether it be better to be loved than feared or feared than loved? It may be answered that one should wish to be both, but, because it is difficult to unite them in one person, it is much safer to be feared than loved, when, of the two, either must be dispensed with. Because this is to be asserted in general of men, that they are ungrateful, fickle, false, cowardly, covetous, and as long as you succeed they are yours entirely; they will offer you their blood, property, life, and children, as is said above, when the need is far distant; but when it approaches they turn against you. And that prince who, relying entirely on their promises, has neglected other precautions, is ruined; because friendships that are obtained by payments, and not by greatness or nobility of mind, may indeed be earned, but they are not secured, and in time of need cannot be relied upon; and men have less scruple in offending one who is beloved than one who is feared, for love is preserved by the link of obligation which, owing to the baseness of men, is broken at every opportunity for their advantage; but fear preserves you by a dread of punishment which never fails.

  • This entire argument is based off of the worst-case scenario, in which people adhere to the most cynical view of humanity. Furthermore, if you act as if people have the asserted qualities, then they will be more likely to have these asserted qualities. There is another trait, however, which is better than either of these, and it works best with being loved. This is the trait of being trusted. If you are trusted, then people will not only offer you their resources, but turn to you in adversity over the people they love and/or fear, but do not trust. If you are trusted and loved, it is far more difficult for them to stop trusting you, and they will give you even more credit. The only time it is better to be feared than loved is in the case that you cannot win over their trust, but similar to other problems, this would not work as well in today's society. Your cruelties and lies might make your people fear you, but it will not silence them. People have been learning that they can rise against oppressors, and once again, other people can communicate and display outrage at your actions when they see that you are causing fear. Finally, fear will also destroy trust in you, keeping people from willingly going to you in adversity.

Among the wonderful deeds of Hannibal this one is enumerated: that having led an enormous army, composed of many various races of men, to fight in foreign lands, no dissensions arose either among them or against the prince, whether in his bad or in his good fortune. This arose from nothing else than his inhuman cruelty, which, with his boundless valour, made him revered and terrible in the sight of his soldiers, but without that cruelty, his other virtues were not sufficient to produce this effect. And short-sighted writers admire his deeds from one point of view and from another condemn the principal cause of them.

  • While this is impressive in that he was capable of doing this, it also shows that he was not trusted enough. Showing bravery, quick thinking, and that you will not waste the lives or health of your army - these will also achieve a similar effect, without harming your own army in the process. Once again, this would not work in the modern day due to communication - the members of the army could see that being in the army is quite possibly a worse situation than deserting. The statement about "short-sighted writers" is included so nobody can use it to say "so you are short-sighted" - this is fallacious, just as much as saying "the bible predicted people would begin to doubt it". After all, if something of what you are saying is horrible or incorrect, then it is not a stretch to assume that people will state that it is horrible or incorrect. This isn't being short-sighted, it's being honest.

our experience has been that those princes who have done great things have held good faith of little account, and have known how to circumvent the intellect of men by craft, and in the end have overcome those who have relied on their word. You must know there are two ways of contesting,(*) the one by the law, the other by force; the first method is proper to men, the second to beasts; but because the first is frequently not sufficient, it is necessary to have recourse to the second. Therefore it is necessary for a prince to understand how to avail himself of the beast and the man.

. . .

it is necessary to be a fox to discover the snares and a lion to terrify the wolves. Those who rely simply on the lion do not understand what they are about. Therefore a wise lord cannot, nor ought he to, keep faith when such observance may be turned against him, and when the reasons that caused him to pledge it exist no longer. If men were entirely good this precept would not hold, but because they are bad, and will not keep faith with you, you too are not bound to observe it with them. Nor will there ever be wanting to a prince legitimate reasons to excuse this non-observance. Of this endless modern examples could be given, showing how many treaties and engagements have been made void and of no effect through the faithlessness of princes; and he who has known best how to employ the fox has succeeded best.

  • There are two points here. First of all, this destroys trust in you, as people can easily pick out your lies and expose you as a liar. This is clear with many politicians recently - it is obvious that they lie to their own benefit. Second, "being the fox" does not require lying by any means. Ideally, it means knowing more than you show and using that information. Realistically, it means misdirection as well - which does not require lying. While this could potentially be revealed by perceptive people and communication, it is far less likely to be revealed than lying, and people can recognize the skill in misdirection through honesty rather than lies. Third, just because others will lie and be decietful does not mean you should as well. If you are, you are simply continuing the behavior rather than improving it. As a leader, you are setting an example - if you set this example, you are merely encouraging the deciet and lies that make more deciet and lies "necessary".

But it is necessary to know well how to disguise this characteristic, and to be a great pretender and dissembler; and men are so simple, and so subject to present necessities, that he who seeks to deceive will always find someone who will allow himself to be deceived.

. . .

Therefore it is unnecessary for a prince to have all the good qualities I have enumerated, but it is very necessary to appear to have them. And I shall dare to say this also, that to have them and always to observe them is injurious, and that to appear to have them is useful; to appear merciful, faithful, humane, religious, upright, and to be so, but with a mind so framed that should you require not to be so, you may be able and know how to change to the opposite.

  • This is a fairly explicit example of the point - this book is based on keeping power rather than being a good leader. Decieving them in suck a way, and considering them to be "so simple", is not giving them the respect due - it is removing a sense of perspective and placing yourself and your priorities above the people and their needs. Furthermore, while it is understandable that you cannot always demonstrate the good qualities, you can be honest when you need to decieve, you can be more outwardly cruel to be more kind, and you can get people to accept less-than-liberal conditions (this was discussed in an unquoted passage of The Prince, as I had no significant problem with it) by explaining the reasons for them. You do not need to pretend to have the good qualities, you can have all of the stated good qualities, with one included - reason. With reason, you can know when it is appropriate to take an action that would be bad in another situation.

