If you do it right, being willing to ask questions of those higher up, like said CEO, is how you get noticed, on their radar, as someone potentially worth watching and investing in and promoting in the future. A secure CEO in a healthy culture is likely to take it as a good sign that employees are aware, intelligent, and paying attention enough to ask clear, well-formed questions.
But if you ask a question in a way that offends that particular individual in whatever way, or makes your direct boss look bad to his direct boss (in either of their perceptions), then that can lead to any of those individuals retaliating in various ways, if their personality or position in the hierarchy makes them feel insecure or like that would make them look or feel better. Asking makes you and them socially vulnerable, and being willing to do so shows you're secure in your understanding of how people will react as well as in your own position/role/status.
Since this was a Zoom meeting, the fact that you asked verbally is also in some sense a status claim, that you felt empowered to ask a question in a way that commanded everyone's attention and interrupted the CEO's talk track. It's a power move, or can be seen as such. If you'd written in a public chat channel, you'd have left it up to others when and how to respond. If you'd back-channel messaged someone higher up in your organization, you'd have given them the option to either ignore it, message you back, or ask the question in the style and at the moment they deemed most appropriate.
Or, and this is what I think happened at the math conference example, if your question is insufficiently well-formed, then a large public meeting is the wrong forum in which to ask it, because the answer may (in the opinion of those better informed) be a waste of everyone's time. Now of course a great speaker will try to hear that kind of question, figure out the source of the confusion, consider whether similar confusions are likely to be prominent among the audience, and either address that source, or gently let you know there are other factors you're missing that sidestep the question, or else point you in the direction of the info that will resolve your confusion (aka "Come ask me after, and I'll list some papers and textbooks you might want to check out on that.") But a less comfortable and capable speaker won't know to or know how to do that, and might shut you down, or get flustered.
Two other examples:
Some forums have a cultural expectation that the option to ask questions is in some sense not real, or not intended to be used, even when it looks like it should be. A colleague of mine was once asked to be on an expert panel in Korea, and asked a fellow panelist a detailed question; he was later told that was a major faux pas, because panels in that context are scripted and no one asks real questions in real time. He got a pass because he was an American and no one had thought to tell him that expectation, but it did interfere with his ability to network at that event and he didn't get invited back.
In a small upper-level college or grad school class, you're supposed to ask detailed questions. If you don't, or can't, you're probably not paying enough attention. But in an intro class of 800 students in a big lecture hall, the lecturer is often going to be pressed for time, and they'd never get through everything if students all felt free to raise questions; the proper time to do that is in office hours or a recitation with the professor or a TA. If the question is important or a lot of people ask something similar, it's their job to filter it up to mention in a future lecture.
1Yeah, there are two different cultures, and it is important to know which one is at your job. For some people, following this advice could cost them their jobs.
I play Go (an Asian board game you can think of as being like chess) at a local club in the city. The rules of hierarchy there are something like “if Joe is much better than Gary, Joe can say Gary’s moves are wrong whenever he wants, and is allowed to launch into a short speech about why Gary’s mistake is such a major mistake.” (There are more cultural norms than that, and Go players reading this will find that a poor description, but for those outside of the culture, it’s close enough). On the other hand, when a weaker player thinks a stronger player’s move is weird, they’ll be very humble in their asking why the move is good. This is the opposite of the situation in corporate!
This is exactly the situation in (Asian) corporate, which is where I spent the first few years of my career at three different employers. In fact, at my first employer (a giant MNC headquartered in my country) juniors were expected to essentially shut up and do as we were told; the mere prospect of clarifying what a very senior person meant was terrifying for most. And at least in the Asian corporate contexts where I worked, what AnthonyC said is correct:
... the fact that you asked verbally is also in some sense a status claim, that you felt empowered to ask a question in a way that commanded everyone's attention and interrupted the CEO's talk track. It's a power move, or can be seen as such.
Given this, when I read what you said here
Back to asking tough questions of the CEO in a giant meeting: he is so powerful - so above me - that I know I can’t threaten him, he knows I can’t threaten him, everybody watching knows I can’t threaten him, and everybody knows that everybody knows this. Boldness has little to do with me asking him a hard question - if you view hierarchy and position how I do, it’s one of the least dangerous group situations in which to ask such a question!
I thought "but he, the CEO, can definitely threaten you. Is the OP not worried at all about this?"
At my first employer, my boss's boss (who everyone in the entire department loved) was fired by his boss (who everyone hated) for repeatedly questioning the latter's decisions (which everyone agreed weren't good) in meetings, in front of others. This happened a month into my tenure, and was quite the introduction to corporate not being college. I have similar stories from my second and third employer, if not quite as extreme.
I'm guessing this ultimately boils down to corporate culture differences.
I am not exactly sure why this difference - a total inversion! -
The boxing and corporate situations don't seem that different to me. In both cases, the higher ups are providing direction and the people lower down are allowed to ask questions -- but might get in trouble for trying to challenge those higher up.
