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What Is Meaningful Leadership

The Philosophy Behind 'Meaningful Leadership'

There is an old joke that goes something like this:

A policeman sees a drunken man searching for something under a streetlight. He goes to the man and asks:

“Is there something that you lost sir?”

The drunken man replies, “Yeaash. I sheem to have… *hick*… lost my keys”

The policeman replies, “I can help you look for them.”

So they both start searching under the streetlight, for 10 minutes with no luck. The frustrated policeman asks:

“Are you sure you’ve lost the keys around here mate?”

To which the drunk man replies, “Well… *hick*… no, the keys are inside the house…”

“So why are we looking out here?!”, the policeman cries.

To which the drunk man says, ““It’s dark inside the house! *hick*… The light’s much better here!”

* * *

If you’ve heard this joke before, that’s understandable. This joke is actually hundreds of years old – the Sufi’s were some of the very first to tell it….

It’s funny, and it has ever since been often stated, because it beautifully illustrates a bias that we’ve long had as human beings – that we prefer to look where it’s easiest to look, (and precisely where the ‘keys’ are not).

This is especially relevant if we would but honestly assess the world of leadership education and training on offer today.

For much of this content has been created by ‘theory-deep academics’, who likewise are trained to look where it’s easiest to look – that is, where it is easiest to measure – as to then write academic papers and PhDs, that will go unchallenged. (After all, who likes to argue with mathematical equations and statistical data?)

It’s in the inherent nature of the scientific method to always favour things ‘well lit’, (i.e. what’s easily measured and quantifiable) – like numbers, structures, processes and so on – and to actively avoid the intangible and hard to quantify things like ideas, ideals, principles or vision… and above all, meaning.

As such, the majority of leadership programs on offer today, are grounded in what appears to be ‘scientific thinking’. And you can easily recognize this brand of leadership education, particularly when it explicitly wears the badge of being “evidence based”, or that it was developed using “the scientific method”.

One common expression of this is the development of lists of leadership characteristics (as tabulated and measured in other leaders), that one is then meant to copy. The proliferation of ‘leadership styles’ for instance, is an example of such a development.

The idea is that if one would but adopt these same observable characteristics, and put these ways of measurable good behaviours into practice – then one would also realize those same outcomes that these leaders also had.

So, a great premium is placed upon how did former leaders present, how did they talk, how did they think, how did they come to decide… and so on.

And so with all this ‘objective knowledge’ about leadership, with all these certificates, diplomas, degrees, master degrees and PhDs – one would now think that we would be drowning in all kinds of great leaders all around us.

So why is it that today, public opinion, (as well as first-hand experience), tells the exact opposite story?

Well, that’s because to copy someone else’s leadership style’ – or for that matter, to enhance an existing pre-disposition of a style – produces little more than a ‘persona’ of leadership, and not the real deal.

‘Persona’, a powerful concept once formed by Carl Jung, essentially means that one fakes the appearance of individuality. It is a mask comprised of collective ideas, and projects nothing real of its own self or being authentic. To quote Jung:

 “[Persona] is a compromise between individual and society as to what a man should appear to be. He takes a name, earns a title, exercises a function, he is this or that. … The person concerned is only a secondary reality, a compromise formation, in making which others often have a greater share than he. The persona is a semblance, a two-dimensional reality, to give it a nickname.”

But great leaders are never two dimensional. Whenever we think of a truly great leader – like with a Mahatma Gandhi, a Martin Luther King, a Mother Teresa – these people evoke something altogether more dimension than even we are. They radiate as to be almost ‘four dimensional’, and this is precisely why so many followed them.

There’s nothing copied. They are entirely original. Each great leader, is of their own unique style as it were.

After all, think of the very best leaders throughout history – the ones that most inspire you the most…

What names came to your mind? What are they like? Can you picture them? Just think for a moment please.

Now consider – were any of these leaders, the product of the ‘scientific management and leadership’ training that’s on offer today?

No? I rest my case.

The Fatal Flaw

The fatal flaw at the heart of all of this, is one issue that philosophy long recognized:

There is a world of difference between the world of things or objects, which is the domain of science || and the world of values and stories, which is the domain of humanities or arts.

