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My (anecdote-based) theory from working with a number of executives that have enough money to never have to work again is that to them corporations are largely some sort of game that they enjoy, like a weird complicated form of Magic the Gathering.
I'm curious to hear about corporate culture in less cutthroat economies. Given how much of managerial BS is about making sure your underlings don't get fired, just making it harder to fire people in the first place would do a lot to remove that incentive.
I worked for a Norwegian Cooperative and it had the most toxic corporate culture and management practices of any company I have ever worked for which included US fortune 500 companies, and it was not particularly close.
I'm the author. I've largely worked in places where firing people is next to impossible, and my colleagues usually think the opposite - in contexts where firing people is possible, the people who lie perpetually should gradually get eliminated. It's hard to quantify which setup has it worse, but tweaking the 'easy to fire people' dial seems like it either does nothing, or needs some other changes alongside it.

I'm still open to the possibility that large enterprises just tend to become terrible, and that's that.

Its easy to see why dictators end up surrounding themselves with yes men and become detached from reality, and make catastrophic decisions.

If bad news is punished, then truth will stop travelling up the chain. Most managers want fewer issues, so naturally even if they say they appreciate honest feedback, their behavior which is closely watched by their subordinates, will indicate they in fact resented the additional headache an issue caused.

There once was a new director giving a presentation in an 'all hands' quarterly meeting about how bad our enterprise stability was. He was absolutely right. If we had 3 of 5 weekdays where all major systems ran acceptably, it was a good week. End users hated IT. You could see half the room nodding in agreement. Finally, us minions would be permitted to fix some things.

Wrong. He was fired and gone the week after. Real advances came from a director a few years later, who started with a 'we're doing good but can do even better' all hands. His slides showed nice green monitoring dashboards with a few yellow lights, even if '3 working days in a workweek' was still very much a fact. Change was very very slow and gradual, but at least it happened.

Very similar to the lesson I had taken away when writing the article. The first director you mentioned was essentially making the same mistake myself and many others make - we think that pointing out the problems honestly will allow us to justify spending resources on fixing them.

The seemingly correct way to handle this is to lie about the current state of things and push for a change anyway. This is counterintuitive to the sane, because things being good means that there's less pressure to change them. The secret sauce evidently lies in agreeing everything is good so that all those involved can agree to your follow-up proposal to fix the obviously bad system without looking like failures themselves.

So the next question is, if change is sufficiently slow (and assuming that you care about whether your work has an impact somewhere), is it worth sticking around? You have to lie a fair bit, which is distasteful, and the time it takes to replace one terrible database could take up 2-3 years of your life. But someone presumably has to do it, and if all the competent people leave, then it'll never get better. Still figuring this out myself.

The article is entertaining to read, but what did you actually learn from your talk with upper management? The story feels so open ended.
Thanks for reading, and I'm happy you found it entertaining.

Firstly, that watching senior management for signs that they know if things are bad, or if they believe their own stories, is a waste of time. Competent managers who want to do well by their employees and grifters behave in largely the same way when talking to the lower ranks.

Secondly, pointing out things that are obviously problems in honest language can be unhelpful to the ultimate strategy of a competent manager. "This project was a failure", while seemingly a way to draw attention to what needs to be improved, may make it more likely for the next project to be a failure.

Thirdly, large organisations may require you to lie frequently if you want to improve things (or at least, not contest lies, which seems to be functionally the same thing).

And yes, if it seems open-ended, that's because I'm not sure if how many clear lessons there were. There are at least a few, namely around the utility of pretending things are okay. But the big questions seem intensely personal. The ones I'm asking myself are, now that I know what the strategy is to improve things:

1. Am I willing to lie for years if it means actual progress?

2. How can I tell when I'm working for a good person when not every organisation is going to have someone that tells me what's really happening in senior management?

3. Is it worth the hassle of getting promoted any higher if this is what good work at that level requires? At the moment, I can at least stick to dishonesty through silence when someone says something I know isn't true. One or two levels up and I'll have to fabricate my own success stories.

4. Is there a way to be a senior manager or executive that can be honest and still see results? Some certainly lie less than others, but the correlation to their success is obfuscated by sheer dumb luck, social skills, etc.

EDIT: And you know what, 5. Is this all just some absolutely bogus justification for collecting a ton of money for not producing anything meaningful? That's an option too.

Thank you very much for taking the time to provide us with this elaborate answer. Though I think there's truth to your skeptical view and tentative conclusions, I believe a more nuanced theory would be closer to reality. 1. Indeed management needs to lie regularly. Probably after a while they will consider them coloured white more easily. 2. You can't. It can be compared to donating to charity, you're never sure if it is well spent. 3. If you already are holding horses to not lie at your current function class, probably it is better to leave than to make promotion. Also, not all companies are the same, some are based on a piramid of lies, other much less so. After being part of different types of organizations, I can safely conclude. 4. Complete honesty is a utopian take. Compare it to honesty in a relationship, sometimes it is better to remain silent, even if you vowed to the contrary. 5. For some, for sure. For most, it is more about power and recognition. That does not nedd be a bad thing.

As a tentative conclusion, to me it is very clear it would be good for your health to look out for another employer. You will see that there is a huge difference between organisations. Your grim outlook will brighten up, I can almost guarantee.

Very much the conclusions I had reached myself over the past few days, where it seems that some degree of dishonesty is necessary and a lot of it depends on the people you're working with (I guess we should be nuanced by default).

You're right though, I've been doing this after finding an employer that has much happier staff than most I've worked at, on a team that actually accomplishes complex tasks. It was a massive improvement to my mental health (i.e, your advice is good), but ultimately, my work is still largely wasted due to organizational issues. I don't consider this outlook terribly grim. I'm always free to pick up another career or start my own business, and I think it's less upsetting to realize that some of the people lying at least have good motivations.

I think 2. is the crux of the matter - if you can't be sure it is time well-spent, it makes a lot of sense to exit structures where that is the case, assuming two things. One being that you highly value your work producing something (as opposed to say, not having much stress at work) and two being that you believe you can reasonably find better work.

On the latter point, as I was discussing with a friend who is quite senior the other day, it depends entirely on whether you've given up on finding a truly impactful/happy workplace. Many of my friends in tech have gone for the latter, and are simply trying to get their salaries high enough to retire ASAP. Some smaller group have been working hard to transform faulty organizations with mixed results. I have friends outside of tech who have no such qualms, and have happily found roles where they know they're having a positive social impact, earn decently, and manage their own time (and being their own manager seems to be an effective antidote to needing to lie - perhaps there's some interface with a customer where they might need to stretch the truth a bit, but it's not like book store owners and barbers are walking around spouting off garbage all day).

In any case, I very much appreciate your thoughts!