The hardest people for founders to hire are so called C-level executives

There's the "grass is always greener" phenomenon, too. Companies are struggling to figure out the next step, so they hire an exec from some other org that's equally struggling but looks shiny from the outside.

Another pattern I see a lot in the tech world is people who jump up the corporate ladder quickly by jumping from the tech side of companies in some industry, e.g., widget-making, to working at tech companies trying to sell software to the widget industry to startups convinced they can use AI to make better, cheaper widgets and then back to some big widget company that just put out a press release saying they're really a tech company that happens to produce widgets. The widget people figure the exec knows tech, the tech people figure they know widgets.

Well, it's also the people still on the ladder are the ones that aren't smart enough to realize there's diminishing returns on personal wealth and a diminishing supply of personal time.

In less than two years I went from my second job out of college to being offered to come up with any role for myself in a 10B cap company in order to retain me as I was getting bored, and after a night's sleep I came back and gave my notice.

The person that offered that position later turned down an offer for CEO of a 100B+ company for similar reasons.

There absolutely are people out there that shoot up the ladder based on skill. But when the people holding the ladder don't realize at a certain point time is worth more than any amount of additional money, it's hard to keep those that do realize it from jumping off.

The problem with filling the C-level positions isn't just that good candidates are obscured by founder Dunning-Kreuger, it's that generally the pool of candidates is going to be biased towards people echoing the BS toxic work culture that is the startup world, and the good candidates are going to have grown past participating in that charade.

WFH and changing attitudes about work life balance may reduce achiever churn moving forward, but I still see the "I'm so busy" posturing with C-levels and their wannabes here and there when I still have to interact with them, so I doubt it's going away soon.

IMHO for start-up to hire a C-level manager the best way is to look at VP / director level at a large company, preferably director level. If a start-up looks for a VP look at senior manager / director level. Basically hire people from large, established companies that a re currently at least 2 level below the senior position you are looking for. Those people are high enough to bring the seniority and low enough to still, maybe, do some of the actual work. Select from this population for the ability to cope with non-existing structures, be hands on themselves and the ability to calmly guide an organization.

The last thing you want is those career politicians that tend to climb the corporate ladder and rely on others to actual do the work.

Work is a type of performance art. Bosses pay to see you suffer. And if you do not act like you are suffering enough, more work will be added to your desk for proper amount of suffering.

I believe that if I tried playing the game, I'd make a pretty good CTO. But as PG is aluding to, there are a lot of really talented people out there (including myself) who hate playing the politic/self-promotion game. For small startups, you can be an effective C level player while avoiding these "soft skills" but the bigger the org the more important these skills get. Avoiding the game, or worse: playing it badly, can kill a startup. I think this is why a lot of founders struggle as their org grows.

> [...]C-level executives have mastered the art of sounding good with minimal set of accomplishments

I mean, they get hired to do the same for the company (internally to potential and current employees, and externally to partners and financiers). The ability to sell is a crucial skill in the C-suite: it's no wonder they can sell themselves.

The CEO is the greatest salesman of the company. So they better excel at selling snake oil. There are positions for technical people, CEO is not one of them.

The real issue for founders is that they think they are looking for a CEO and they end up selecting for skilled liars.

You always need references, and those references need to be trustable.

> but the person who knows how to sell their work

And very often: how to sell the work of others

Actually they genuinely believe they have accomplished things!

The people doing good work are too busy doing working and increasing related skills that they have no time to improve their skills in selling themselves. Those without skills have nothing to do other than sell themselves so that is what they get good at.

I'm very mixed on this as I agree a lot of C-Levels mostly have mastered the art of selling themselves and I find most announcements of new C-Levels in my company to just be a waste of an email and likely salary.

But your last part strikes me as falling to a common misconception that climbing up the corporate ladder from inside is best done based on merit, as leadership is not always compatible with the actual work being done at the lower levels.

C-Level leadership tends to be more about company growth and being able to understand which parts of the company do need to change/evolve to reach that next level, sometimes with hard decisions. I've gone up the ladder like this from a very low level to a few reports away from the CEO and definitely it changes your perspective a bit on how you approach things.

