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> I tell my engineers that if they know I’m about to do something stupid, they have to tell me, so I don’t do it.

My career advice: If your boss tells you to not be afraid to disagree with them, don't do it. It's a trap. I've been suckered into this one numerous times, and there was not a single occasion where it didn't backfire. People like to think of themselves as being that enlightened, but rarely (in my personal experience: never) are.




And the worse are often those that brag about how "open to criticism" they are.

It's a trap for literally-minded/low-EQ people.

There are those that are indeed open to criticism, but those are almost never the one's that are gonna tell you about how open they are. Rather they are the ones that will actively engage in such discussions and technical arguments with you, and even enjoy it. You wont be "invited to criticize" them, you will be criticizing stuff and arguing together all the time, as if you're peers.


This is a bad attitude, and doesn't acknowledge the importance of collaboration.

Now in a given position you may not have appropriate communications skills (or missed a memo, intent, constraint) but if you keep your criticisms objective and organized, this probably isn't a trap.

Leveraging some hard to address criticism in a public setting, too late, and viciously is very different from a timely, short, semi-private email. It's rule 1 of communication: know your audience.


I don't see this view as being an indicator of a bad attitude. Actions are louder than words, and that is acknowledged in their post.

(That said, I do view the implied motive as a negative. The intent of open communication may be honest, while the actions may not reflect it.)


> It's a trap for literally-minded/low-EQ people.

So many things in everyday communication are just this. Sometimes I think politeness is overrated: 'Maybe later' when you mean 'never' still confuses me. You can let someone down gently whilst being unambiguous.


Also, sadly:

"HR is your enemy. The role of HR is to protect the CEO and his team when they do something unspeakable and to smooth the way when firing people."


HR is not your friend, but to say they are your enemy is overly reductive.

The job of HR is to protect the company, which often means ensuring things are done by the book, or that enough compensation is given that it is better to take the money than argue.

They aren't your friend, but they aren't your bosses friend either, and if your boss is trying to do something that will get the company in trouble then you may find that you and HR are on the same side. I've seen this happen when a friend's manager was trying to put somebody on a PIP without a good reason and it did not end well for the manager.


> They aren't your friend, but they aren't your bosses friend either

To be clear, sometimes they are close friends with your boss. Sometimes they are also the corporate lawyer.

I've encountered this situation in the past.


That's true, though I think statistically, the higher up the food chain you are, the more likely HR is going to be your friend. Leadership tends to band together and influence HR policy to favor managers over do-ers.


I feel like a lot of people I’ve known who work in HR are very much into the high school popular kids clique mentality. Not all. I’ve known very wonderful souls who work in HR but it attracts “people person” types who seem to thrive on gossip and secret communications not unlike a bunch of high school girls.


HR in large firms is the “people risk department”. People introduce all sorts of risk to a company. They sometimes don’t perform, they have bad behaviours that cause secondary effects/blowback on the company (you didn’t protect me from employee X with bad behaviour Y causing me problem Z).


To be clear, the official role of HR is to protect the company, which objectives are defined by the owners, represented by the board, not the CEO. Goals of the CEO and the board may align, but they may not, in that latter case a non-corrupt HR function sides with the board. At the end of the day, the CEO is just another employee.


>which objectives are defined by the owners, represented by the board, not the CEO

You'd be surprised how non-involved the board could be.

>At the end of the day, the CEO is just another employee.

In many cases they can also have a controlling share of the company, and most of their board and C-level be their pals and picks, so there's that.


When our company hired HR, a lot improved. They were not my friends, but they did a much better administrative job then the chaos previously.


It works with good bosses. You will know pretty quickly if they're good by how they act. I've told good bosses what they need to hear and it's gone down well. Mind, the good ones are not common; the bad do predominate.


It's highly culturally dependent too. I found that in Singapore nobody with authority tolerated it, whereas authority in the US and UK was more tolerant.

Even more than culture and the nature of the boss, though, I think how many other people hear of the criticism. The optimal number is 0.

Bosses who don't have anything to prove tend to be more receptive, too. Vint squarely falls in that category. I'm not sure he'd be as receptive if he was at the tail end of an unimpressive middle management career, being challenged by some younger employees.


> It's highly culturally dependent too. I found that in Singapore nobody with authority tolerated it, whereas authority in the US and UK was more tolerant.

That's interesting. I think I would actually do better in such a culture. I actually have no problem at all respecting "chain of command" if that's part of some body of rules that are clearly stated or at least culturally implied. What I tend to have a problem with is power structures that are based on a web of humans manipulating each other while claiming they're not.

If you folks could help me brainstorm ideas for companies, geographies, social spheres and such, where strong hierarchies and little politics and psychological-level human manipulation is part of the culture, I'd certainly appreciate it. Some place where no one will ever say to me again: "Feel free to voice your disagreement. You're safe." I'm serious, I think it would help me out.

I'm a pacifist and strong believer in civil rights though, so anything in the armed forces or intelligence community is out.


They'd still protest that they're open to criticism of course. There were, if anything, more idiotic mind games centered around enforcing power structures. There was a rigid implied racial hierarchy too.

