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An Ironic Perspective on the World of Work

Is this the Future of Leadership?

Is this the Future of Leadership?

What makes one leader sustainably great whereas another is only temporarily great, one moment a god amongst mortals, the next, like Icarus, hurtling back to the ground, his wings scorched and blackened by the sun, hoping the landing isn't too hard?

As with all questions about greatness, the answer to the second part of the question (why does a once great man fall?) is the easier. 

Reason One: The smartest leaders tend to get self-dazzled by their previous successes and end up in a myopic wonderland, feeling invulnerably magnificent in their sycophantic towers of luxury (as discussed by Dr. Travis Bradberry here and wonderfully illustrated in The Big Short, as detailed here).

Reason Two: If you become concerned and speak freely about what you see happening, you risk losing your head (as analysed by the Harvard Business Review here)

Reason Three: Because of problems one and two, irony, cynicism, sarcasm, mockery and ridicule manifest in the workforce as they are the only way to safely express what you are thinking about the increasingly obvious shortcomings of the powerful (as discussed by me, here). 

Consequence: The once mighty company begins to struggle, management can't find a way out, nobody else who might be able to help risks speaking up, and everything goes to hell in a handbasket. 

This sequence of events uncannily parallels the plotline of classic Greek tragedy, in which a leader, having risen to power through his exceptional qualities, becomes too self-confident and unreflective, and, flattered by his courtiers as to his strengths, loses everything by failing to see anything of worth beyond the qualities he possesses. With 2,500 years of evidence (what is great literature other than a crystal clear window into human behaviour) supporting a readily observable, oft repeating pattern of CEOs, companies and even industries rising and falling, we perhaps need to start imagining new ways to lead if our future is to be bright enough to need shades.

Which takes us back to the first part of the question and the quest to find a model of sustainably great leadership. 

This is trickier. I've never been comfortable with the populist literature talking about vision and charisma, culture and behaviours. It always brings to mind a kind of religious cultism in which the group should unswayingly pledge loyalty to one man's perception of how the world should be. For me, great leaders should be able to hold personal vision, organisational activity and critical dissent in permanent and energetic tension, leading from the top and learning from the bottom, knowing everything yet happy to be taught. Which is why irony, sarcasm and cynicism have so long appealed to me and why I ask if it is possible  to tap into the creative intelligence of these authentic dissenters and use it to further energise leadership.

It's not an easy question to answer. I've researched and written on Steve Jobs, Richard Branson and Nelson Mandela, but never found my conclusions convincing enough for myself, let alone a wider audience. I found most success writing and presenting about Jon Stewart, for which I won an award at a leading organisational research conference, but was unsure whether it would translate into the wider management arena. 

Then I read this article: Billionaire Ray Dalio had an amazing reaction to an employee calling him out on a mistake.

And it hit me! The answer is in the operationalising of irony in the decision-making process, not in the ironic character of the leader. 

Which makes things much easier. Why struggle with trying to develop a framework to operationalise ironic leadership when a billionaire hedge fund manager has already done it? Because if you can't trust a billionaire hedge fund manager, who can you trust? 

Now, I don't know if Ray Dalio has all the personal qualities I was looking for in an ironic leader. I want him to be humble and witty, ruthlessly interrogative and generously pedagogical, innately concerned with ethics and the nature of knowledge, and utterly willing to challenge the myopically self-dazzled. However, I no longer care. What matters is that he has operationalised irony in the leadership structures of his company. It doesn't have to be part of his personality as its intertwined throughout the strategic decision-making environment. And it's genius. 

NB: If you haven't read my article on the difference between irony and sarcasm, it might be a good idea to give it a quick once-over before moving on. In basic terms, irony works around this conceptual framework:

  • The ironic perspective: perceiving the gap between expectations and reality
  • The ironic performance: transmitting that perception by saying one thing and meaning another
  • The ironic personality: being comfortable living with such gaps

My argument here is not just that Ray Dalio has designed a decision-making framework that parallels this conceptual framework, but has also provided some compelling answers to the problems that have bedevilled those that have tried to employ irony against self-dazzled authority throughout the ages. 