The simplest example is realizing you have a lot more decision power over how you interact with your customer base, and options like "we simply won't support this" are a viable option when before you didn't have such options. How you allocate your people towards projects becomes far different when you introduce a new product/feature, and so on. It becomes a lot less about the minutia of the day to day work and instead about the long-term sustainability and health of the people and the company. Learning to take in a larger scope of understanding is not easy and not everyone naturally learns it, yet many companies still follow the time-based seniority model or promoting to leadership persons who really don't have basic leadership qualities.

You also have to consider your top people and how to evolve your strategy without ostracizing them or causing disinterest; too much workload on your top-tier team members and you'll start to bleed such people. Same with adding in too many things not related to their interests. Ideally, in such a high level position you're listening closely to the feedback from the lower managers and making decisions that try to balance both aspects and pushing only on situations where the growth is very essential, but there in is the catch: how can you know what is essential until you try it and see the result? What worked for one company doesn't work for another as no matter how similar the product/services might be. I've seen this happen tons of times with support and RND teams that were basically modified to include professional services aspects which is not what any of those people signed up for, and there was a huge exodus. The justification was that the C-Level who made the call had success with this at another company X, but the scope of what had to be managed was far more narrow at X and the client base with a support package was significantly smaller. The results at X were undeniable, but the conditions under which such a change were effective were quite different, and the C-Level just failed (refused?) to recognize this.

Leadership is very hard to grow properly, and personally I'm of the opinion that people who seek leadership are to be treated sceptically, as it's something that grows with familiarity and organically, not in a classroom. The Classroom helps with the fundamental skills (statistics, financial studies, etc), but my personal observation is that what gets lost in these classes is that such knowledge then needs to be heavily customized to the environment you're in. It doesn't really matter how many tools you have for leadership if you're using the tools incorrectly.

I worked at the same company.

This company has uniquely terrible CEO leadership who systematically have a track record of very poorly choosing senior leadership, recklessly changing the culture and doing zero to curate innovation, people development.

All of the talent left, mostly to direct competitors who will now be super charged to annihilate them.

This May one day become one of the saddest case studies, along with how Intel has shaped up, but the damage is going to show up everywhere for years to come.

Having burned very significant energy at this company, I am deeply sad to see the most garbage humans left in charge and also deeply glad to see the talented people effusion to great roles where they will mop the floor with this company.

Pretty sure I was your coworker.

The interesting thing about that company is how badly it failed at filling executive roles with promotions from within OR experienced hands.

Fundamentally, the CTO failed because in their previous success, they built it from the ground-up. They had zero experience trying to take over a large org, came in like a bull in a china shop, and worst of all, made a lot of very costly, morale-destroying mistakes.

But see also the Chief Product Officer who left in disgrace or the quasi-COO who also left in disgrace. They were both promoted from within well past their level of proven competence.

The common thread? The CEO who made all of those decisions. Executive hiring requires a CEO with the ability to reflect on their personal shortcomings and those of the team. And then, they need the ability to attract and evaluate candidates. And even if they do that successfully, they need the ability to meld a group of these execs into a highly functional team.

Our CEO only had the ability to hire people he saw as junior versions of himself.

Were we at the same company?

I joke. I probably wouldn't have called us "large", but otherwise your story matches my experience word-for-word, which says something about the industry...

Uber?

I worked at a company that mostly matches this story, but I think is probably not the one you mean.

It’s insane how many don’t realize this when it’s so obvious. Seen so many big shot c-levels wander in from Amazon, Microsoft and the like, institute some changes to make a mark and hit promises they made coming on, then leave 8 months or under 2 years later with the thing they were in charge of in disarray only for another to roll in and do the same.

Company I work at was almost ran into the ground until we fired all the c-levels for hire and empowered the top levels of individual contributors instead.

> ensure that your early hires are all top notch with the potential to eventually build out to become your C-suite

Are we talking about developer early hires, or sales, or whom?

The skills and character required to be a succesfull developer are totally different than whats needed for C level. Thr training required to get there is a lot. Finding the right people and keeping them is hard enough.

But all means try to grow them internally and probide training, but as a 'solution' it is not realistic.

If someone is already handling the functions of the CxO role internally and doing it well, they should be considered as a forerunner for the position.

