Great Performance and Results
Whether you’re a startup founder or an investor in venture capital, data shows your future success is ultimately tied to one thing: your company (or portfolio of companies) needs to be an outlier that outperforms the competition.
Outperforming, in the world of companies, ultimately means one thing: growing your financial value multiple times over.
Since the person responsible for this growth is ultimately the CEO, in today’s article I’m going to share with you 12 leadership lessons some 500 years old ─and why they are still relevant today.
These lessons come straight out of the infamous treaty “Il Principe”, better known to English readers as “The Prince”, by Renaissance diplomat and political writer Niccolò Machiavelli.
In this article, we will look at what these key lessons are. Then I will go through why they are still relevant today, and what we can do to improve our leadership skills through their wisdom.
The 10 Lessons from Machiavelli
1. It is better to be adventurous than cautious
Machiavelli argues that great leaders need to adapt to changes in times and fortunes. Those that stand better chances of doing it well are those that don’t fear to be bold.

2. Be a constant inquirer, and… a patient listener
Leaders should encourage their subordinates to come up with ideas and counsel. However, a leader should never tolerate those that do so dishonestly: Flatterers should always be avoided!
Machiavelli devotes several passages to stress that surrounding oneself with great aids is the “trademark” of a great leader. Leaders should make it a priority to treat them well and yet to maintain authority over them.
3. Irresolute [leaders]… are generally ruined
Strong leaders always seek to build up respect and reputation: they are never neutral. They know that it’s much better to make a stand and lose, than to act weakly and irresolutely.
Machiavelli makes it clear that you will gain tremendous respect when you are either a true friend or a downright enemy. Your allies will not forget it and your opponents will at least respect your courage and straightforwardness.

The Prince also recommends to avoid alliances with someone stronger than oneself for the purpose of attacking others. Smaller players will hate you and the bigger ally will always pick the terms.
4. Avoid… [doing what will make you] hated or contemptible
You can’t please everyone all the time, which means that you can’t be loved by everyone.
Sometimes, you might even need to be tough, which will probably attract some hostility.
What you MUST avoid, though, is to be hated by everyone. This normally happens NOT when you are tough, but when you are fickle, frivolous, mean-spirited and when you do not give your people what’s due to them or disrespect their property.
5. It is necessary… to know how to do wrong, and to make use of it or not according to necessity
You probably expected it: here, just like in other infamous passages, The Prince advises leaders that, sometimes, for the greater good, they need to be able to play tough.
Machiavelli specifically argues that leaders should be prepared to show the ruthless strength of a lion, when confronted by “wolves” threatening what they built, and the cunning deception of a fox, when dealing with the traps and machinations of their adversaries.

6. Injuries ought to be done all at one time… benefits ought to be given little by little
Cool, so occasionally you might need to play hard. Here Machiavelli tells you how: don’t delay and act quickly and at once.
If you need to bring under control a difficult situation or take difficult decisions to steer you ship through difficult times, you should clearly assess what is the extent of the damage you need to inflict and aim to deliver it all at once.
In today’s times this principle can apply in a myriad circumstances. In business, for example, when you need to make redundancies, or in politics when your population’s welfare requires you to take unpopular decisions (covid restrictions anyone?) .
When it comes to “giving”, instead, make sure you can you show your approbation gradually and incrementally.
7. Encourage… people to practice their callings… [and] entertain [them]… at convenient seasons
Machiavelli encourages leaders to be liberal and let people build up their fortune, but also not to forget their “mental health”. In our times we find parallels to this approach in both in politicians who encourage free enterprise and in business managers who let their subordinates try their own ideas and be rewarded for their successes.
8. Endeavour in every action to gain… the reputation of being a great and remarkable man
There are no two ways around this: if you are to lead, you can’t stay in the shadow. You must have an ambitious vision, be at the forefront of the action and lead by example.
Great leaders strive to make a positive impact in the world by accomplishing great enterprises.
People are quick to forget countless shortcomings when you achieve something remarkable and for the greater good. Thus, focus on making an impact, rather than on avoiding failure, mistakes, or causing offence.

9. Men ought either to be well treated or crushed
If it weren’t clear by now, Machiavelli’s analysis of power shows half-measures don’t pay.
You either treat someone well and support them all the way or, if you’ve decided they are a threat to your endeavours, you should be upfront and clear them out of your way completely.
10. The chief foundations…[of all rules] are… good laws and good arms
In international politics, Machiavelli’s advice is still true today in a literal sense. Powerful nations have both a strong army and a strong system that upholds a fair rule of law.
However, if we take “laws” and “arms” in a more metaphorical sense, this lesson can be applied to pretty much any organised groups in competitive landscapes, from companies to organised movements. Specifically, good leaders should always strive to build and maintain two things above all else:
- A strong yet fair internal management system
- A solid “growth engine” that can beat the competition

11. Mercenaries and auxiliaries are useless and dangerous
Paying for growth and reliance on external supporters is never a good long-term strategy.
In business this can happen when a company relies too much on contractors and agencies, rather than building a loyal and vested-in workforce. That’s why culture is so important in startups! In politics too, one should aim to build grass-root support.
Ultimately, good leaders recognise that paid marketing of any kind, both internal or external, is not reliable. Organic sales trump paid advertisement. Loyal employees believing in your mission outperform money-driven consultants. Active fans and followers believing in you can help you win ground against bigger and richer adversaries.
12. [You] should…study… the actions of illustrious men
Finally, The Prince gives leaders an advice for self-development: learn from those that accomplished great feats.
Machiavelli writes:
A wise man ought always to follow the paths beaten by great men, and to imitate those who have been supreme.
Niccolò Machiavelli – The Prince
Why Bother Learning From A Guy Who Died Half a Millennium Ago?
Let’s start in reverse. Why should you bother listening to leadership tips given when Chief Officers did not even exist?