One prince(*) of the present time, whom it is not well to name, never preaches anything else but peace and good faith, and to both he is most hostile, and either, if he had kept it, would have deprived him of reputation and kingdom many a time.

  • This is a direct example of deciet and lying as a good thing. It is not, as it is going against concepts which would help the world. Again: Set an example - if you cannot be expected to be honest (or to support peace and 'good faith'), nobody who follows you can be reasonably expected to do the same.

Turning now to the opposite characters of Commodus, Severus, Antoninus Caracalla, and Maximinus, you will find them all cruel and rapacious-men who, to satisfy their soldiers, did not hesitate to commit every kind of iniquity against the people; and all, except Severus, came to a bad end; but in Severus there was so much valour that, keeping the soldiers friendly, although the people were oppressed by him, he reigned successfully; for his valour made him so much admired in the sight of the soldiers and people that the latter were kept in a way astonished and awed and the former respectful and satisfied.

  • Once again, cruelty supported and implied to be 'good'. Successful keeping power at that time, yes, but in the current day there would be quite a few more problems for him.

A prince is also respected when he is either a true friend or a downright enemy, that is to say, when, without any reservation, he declares himself in favour of one party against the other; which course will always be more advantageous than standing neutral; because if two of your powerful neighbours come to blows, they are of such a character that, if one of them conquers, you have either to fear him or not. In either case it will always be more advantageous for you to declare yourself and to make war strenuously; because, in the first case, if you do not declare yourself, you will invariably fall a prey to the conqueror, to the pleasure and satisfaction of him who has been conquered, and you will have no reasons to offer, nor anything to protect or to shelter you. Because he who conquers does not want doubtful friends who will not aid him in the time of trial; and he who loses will not harbour you because you did not willingly, sword in hand, court his fate.

  • There are actually situations in which staying neutral is good. If you are more powerful, and wish to not engage in war, then become a refuge for those that need it. Otherwise, defending the disadvantaged will have them support you more strongly than aiding the stronger ones. Furthermore, sometimes you must stay neutral because you cannot fight, or you have had too many wars recently - fighting while rebuilding your people, or staying locked in constant wars, will be problematic and easily cause ruin. Peace IS necessary sometimes. Beyond that, however, this is good advice - it does apply in most cases.

Therefore a wise prince ought to hold a third course by choosing the wise men in his state, and giving to them only the liberty of speaking the truth to him, and then only of those things of which he inquires, and of none others; but he ought to question them upon everything, and listen to their opinions, and afterwards form his own conclusions. With these councillors, separately and collectively, he ought to carry himself in such a way that each of them should know that, the more freely he shall speak, the more he shall be preferred; 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.

  • This is foolish. It does not account for the possibility that councillors may see something you miss entirely - if they are not allowed to advise you except in what you ask about, they cannot show you what you missed in other topics. If you ask them about very general things, that is barely a change from allowing them to simply advise in general, without needing to be asked. Furthermore, people outside councillors can have valid advice that is not thought of by you or your councillors. It would be a better course to consider what all people say with your own thoughts, and consider it fairly - only giving some extra weight to the councillors' advice. If you show that you will consider information in the light of other information, and consider it honestly, then you will show your capability far more strongly, and people will be far more honest.

Once again, this is not necessarily an exhaustive list of examples. These are merely ones that caught my eye while writing this up.


Some defenses of The Prince that I've recieved

Please go to this link. It couldn't fit in this news post, apparently.


Final Thoughts on Good Leadership

Note: "he" will be used occasionally, and in such a case the normally-gender-inspecific person will be referred to as male. This is for grammatical purposes, and constitutes no belief on my part about the fitness men to lead vs women.

1. A good leader needs quick thinking capability, honesty, trustworthiness, charisma, and good judgment of character and skill.

2. A good leader needs support from skilled individuals to make up for his failings, and needs to be capable of admitting when he has done wrong or failed.

3. A good leader needs to acknowledge when there is another person more suited to his job, and needs to be willing to step down to raise this other person to his place.

4. A good leader does not force people into actions unless he needs to - instead, he will convince and demonstrate why people should take the action he wants so that the people do so willingly. If the people are taking an action willingly and gladly, they will do better than if they were forced into it against their will.

5. A good leader will use fear sparingly, as it is a powerful tool that has great effects and cuts the one that weilds it.

6. A good leader works for the people more than themselves. He is less inclined toward personal glory and more inclined toward improvement of their people and the world.

7. A good leader is compassionate and treats the people with the respect they are due. After all, the leader is a person himself, and respecting the people they lead as people shows that he 

8. A good leader recognizes the value and power of education, and will be able to use it to empower people to make their own strong judgements.

9. A good leader will always be striving for improvement of himself and others.

10. A good leader will not waste his people's health, lives, or resources.

11. A good leader should punish people who cause trouble quickly and strongly, but not stronger than necessary, and not without strong justification.

12. A good leader should not waste his breath and time saying more than necessary, but should not be so quiet that people don't know what he is thinking.

13. A good leader will show others that he is a person as much as his people, and not live as if he is something more than a person. Being a leader does not change him from being a person.


If I think of more to put on this list, I will. I'll also add any more traits that people suggest which I agree with.


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Skye man... you're a cool guy, but sometimes you just say too many words. :P

3/25/14 SkyeWintrest responds:

They explode out of my fingers, just like music. :P