Anyone hired externally must be expected to meet a substantially higher bar than the existing employees. Bringing in an external CxO who is less qualified than internal candidates will destroy morale and lead to attrition.

However, there’s a lot to be said for bringing in an external CxO who can take the team and the company to the next level.

A CxO role is quite different than a traditional manager role. You can’t expect good managers to automatically be good C-level executives because the work is just too different. It’s the same story as promoting ICs to managers - Different responsibilities and different skill sets.

But internal employees should always at least be considered and given a fair shot.

Well one of the problems is that you're often hiring a CxO to bring characteristics of a bigger company to your smaller company as it grows. For example, if you have a haphazardly grown sales team doing about $10 million in revenue, you might want to bring in someone who has been a Director in a $100m sales org to be your Chief Revenue Officer to bring some of the sales force management and compensation practices that you need to develop as your sales team gets bigger. There's nobody in your organization who really knows that.

I must disagree. What I have seen is what you are saying enables bad internal culture, decision making and technical habits to become more ingrained into the very soul of the company.

I see well meaning senior technical people disregard my advice on technical matters because that's just not how things are done there ever, some things are so far out of the box they can't even conceive of it as a possibility. Manager after manager telling you the same answer because that's what whoever they ask about tells them because everyone at that dept/company is 15+yr tenured.

If you want to keep things as they are but maybe slightly better or to make different internal people happy you promote from within. If you want fresh thinking and new directions you gotta hire from the outside.

I can't emphasize this enough. The only analogy that comes to mind is eskimos that have to traverse a desert but only want other eskimos in their team.

> Q3: Why can't we promote from the pool from the answer to Q2 instead of hiring externally?

To offer a few potential answers:

* Because the existing company culture is not conducive to taking a step forward, and you intentionally want to bring in outside ideas (e.g., bigger-company experience).

* Because the people who are the answer to Q2 don't get along all that well, or are worried about their individual career paths, and promoting one of them above the others will make them upset in the short term.

* Along the same lines - because you don't trust the people from Q2 to level up and handle the full scope, and will instead always favor "their" organization.

Anecdotally, I've observed that man CxO roles are created at the behest of the board or to acquire prestige for some purpose. It would not surprise me that it's easy to find highly successful people who will trade Prestige for money and WLB after a certain point in their career.

Promoting internally won't buy your firm more prestige/credibility.

That seems unsurprising. It reminds me of that bit from one of Ben Horowitz's old articles [1]:

> Things go wrong, because building a multi-faceted human organization to compete and win in a dynamic, highly competitive market turns out to be really hard. If CEOs were graded on a curve, the mean on the test would be 22 out of a 100. This kind of mean can be psychologically challenging for a straight A student. It is particularly challenging, because nobody tells you that the mean is 22.

[1]: https://techcrunch.com/2011/03/31/what%e2%80%99s-the-most-di...

I think a lot of people fall for this kind of fallacy (no offense meant to your acquaintance).

1/ You really cannot grade absolute values on a curve. As others have pointed out, your A players are only in comparison to others in your team. Maybe they are actually C players, who knows? Maybe they are A players only in the environment you created etc, etc..

2/ And a more important point is that a lot of work is being done by people that are not A players. Whom I would call net positive is only in relationship to what I can measure. I know of many people in my team who were not exceptional at software, but got things done due to building relationship with other teams, ability to see things to completion etc. I think Amazon fell into the trap that only type A personalities get things done and I see it in other places too. It is easy to see the extremes, but a lot of times the glue that holds things together is almost invisible.

It is hard to gauge value and I personally am refusing to judge anyone (to the extent possible).

I would say this is true of almost any position. Ask any manager and they will probably say this is usually how it shakes out. 33 percent of hires are A players, 33 percent are B players, and 33 percent are C/D/F players.

It is grading on the curve. An A player at one company might be a B player at another. If someone is an excellent CxO they are probably a good candidate for a bigger and better company or the CEO job somewhere else and so will leave after some time unless given large incentive to stay or otherwise have reached their career ambitions.

It's like any employee, vitality curve and all. The top 10-20% are responsible for 90-80% of positive results and the bottom vice versa while everyone in betweek keeps the boat afloat.

