Why Epistemology is Important in Leadership (And How to Apply It)
Knowledge brings success. Anti-knowledge brings failure – or valuable secrets! • Why don't we teach anti-knowledge to new leaders? • Information asymmetry and weaponized anti-knowledge
Do you know what knowledge looks like?
Think about that for a moment, and the following may come to mind:
A teacher or professor instructing a room full of students
A library bookshelf laden with heavy volumes
A wood-paneled wall adorned with diplomas and certifications
An expert confidently answering questions like a machine gun firing light bulbs of insight
Now let’s approach this from the opposite direction: do you know what anti-knowledge looks like?
This question required more thought, didn’t it? Maybe you thought of ignorance (a lack of knowledge), manifested as:
The last time you had to clean up someone’s incompetent work
A child’s innocence or an adult’s naïveté
An act of egregious stupidity worthy of a Darwin Award
Or maybe you put on your lateral-thinking cap, went meta, and figured that if you knew what anti-knowledge was, it would no longer be “anti-knowledge”; it would just be knowledge.
Welcome to the weird and wacky world of epistemology, which is a fancy term for the study of knowledge. Philosophers have debated about the nature of knowledge for thousands of years. There are multiple branches of epistemology that disagree about what knowledge is, how much you actually know, and how much you should trust what you (think you) know.
The ocean of epistemological debate is deep and sometimes interesting, but we’re going to avoid most of it. After frolicking in the philosophical kiddie pool, we’re going to focus on how epistemology is relevant to the practice of leadership.
Epistemological Dilemmas in Leadership
Even if “epistemology” is new to your lexicon, it deeply affects you as a leader. Every day, you make decisions despite having incomplete knowledge of a situation. Does the following sound familiar?
Your decision depends on the reliability of recommendations prepared by your subordinates. Are they telling you the truth, telling you what you want to hear, or telling you what they think you want to hear? Should you conduct a firsthand inspection before making the call?
Your analysts predict an 80% chance of success. That means in 1,000 parallel timelines with 1,000 potential outcomes, you will be successful in 800 timelines and a failure in 200. You will only experience one timeline out of this multiverse of 1,000, and you don’t get to choose the timeline. What fate will the random number deities bestow upon you?
Even if your new policy achieves its intended purpose, will it have unintended consequences? Will the unintended consequences ripple outward and trigger additional consequences?
A competitor launched a new product line they’ve apparently been developing in secret. It wasn’t even on your radar, and the emergence of the new threat proves that your organization has fallen years behind the curve. What the hell do you do now?!
For each decision, you must weigh what you know (knowledge) against what you don’t know (anti-knowledge). Note that anti-knowledge is not the same as ignorance, which is a lack of knowledge. Anti-knowledge isn’t an absence of knowledge; it’s the presence of something you don’t know or understand. Anti-knowledge and ignorance are interchangeable in most contexts, but we’ll point out a few instances where the distinction matters.
Remember last week, when we covered fragility and anti-fragility, the secret asymmetries of leadership? When you’re trying to accomplish something fragile (more to lose than to gain), anti-knowledge will derail your efforts more readily than knowledge will help them. Imagine trying to protect your career, reputation, and organization from an adversary you can’t see, can’t hear, and can’t understand. Fragile things are more likely to break when you’re blindsided.
The higher you climb from the Boss Forest → Middle Management Foothills → Executive Mountain, the more you’ll wrestle with fragility. The Sword of Damocles suspended over your head grows larger and heavier as anti-knowledge exerts increasing influence on your decisions. Perhaps the greatest cruelty of leadership is that you’re not merely responsible for what you know; others will hold you accountable for the impact of unknown factors beyond your control and unknowable forces beyond your comprehension.
You Can’t Teach What You Don’t Know
How do you evaluate something that, by definition, you don’t know about? For most people, the solution is simple:
They don’t.
Our schools teach knowledge, not anti-knowledge. The Institute of Conventional Wisdom’s motto is Sola lux et veritas (“Only light and truth”) because conventional education only focuses on knowledge. Upon reaching an educational milestone, you receive a report card or transcript that serves as a record of your knowledge. Have you ever seen an anti-transcript that contains a record of your anti-knowledge? Of course not; the Institute doesn’t measure anti-knowledge, so it may as well not exist.
