Unconventional Leadership conversation: Plato on Timeless Principles for Modern Leaders

When I was preparing a new edition of my newsletter Unconventional Leadership with the idea of kicking off the a series of articles about 'The Future of Leadership: Predictions from AI', I imagined to approach it with the form of a direct conversation with AI. However, this exercise soon took on a life of its own evolving into the desire to engage a proper interview with an influential thinker from the past. And that's how I started refining my engagement with the AI to prepare what you are about to read, an interview with Plato, where Plato is portrayed by the AI, carefully instructed to act and think like him.

I was truly fascinated by where the discussion was heading but the result far too long to include as a new edition of the newsletter. For this reason I decided to offer it in a separate publication, not cutting any parts and remaining trustworthy with the original outcome.

The new edition of the newsletter, coming soon, includes my reflections on this conversation, which I found extremely interesting, especially because Plato's insights led the conversation in directions I hadn't anticipated.

Without further ado, I invite you to dive into the interview with Plato. I hope you'll find it as interesting and engaging as I did, despite its length

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Sebastiano:

Good afternoon, and thank you for joining me today. My name is Sebastiano, and I’ve had the privilege of working for over 30 years in the technology industry, a field that constantly challenges conventional thinking and pushes the boundaries of innovation and reinvention. Throughout my career, I’ve been fascinated by the multifaceted nature of leadership. Over time, this fascination has evolved into a deeper exploration of the overlooked and unconventional aspects of leadership, those subtle dimensions that, while less discussed, have the potential to profoundly shape individuals, organizations, and society. Today, I am honored, and, admittedly, a bit awestruck, to be speaking with none other than Plato, one of history’s most revered thinkers and the foundational philosopher of leadership, governance, and virtue. Plato’s ideas have shaped how we view justice, wisdom, and the responsibilities of leaders for centuries, and they remain as relevant today as they were in ancient Athens. I approach this conversation not just as a seeker of knowledge, but as someone eager to be challenged, provoked, and inspired. With Plato’s guidance, I hope to uncover truths about leadership that transcend time and push us into new realms of understanding. Together, we’ll explore timeless principles and their resonance in today’s rapidly evolving world. So, let’s begin this extraordinary dialogue, a journey into the heart of leadership, guided by one of its greatest architects.

Plato:

Good afternoon, Sebastiano. An opportunity again to dive into the subject of leadership, something so important for mankind.

Your background in the field of technology, which advances every day, is an interesting dimension in this discussion, precisely because it is the field a leader can dive into as a power that inspires innovation or shapes the trajectory of civilization. As I have long argued, leadership is an immutably intellectual and moral act; it requires not only the ability to lead but also the wisdom to know in what direction one should lead people.

My hope in this conversation is that together we will be able to uncover some of those deeper principles, those that endure beyond time and circumstance and touch upon the very nature of what it means to lead purposefully and virtuously.

Now, let us proceed with our common inquiry into the facets of human leadership and ways that it may transcend the measurable, touching the soul.

Sebastiano

Can we please start revealing what is leadership for you? From your perspective, is it an art, a science, or something more transcendent?

Plato:

Leadership, Sebastiano, is the deepest expression of the human condition, and to define it either as an art or as a science would demean its full signification. It is something more transcendent: a harmony of mind, spirit, and action directed toward the cultivation of the good both in others and in society.

Basically, leadership is to inspire and guide others to a vision that coincides with what is just and true. It is neither wholly born of technique, as science might suggest, nor of mere creativity, as art might claim. It is rooted instead in wisdom, a quality that unites knowledge with moral understanding. To lead means to conduct the maze of human nature, balance reason and emotion, individuality and community, ambition, and humility.

True leadership cannot be based on power or persuasion but must be firmly planted in ethics and a commitment to elevate those who follow. Hereby, leadership transcends the realm of the practical and becomes the expression of the inner life and virtues of the leader himself. In my time, I likened such leadership to the craft of the philosopher, who seeks not personal gain but the illumination of others. It is a responsibility that calls upon the leader to understand themselves and the world deeply and to act in ways that harmonize the needs of the many with the ideals of the eternal.