As long as you can identify which are which quickly and action then 33% hit rate can stack your roster pretty quick. Hiring takes time though, in most cases.

Sounds as if he did not fire the 33+33% ? The board or the investors wouldn't have liked that? (Or why not)

The rings true, most of the problems I've seen tend to come from a CEO who refuses to get rid or fails to notice the poor ones though

For the second two categories, did he think they should fire/fire immediately and promote within? Or hire externally again?

I guess you comment as an exec but this comment does not help make the case. Without being an engineer myself, I would be very frustrated with the last paragraph. It uses a statistically true fact to make a meaningless argument (how is optimising for top 50% different to e.g. optimising for bottom 50%?). Furthermore it demonstrates a view of a team of engineers as a bag of individual contributors. In a team, skill and talent are only one factor in optimising team dynamics. You don’t trust in numbers, you trust in dynamics and collaboration and in people growing within your organisation. I recently hired a PhD and a bored junior admin whose most exciting piece of work was scripting his boring work away at the same day. Also to your core intended argument, you hire an engineer in a couple of interviews, an exec would go through an extensive round of meetings and interviews and therefore you would optimise the process across different dimensions. The margin of error should be pretty similar, given fundamentally organisations have an underlying risk appetite even if it is implicit. The issue is that execs have more experience manipulating your perception of risk and therefore you should go with your eyes open, because this is part of the skillset you are probably looking for anyway.

"- founders, especially first time founders, often have middling experience hiring for any role, and zero experience hiring execs."

These seem like (and this one especially) exactly the sort of problems a VC would be positioned to help solve.

So I wish PG would give advice instead of just complaining about bad execs here.

Sounds like a strong argument for delaying hiring exces till your larger. Unless they have contacts you need to tap.

This is sort of the discussion I wanted to hear from this thread. What separates a a product manager paired with a data analyst from say, a CEO or CPO (product)? Surely the PM and DS are better armed to make decisions with data and talking to users, etc.

as a fellow skeptic, this oversteps. your mistake is that smart = value. connections do have value, as does experience and other leadership qualities than domain expertise. your criticisms will be stronger if you recognize this.

This is the thinking that technical folks often fall into - raw intelligence is the best indicator of performance.

At the core, C-level roles are often sales roles. They need to sell their ideas both up (to the CEO and board) and down (to their org).

If your goal is to become a C-level executive, start your career (and excel) at McKinsey, BCG, Bain, or similar elite management consulting firms.

Maybe that is the way to hire good ones. Exclude all candidates who went to a 'brand' university.

They also work very hard as in spending enormous amounts of time working.

One aspect is that companies can grow much faster than people do. Someone who's decent at managing 5 people will need many years of experience to become capable at properly managing 500 people, and a company can grow to needing such a manager much faster than that. Just as you can't expect a skilled individual contributor to be able to instantly become a good manager (they can, but that's a different skillset that needs both learning and practice which will take some time), so if you suddenly need a bunch of good managers now then you have to hire them instead of promoting your contributors; and in the same manner you can't expect a skilled team-lead to become a good CxO in a large organization (the difference in the daily work and skillset is comparable to that of IC to manager), so if you suddenly need CxOs to become a larger organization from a small one, it's exceedingly likely that none of your managers are qualified at the moment - they might become qualified with, say, two years of personal growth if targeted at that, but a fast growing company likely can't wait those two years and need a CxO that can start doing these things properly now.

"What do they bring to the table? Why not promote leaders from within?"

Both carry risks: the former can cataclysmically change internal culture and make a cascade of errors rapidly (usually during the idiotic 'empire building' phase many start from), the latter can sometimes be pushed up on questionable grounds and do much the same (e.g. worked for a firm where the CRO left abruptly after 18 months and because executive search was so expensive and lengthy, opted to promote the head of a region to CRO, who proved to be at best a mediocre sales leader in terms of actual revenue, but proved perpetually toxic to everything they touched. An almost cartoonishly corpulent and caustic incompetent from central casting. When he was regional lead he was problematic but contained, but when promoted turned into a total 'Enfant terrible')

The arguments you often hear are:

- new set of eyes / people that aren’t colored by biases from previous experiences

- external networks and resources

- right background and experience for the task

Etc.