This blindness to anti-knowledge continues after you graduate and establish a career. Got a problem? The solution is simple: more knowledge. More self-help books. More TED talks. More continuing-education training courses, all available if you unload a dump truck full of money into the Institute of Conventional Wisdom’s pockets!
We’re proponents of lifelong learning, but there are critical limitations to acquiring knowledge. Human brain capacity is too low. Human lifespans are too short. New books are being published faster (and in more languages) than one person could possibly read. No matter how much knowledge we acquire, there will always be a vast ocean of anti-knowledge surrounding our little islands of comprehension. Seeing as how fragile endeavors are more harmed by anti-knowledge than they are helped by knowledge, is tending to our little islands of comprehension the best way to achieve success? What if we studied the ocean of anti-knowledge itself to avoid harm?
If you can’t beat anti-knowledge, embrace it
Our inability to reach omniscience is why epistemology matters in leadership, and one reason why the distinction between ignorance and anti-knowledge matters. It’s not enough for instructors to reduce ignorance by illuminating new concepts; they need to teach new leaders about the nature of darkness itself. Leaders should continue studying conventionally to brighten their islands of comprehension, but that’s not enough; they must also survey the unlit ocean of anti-knowledge that stretches to the horizon. Brightening the island increases the chance of success; studying the ocean is for risk assessment and avoiding failure (assuming fragility; more on anti-fragility later).
It’s impossible to know exactly what anti-knowledge is; if you did, that would make it plain old knowledge. However, you can glean information indirectly, like how astronomers study dying stars to deduce the characteristics of invisible black holes lurking nearby. Likewise, you can gain knowledge about anti-knowledge by studying how it affects the things you can see, hear, and comprehend. It’s like trying to guess what’s inside a gift-wrapped present based on its shape and size, or based on the habits of the sender. Or analyzing the metadata of encrypted data.
Unfortunately, if you have no way to impart knowledge about anti-knowledge, you can’t share what you learned about the sea of dark anti-knowledge with anyone else. This limitation leaves you with only one way to build up capable leaders:
Promote someone by one rank
Reduce their ignorance as much as possible
Let them be batted around randomly like a ball of yarn at the mercy of a hyperactive cat
Promote the survivors up another rank and repeat the cycle with a bigger, deadlier cat.
That’s pretty much how everyone does it. Or they steal capable leaders from a competitor.
Part of the reason we started writing was because we thought there’s gotta be another way to do this.1 We created the Leadership Land metaphor to ease newcomers into topics not covered by the Institute of Conventional Wisdom, including epistemology. We use the Fog of Uncertainty and the Unknown Abyss to de-abstractify the concept of anti-knowledge. The Fog and the Abyss represent the presence of anti-knowledge, not the absence of knowledge (ignorance).
If Knowledge Is Power, is Anti-Knowledge Powerlessness?
So far, we’ve portrayed anti-knowledge as antagonistic to leadership. The Fog of Uncertainty oppresses you, induces anxiety, and ruins your carefully-laid plans. The Unknown Abyss evokes a primal fear of the dark. Wariness of the unknown is appropriate because, so far, we’ve only been talking about the first secret asymmetry of leadership: fragility.
If fragile things have more to lose than to gain, then building something fragile is more difficult than breaking it. Even if your role is not to build but to maintain, maintenance of a fragile and complex organization is no small feat. You’re constantly fighting against external threats; internal drama; and socioeconomic, geopolitical, or cosmic forces beyond your control. You also have a Sisyphean struggle against the second law of thermodynamics, which causes systems to steadily decay unless someone spends a lot of energy to reverse the rot.
When it comes to building or maintaining fragile things, knowledge really is power. Anti-knowledge does confers powerlessness.
Harnessing power from the unseen, unheard, and unknown
Let’s move on to the second secret asymmetry of leadership: anti-fragility. Recall from last week’s article that anti-fragile things have more to gain than to lose (the opposite of fragility, which is more to lose than to gain). Anti-fragile things are easier to build than to break because they are improved by the same unpredictable forces that break fragile things. Anti-fragile things benefit from anti-knowledge, not in spite of anti-knowledge.
In the realm of anti-fragility, anti-knowledge does not confer powerlessness.
Anti-knowledge becomes a source of strength, not weakness.
When you’re anti-fragile and have more to gain than to lose, anti-knowledge can further enhance your situation. Let’s look at some examples.
