Machiavellian Leadership

The Prince Original Cover

The past few weeks my read of choice before bed is The Prince, by Niccolò Machiavelli. While the book speaks volumes to the monarchy of yesteryear, the implications for a “Prince” like myself are astronomical. The book has had a direct impact on my leadership outlook and helped me to better understand roles. Forgot the cheese and focus on a classic.

The book is a chapter-by-chapter breakdown on leadership principles for Princes of the post-Roman empire. Machiavelli does a wonderful job showcasing both sides of a coin. For example Machiavelli correctly points out that a leader must strike a balance between cruelty and mercy. A leader cannot be totally loved and respected and likewise cannot be totally hated and respected. This same chapter discusses the implications of the people loving or hating you and assassination. A very inclusive chapter.

As with all principles it is important to take them in small doses. A modern day leader can lean upon the ideals portrayed but not engulf them. My teams would certainly be opposed to my hanging them to deal with disgruntled employees. Or maybe I am just a weak modern leader, a good hanging never hurt anyone.

Defense and Military

Machiavelli states two key points:

  1. A fortified city is very unlikely to be attacked
  2. Mercenaries are without loyalty and should not be used under most circumstances

A house in order is unlikely to breed confusion. It is of the utmost importance that your city/house/team is fortified. That means being aware of your teams strengths and weaknesses. Think of your personnel as a wall and where best to place them. An example would be that one of my leads is an amazing engineer, but lacks personable communications. I place that portion of the wall in the valley of my city and put the big smiling presenter on the front line. Thereby my city is fortified in key locations.

In the event your fortification has shortcomings you may desire to bring in temporary embankments. There is a point where you are given no choice due to time and money, but in all cases you should first attempt to grow that from within. Any talent grown from inside the city/organization will be stronger and more loyal to the cause.

Reputation of a Prince

Perception control is the paramount when ensuring your people respect you. This turns into a difficult balancing act as your role calls for a leader to act against the humane, merciful, and faithful qualities. That is where the perception of qualities is important as you must ensure that is your going in baseline.

I will admit this is the chapter that had the most impact on my own psyche. My religious upbringing and soul make it difficult to emotionally separate from the needs of my team. Learning what makes people tick is the only way to ensure that the reputation of yourself is kept. Most revealing is that a bad reputation does not inhibit power or control, rather it just needs to be offset by other qualities.

My personal opinion is that a leader who upholds ethical and moral responsibilities is stronger than the one who does not. It breeds a culture of honesty and team work.

Generosity vs. Parsimony

It is better to be hated for being stingy than hated for not keeping the generosity flowing. I am lucky enough to be surrounded by one of the best groups of people I have come in contact with. When I ask them to reach a benchmark, they exceed it. I ask a great deal of my people’s time and resources and they never fall short. It is difficult to not praise them and be generous with the thank fullness.

What I found is that the effect was less felt the more it was given. The new tactic is to establish that this baseline is the default. There is no choice than to meet the expectation and in the event you outshine your fellow team members the praise will flow.

From the podium this must be preached to your team, but this is not to say the reality will necessary hold true. A leader must accept that everyone cannot uphold the same principles due to the peripheral dependencies of life. In these cases there must be personal generosity. Pull your team members aside and ensure they feel appreciated, but knowing that it is self customized due to them not meeting the expectations of the team as a whole.

Cruelty vs. Mercy

In the course of history there have been few leaders that were both loved and feared. There is the portrayal of such things in photographs and paintings, but the case is never so cut and dry. Alexandria the Great was a prime example of the embodiment of these. When a leader can uniquely portray this, align yourselves with them. They will perform great things in their life.

When you can not be both loved and feared, it is safer to default to fear. To be loved with no fear in hearts does nothing but permeate dissent and lack of regard. An business arrangement made in amicable terms is not as strong as those made in fear. Your associate will not break an agreement fashioned in fear, due to the emotion transcending the entrance and exit.

Being cruel exhibits that you are simply an asshole. There is only so much push you can successfully give as a cruel leader. Never be cruel to the point of hatred or you have lost the ability to maximize potential.

Avoiding contempt and hatred

Keep your people happy rather than your leader when at all possible. When your people are contempt there is less likely to be internal conspirators.

Gaining Honors

Neutral positions in a fight will leave you with all the negatives of each side. Picking a side in an internal struggle ensures that you have an ally in either case. Having a stronger ally brings up the level of strength of your own organization. Being the stronger ally means that your friend in the fight will always feel the need to assist you and prove the alliance is worth keeping.

Sometimes though the chips fall differently and you end up loosing. Misery always needs a friend and your ally will be close at hand. Be smart though and teaming with a stronger partner as you run the risk of their power engulfing your own.

My Father always told me to take a stand, more than anything it is the honorable thing to do. Where Machiavelli falls short is in understanding human nature. There is something to be said for deciding to be the underdog. The underdog is given a free pass in the event of failure or a parade of roses in the event of success. Loosing isn’t always the worse place to be.

Nobles and Staff

A good leader gathers good teams. My current boss told me that when a leader is given the opportunity to hand select persons and choices poorly it is indicative of the overall leaders abilities. When selecting a team it is important that the leader either knows the subject purely on their own or is smart enough to select others that do. Picking people for any other reason breeds failure.

Avoiding Flatterers

When you are put in a position of oversight everyone is attempting to please you. Trusted council becomes imperative to the success of a team. Finding someone who will call your bullshit and advise to the contrary should be integrated into your inner-sanctum. The inner portion is important though, as a member of your council that becomes displeased when you do not take their counsel and shares the information with others will undermine your authority.

Hit the ground running with 70% of the knowledge and figure out the rest as you go. My Father taught me that there is at no point a moment when you are 100% ready for anything. Likewise when under counsel you make a decision you must stick with it. Constantly changing your mind or altering course showcases your ineffectiveness. Flattery is no reason to make or change a decision.


Machiavellian uses force-fullness throughout the entire book and then leaves the reader with a catchall for the ages. It is significant to emulate the greats of the past and their lessons, but understand it is not always a direct ratio. As with the above, there are a great deal of teachings to be gathered from The Prince, but not all directly correlate today.

In the end it is a 50/50 quotient. There is half of our success that can be attributed to learning and emulating while the rest is left to dumb luck or fortune. Some people are destined for greatness. Keep your eyes raised as good fortune is a blessing. Frankly none of us are that exceptional to succeed without an authority above us.