You're asking for a geographical location or a company where humans dont act human. I dont think it exists.


> There were, if anything, more idiotic mind games centered around enforcing power structures. There was a rigid implied racial hierarchy too.

Oh, I misunderstood you then.


> ideas for companies, geographies, social spheres and such, where strong hierarchies and little politics and psychological-level human manipulation is part of the culture

Where there are humans, there is politics and psychological manipulation. In strong bureaucracies, this happens at the level of dictating what the rules are and how they should be interpreted, as well as in squabbling over titles and fiefdoms, instead of in each interaction around the actual work and resource allocation. So in some sense, it's actually worse!

----

Unrelated to the observation above, I struggle squaring the idea of a pacifist that prefers hierarchies of dominance, since they're almost always founded on a thickly veiled threat of violence. (Even in a strict bureaucracy, you can hear the walls whisper "fill this form, or else...")


> I'm a pacifist

“Everyone has a plan until they get punched in the mouth.” - Mike Tyson


As far as opinions and feedback you are in a advisory role to your boss. Meaning you can disagree with him but ultimately the decision is his to make because he is responsible for the outcome. So you are free to disagree, but you are not free to insist and press the issue.

Now what happens when you disagree so hard on an issue that you simply can't accept your boss's position? First make sure it's really a make or break situation an not just a useless hill to die on. Then just state the fact as calmly as possible.

If telling your boss he's about to do something stupid means you will no longer be working working with him that's a good thing too. Not even close to a trap. If the stupid thing is not compatible with your principles (happened to me while working for a casino) then you should move on to something else. And if the boss is a proud idiot who can't take no criticism (I don't remember meeting one in 25 years) then you don't want to work with him either.

So no matter what, speak your mind. Even if you do it in a horrible way (I suspect this is the case with the parent poster), or you yourself are wrong, it is still better that you open your mouth and receive outside feedback than to develop an ugly hidden persona.


I think it depends a lot on your approach. Raising some concerns in a one-on-one and allowing them to change course or not will go over better than just shooting their idea down in a big meeting with many people.


I've tried many times, with many different approaches and many different people over the course of a 20-year career.

The variation in outcomes was absolutely zero.

To anyone who wants to believe that bosses are fundamentally capable of tolerating independent thought among their underlings, I would recommend the book "Disciplined Minds" by Jeff Schmidt [1].

[1] https://www.amazon.com/Disciplined-Minds-Critical-Profession...


I guess theoretically I could have had a career that's gone even better than the one I have had, but I haven't had any real problems with my approach so I think I'll stick with it.


Were you trying to say "My success proves me right"?

Because the other reading is: You're not good at independent thinking, therefore you've never had those independent thoughts that made your bosses dislike you, and that explains why you had a good career. So, your success proves me right.

Now enter into some introspection. Do you dislike me, now that I've suggested this? Or do I get brownie points from you for being an independent thinker and voicing my disagreement?

Because I genuinely believe that there's a valid and interesting thought in what I just said that we can all learn from. Also: If you were my boss, I would have just killed my career prospects.


If your approach is personal insult then I can see why it isn’t that well received. To answer your question, though, I was saying I feel I have had success raising disagreements and didn’t ask for or particularly want to read something explaining to me why I should ignore over a decade of my own experience. Hey maybe I’m just really dull like you suggest.


If you really want to call in the tone police on this: My initial comment was reacting to the article saying "This doesn't match my experience" in which I've simultaneously made myself vulnerable to ad-hominem attack because it was implying that my career wasn't going so well. And your response was to step on that vulnerability and say: "Well, take it from someone whose career is going great: If you're the sort of person who has experience X, you're probably the sort of person who would make mistake Y." What do you know about whether I use one-on-ones for voicing disagreements with my bosses versus making them look bad in public?


> your response was to step on that vulnerability and say: "Well, take it from someone whose career is going great: If you're the sort of person who has experience X, you're probably the sort of person who would make mistake Y."

No. No one said that. Don't make up quotes.


I didn’t say any of that and that was just one illustrative example of how your method of delivery can have a big influence on whether your suggestions are received as well intentioned or hostile. If you are this prone to seeing attempts to offend you where none are there and responding in kind then I do think we’ve found the root of your problem.


FWIW, I think resistance, as hinted at in Disciplined Minds, is a weak basis for an identity. A "truth to power" speaker is only good for certain kinds of truths and certain kinds of power. Its a role that doesn't mean much outside of that; it doesn't hold up in the long run.


I am not the OP, I am not your boss, we are not even in total disagreement, and yet your short comment already rubs me the wrong way.

Maybe your streak of bad results isn't a result of disagreement per se, but of your attitude. If you usually present your disagreement in the same way that you wrote this comment, the I-Win-You-Lose attitude is a good way to needlessly alienate other people.


It's almost as though you're saying that offering contradictory advice to the boss is akin to arguing against the orthodoxy on HN.

Your moderation score is the wages of sin, son.


Yes, bosses, in the end, don't really care. They'll "appreciate" it in their minds (in the manner of a process being completed) but then not do anything with it, because that's not their job. They exist to create confusion and order from it and anyone honest enough to be a Good boss is quickly dethroned.

