To be called Machiavellian is to be considered unscrupulous, immoral and deceitful. This is a man that wrote that ‘since love and fear can hardly exist together, if we must choose between them, it is far safer to be feared than loved’, and ‘if an injury has to be done to a man it should be so severe that his vengeance need not be feared’. Machiavelli did not see people as inherently good, but wrote that ‘of mankind we may say in general they are fickle, hypocritical, and greedy of gain’.

But in spite of this jaundiced worldview, or maybe because of it, Machiavelli has been called the founder of modern political science and realpolitik, and I believe teaches 5 lessons that can benefit the strategist.

Niccolò Machiavelli was an Italian Renaissance historian, politician, diplomat, philosopher, humanist, and writer. He was for many years a senior official in the Florentine Republic, with responsibilities in diplomatic and military affairs. He also wrote comedies, carnival songs, and poetry, but is best known for his masterpiece, The Prince (Il Principe), written in 1513. It is these writings from which we can draw our lessons.

The first lesson is to be the agent of change. Machiavelli wrote that ‘I’m not interested in preserving the status quo; I want to overthrow it’. He understood that the world doesn’t stand still for anyone, that the only constant is change, and that if we don’t embrace this change and drive it, we will be caught unawares and swept aside by it. He could be talking about our lives in the digital age when he writes that ‘whosoever desires constant success must change his conduct with the times’. The digital revolution has brought unprecedented levels of change, all happening at disorienting speed. The strategist needs to recognize and embrace this.

The second lesson is to understand that you will always face resistance to the change you are driving. He writes, ‘it must be remembered that there is nothing more difficult to plan, more doubtful of success, nor more dangerous to manage than a new system. For the initiator has the enmity of all who would profit by the preservation of the old institution and merely lukewarm defenders in those who gain by the new ones’. Enterprises, and the people that work within them are not wired for change. They are designed to maintain and build on the status quo, particularly when it works to their advantage. It is far too easy to grow comfortable within the machine. And the graveyard of history is littered with the bodies of technology and business giants that became complacent and resistant to change that can happen incredibly quickly. Recognize that there will be resistance to your efforts to drive change and you can plan accordingly.

Which brings us to the third lesson, that of speed. Machiavelli writes that ‘the wise man does at once what the fool does finally’. We have often discussed the need for the strategist to act decisively, to move quickly, to test, to fail fast and to move on. The digital fingerprints of failure are impermanent, so the stakes are lower. But the impact of inertia can be crippling.

The fourth lesson is an understanding of the capacity of people to react to both good and bad news. He writes that ‘the new ruler must determine all the injuries that he will need to inflict. He must inflict them once and for all’. Later, he adds that ‘benefits should be conferred gradually; and in that way they will taste better’. This is an interesting one, and bears some explaining. It is based on the idea that as people, our capacity for anger or happiness is limited. That is to say, that we can only get so angry or happy at one time, and that as strategists we should use this to our advantage. So if you have bad news, give all your bad news at the same time, because the recipient will be just as angry with a single piece of bad news as they will with three. The inverse is the case with good news. Spread out sharing your good news over time, since we can only achieve a certain level of happiness at one time. By spreading it out, you give your audience a heightened and sustained sense of well being and are able to drive your change agenda more consistently.

The fifth and final lesson is to be subtle and pragmatic. Machiavelli writes that ‘Men judge generally more by the eye than by the hand, for everyone can see and few can feel. Every one sees what you appear to be, few really know what you are’. He builds on this theme of subtlety by reminding us that ‘no enterprise is more likely to succeed than one concealed from the enemy until it is ripe for execution’. Machiavelli is not alone in emphasizing subtlety; we have previously explored this theme in the writing of Sun Tzu. He combines this focus on subtlety with an emphasis on the need to be pragmatic. As he writes, ‘The promise given was a necessity of the past: the word broken is a necessity of the present’. It is this pragmatism that makes much of Machiavelli’s writings so controversial, specifically his perspective that a promise is just a lie that is waiting to happen when necessity dictates. While I don’t subscribe to his worldview of being unprincipled, I do believe that it is important to not be rigid or ideological. To be pragmatic is to acknowledge that circumstances change and that the future is unpredictable. To be pragmatic is to be supple enough to change course when necessary. To be pragmatic is to focus on the goal, on the outcome and not the individual steps. In short, to be pragmatic is to be strategic.

Most revisionists will write that someone controversial was a man of their time, that their views and opinions need to be considered through that lens, and not from the perspective of a modern sensibility. My interest here is not to do that, not to gloss over Machiavelli’s more controversial and less palatable views. My interest is to understand how some of his core ideas remain vital in the digital age, and how applying them make us more effective strategists. Machiavelli did not have a high opinion of human nature, but he did understand many of the fundamentals of what it took to succeed. As he wrote, ‘he who wishes to be obeyed must know how to command’.

Next week on octopus, we will continue to explore the role of the digital strategist. Please be sure to comment below. I’d love to hear from you. Please subscribe for alerts about new episodes and content. Thank you for listening to octopus. I’m Nasser Sahlool.

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