Lol Bob Smith (CEO of Blue Origin) is the pinnacle example of this.

These people need to be publicly named and shamed, enough to show up as a huge black eye in their Google/due diligence results.

I have suffered under a few such C-levels and their incompetence is maddening. It is hard not to see the C-level social network as one big circle-jerk, and they get to walk away scot free. These folks are only worthy of spending the rest of their life as a clerk at a gas station, not (mis)managing million/billion dollar companies.

that’s what happens when you hire people not based on their talent but on nepotism

It's a game theoretical ratchet:

- My friends will tell me who they know

- People are responsible for their own hiring

- If I recommend this guy and he's at least acceptable, my network grows

- If the guy I recommend is not that good, all three will make excuses: my mate who hired him (will blame chemistry/randomness or me), the dude himself (will blame chemistry/randomness or me), and me (will blame chemistry/randomness). Since we're all adults, you can't blame someone else for your lack of due diligence, so it's a shame their styles were so different and the market turned against their brilliant plan.

- Nobody ever gets blacklisted for bad recommendations

- Everyone is complacent about who they will recommend

- My network grows, and I don't need to grill everyone. So my network grows.

Of course what this also means is if you don't happen to be in one of these networks of mediocre people, you are totally out of luck because those networks are big enough that someone will be found, just not you.

Your compensation is determined by your power within an organization, not your contribution to it.

What blows my mind is the degree to which people believe that perfect competition exists everywhere and “the market” will fix all inefficiencies.

Edit: I want to make clear that I am not denigrating the value of markets, I’m only looking to point out the idealization that exists in many people’s minds, especially as I have encountered on this exact forum.

If a CEO or other C-level sets some targets, then you’d think they would be held accountable for missing them. But from what I’ve seen, this is very rare. So the board is just as responsible for what happens as the CEO.

I have seen cases where the board holds executives accountable, and that results in a better company lead by competent executives. But that kind of accountability is unusual in small companies because the board and executives are often one and the same group.

If there’s anything I’ve learned over my career it’s that the theoretical structure of a company has no inherent relationship to reality. If the CEO, chairman and board members are all mates then they will pat each other on the back until well after the iceberg has ripped a hole in the side of the ship.

> 2. There's no good objective way to measure C-level performance.

> On top of that, the best person for a given CXO job often just so happens to be a golfing buddy and/or have outside business dealings with half the board.

> C-level hiring market [isn't] some sort of efficient meritocracy

Those 3 things aren't contradictory, they each follow from the other. In absence of an objective way to measure performance, the best thing is "I have experience with this person, and can vouch that they're good." And so it totally makes sense that this sort of network-based hiring is what we see instead of a meritocracy.

It’s game theory and asymmetric information at its finest. Throw in a healthy dose of survivorship bias, a pinch of appeal to authority, and you get a perfect recipe for astronomical out of whack compensation packages.

I am convinced that we need to move companies from effective hierarchical dictatorships to more democratic institutions. A CxO should be like an elected politician - representing some manifesto that is a coherent (!) package of measures and gets appointed maybe by an election amount employees / shareholders.

As such they need to persuade a majority of people who will supply the (human / financial) capital that their manifesto is the best option. They essential earn their way into the office.

Edit: I am also semi convinced that the hierarchical thing is half the problem. Having a single person make "the hard decisions" is usually a way to have the wrong decision made about 50% of the time. Somehow humanity has found science as good means of improving those odds. But for the sort of decisions we make in business (very little hard science) then I suspect democratic consensus might be a much better way to get a good decision.

(no this is not about decision by committee.)

Playing devil's advocate here.

Maybe being a golfing buddy does qualify for being a good CXO. To be a "golfing buddy", you need money and connections. Connections are important for that job, and wealth correlates with success and good finances, again important. Some of them are just born in wealthy families, but this is a positive, not a negative: wealthy family often give their kids good education, have lots of connections, and are used to being leaders. Golfing buddies also need to make good conversation, including on business topics, otherwise they won't stay buddies for long, again a valuable skill.

