Overconfidence, and Executives as Personality Defect


I've been thinking a lot about confidence and how absolutely Gross (capital G intentional) it is, and how unpleasant so many of executives I've spoken to have ended up being.

In my experience, and I would wager most people's experience, confident people succeed. They succeed in degrees that are generally far greater than whatever their actual competence would indicate that they should. They'll succeed despite being obviously and aggressively wrong to thinking people, time and time again. This is Gross.

At the same time, it's generally considered to be good advice to 'fake it until you make it', especially for chronically underconfident people. This advice doesn't feel like it's morally wrong to give out. This doesn't seem absolutely gross.

It seems to me that we're discussing two kinds of confidence...

  1. Confidence: Refraining from being too shy to state your mind, or speak up in front of a crowd. The simple ability to speak without appearing rushed or panicked.
  2. Gross Confidence: The absolute inability to even notice that you don't know what you're saying, but sincerely being able to convince yourself that it is probably true, and anyone that disagrees is being a difficult idiot.

And two kinds of success...

  1. Success: Being able to accomplish something that is difficult, despite whatever barriers reality has put in your way. This could be anything from engineering tasks to social problems.
  2. Gross Success: Being able to achieve nothing more than convincing other people to elevate you. Sometimes this requires success of the non-Gross variety, but it will be delivered by someone else.

The confident person is the one calmly stating their opinion, having done some reading on the topic. They can be reasoned with because they're interested in the problem, and don't shoot 100ccs of ego straight into their veins every morning.

The Gross confident person, on the other hand, I've heard them described as simply "running over" reasonable people. This usually takes the form of being willing to go to war on every issue so aggressively that everyone else simply backs down. Someone starts saying something you don't like, and you fucking floor that gas pedal, making it clear that you will never back down, that this person is slowly earning your personal enmity over this minor issue, and you will all be tied down arguing this for hours. The reasonable person backs down. Splat.

These two sets of behaviors naturally lead to the two different types of success. The former person, being reasonable, is much better at navigating an actual problem. Were I to say "customers really don't like the redesign your team rolled out" with adequate data, they would likely just change it back. The latter person is going to go to war with me, personally, because I've said that they've made a mistake.

In a small company, where it really matters what those customers think, the latter person sinks the company. I've seen that happen once.

In a company large enough to have an extensive layer of politics and minimal accountability, the latter person is totally fine. Everyone backs down from the fight because it isn't worth their time to argue with this absolute psycho. There are no consequences.

In the case of a large enough organisation for failure to be survivable that does have tracking of any sort, they'll just assert that Bad Things weren't their fault but Good Things are totally their doing. Or, a line from Patrick McKenzie's advice for young engineers that is so much truer than I'd ever imagined upon my first reading:

Status in well-run businesses generally is awarded to people who successfully take credit for doing one of these things. (That can, but does not necessarily, entail actually doing them.)

Status in a well-run business can still be hijacked this way. It just takes a little bit more work. How many businesses are even well-run?


I have, for various reasons, access to an anomalously high number of executives in casual settings. My specialty is technology, so most of them are doing work approximately in this space. My time with them is very limited for the most part - they're willing to advise me on many issues, but the total time I've spent talking with each of them probably ranges from an hour to fifty hours.

All but one of them has, at some point, despite not that many contact hours, expressed absolute confidence in something around technology that they were totally fucking wrong on. I mean, not a little bit wrong, just dead to rights caught talking absolute nonsense. To a degree that people I have spent much more time than that with have never been with such certainty. Executives seem to get things confidently wrong at astonishing rates.

The most recent example, with only minor obfuscation, is a Chief Technology Officer of an organization being absolutely convinced their security team has been capable for years of breaking through a security measure that every cryptographer in the world hasn't been able to.

On the occasions where I've offered any form of gentle correction they have almost always doubled down, and in some cases revised their opinion of me downwards. Usually they have then gone to another party and said something disparaging about me, but they quickly forget about the slight and we're on good terms the next day - the capriciousness of it all is even more unbalancing, and makes one reluctant to offer contrary opinions, though that's an element of the dynamic for a psychologist to unpack.

But why am I going to them for advice if they're so wrong?

Briefly stated, the Gell-Mann Amnesia effect is as follows. You open the newspaper to an article on some subject you know well. In Murray [Gell-Mann]’s case, physics. In mine, show business. You read the article and see the journalist has absolutely no understanding of either the facts or the issues. Often, the article is so wrong it actually presents the story backward—reversing cause and effect. I call these the “wet streets cause rain” stories. Paper’s full of them.

In any case, you read with exasperation or amusement the multiple errors in a story, and then turn the page to national or international affairs, and read as if the rest of the newspaper was somehow more accurate about Palestine than the baloney you just read. You turn the page, and forget what you know. - Michael Crichton

I work hard to exercise some level of humility (and, like many engineers, this has been hard for me in the past), and this resulted in me just assuming they know what they're talking about in other domains. They have a lot of experience, after all. Sure, they're kind of full of shit on topics I know about, but the rest of what they're saying makes a lot of sense. Which topics do they make sense on? Only the ones I don't know about? Oh fuck.