Good question: it turns out there are striking similarities between modern business leaders and the renaissance rulers of Machiavelli’s time.
You can see proof of it in the very enduring popularity of The Prince, which continues to be in print even today and has, since its publication, inspired leaders of all kinds. From philosophers to politicians. From crime lords to… business executives.
Perhaps most importantly, though, recent studies confirmed the relevance of (at least some of) Machiavelli’s reflections on what makes a successful leader.
In short, we can summarise such reflections with something like this:
Unsentimental realism trumps abstract moral absolutes. As long as a leader has the vision and capability to build a stable and prosperous rule, we might excuse such leader if they use single-mindedness and even (occasionally) “brute force” or deceit to crush those who undermine them.
Now, a bit of contextualisation for these principles. Machiavelli wrote at a time when:
- Moral leaders like the Pope had unapologetic worldly goals and countless mistresses;
- Murder was a fairly common practice for resolving issues; and
- Internal succession and political chaos ravaged an Italian Peninsula divided into competing principalieties
Times change, people don’t
Today, thankfully, the world is in a much less brutal state of affairs. The murder rate is exponentially lower and the justice system more or less able to regulate most business and political disputes, without people resorting to killing off one another.
One thing stayed constant, though. Even if we focus on the world of business alone, the competition to carve out a substantial space in the world economy is not necessarily less than it was back then to conquer a piece of land ─and neither is the responsibility on the the shoulder of modern leaders and CEOs.

Specifically, today’s business leaders are responsible for the ultimate success of their ventures. They are also responsible for the livelihood of themselves and their family, and most importantly of their employees. They are accountable to their supply chain partners, shareholders and financial backers. Finally, they are accountable, by extension, to the broader economy and communities where their venture sits in.
Business leaders are also responsible for the impact (big or small) their vision and efforts will have on the rest of the world.
These are no light burdens and, as a result, success rate is also slim. Failure is much more common.
Key Takeaways: strive for being a GOOD leader BUT make sure you are at least a STRONG one
So how can entrepreneurs turn the odds in their favour and maximise success in their endeavours?
That’s where Machiavelli’s observations strike as extremely relevant.
A University of Chicago study in 2008, for example, measured the financial performance of 316 CEOs, depending on their personality traits. The study divided candidates into two groups:
- those who mastered the ‘softer’ skills of management, such as demonstrating openness to feedback, possessing great listening skills, and treating people with respect; and
- those who mastered the ‘harder’ skills of execution, quickness, aggressiveness, and tenacity.
The candidates were actually skilled in both fields, but only highly skilled in one or the other. The researchers called the first group “Lamb CEOs” and the second group “Cheetah CEOs”. They might have as well called them Likeable CEOs and Asshole CEOs but these terms could have caused offence.
The result? According to Chicago business professor Steven Kaplan, the “Lambs” succeeded 57% of the time. Not bad. The aggressive, hard-nosed managers, or “Cheetahs,” however, succeeded 100% of time.
Does it mean you should strive to be an asshole when you lead?
Not necessarily. According to Geoff Smart and Randy Street of ghSMART, a top management assessment firm that conducted the in-depth CEO interviews, different situations call for different leadership characteristics.
The Chicago study, for instance, focused on CEOs at private equity-owned companies, which PE groups frequently purchase with high debt-loads and expect to achieve fast results through aggressive restructuring that require tough-minded managers. In other situations – whether building teams, motivating people, or managing relations with diverse constituents – interpersonal and team-oriented skills (aka. Emotional Intelligence skills) are crucial. The World Economic Forum and sales experts agree.

The conclusion from all this modern-day research?
If you need to manage a large team, restore or maintain order, and drive results, you need to have a strong leadership that focuses on results above everything else –including the “moral obligations” to be nice to people.
If you want to sell more, build stakeholder relationships, and attract and retain talent, then mastering Emotional Intelligence interpersonal skills is key.
Now, what did Machiavelli advise some five centuries ago?
Upon this a question arises: whether it be better to be loved than feared or feared than loved? 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.
Niccolò Machiavelli – The Prince

By observing the nature of humans and effectively doing an almost “statistical” study of both successful and failed leaders, Machiavelli understood that a great leader must muster both skill sets. Yet, to avoid losing control in difficult times and in situations where one cannot be both, being tough maximises your chances to get out wining on the “other side”.
That’s the power of Machiavelli’s writings. He preceded psychological sciences by centuries in using empirical data on “what has worked” and “what has failed” in what situations to make his observations.
Instead of writing about what “should be”, he wrote about what worked for rulers A, B and C, versus what failed rulers X, and Y.
Winners focus on winning = winners focus on results (and on the greater good these will bring)

In the end, perhaps all the infamous Florentine author wanted to tell leaders was to develop ones’ virtue and valour and to achieve something remarkable for their people.
I like to think that it’s to to that end (and because of the greater good that such end might bring) that Machiavelli (like Smart and Street’s research) pointed to the importance of focusing on results –and on proven (not moral) ways to get them.

Like Machiavelli’s scholar Maurizio Viroli once said:
A true ‘Machiavellian’ entrepreneur or executive would be an innovator capable of creating new and better ways of producing and distributing products and services.
In Machiavelli’s view, such a leader might be excused, not justified, if he or she violates the principles of honesty. But only on condition that it is absolutely necessary to accomplish a great deed of innovation that would benefit a great number of human beings, like the ideal prince whose highest value is the good of the people of his country.
M. Viroli – interview on “Strategy+Business”