Being a golfing buddy certainly isn't an objective criteria, but it is not completely worthless, and it is easier to detect fakers when you spend a lot of time with them, or at least, it requires more effort from the faker. Objective criteria typically include past work, and CXOs usually have that too.

It's also pretty hard to measure the performance of software engineers at the senior level. When hiring, I don't feel like it's wrong to encourage good software engineers to refer former colleagues they think are good.

I don't see why that would be wrong for C-level executive jobs either. It's really the same thing -- trusting the opinion of people you know and think are good is a better bet than drinking from a fire hose of job applicants of widely varying quality.

At any job where your purpose is "leadership" and "impact" it is difficult to quantify success. People have tried to measure with things like OKRs, but ultimately a lot of what successful senior people bring to the table is hard to measure.

One measure of a high-quality C-level performer is the quality of their teams. The best C-level people can bring in very high-quality managers and individual contributors underneath them. Below average C-level people really struggle on this front.

Also, for some C-level roles there are good and objective ways to measure performance. For example, for a Chief Revenue Officer you have (obviously) revenue. There are a ton of confounding variables of course but in general CROs who consistently out-perform plan are better than those who consistently under-perform plan.

My theory about the giant comp packages:

1. The board is constantly dealing with the CEO, and CEOs are very good at taking credit for things regardless of their actual impact. So they create a subjective impression of being very important.

2. The CEO is only one person, so throwing (say) 1% of the company's profits at them seems like a great investment for all that stuff they're "doing".

If enough boards play this game, CEO pay is driven through the roof.

Most CEO compensation is equity which is directly tied to company performance.

If you look at Pfizer’s CEO who had a total comp of $24.3M of which his salary was $1.6M.

This is a really great list, and matches most of my "corporate" experience.

I would add one simple caveat, though. It's usually difficult to observe and measure all the listed items, unless you have been working with such executive for a long period of time.

The hard part is to figure this out in months, not years.

Edit: or possibly, to figure it out before actually hiring the fraud.

That happens, but I don't think that's really relevant to pg's tweet. I mean, if a founder is willing to hire a buddy and deliberately overtitle them, that's easily the fault of the founder and, for better or for worse, shouldn't be a mystery if things go south.

That's very different from what pg is referring to, where, even through all the best of intentions and due diligence of a founder, a shitty C level is hired because they excel at bullshitting.

It depends on the stage of the company. Hiring a buddy early in the company's life might make total sense, especially if willing to work for primarily sweat equity compensation.

An early joiner will get a grandiose title.

nepotism at its best

Because you need specific skills and experience, not only motivation?

When you need an accountant, you don't invest in a motivated office assistant to learn accounting, you hire someone who already spent the years to do it properly, since there are many steps between a random person and an accountant and most likely none of your current employees are "almost-accountants" who are ready to take the next step. And when you need a CFO, you don't invest in a motivated accountant to learn how to do that, you hire someone who has already spent the years to do it properly, since there are many steps between an accountant and a CFO and most likely none of your current employees are "almost-CFOs" who are ready to take the next step.

Startup founders hiring random "good people" without competence at the appropriate scale as their CxOs is a good way to disaster.

Because Executives are (besides other things) the voice of the client in a company. Engineers typically have a very bad understanding of the clients they are made to serve. Of course that doesn't make them bad engineers.

Someone who has never been an IC or has no technical background makes me doubt their competence.

While I agree with a lot of what he says, I also think there is a bit of wishful thinking when it comes to "world class leaders".

Just like you can't hire the top 1% exclusively, your leaders won't be top 1%. Chances are they will be somewhere in the middle. Creating a "culture" that allows for initiative at different parts of the company is going to do a lot more for you than rolling the dice on getting exclusively top quality leadership.

Re: "Culture": I mean this in the group dynamics sense, not the meaningless corporate-speak sense.

There are 3 options.

* Fit in

* F-off

* Fight

The primary benefit of F-off is that if you play the game correctly you can be well compensated for doing so and maybe even get hired back to fix the mess 18 months later.

Sounds like you've met "Action Jack" Barker.

I worked for a place whose former CEO (before I joined) basically committed the company to sales contracts it had no hope of fulfilling, then gtfo'd before the delivery dates, to pump up his CV with "closed so many millions in sales with company X".