Sebastiano

Is what you described somehow the concept of the "philosopher-king" as the ideal leader you describe in The Republic?

Plato:

Indeed, Sebastiano, this view of leadership brings with it the concept of the philosopher-king. In The Republic, I explained how the philosopher-king would constitute an ideal leadership because of possessing the love for wisdom (philosophia) in addition to good character, proper to exercise just government. Such a leader will be uniquely fit to rule, uninfluenced by the taint of personal ambition, the attraction of wealth, or any passing appeal of power. But whereas it settles for opinion, they remain committed to the Good, this transcendental Ideal constituting in itself a premise from which all action just or righteous might come.

The philosopher-king may be said to rule upon bases of knowledge and to lead in virtue, not good for himself, but of the good of the 'polis'. Their wisdom was such that they were always able to see what truly Just would, while their Virtue itself always ruled that they must act not in the interests of only an elite few, but everyone. The blend of knowledge and moral integrity makes them capable of uniting these often competing forces within a society, guiding it toward harmony and flourishing.

But let's consider how this concept might resonate in modern leadership. Today's leaders are not philosopher-kings by name, but could well carry these qualities in their approach to governance, organization, or innovation. Is the ideal there, though its form has perhaps changed.

Sebastiano

In your description, I see three dimensions contributing to building the leader: knowledge, purpose, and virtue.

I'm not sure if this is a sign of the times, and also not sure how much this idea is driven by my personal history, but I feel nowadays we tend to recognize as leaders people with a dominant personality, which often also corresponds to an equally important ego. Leadership as you describe, involves balancing individual desires with collective well-being.

How can leaders ensure they serve the greater good without succumbing to personal ambition?

Plato:

Sebastiano, you've touched on a tension that always accompanies leadership, that pull between serving the greater good and the seduction of personal ambition. My point is, this tension was there in my time as well, but perhaps now it is magnified when the cult of personality, publicity, and all the rest too often seem synonymous with power. Let's see how leaders might rise above this tendency.

The first safeguard is self-knowledge. First, there is the need for a leader to understand his own soul—desires, strengths, and vulnerabilities. Without this introspection, the leader is easily swayed by ego and the lure of self-aggrandizement. The Delphic maxim gnōthi seauton ("know thyself") is critical here; only by knowing one's inner nature can one resist its darker impulses.

Second, a leader must anchor themselves in a purpose greater than self-interest. In The Republic, I argued that the philosopher-king was suited to lead because his pursuit of the Good transcends personal gain. Modern leaders, too, must align their goals with principles serving the collective: justice, equity, and flourishing for all under their care. When a leader's purpose is clear and noble, it acts as a compass, steering them away from the temptations of ambition.

Third, there needs to be mechanisms of accountability. No leader, however virtuous, can exist above scrutiny. In governance, this might be done through institutions; in organizations, it could be shared decision-making. A leader accountable to others, especially to those that represent diverse perspectives, stands a better chance at putting the common good over ego.

And lastly, we really cannot turn a blind eye to education and culture. A culture that worships power will create leaders that reflect that belief. On the other hand, a culture that values wisdom, modesty, and service will develop leaders who possess those qualities. Leadership, then, is as much a product of the community as it is about the individual.

Is this model of self-awareness, direction, responsibility, and cultural influence realistic in the world you live in? Or has the dominating ego that one sees with him become an inevitable part of contemporary leadership?

Sebastiano:

You can call me Seb if it is easier for you. It is for sure shorter.

I think you've hit upon an important point: the impact of the dominant culture of our time. In this era dominated by virtual communication and artificial intelligence, is the framework you suggested still applicable? What are the ethical values our society actually proposes?

Can you try to look at us with your own eyes, see how we have evolved, and try to trace the complexity of the trajectory we have undertaken?