How anti-knowledge benefits you in non-competitive environments:
Anti-knowledge is the source of pleasant surprises. We hide gifts in bags or mummify them in wrapping paper to build up anticipation for the big reveal. A “just because” gift from a loved one on a random day feels more special than an unimaginative gift on Obligatory-Show-of-Affection Day. Even if two new hires have the same knowledge, skills, and abilities, you’ll be much more impressed by the one who under-promised and over-delivers than the other one who over-promised and under-delivers.
The Fog of Uncertainty is the source of serendipity and delightful randomness. There’s always something novel going on in large cities; you can always find new things to explore with each visit2. Treasure hunts are fun because the rewards are variable and randomly distributed. Taken to the extreme, random rewards become pathologically addictive (e.g. compulsive gambling).
The Unknown Abyss is the source of scientific and technological discovery. Researchers, tinkerers, and artists who delve deep into the Secret Grottos can extract Cerebrium (crystallized secrets) from the uppermost part of the Unknown Abyss. These chunks of Cerebrium can be secrets about nature (natural phenomena and methods for applying them) or secrets about people (hidden agendas, self-deceptions, emergent behaviors that only appear when groups of people interact3).
Anti-knowledge is a major driver of personal growth. Good judgment comes from experience; experience comes from bad judgement. Your biggest, most painful screw-ups (courtesy of anti-knowledge) are probably the best lessons you’ve ever had. The consequences of anti-knowledge tend to be great teachers, assuming you survive them.
How anti-knowledge benefits you in competitive environments:
“Information asymmetry” is the term for when one party has more (or better) information than other parties involved in a transaction or conflict. When one party possesses knowledge that the other parties completely lack, the privileged party holds a secret. Information asymmetry forms a spectrum between 100% transparency and 100% secrecy.
Let’s look at some examples of benefiting from information asymmetry:
Most people spend all their time on the brightly-lit surface of Leadership Land, studying in the Institute of Conventional Wisdom. By definition, “conventional wisdom” is widely known and accepted, and thus cannot be a secret. If you’re willing to travel underground to edge of darkness and labor alone in the Secret Grottos, you can discover secrets buried within the Unknown Abyss that give you a competitive edge. This is true of both secrets about nature (which can be patented, monopolized, and monetized) and secrets about people (which allow you to win hearts and minds to your cause).
You can weaponize the Fog of Uncertainty against your opponents. The Art of War summarizes this nicely with its opening line: “All war is deception.” You can manufacture anti-knowledge by obfuscation, misdirection, and deceit. You can thicken the Fog of Uncertainty to confuse your opponents, weaken their morale, and slow down their progress. If you target the people who are most afraid of the dark, their fear, uncertainty, and doubt will infect others.
If the rules of engagement or your personal ethics don’t allow you to weaponize anti-knowledge, you’re disadvantaged against adversaries who have fewer scruples. That’s your signal to disengage from direct confrontation (symmetric) and use guerilla tactics (asymmetric). Make yourself as robust against anti-knowledge as you can manage, following the framework from last week’s post. Bide your time until your adversary’s superior knowledge makes them overconfident, and they overextend on a fragile endeavor.
Expect the Unexpected: How to Apply Epistemology to Leadership
The first part of this section will be geared for new and aspiring leaders. The second part will be mostly for experienced leaders. The third part applies to everyone.
Touchy-feely epistemological matters for new leaders
In our first-ever article, we warned new leaders to be wary of the unseen, unheard, and unknown. Most newly-minted leaders are fragile, i.e. they had more to lose than to gain. During the first 6-18 months, we believe new leaders should focus on:
Learning to robust-ify themselves against the Sword of Damocles that suddenly appeared over their heads
Training their emotions to cope with anti-knowledge. So far, this article has been 100% “how to think about anti-knowledge” and 0% “how to feel about anti-knowledge.” Generally, anti-knowledge feels bad. The Fog of Uncertainty is oppressive and anxiety-inducing. The Unknown Abyss is dark and scary. To cope with anti-knowledge (and eventually benefit from it), leaders shouldn’t suppress their fear of the unknown; the key is to treat fear as data. Terror is your body warning you that you’re in a fragile position – you can choose to heed the warning and find ways to beat a hasty (and orderly) retreat, or to dig in and robust-ify yourself against fragility. Or you can choose to panic PANIC PANIC. We previously wrote about this in Living With Uncertainty – How Leaders Can Manage Emotions.