Leadership primarily belongs in the later category, and not the former. Leadership is first and foremost an art.

Naturally a good leader needs to be aware of the world of objects and think scientifically about these, but leadership itself is concerned with the choices or actions that ought to be undertaken – as the leader recognizes, along with the team he or she influences.

This insight of ‘ought’ does not emerge from the material data or the object themselves. There’s nothing there to ‘value’. The ‘ought’, emerges from the hidden, subjective pursuit of values – in what the leader recognizes to be significant, and what he or she then influences others to also value.

The process of valuing is a process of meaning recognition. While science is able to categorize properties of objects and then to develop practical applications from it – this later aspect in itself is a function of the story we tell ourselves about the utility of this or that aspect.

For example, Albert Einstein as a physicist discovered that the property of matter and energy is interchangeable, that E=mc2. It was then leadership of Robert Oppenheimer that took this idea, as to then build the first atomic bomb through the story he told others about its potential.

It was then the leadership of President Truman that made the decision to use this built nuclear object, in Hiroshima and Nagasaki, after the Japanese leaders themselves, rejected the Potsdam declaration.

And on and on…

Great leadership uses both modes of interpretation – the world of objects and values – as to get a most comprehensive picture of the situation. Both are necessary, and pitting one against the other is a demonstration of failure to understand first principles – i.e. that what is and what should be, that these two perspectives are poles apart.

But the essence of leadership is about the recognition that our outcomes first begin in the subjective realm, in what comes to be valued ahead of another.

The explosion of an atomic weapon did not merely emerge out of scientific enquiry and application, as if these things had a mind of their own. It began from an idea in Einstein’s mind (through his of valuing the world of physics and finding meaning therein), to ultimately, Robert Lewis, the pilot choice who pressed to drop from inside the Enola Gay bomber (through his military value structure).

Why throughout time, the great leaders sought counselling, is because it is through these interactions one comes to find optimal meaning – what ought to be done – i.e. one discovers the most optimal schema of interpretation, that can guide the optimal emotion and optimal action.

Here is for instance 3 proverbs from King Solomon – a man who is culturally held by many as the embodiment of wisdom – who states this same truth in different forms:

“Plans fail for lack of counsell, but with many advisers they succeed.”
Proverbs 15:22
“Plans succeed through good counsell; don’t go to war without wise advice.”
Proverbs 20:18
“Where there is no counsell, the people fall; but in the multitude of counsellors there is safety.”
Proverbs 11:14

As such, there is a fatal flaw whenever one tries to derive ‘the keys of leadership’ from mere statistical probability of crunched data, as to what makes for a good leader.

It’s no surprise then that the majority of today’s leadership programs that are systemically grounded in easy to measure assessments, in empirical theoretical frameworks – in reality, these address none of the deep-seated problems that leaders actually need to resolve.

The real problem of leadership is in how to recognize with clarity the optimal hierarchy of values, in how do we connect with the optimal meaning, and how do we practically share this meaning with others.


The Classic Case of Robert McNamara

A classic example of this flaw in leadership thinking came from Robert McNamara – the US Secretary of Defence during the Vietnam War.

Previously McNamara served as the leader of Ford Motor Company, where he was very good at scientifically managing all things, as ‘things’. His leadership knowledge was grounded in the excellent management of the ‘conveyor belt’ on an assembly line, and coordinating the movements of complex mechanical parts.

When appointed as the leader of the war effort against the Communist problem in Vietnam, he decided to place the same scientific quantitative measures like he placed at the Ford powerplant.

McNamara thought to treat war like a maths or engineering problem, because like the saying goes, ‘he who is good with a hammer, thinks that everything’s a nail’.

So he restructured the military complex, in line with the factory assembly line. As a scientific manager, ‘IN’ went in things that were easily measurable and quantifiable, like enemy kills numbers. And ‘OUT’ went all the hard to measure qualities and hard to measure things like values or the feelings of the rural Vietnamese folk.

And what was the end result?

Well ultimately, it resulted not just in the defeat of the US militarily in the 1970s. For ever since the Vietnam War, culture itself has fundamentally shifted as a result.