Perhaps they're right on some topics, but they sound equally right across all domains by projecting Gross confidence, and despite their stories about all their great victories, I've never seen evidence they can achieve anything other than Gross success. To be clear, I haven't seen evidence that many of them can't achieve regular success, but at some point you begin to wonder if they just got to where they are by talking a good game and stealing credit.

Practically, any CEO who "rose through the ranks" is competent at being an actor. No exception. - Nassim Taleb, being his usual self

I found this quote after writing most of this, and in this context, Taleb talks about "rising through the ranks" as starting at a large organization and working your way up, as opposed to creating your own business where you need to be able to achieve non-Gross success.

(And, if I'm being honest, a lot of the entrepreneurs I meet, at least the charismatic ones in the tech space, hardly strike me as being wise or reasoned, so maybe that elevates people to power who are awful in a different way.)

Personality Defect

The last thing I'd wondered about is whether this behavior is a deliberate strategy or not.

At my first job, I got to spend a lot of time working with salespeople. It was at a small startup, and the product was not good. I remember walking out of the first failed sale we had, and being struck by how annoyed the guy teaching me was at the potential customer.

"They're small time players, and don't know a good opportunity when it's knocking right at their door."

This otherwise smart guy had honest-to-God convinced himself that our product was good. He believed it, and that was why he was generally an effective salesperson. It has been years, but I haven't finished wrestling with the implication that people are capable of doing this. Of course, we all believe things that are stupid when it's emotionally convenient, but this product was bad, and it also wasn't like it should have meant that much to him. He could get another job easily.

Years later, I was approached by the executive suite at a major cryptocurrency platform to be their lead analyst in a market expansion. I personally think the technology is vaguely interesting, but that the majority of the people working in this space are disgusting grifters, frothing at the mouth at the prospect of easy money - but I needed job security given my immigration status.

For political reasons, a ton of the C-suite wanted to interview me personally. All but one of them expressed extreme stupidity around topics they should have known much more about, and the smart one was removed in a coup within a month. In particular, I recall their CFO asked me if I (one person) could build a real-time machine learning platform to perform sentiment analysis on news sources and thus beat the markets for them.

I feel like a CFO should, without having any technical knowledge, understand that it is extremely unlikely that one guy under the age of 30 isn't going to be able to hack for three months and consistently beat the market... I'm not going to waste anyone's time explaining the technical reasons for this or why the CFO can figure this out without those reasons.

But more importantly, after all those discussions had dropped off, and I'd resumed normal life... I realized that the guy originally teaching me sales had moved into cryptocurrency. In fact, all the salespeople I worked with had moved into cryptocurrency except the ones who ever expressed any doubt. It's just striking me now - that CFO was in a one-on-one conversation with someone who had nothing to really offer them. There was nothing to gain from talking to me about A.I in this way. She had simply convinced herself that their terrible crypto platform had value, that they could beat the market if they tried for two months, and that crypto was going "to the moon", and this mindset manifested as saying total nonsense to me.

There's just a personality that will just decide whatever attracts money and status is correct. The latest manifestation of this I've seen in the workplace has been trying to talk about ChatGPT as much as possible, from people that barely know what a LLM is, and frankly have never used the product beyond ten minutes of playing around.

And, to make things worse, it can't be turned off. In the above, they've obviously made out like bandits from their poor behavior. But I have, and I swear this is true, seen an executive in a similar position (who now holds the equivalent of a knighthood in the country we're discussing) eat a dish at a restaurant that was incorrectly delivered to their table. They then asked the waiter to bring the right meal at no additional cost, and when a small child at the table piped up to point out this terrible behavior, they shushed the child. Like, what?

It doesn't seem to be a strategy. These people are surely capable of some degree of strategy, but the fundamentally terrible nature of their being comes naturally to them. There is no reason someone in their position should ever behave that way. It's embarrassing and actively harmful to their reputations, but they just can't stop.

The security team can crack that cryptography, because saying that right now gives me status in the conversation. You're wrong if you say that's not possible, because that lowers my status. Argument over.

Of course you're an idiot for not buying this product - it can't be my fault we've lost money, and I'm not a liar for saying the product is good. Argument over.

Yes, of course we need better analytics at the organization, I'm data driven. No, I'm not going to invest any time in making the data accurate, that would require not ticking as many boxes off in the next status update. There is no contradiction.

Of course, we should talk about ChatGPT, because it's the trendy thing and makes me seem like an expert. No, I'd never read about how it works despite claiming it's the most important thing in the industry at the moment. There is no contradiction.

All our social processes seem to be largely selecting for absolute lunatics at the wheel.

As always, if you have any experiences that support or contradict what I've written, I appreciate, read, and respond to all emails sent to