The Prince

By: Niccolo Machiavelli



We’ve all heard of people being called Machiavellian, and perhaps even described someone in that way ourselves. The description conjures up unscrupulous, opportunistic, amoral characteristics... those we perhaps wouldn’t want ourselves to be identified with. But, in all fairness to Niccolo, these broad definitions are out of context.

Machiavelli’s book, The Prince, from which most of these interpretations have arisen, was written at a time of strife in pre-nation Italy when power was held by key city states including Venice, Florence and Rome.

Each of these domains was led be a prince who needed to be unscrupulous, opportunistic and amoral to maintain and increase his power in troublesome times. Perhaps then being Machiavellian was beneficial. Indeed that is where his book focussed. It was written for the elders of Florence, defining best practice leadership techniques of the time.

So where does it fit in today’s world? Well, if we replace competitive city states with competitive businesses, ambitious growth plans for territory with ambitious growth plans for market share and attainment of assets though conflict with attainment of assets through mergers and acquisition... then the parallels are there for all to see.

So join us for the next ten minutes or so as we re-interpret the best practices of The Prince and determine whether being a modern day Machiavelli is a badge of honour.

So join us for the next ten minutes or so as we re-interpret the best practices of The Prince and determine whether being a modern day Machiavelli is a badge of honour.

Mergers and Acquisitions

Machiavelli describes the challenges faced by a leader taking over new territories or domains.

The first challenge is that of expectation. As Machiavelli puts it, “men willingly change their ruler, expecting to fare better”. The honeymoon period in M&A’s is well recognised: periods of back slapping, bi-directional praise of success, statements of synergies and future plans abound. Staff look principally at the changes in their own area of responsibility and ask: what’s in it for me?

Machiavelli identified this challenge: “no matter how powerful one’s armies, in order to enter a country one needs the goodwill of the inhabitants”. New leaders need to gain the trust of the new team by ensuring their needs are met, either by improving their situation or maintaining the status quo, “so long as their old ways of life are undisturbed and there is no divergence in customs, men live quietly”.

So the Machiavellian approach to M&A’s is not necessarily dictatorial, but places emphasis on positive change where necessary, with maintenance and exploitation of what is good: a 15th century SWOT analysis.

Leading by “Being There”

Machiavelli identified the challenges faced by a remote leadership team:

..when states are acquired in a province differing in language, in customs, and in institutions, then difficulties arise; and to hold them one must be very fortunate and very assiduous. One of the best, most effective expedients would be for the conqueror to go to live there in person."

So the Machiavellian approach to M&A’s is not necessarily dictatorial, but places emphasis on positive change where necessary, with maintenance and exploitation of what is good: a 15th century SWOT analysis.

He spotted the advantages, the same advantages attained today:

Being on the spot, a leader can detect trouble at the start and deal with it immediately. If absent, problems are identified only when they become serious, and then it is too late; When issues are identified early, they can easily be remedied. Wait too long and the disease will have become incurable.

In today’s workplace, managing by walking around, strong social communication, authentic leaderships and other practices are proposed by our latter day gurus. Which of them have ever been described as Machiavellian?

A quick word on motivation When it comes to motivation and discipline Machiavelli is quite clear: “Violence must be inflicted once for all; people will then forget what it tastes like and so be less resentful. Benefits must be conferred gradually; and in that way they will taste better”.

Short sharp shock for deviants: progressive praise for compliants. We’ve all experienced the good-bad-good sandwich of personal appraisal. Get criticism over with quickly and get on with business. It’s another excellent “Machiavellian” practice, now in common use in business.

The leader’s A-team

Machiavelli discusses how best to create the leader’s support team. He identifies two options: work with a group of equally powerful individuals or become the focal point and gain support from lower levels of responsibility.

He presents the latter as the better option: “A man who becomes prince with the help of the nobles finds it more difficult to maintain his position than one who does so with the help of the people”.

Why? Because in the former, the leader finds him or herself surrounded by many who believe they are his equal, and because of that the leader cannot command or manage them the way they want.

The worst that can happen to a leader when the people are hostile is for him or her to be deserted; but from hostile nobles, the leader has to fear not only desertion but even active opposition.

Machiavelli’s answer is to ensure that the nobles (or today’s Vice-Presidents) conduct themselves in such a way that they become dependent entirely on the leader’s fortunes. How? By sharing risk and reward, build an A-Team with separate yet co-dependent skills, experience and shared ambition.

Machiavelli and good governance.

Machiavelli states: “The first way to lose your state is to neglect the art of war; the first way to win a state is to be skilled in the art of war”. It’s clear in the context of the original publication that this relates to dictatorial aggression but with a little extrapolation and consideration of our own modern business context his comments directly relate to good governance.

If the leader focuses on the constraints of his business domain, the external influences, rules and regulations to which alignment is necessary and the influence of local conditions will make it much easier to progress and develop.

Machiavelli also suggests intellectual training: assessment of other successful leaders from other domains or times, “to discover the reasons for their victories or their defeats, so that the prince can avoid the latter and imitate the former.“ It’s benchmarking by any other name.

Machiavelli and Authenticity

Machiavelli suggests the leader should appear to be compassionate, faithful to his/her word, kind, guileless, and devout. But his/her disposition should be such that, if he needs to be the opposite, he knows how.

Now this is more like the common perception of being Machiavellian, but let’s read into it a bit. Everyone agrees it is praiseworthy for a leader to honour his or her word and be transparent. None the less, many who have achieved great success have been less open in their approach.

An example? Look no further than Apple and Steve Jobs. Despite being externally praised, there are many Apple employees who could describe the “dark-side” of Jobs leadership’s style.

But as Machiavelli puts it, 

“a prudent ruler cannot, and must not, honour his word when it places him at a disadvantage and when the reasons for which he made his promise no longer exist.” 

Change with the times. Be open to continuous improvement.

Conflict and Contest

Machiavelli suggests that: 

“There are two things a prince must fear: internal subversion from his subjects; and external aggression by foreign powers”.

To combat the latter, the leader needs good allies — especially within his or her own organised. Again good internal allies are key.

Don’t get lost in self-belief

He writes, “Men are so happily absorbed in their own affairs and indulge in such self-deception that it is difficult for them not to fall victim to this plague”. There have been many similar personalities in our modern times.

Machiavelli believed the only way to safeguard yourself against flatterers is by letting people understand that you are not offended by the truth, while recognising if everyone can speak the truth to you then you run the risk of losing respect.

He suggests a prince (or leader) must never avoid seeking advice. But he must take it when he wants to, not when others want him to. At the same time, he should be a constant questioner and must take note of the answers given.

In today’s world no business stands alone. Success is based on strong equitable partnerships. As Stephen Covey suggested, success is based on First seeking to understand, then to be understood.


So is it wrong to be Machiavellian? We can suggest that he has been misrepresented and like a stranger in a strange land, his alternative perspectives set him apart. But sometimes, the outliers succeed. If we do the same things, we get the same outputs. Time for a change?