We had one of those at my previous company! I didn't realize until now.

It’s even worse when the IL is the CEO.

While your point about jealousy is a good one, MBA-ification is real and has real consequences, many of which might reasonably provoke frustration

I do agree the anger is ideally channeled into some attempt to productively frame, understand and solve the problem, but dismissing it all as sour grapes doesn't seem very helpful either

I saw the issue pithily summarized recently:

> Salesmen, in any field other than sales, are like an invasive species who outcompete the natives with their superior social polish, but who struggle to actually do anything, which leads to systemic underperformance and the erosion of trust, which only makes the competitive necessity of salesmanship even greater

We need to build social systems which don't select preferentially for relentless salespeople and smooth talking charlatans if we want to live in a prosperous, harmonious society. The optimal proportion of these is in all likelihood not zero, but does anyone believe it's as high as we see now?

Without fail, there is always one comment on HN that is faux-insightful but really just being contrarian towards the general tone of other comments without much substance.

You don't need to advocate for capped compensation or removing autonomy to be righteously angry over inept leadership. You should be angry over inept leadership, it's essentially corruption, and hurts everyone else in the organization. I don't even know what the point of this comment is.

No it’s just years of watching some average guy make millions for literally nothing

Even though I think some people are jealous there are plenty of legitimate reasons to be mad. Often highly paid people are where they are due to nepotistic inertia. It's extra infuriating because they all pretend it's merit, and those that admit there's a broken system that enables their wealth ignore any personal responsibility for it's existence. Everyone else is working the system after all, don't want to be left behind. In general many (most?) highly paid people are in that position because of a system of exploitation that they're tacitly involved in and turn a blind eye to. So yeah, plenty of reasons to be mad.

At a startup the most common failure mode I've seen is hiring someone who, even if they were good at there last job at BiggerCo, is terrible at what the startup (in a different business development stage) needs.

Hiring a person who's been running a thousand-person org to take over a 1-10 person org is often insanity, but it can look smart because "wow, they were doing so much at such a successful place and have so many great stories to share." Run a 1000-person org and after all, even if you suck, some of your sub-departments are likely to hit on some great results that you can share in future interviews!

As a worker, I create wealth. There is also a parasitic class of heirs who are LPs for VCs, or who get dividend, rent and interest checks - rentiers expropriating surplus labor time of those who work. Yes, my attitude towards them is about what Lenin's were for the tsar and his parasitical family.

I can care less what those who are parasites off my labor think of me, and their cadre who somehow benefit off this paraditism. Workers work, create wealth and have no need of these parasites. Yes we resent them, and will eventually eliminate this parasitism.

We live in a society ... where humans do human things. Cronyism, nepotism, and tribalism are normal human behaviors, regardless of how some people think humans should behave. Our fellow humans are under no obligation to surpass humanity and behave altruistically. I think a more useful question is how do we utilize or exploit our human behavior to improve ourselves and our societies.

I doubt that most people here are angry about this. For me, at least, my anger arises from the opportunity cost.

First, if you spend a lot of money (and time) supporting a dud executive then you you’ve lost a bunch of runway. These people are often in a position to put startups into a death spiral from which they will never recover.

So it follows that as a founder that idea is dead - it’s almost impossible to restart. If you’ve put your heart and soul into a business, spent a year raising funds and putting a team together, and then some bozo is parachuted into a position of authority and proceeds to throws all your hard work out the window as they miss their own targets and crash into the terrain, yeah that’s gonna make you pretty pissed off because you won’t get that opportunity ever again.

It’s not about jealousy. It’s about the destruction of value.

I think there's justified anger on the part of people who have seen companies they enjoy working at be damaged, either in culture or in more direct results by a poor C-level hire, and most people have experienced situations where this has been abundantly clear from the outset.

It's completely reasonable to want to see a company you work for succeed, and it's completely reasonable to be frustrated when those companies make obviously bad decisions that put your job in jeopardy or make the company a worse place to work for. Particularly with startups, a lot of your career success is fairly closely tied to the success of the companies you work for (no one cares about hiring a eng or other role from a startup who crashed and burned).