Operationalising the Ironic Perspective

The ironic perspective: perceiving the gap between expectations and reality

Ray Dalio is a brilliant man who is almost always going to be one of the smartest guys in the room. He's been called the Steve Jobs of investing. His company, Bridgewater, has made more money for its clients than any other hedge fund anywhere. In 2010, it made more than Google, eBay, Yahoo, and Amazon combined. It was one of the few entities to predict the 2007 financial crash. An awful lot of reasons for somebody to feel inordinately proud of himself and start trusting his own leadership exceptionalism. 

Yet, after a meeting with a client, he received an email from one of his employees, which said,

It was obvious to all of us that you did not prepare at all because there is no way you could have and been that disorganised."

Instead of harrumphing, hawing, kicking up an almighty stink and punishing his critic, Dalio reflected on the message, asking everybody who attended the meeting to critically feedback on his performance,  then copying the email exchanges to the entire company so that everyone could learn from the situation. 

Dalio had fallen short of his company's expectations of him, leading to a reality in which he had let his company, his team and his client down. Instead of brushing it off, he (a) accepted the critique, (b) sought further data to ensure that it couldn't happen again and (c) shared that data with the entire company. 

The ironic gap between expectations and achievements, if left unidentified, is one of the biggest and quickest killers of performance, reputation and income. By reacting so quickly, Dalio sends a message to everyone in the company that authentic critique is demanded when anybody falls short of the expected standards.Even if it's him.

Operationalising the Ironic Performance

The ironic performance: transmitting that perception by saying one thing and meaning another

It is doubtful that Ray Dalio's employees have to use irony, sarcasm, mockery, ridicule and satire when trying to get critical points across (although they sometimes may) because Dalio has developed a system that enables authentic dissent to thrive rather than be punished. The workings of this system and how it relates to irony are located in Dalio's quote:

"The greatest tragedy of mankind comes from the inability of people to have thoughtful disagreement to find out what's true."

This is especially true when there are power differentials between the discussants. It is very difficult for somebody of perceived lower status to challenge somebody of perceived higher status as (a) hierarchical rules often forbid it and (b) even if the challenge is acceptable, if the higher status individual gets made to look foolish, the lower status individual risks losing his head. The method of protection is the ironic performance, in which the ironic speaker cannot be punished whether the listener gets or doesn't get the irony. If he gets it, he's worked out for himself where the folly lies, so can't take retribution without losing legitimacy. If he doesn't get it and remains none the wiser about the criticism, then no harm done. The ironist walks away with his head still attached to his neck.

In theory, anyway! 

This theoretical understanding characterises the method through which Socrates interrogated the great and good of Athens, in which he uses ironic techniques to help them come to terms with their weaknesses and follies without taking great offence and retaliating. Socrates's ironic technique has two elements:

  1. Revealing that the person he is interrogating cannot be wise by illustrating the absurdities in the person's conceptual definitions
  2.  A manner of speech that keeps the conversation going through “pleasant rallying” or "soft sarcasm". 

This method, of course, worked extremely well. Right until the moment the Athenians made him drink hemlock! Others that tried it haven't necessarily ended up that well either. For example, Cicero was murdered, Voltaire executed and Oscar Wilde imprisoned. Yet, we celebrate them, not those who persecuted them. It seems irony is worth it if you don't mind dying for it!

By celebrating authentic dissent and thoughtful disagreement as being the core tools in the pursuit of truth, Ray Dalio has created an environment in which reflective, critical and ironic though can flourish without risking the severe sanctions of upset authority. Ironic performance is not required because reflective, critical and creative ironic thinking is admired, encouraged and cultivated. How that is done is where Ray Diallo's real genius lies.

Operationalising the Ironic Personality

The ironic personality: being comfortable living with such gaps

As we all know, the Athenians executed Socrates for being a wise-cracking, snarky know-it-all who made the great and good look foolish and taught and encouraged the kids how to laugh at, mock and ridicule them. 

Or, rather, for being a Sophist and corrupting the youth of Athens. Pretty much the same thing, though. And also exactly why irony can't be employed to structure an organisation. It will lead to chaos, in which everybody mocks the leaders and everybody thinks they can cleverly manipulate decisions to go their way. 

