In my org at work, we are currently going through a Dare to Lead workshop, based on Brené Brown’s book of the same name. It’s got some nuggets of wisdom, but this part of Section 3 on “armored leadership” and cynicism had me scratching my head and disagreeing vehemently.

6. Armored Leadership
Hiding Behind Cynicism

Cynicism and sarcasm are first cousins who hang out in the cheap seats. But don’t underestimate them – they often leave a trail of hurt feelings, anger, confusion, and resentment in their wake. I’ve seen them bring down relationships, teams, and cultures when modeled by people at the highest levels and/or left unchecked. Like most hurtful comments and passive-aggresiveness, cynicism and sarcasm are bad in person and even worse when they travel through email or text. And, in global teams, culture and language differences make them toxic…

In a world roiled by incessant and tumultuous change, swamped by boatloads of fear and anxiety and rampant feelings of scarcity, cynicism and sarcasm are easy and cheap. In fact, I’d say that they’re worse than armor – we use cynicism and sarcasm as getting-out-of-contributing-free cards.

First of all, the author is conflating sarcasm, skepticism, and pessimism with cynicism, while these all have very different meanings behind them. For example, later on, she writes:

Cynicism and sarcasm often mask anger, fear, or feelings of inadequacy, and even despair. They’re a safe way for us to send out an emotional trial balloon and if it doesn’t go over well, we make it a joke…

And later this:

Again, while a cynic might argue that someone who clings to hope is a sucker, or ridiculously earnest, this type of armor typically comes from pain. Often, people’s cynicism is related to despair. As the theologian Rob Bell explains, ‘Despair is the belief that tomorrow will be just like today.’

This is pessimism, for sure, and potentially skepticism (doubt in the face of truths that show tomorrow will be different), but this is not cynicism.

Understanding Cynicism and its Roots

Cynicism is an ancient Greek philosophical school of thought. The ancient Cynics aimed to live in harmony with nature, and to eschew wealth, fame, fortune, and power, often via ascetic practices. Ancients Cynics would often point out the hypocrisy of others, exposing their motives and pretensions underlying the norms of society. Their goal was to achieve happiness through virtue.

There is nothing in ancient cynicism around despair, hopelessness, pessimism, inaction. Rather there is the challenging of norms and conventions, and the questioning of motivations of others, and whether they are acting solely out of self-interest, or out of virtue. Reading about the prototypical Cynic, Diogenes, one can see the true roots of this school of thought.

In modern or contemporary meanings, cynicism has evolved to mean a questioning or distrust of the motives of others. A line from Wikipedia stands out to me:

Cynicism is often confused with pessimism or nihilism, perhaps due to its distrust in others. The differences between the three is that cynicism is a distrust by prudence; while due to a sense of defeatism, pessimism is the distrust of potential success. Nihilism on its part have distrust cast upon the belief that life have any valuable meaning.

Wikipedia: Cynicism (contemporary) – Wikipedia

I think in the case of Dare to Lead, cynicism is being miscast as pessimism, and while I can certainly agree that pessimism is an undesirable quality in an organization, along with sarcasm, I do think that cynicism has an important role to play as a check and balance against corruption.

Cynicism is a tool that can point out injustices, inequity, and expose selfish motivations behind decisions in our workplaces. It is cynicism that enables us to ask “why is my company’s Political Action Committee donating money to senators and congress people who actively supported insurrection against our country?”, or to question the motivations behind the differing response of force at the Jan 6th insurrection, vs the BLM protests in the same area, or whether this licensing change is actually a bait and switch for our customers and will really tick them off.

In fact, our constitutional democracy is based heavily on a Madisonian cynical view that assumes that people in government are motivated by self-interest, and that earlier democracies had been failures for not taking this into account.

But it is wrong to assume that cynicism has no place in a well-ordered constitutional system. In fact, the opposite is true. Cynicism about governmental abuse of power as well as the tendency of interest groups to influence and control government inspired the Framers. In fact, a dominant theme of The Federalist Papers is “the desirability of adopting the Constitution as a means of controlling interest groups.” In The Federalist No. 10, James Madison “expressly embraced the notion that what would separate his constitution from those that had gone before it would be a more realistic [i.e., cynical] conception of human nature.”‘ As I previously observed: The problem confronting the Framers was that, on the one hand, they did not want to organize another monarchy, but on the other hand, the earlier democracies had all been abject failures, nothing less than ‘spectacles of turbulence and contention.’ Madison’s view was that the problem with previous democracies had lain in the assumptions made by their organizers. Specifically, prior to the Federalists’ construction of our political regime, ‘the whole of political thought had turned on ways to inculcate virtue in a small class that would govern.’ In stark contrast, the government that Madison had in mind (and the one that ultimately emerged) would be based on the [cynical] assumption that the postconstitutional world would be populated by people motivated by self-interest rather than by virtue. The Framers frankly and self-consciously took the view that they had to construct the Constitution to deal with the corruption and ineptitude of the leaders who would govern the postconstitutional order.

Jonathan R. Macey, Cynicism and Trust in Politics and Constitutional Theory, 87 Cornell L. Rev. 280 (2002) Available at: http://scholarship.law.cornell.edu/clr/vol87/iss2/2

I would argue that in discouraging cynicism, and not listening to the issues raised by the questioning of motives and intentions can actually be one of the root causes of anger and resentment in the organization, and a barrier to real effective change. Trust is necessary in any organization, but so is a healthy dose of cynicism to keep any corruption in check.

This book, Dare to Lead, is about the qualities necessary to be a brave, empathetic, and effective leader, through listening, having tough conversations (“rumbles” as they are referred to in the book), “being vulnerable”, and “living into our values”. And so I question why this same book is discouraging cynicism, which is one of the tools that employees have at their disposal to speak truth to power. It’s very easy to avoid hard conversations as a leader when you discourage the people underneath you from questioning and challenging your motivations that drive your decision-making.

I was honestly enjoying the setup to this section of the book, which included having “hard conversations”, embracing vulnerability, building a “Safe container” so that employees can share difficult or challenging things without fear, and yet I come to this part of the book and am essentially told that no, it’s not ok to have a questioning attitude. If we can’t question motives, then we are all just essentially “yes-people” in the org.

This immediate dismissal of cynicism has the Cynic in me now fully awake, and questioning the motives of leadership for even assigning me this training. Is it to create a culture of “yes-people”? I know this is most likely due to the author not really taking the time to understand cynicism, and conflating it with other behaviors, but I would expect the author to understand the difference, and to recognize the unique meaning of cynicism and its necessity in an organization.

I for one feel that we need a little more cynicism in the workplace, and I would hope that my leadership would exercise cynicism and question the motives of their leaders, so that we have accountability all the way to the top.