Culturally, ever since we live in a very cynical time about all the leadership that surrounds us. There are poor leadership examples on display – from the highest levels of political office, to the many Fortune 500 companies that spectacularly collapsed due to the weight of sheer corruption – i.e. from the energy company Enron, to the behemoth investment bank Lehman Brothers, to the mega start-up Theranos, to the crypto exchange media darling, FTX…

Worse than cynicism still, many see no way out of this mess. For there’s also a cultural ‘learned helplessness’ at play that undermines any attempt to even change it.

But I propose that much of what’s present today has been in no small part, due to this kind of leadership education that most leaders today get.

When leadership ethos mirrors the Machiavellian mindset that states that, ‘there’s no reality, only perception’; or that ‘ethics’ is merely that which is expedient; or the ‘learned meaninglessness’ found in most academic centers which affirm life as nothing more than ‘a tale told by an idiot, full of sound of fury, signifying nothing’…

How can leadership that emerges from these ideas, be little more than pretences?

Today’s leader is a very precarious position. Most leaders do not have a rock-solid foundation for what to do and what gives life genuine meaning. We have lost touch with the principles that tell us what excellent behaviour is all about.

As such, leadership lacks conviction amidst a culture that’s rife with cynicism. When the last ‘leadership program of the month’ created little more than cosmetic changes, we set our sights lower and just go through the motions of ‘the corporate thing to do’…

The Idea of Meaningfulness in Leadership

Considering the convergence of life altering technologies already at play, and their seemingly unstoppable accelerating growth into our world – great leadership in today’s world matters more than ever. Most of us already know this.

But beyond the global issues that affect us – the issues that seem mostly beyond our control – at the most personal, tangible level, leadership first and foremost needs to be able to connect us to a meaningful life.

After all, for most of us, work takes up (and will take up), the biggest and best share of our life. It’s what we give up our time for, (which is our life in essence) – ahead of seeing more of the people we love, like our spouse, children, friends… or in doing activities that we really love, like playing sports, or attending religious services and so on.

For most of us, our identify and purpose in life is intimately married to our work. The quality of meaning that we extract from what we do with our lives, makes up the bulk quality of our lives.

As such, leadership is intimately and inextricably linked to pursuit of meaning.

After all, how can we increase engagement and enrollment into a project, except through a genuine increase in meaning?

How can you increase your own capacity to give your best, for the team to participate more fully, as to then create better work, except by being able to mine for more meaning?

How can you increase loyalty to an organization and commitment to quality, except through a greater magnitude of greater meaning, than the alternative?

And furthermore, how can an overall increase in meaning NOT translate into direct bottom line dollars – from the cost reduction achieved through less waste, less turnover, less mediocrity… to the opportunity cost gained though enhanced quality, creativity, productivity, satisfaction, and effort?

Meaning is the beating heart of genuine leadership. It’s meaning that moves simultaneously the body, the mind, and above all, the heart.

Nothing else can do that.

Coercion and force can move a body. Persuasion and propaganda can even move the mind. But only true meaningfulness can move the heart.

The heart of leadership is in mining for more meaning.

You know that if you as a leader cannot find meaning in your work, you cannot be truly effective in your role.

And this is just as true for the employees and the partners that work with you – for if they too don’t find their work meaningful, in some way, excellence in a free marketplace is just a pipedream. The company that is able to mine the heart for more meaning in the long run, always wins.

And all we need to do is listen, because survey after survey, from localized to transnational say the same thing – for most people, meaningful work is much more important than money.

And how can this not be – for would we ourselves not want to live a more meaningful life?

(And let us remember, that if one would choose money ahead of meaning, this does not reflect a mere inconsequential, subjective aesthetic preference – like preferring vanilla over chocolate – but this is a deep-seated pathological orientation. This is the motivation behind so many tragic stories, like ‘Citizen Cane’ or ‘There Will Be Blood’.)

Let us therefore be glad that we have around us people who value meaning, above all else. For this is the foundation for good mental health. Let us now build on this.

Let us go forth and lead with meaning – to support others to live a life that matters, a life of beauty, a life of truth… a life that transforms our world for the better, because we would choose first, to be the change we want to see in the world.

Let us return to the great ideal of meaningfulness.

That’s what we’re here for.

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