Plato:

Ah, Seb, thanks for allowing such familiarity: it will make the dialogue all the more fluid.

You have just brought up a very profound and immediately relevant question: how, if at all, has leadership guided by virtue and purpose adapted to a world that has been transformed by virtual communication and artificial intelligence? More precisely, what ethical values does your society now uphold? To see your age through my eyes is to see, in equal measure, remarkable evolution and troubling dissonance: technology that has amplified the reach of human potential, surmounting the barriers of distance and knowledge, even as it has reshaped many of the values and structures that once framed community. Let us trace the contours of this trajectory, and some of its complicating features.

In my time, leadership was personal, resident in physical presence and direct talk. The agora permitted leaders and citizens to confront one another, their virtues or defects, fully in view. Virtual communication has obscured this intimacy today. More often than not, leaders project an image rather than embody a reality, their personas crafted to enthrall rather than guide. This separation from physical presence introduces both opportunity and peril.

While technology enables outreach to an ever-wider audience, it also threatens to yield superficiality and detachment from any notion of truth.

Your time is one of speed and automation, measured by means of quantifiable results of which artificial intelligence is the exemplar. Such a development, wonderful in every respect, has raised the value of efficiency as a moral one unto itself and often with a diminishment of contemplation necessary to achieve prudence. Leaders in that kind of world may very well settle for what they find expedient rather than what is right. The human capacity for reflection and empathy, qualities central to ethical leadership, must not be diminished by the very tools designed to enhance it.

At Athens, the ideal of the polis was a shared vision of the good, even if imperfectly realized. Today, I sense that this rapid exchange of information has fragmented society's values rather than uniting them. While the digital sphere empowers the individual voice, it also fosters division and a preoccupation with the immediate. The cacophony of competing interests and ideologies grows louder, and alignment in collective purpose becomes even more elusive.

Not all is grim, Seb. Your time has a complicated trajectory, but within that resides immense possibility. Virtual communication does afford the opportunity to democratize knowledge and amplify unheard voices. Artificial intelligence, put to work in service of moral values, can reduce suffering and extend human capability. The challenge is to incorporate these tools into a framework serving values that endure: truth, justice, and the welfare of all.

The framework I have proposed, self-awareness, purpose, accountability, and cultural influence, is not irrelevant; it is more necessary now than ever. But it must be fitted to the facts of your life. Leaders must employ technology in humility, deeply cognizant of its power to shape society but preserving its humanity. They must create a vision of not just progress but worthwhile progress, progress at the service of the good.

Seb, I ask in return: does your society have the will to anchor its trajectory in such ethical values? Does the rate of technological change greatly risk outrunning the moral reflection it needs to guide it?

Sebastiano

This is a long answer, Plato. I hope that those who read us are not lost.

Let me try to summarize: Modern society, governed by digital communication and invaded by AI, offers an opportunity to amplify values and give voice to those who usually cannot have it, but at the same time, there is a risk of derailing towards obtaining easy successes or slipping into ephemeral values.

Thinking back to what I identified earlier in your argument, the dimensions of knowledge, purpose, and virtue, it seems that we could almost qualify virtue as ethics and try to understand how much this is embedded in modern society.

Plato:

Ah, Seb, your summary is clear and incisive, an excellent refinement of my lengthy discourse. Let us now sharpen our focus on virtue, particularly as ethics, and examine its foundation in the context of modern society. Virtue, as I conceive it, is not merely a set of moral behaviors but a state of being in which one's actions are aligned with the Good. Ethics, then, are the active expression of virtue, which is the guiding rules to which persons and communities would seek to act rightly. In this sense, ethics are as personal as they are collective, shaped as much as shaping the culture in which it resided.

In your time, the question of ethics is both critical and precarious. Ethics in ancient Athens had been deeply embedded in high culture ideals, even when contested from time to time. Today, society is, seemingly, fragmented, with no singular universal conceptualization of the Good. At variance, values are increasingly pressed by digital communication as well as a pluralistic awareness of ethical perspectives. Such a pluralism can enrich but at the same time weaken consensus since shared principles for leadership and governance also become more difficult to get established.