Hang on a second! Haven't I just been saying that great leadership is ironic and praising Ray Dalio for operationalising irony. Surely you can't have it both ways!

I did say it was genius!

The main tension in any culture in which ironic thought and communication emerges is in its relationship with democracy. On one hand, you have Sophists, who exist purely to "make the weaker argument seem stronger". They use their exceptional power with words to beef up the argument of whoever is paying them, whether they believe it or not, to aid self-interested pursuits of power. A bit like spin doctors today. You can no longer believe in the authenticity of any statement because you cannot trust that it is believable because of deep thought and reflection, or believable because of somebody's ability to manipulate words into pretty shapes. On the other hand, you have the youth, who borrow these techniques purely to laugh at, mock and ridicule any statements that claim authenticity or sincerity of any kind. They question everything, believe in nothing, and undermine somebody's thinking just for the pleasure of undermining it. 

As many commentators have observed, once out of the hat, irony corrupts attempts at seriousness completely and irrevocably. It seduces people into unreflective, never-ending mockery, resulting in absurdity and nihilism. Yet, without it, there is no critical or reflective thought as there is no perceived gap between aspirations and achievements in which either can flourish. How to tame irony so it contributes without corrupting and is as constructive as it is destructive has consumed thinkers in this space for centuries.

It might be that Ray Dalio has discovered the answer.

The answer is framed around these two quotes considering democracy and believability:

"Democratic decision-making — one person, one vote — is dumb, because not everybody has the same believability."


When you express an opinion, it's weighted by whether you've established yourself as believable on that dimension. Your believability is a probability of being right in the present, and is based on your judgment, reasoning, and behavior in the past.

These conceptualisations reward the reflective, critical and creative aspects of ironic thinking whilst handicapping its destructive, nihilistic and seductive qualities. By having a sliding scale voting system that awards different numbers of votes to those who have a history of having sound judgement, good reasoning and rational behaviour about a certain subject in the past over those who haven't, Dalio achieves two things.

Firstly, he prevents the surge of Sophistic thinking and youthful impetuosity from having long-term impacts. Ironic thinking is not enough in itself. Without the weight of believability, you can prick the ox into thinking about moving, but not make it move. You must have more than clever words or youthful queries if you want to taken seriously. 

Secondly, he rewards people for thinking critically in all aspects of decision-making by assigning them greater believability. Those who aren't believable in the field aren't expected to hold opinions, but they are expected to intelligently question and challenge conventions. Thos who do have believability are supposed to hold convictions, but be ready to be interrogated on their reasoning. Over time, the former might become the latter, but only after they've proved their qualities. This (a) prevents the experts from getting arrogant and short-sighted about their assumptions, (b) stops the impetuous youthful from getting above themselves whilst encouraging them to keep thinking and (c) banishes Sophistry completely. 


The decision-making model arranged around Dalio's leadership ensures that Dalio can't become self-dazzled and group-think can't emerge, whilst protecting the organisational from the seductive and nihilistic excesses of authenticly critical ironic thought. If every decision is interrogated through this model, it should perhaps not surprise us that Bridgewater outperforms all the other hedge funds and predicted the financial crisis, as it prevents hubris and keeps thinking fresh.

It is not often I fawn enthusiastically over a model of leadership as I am so often disappointed by the lack of rigorous thought and anti-intellectualism that sadly permeates much practice, leading to an overreliance on hideously simplistic but cleverly marketed concepts (the Sophistry of management?). In this case, in which the model, perhaps uniquely, seems to fully address a core aspect of the human condition that emerges and re-emerges in the rise and fall of kings and cultures throughout the centuries, and has succeeded to a remarkable degree, I have suspended my scepticism. 

Ray Dalio has given me hope for the future of leadership. For that, I thank him. 


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The Ironic Manager seriously rethinks how organisations work at the most fundamental level and offers a variety of solutions for businesses struggling to cope with the ambiguity and stresses inherent to contemporary organisational conditions of constant change.

Richard has been helping businesses and people deal with leadership, management, communication, technology and change for over twenty years through his training, coaching, speaking and consulting services. 

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Over twenty years helping people managing change understand why resistance happens and develop quality vital communication skills that aid successful business transformation.


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