After learning to manage (not eliminate!) the fear of anti-knowledge, leaders can transition into…
Epistemology as a positioning tool for experienced leaders
The ideal state is to swap seamlessly between being wary of anti-knowledge (if fragile) and embracing anti-knowledge (if anti-fragile). Transitioning fluently between the two mindsets is key to proper positioning. You don’t know what anti-knowledge is, so you can’t predict or control the who-what-when-where-why-how of the unknown. You can, however, control where you are. You can position yourself far, far away, behind two blast doors and three insurance policies when anti-knowledge starts breaking fragile things. You can also position yourself to be “in the right place at the right time” when anti-knowledge brings prosperity and golden opportunities. Identify where you’re fragile and anti-fragile today, so you’re properly positioned when anti-knowledge strikes later.
The old cliché “expect the unexpected” is thought-provoking, but it isn’t very actionable. Let’s unpack the wisdom inside those three succinct words:
You can’t know what anti-knowledge is, but you can expect to be impacted by it – for better or for worse.
When you feel anxiety, fear, or terror – listen up! That’s your body’s instinctive fragility detector blaring. If you’re in a position with more potential downsides than upsides, beware of anti-knowledge. Figure out if you need to relocate to a safer position (literally or figuratively), fortify your current position, entrench yourself after relocating, or do nothing.
When you feel excited – listen up! That might be your body’s instinctive anti-fragility detector blaring4. If you’re in a position with more potential upsides than downsides, embrace anti-knowledge. Seek it at every opportunity, within reason.
The “greatest cruelty of leadership” revisited
Earlier in this article, we wrote:
Perhaps the greatest cruelty of leadership is that you’re not merely responsible for what you know; others will hold you accountable for the impact of unknown factors beyond your control and unknowable forces beyond your comprehension.
That was in the context of leaders taking blame for the negative impact of anti-knowledge. The reverse is equally unfair – many people will hold leaders responsible for the positive impact of anti-knowledge they couldn’t possibly control or understand. As a species, we sure like blaming scapegoats for bad outcomes and worshipping anti-scapegoats (i.e. idols and deities) for good outcomes!
Recognizing this tendency, some leaders make themselves anti-fragile by claiming credit when things go well and blaming others or the random number deities) when things go badly. We recommend against this (mis)use of anti-knowledge, and not just because of ethical misgivings. The strategy of “heads, I’m skilled; tails; I’m unlucky” will probably help one’s career in the short term. But in the long term, it leads to a misbegotten sense of superiority that suppresses the ability to learn. The eventual crash-landing in the Career Swamp will be all the more painful because the disgraced leader didn’t expect the unexpected.
Next week, we’re delving deeper into epistemological matters. What better way to study epistemology than by studying what artificial intelligence (AI) can and can’t do? Check back next week for Artificial Intelligence (AI) Can't Tell You Secrets to discover the limits of what AIs can do (in 2025, anyway) and whether they pose a greater threat or benefit to leaders.
This is post #3 in the Leadership Land Consistency Experiment, Phase I. We’re building better writing habits by publishing weekly between 12/20/24 – 2/28/25, instead of once every someday. Are we compromising quality for increased quantity? Was this post any better or worse than usual? Please share your comments below or reply directly if you’re reading the newsletter!
To clarify: we don’t expect Adventures in Leadership Land to fully replace the value of first-hand experience. There will always be value and valor in earning one’s battle scars. Sometimes we learn best by touching the grown-up equivalent of a hot stove and deciding we’re never doing that again…unless you’re a crazy scientist who must repeat the experiment because you’re allergic to anecdotal evidence. Or a masochist.
Interestingly, your anti-fragile serendipity arises because many city attractions are fragile. Why is there always something novel in cities? Because the life expectancy of existing attractions is very short. New restaurant? Previous one went out of business. New fun activity? The previous one became boring and people stopped going.
We briefly covered emergent properties in The Lollapalooza Effect: When 1+1=2 Becomes 1+1=11.
We say “might be” because the anti-fragility detector can be mis-calibrated to favor short-term gains at the expense of long-term viability. You can be excited to have unprotected sex with a dirty syringe full of addictive drugs, but no reasonable person would consider that situation as having more upsides than downsides. Your body is fragile, but the addiction is anti-fragile (deprive it, and it will grow stronger).