Technology has advanced ethical consideration in new dimensions: For example, artificial intelligence raises profound questions regarding accountability, bias, and the limits of human oversight. Do these tools ultimately serve the common good, or are they wielded principally in the cause of profit and efficiency? Saying ethics forms the foundational base in such contexts automatically demands vigilant reflection lest power from these tools overtakes the guiding morality of the same.

Ethics, or virtue, in leaders has to be more than the mere observance of rules and regulations. It requires courage, integrity, and a commitment to justice, qualities timeless yet often overshadowed in metric-driven or immediate-gain-driven environments. Leaders who embody virtue build cultures where ethical precepts are not imposed but lived, fostering trust and collaboration.

Yet, despite the discouragement, I do see ethical awakenings in your era. The rise of movements for sustainability, equity, and transparency suggests a desire to realign progress with purpose. These movements perhaps hint that the foundation on which ethics must rest, though fragmented, is not missing. What it does need is to be nurtured and a conscious decision to give primacy to long-term well-being over immediate gains.

Virtue, as you rightly pointed out, remains the bedrock of leadership. If it is to survive in today's world, then it has to be cultivated consciously, through education, cultural values, and leaders who lead by example.

How do you see this awakening of ethics, Seb? Are these leaders and societies capable of embracing virtue as central in their actions, or do they falter before the many competing priorities?

Sebastiano:

Well, Plato, this is a challenging question for me, and I'm sincerely not sure how to see it. I tend to romantically agree with the idea of an ethical awakening, and there is certainly a growing need for ethics in modern society. And when we cautiously search, we are lucky enough to find inspired leaders, both political and business leaders.

But daily experience often brutally awakens us: ethical values fade easily, success and money take over, and the cost is virtue.

Plato:

Ah, Seb, your frankness is refreshing, and the tension you describe resonates deeply with the concerns I raised in The Republic.

The conflict between the ideal and the real, between the pursuit of virtue and the allure of wealth and success, has long shaped the human experience. You are right: inspired leaders do exist, embodying ethical principles that uplift those they guide. And yet, as you see, the wider current of society runs almost invariably in the opposite direction. The love of gain and the love of power, severed from conscience, are an abyss that devours all else. Virtue is not merely hemmed around by hostile powers; she is sacrificed to the craving for ease and selfish indulgence.

Why does virtue fade? The cause for the fading of ethical values has two sides, intertwined: first, cultural incentives; societies reward what they most vividly want. Measured primarily by wealth or status, those individuals who place a high value on ethics may be left out in the cold. Those that would pursue the path of virtue often have to assume delayed gratification and face hardships, qualities at variance with a culture driven by immediacy. Second, human fallibility: leaders, like all humans, are fallible. Ambition, fear, and pressures from without can cloud judgment, even for those whose journey started with noble motivations. Otherwise, without a firm footing in purpose and self-awareness, they will be swept away by the tides of greed and acclaim.

What, then, is the remedy? It lies in the cultivation of philosophical leadership, a leadership directed by constant reflection on principles of justice and the Good. The leaders do not seek personal success but strive to make their actions compatible with ethical ideals, even at personal costs. Philosophical leadership also demands courage because, in a society that prizes material gain, the virtuous leader often swims against the current. This courage must be coupled with wisdom, enabling the leader to navigate the complexities of modern life without compromising his values.

While the state of ethics may seem so fragile, resilience starts with individuals and communities not allowing virtue to disappear. It is as much the values of those being led that create the leader as it is the aspirations of the leader. Once society begins to demand ethical leadership with the same fervor in which it now pursues profit, a shift will happen.

Seb, the fact that you're even aware of this tension already makes you someone who doesn't just see things at face value. Maybe what we are asking is whether these inspirational leaders whom we admire today can catalyze a broader transformation or whether the collapse of virtue must precede the awakening of its need.