As a CIO/CTO, I am very hands-on, but I don't feel offended by this statement; I do agree that there are many companies where the CIO/CTO are often vendor management, and more administrative than technical.

I'm not sure I agree about COOs though. My experience with COOs is that they typically have the pulse of the company and are actually quite close to the ground.

Didn't even mention "Chief Customer Officers". We hired a CCO out of a friendly F500 with absolutely no experience. The unscalable support costs alone have him as a top contender for why we're at risk of running the whole company into the ground. Conveniently, everything in the org is the problem except him.

> He is a platitude robot saying nothing more than 'Crypto will lead to economic freedom' and 'now is the time to build'. Before the crypto crash it seems like the only motivator was money

Yes, that's what it's always been about with coinbase. That's why they sold their equity on a traditional finance platform for USD $ and why Brian bought a $130m mansion. 10 years later what has crypto accomplished besides grifting people out of their savings through 3% commissions and scams? Do you know how useful Google, or like any other company, was after 10 years?

How else could Coinbase have ended up? It's a company for people to speculate on digital tokens. There's no grand mission to the thing, his rhetoric has always struck me as hollow and self-serving. "Create more economic freedom" lol. I have an account, the app didn't even show you your return till fairly recently.

Coinbase will die, even if crypto survives. But he's already taken out his millions.

at this point I wouldn't be surprised if some of them are cooperating with the feds

Same for CTOs. Reason, I am one and this comment thread is a very depressing read.

Surely someone must have examples of when a C-level leader actually made things better?

This is not so unusual compared to other jobs - I've worked with crappy engineer coworkers who went on to bigger and better jobs. Always a fun day when your peer who you thought was slowing the team down announces they're leaving for Google, say! Most people fail sideways at worst, vs flunking out of the ability to tackle a role again ever in the future.

If the assumption is that other people would be better at these roles and the hiring is broken (this is PG's assumption, as far as I can tell from the tweet), how would we better identify those people who'd do better?

(Personally, I think we're under-estimating the amount of it that's caused by "it's fucking hard.")

it happens with CTOs. At many companies, CTO is less of a management role and more of "the leader of all of the principal engineers and source of innovation for the company". VPE reports to CTO and does the administrative side of things, CTO sets technical vision. Most other c suite type roles are generally bucketed into sales, marketing, operations, and if you are particularly unlucky: product, "Information", and human resources.

I’m just past the year Mark in being a CTO after a career as an engineer / architect. I won’t claim to be an amazing exec, but I still don’t understand how anyone could succeed in this role without having significant engineering experience. I approach this as “my turn” at playing the executive role - because I finally said to myself that there has to be someone who can code in the exec team of my next job. I intend for this to be my one and only time in a role like this - to do it well just requires more time and energy to sustain it for decades.

Pat Gelsinger, recently. But he's been an executive for a long time already. Carmack is a part-time CTO these days.

Unless you network like it's 1999.

Define decent size? I’m CTO a a ~450 person company, but the the tech team is more like ~60.

My job is to set the technical tone about how we’re building software for the engineering teams, to determine our technology strategy from the business strategy set by the CEO, sometimes to just be a technology handy man for the rest of the company. I stay quite close to what my teams are doing, and I call out hopefully helpful direction from the sidelines to make sure that they’re all pulling in the right direction and don’t get pushed off course by other stakeholders.

He also put together the Schlieffen plan that led to Germany wagining a 2 front war against superior adversaries that had time tables planned down to the hour that ended up not taking in to account numerous factors that ended up leading to the most horrible experiences in human history.

... but in the military, it's generally not possible to 'fail up' into a similar role in another organization when things become uncomfortable. A clever lazy Prussian officer can't build out their resume for a couple years and then go work for the French, so they have to actually stick around and make those difficult decisions. Whereas in tech, it's not just possible but normalized to change companies with some frequency, and a lazy clever C-level exec may not stay around long enough to see the outcome of their difficult decisions.

My grandfather used to say "there are two types of people in the world: lifters and leaners."

I was skeptical when I first heard it. I still question the many special cases or situations that fall somewhere in between. That said, the longer I live and work, the more I see (or hear of) the leaners ... and their enablers.

as a clever and lazy person this gives me lot of hope