Thanks for the book recommendation!


I'm a "boss" of people that report to me and I oversee, and I certainly care and appreciate feedback and suggestions and criticism.

But that's where it ends. I am under no obligation to do what this subordinate wants or thinks is best. It isn't a democracy or a decision by committee when we have hierarchical structures in place. You give your best advice, suggestions, opinions and recommendations...and then it's up to the leader to make a decision; wrong or right. That's leadership.


The question is not so much whether you do as you're told by your subordinate but how you handle the "disagree-but-commit" state.

Ideally, the way it should work would be for the boss to say: "Okay, I think the right course of action is X, you think it's Y. We're in disagreement, but because I'm the boss, we'll do X. As you go about doing X, I won't intrude on your sphere of autonomy but will instead trust that you're a professional and will execute on X faithfully. If you frequently disagree with me and you're up for a promotion, I won't hold the disagreements against you. It might even work in your advantage, because we need to increase diversity of thought in management, rather than filling management roles with yes-men."

The way it usually works, in my experience, is: "I want you to do X, but you think you should be doing Y. That makes you a risk, because there's a danger you will sabotage X and execute on Y instead. I'll subject you to extra-close supervision to counteract that risk. When you're up for a promotion and you frequently disagree with me, I will fight your promotion, because if we increase your level of influence, it'll create more work for me, because I'll have to double-check your judgment and countermand your actions as a manager whereever I disagree. Having people in management who aren't yes-men just makes management more work, and we don't need that."

If your boss is of the latter kind and you disagree with them, then it's a mistake for you to ever "show your hand" to them by telling them about it. It's then better to just keep your mouth shut, and do as you're told. -- And this "shut your mouth and do as you're told" is my career advice for young people. This makes me look bad, and reflects poorly on the companies I've worked for. But that's the difference between career advice and hagiography.


I think the way the disagreements are voiced and handled by the disagreer matter a lot in which of those two responses you would receive.

Also, I think it would matter a lot on how X vs Y turned out later. I.e. the difference between always disagreeing but also always getting it wrong. Or sometimes disagreeing but then getting it right and handling being right gracefully.

In my experience "shut your mouth and do as you're told" people are appreciated, more than employees who just disagree to disagree. However, the employees who voice their opinions, are able to articulate their stance and know when it is important to budge or when not to budge are always valued higher.


> how X vs Y turned out

There's a cool idea that's related to that which also comes up in Ray Dalio's "Principles", which is to keep a log and do some kind of bean counting on who turns out to be right vs. wrong in situations of disagreements. The idea is that people who frequently turn out to be right should be given more influence. It's also a question that has been on my mind a lot in reflecting upon my career.

My observation has been that people have a very acute awareness of who the people are who they frequently find themselves disagreeing with versus who the people are who they seldom disagree with. And they have terrible memory when it comes to remembering what those disagreements were even about, let alone who ended up being right. If you are the "wronged party" in that dynamic, then bringing up your track record of disagreeing and being right is one of the worst things you can do.

People who disagree just for the sake of disagreeing are, in my mind, a myth, especially in the workplace where the stakes are high and disagreement tends to go hand-in-hand with conflict and power struggle and is therefore uncomfortable territory. Nobody would put themselves through that discomfort for nothing.


> People who disagree just for the sake of disagreeing are, in my mind, a myth, especially in the workplace where the stakes are high and disagreement tends to go hand-in-hand with conflict and power struggle and is therefore uncomfortable territory. Nobody would put themselves through that discomfort for nothing.

Maybe so, but the persistence of this myth among people who work suggests my original point about the delivery of the message as important has some truth to it, as some people are perceived this way.


What I meant was that there's a very marked disconnect between being a boss and being an employee. Most people are often both. Yet, when one's a boss, one forgets what it's like for the employee on the other end, and vice versa.

Work by / working with people that can bridge this gap is what startup culture (in tech) used to be all about.


I think your advice is a safe assumption that has some truth to it. For a rare counter-example, there's this fascinating article about a strongly opinionated minister who disagreed with the Tang Dynasty Emperor:

https://en.wikipedia.org/wiki/Wei_Zheng#Emperor_Taizong's_re...


Yeah it could be with some managers. But, I've met Vint, asked him to sign a copy of his TCP/IP paper and even asked him if he'd get Robert Kan's signature and he did it. He's an incredibly nice and sincere human and very self aware. I would trust Vint as a manager.


I've never had a problem doing this

sometimes they don't agree, and that's fine

maybe it's your approach


I think if someone wants that, they need to be under someone else's tree as part of a 'watch dog' / 'watcher' structure.

As far as leader's go, I thought 'we' had this solved with frequently rotated elected presidents. Though maybe not with the current balloting system (better have been proposed, 'path vote' is my current fave). However the political party, or corporate ownership, systems seem to wreck that idea. This might be a spot where least privilege is the best answer.


Weird take. I tell all my employees this, and they teach me a lot in return. Same goes for my relationship with my boss. Maybe it's the way you've interacted with them in the past that has jaded you? It helps to be tactful.




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