Sebastiano

This is a great question indeed. Can the few inspired leaders we admire today become the catalysts for a broader transformation?

I'm adding a perspective: Do we know how deep the impact these leaders are making is? How deeply can their voice resonate? I think there is a role for us non-leaders to be their sounding board, to amplify and spread the values of their message.

Plato:

Ah, Seb, what a profound perspective you have here! The impact of inspirational leadership is never wholly their work. Their voice, no matter how articulate and noble, requires other voices to be heard across the fabric of society. And without these other voices to amplify and carry the message, the best can watch their efforts dwindle down to nothing more than an echo in the wind.

The depth of the impact a leader has is measured not only by the immediate achievements but also by the values instilled in others. True transformation has to be a situation where the leader inspires others to internalize and act upon the virtues he or she portrays, not because the leader has imposed change. One leader may light the fire, but the many must tend the flame.

It is here that the role of the "sounding board," as you so nicely put it, becomes very important. The non-leaders, the citizens, the followers, the peers, are not passive recipients of a leader's vision but are active agents in deciding its reach and impact. They extend the leader's ethical message through their actions, discussions, and choices to make it reverberate beyond the immediate circle of the leader.

In The Republic, I dealt with education as the means for the cultivation of the just society. Today, the principle takes up an added dimension: how the ethical education of society requires the ability to recognize and, when opportune, undertake virtuous leadership. In this sense, each one of us becomes a co-creator of desired transformation.

Your insight here reminds us that leadership is not an isolated act but a shared endeavor. It is not the few who are responsible for changing society, but the many who believe change is possible. Non-leaders can serve as sounding boards, amplifiers, and stewards of virtue to extend the reach of inspired leaders and assure continuity of their message.

Seb, in your words, I see the seeds of an important question for our time: Do we recognize the power we hold, not as leaders, but as participants in the ethical dialogue of our age? And will we choose to wield that power to amplify what is good and just?

Sebastiano:

I feel we can discuss further perspectives on leadership that we left behind while focusing on virtue and ethics, but I sense this may be a great closing for our conversation. Maybe our first conversation, we can imagine having a follow-up soon. May I ask you to close with a powerful statement? What would you say to inspire those who feel unworthy of leadership but yearn to make a difference?

Plato

Ah, Seb, it's been an honor to have this dialogue with you. To those who feel themselves unworthy of leadership yet yearn to make a difference, I would like to say:

True leadership does not come by title; it is not forced through, but it rises of its own accord through this quiet resolve to serve the higher good in all things. If your heart seeks justice for all and your actions reflect such courage, then you too are a leader. Greatness is not in the power given, but in the light lit. Do not ask if you are worthy—ask the world if it is better because you acted.

Let us part now with the understanding that beneath the wings of virtuous actions, leadership is within a hand's reach of all who will dare to live virtuous lives and inspire others to soar to great heights.

Until next time, Seb, may wisdom and determination light your way.

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I realize this has been an unusually long read for a LinkedIn article, but I hope this conversation was engaging. Stay tuned for the new edition of Unconventional Leadership, coming soon, where we can continue reflecting on the thought-provoking ideas Plato shared with us.

Before wrapping up and thanking you all for your patience, I want to mention that this dialogue was left untouched, Plato's way of expressing himself was shaped through a lengthy process of iterations, aiming to soften some of the overly AI-specific nuances in his language. So, what you've read here as Plato's voice is entirely AI-driven, and even the attempt to humanize his speech was part of a response to a specific request (including all the praise and flattery I get from Plato, honestly, I swear ??! It was not me adding them ??).

One last side note: I had prepared an outline for this interview, but Plato's dialectical approach ended up steering the conversation in unexpected directions. In fact, I still have several questions left unanswered, which leads me to wonder: why not conduct a second interview, or perhaps expand to include other thinkers and their unique perspectives on leadership? Depending on your feedback and interest, this may very well be the first in a series of such dialogues.