In the situation where you describe talking to a senior statistician, "Why'd you use the mean instead of the median?" sounds a whole lot like "Why don't we stand like this instead?" in a boxing gym. Those are both "Hey expert who is deservedly above me, please enlighten me", and both work. If you say to your coach "You're wrong, this stance is better", that sounds more like "Really, you should be taking direction from me because I know better than you". If instead, you were to tell the senior statistician "You're wrong, in this case the mean is better" in that same tone, I could see him being shocked and annoyed with your arrogance. Especially if you try to condescendingly explain stats 101 considerations that he obviously has taken into account.
I asked the speaker - a mathematics professor I didn’t know - a direct question. He took it poorly, and rejected my question with a cutting remark [...] Part of the problem is that it’s just too easy for the senior. Imagine an undergrad, giving a math talk, trying to do the same thing to a mathematics professor in the audience who asked a question. Be as cutting as you want - nobody is going to laugh at the mathematics professor!
Okay, I think I see where the confusion is coming from now. You seem to be assuming that status markers like position as a professor accurately track actual ability/knowledge that supposedly justifies this position. If you have an bright undergrad and a math professor who doesn't know enough math to be respected as a math professor, then the undergrad's position doesn't stop him from being able to expose the professor as a fraud. Imagine that situation again, where the undergraduate's criticisms are spot on and the professor can't address the question without exposing the fact that they don't actually know math.
This stands out to me pretty strongly because as an undergrad I never shied away from pointing out where my professors made mistakes, and I've had it go both ways. My physics professors actually knew physics, and as a results were always secure. On the other hand, my philosophy of science professor didn't actually know philosophy of science, so when tried to roll me over by posturing I could just keep poking holes until he was visibly fighting back tears and he explicitly asked me to stop correcting him.
Questions of “who is better” in Boxing can be resolved by spending three minutes in the ring with each other (and Go is the same, except it takes an hour). Skill differences in programming, or god forbid project management, are much harder to measure.
Philosophy is even less concretely resolvable than programming yet that was resolved so I don't think it's a huge deal, but I do think having a three minute definitive test available does help make these dynamics more clear.
In jiu jitsu, for example, you're supposed to be nice to the lower belts but you can never offend them as an upper belt beating them up. Nor do you have anything to worry about when rolling with an upper belt that can mop the mat with you at any time they want.
But when a lower belt can demonstrate superiority over an upper belt, that's when things get tense. That's why jiu jitsu people can sometimes be weird about strength/quickness/wrestlers/leg locks. Any time a white belt can beat a brown belt, the brown belt has to find a way to square that with their social position -- and sometimes that's tough.
I think the bigger difference is who pays for poor performance. If you're my boxing student, then your poor performance just means you get punched in the face. So if I'm criticizing your actions I'm just trying to help you achieve your goals of not getting punched in the face. If you're my employee then your performance hurts my bottom line, and you don't feel it unless I take action to make you. So if I'm criticizing your actions it's because if affects me, and I'm probably going to do something to make sure it affects you -- so you know there's pressure to do better or else risk getting fired.
So I realized Amad’s comment obsession was probably a defense against this dynamic - “I have to say something to my juniors when I see them”.
I think there's a bit of a trap here where, because Amad is known for always making a comment whenever he ends up next to an employee, if he then doesn't make a comment next to someone, it feels like a deliberate insult.
That said, I see the same behavior from US tech leadership pretty broadly, so I think the incentive to say something friendly in the elevator is pretty strong to start (norms of equality, first name basis, etc. in tech), and then once you start doing that you have to always do it to avoid insult.
I like this post. But I think it is somewhat common that the CEO can often feel insecure despite being all powerful and cannot be threatened by you.
Case Study: Elon Musk and disgruntled Twitter Engineer
Elon Musk is the majority share holder (along side with his consortium) of twitter, yet he is left flustered by an engineer asking technical questions in an aggressive manner. He had all the room to be magnanimous, caring and respectful - he could've turned a confrontational situation to one where he concedes that he knows little about the technical stack and turned an enemy into an ally a la Julius Caesar style. Yet, after mumbling for a bit, he just calls that person a jackass and removes him from the call. In his world, face is extremely important and he just thinks very little of the existing twitter engineers and their competency independent from truth.
The world of public opinion and perception of power is a funny thing. I think for many CEOs who have built their personal understanding of themselves around their force of will, it is often hard to take any criticism/doubt from their underlings even when they are technically invulnerable - they simply don't want to appear weak to their underlings (whether for true or ill).
That’s an interesting example. The CEO I had in mind while writing this was a buff guy with a very force-of-will kind of character, but he appreciated such questions.
I guess all our examples were non-public, company-only meetings. I don’t know the Musk example you describe, but since we know about it, I’m guessing it was more public? Or was it secretly recorded and leaked later?
My intuition was that it was a semi-public meeting. My memory is hazy but there was a lot of people, and they were on twitter spaces (a mostly “public forum” style audio chatroom). So I don’t think it is a secret per say.
Kinda related: You might enjoy the book The Culture Map by Erin Meyer, e.g. I copied one of her many figures into §1.5.1 here. The book mostly talks about international differences, but subcultural differences (and sub-sub-…-subcultures, like one particular friend group) can vary along the same axes.
You're allowed to ask your CEO "why'd you do X", you're allowed to ask a senior Go player "why'd you do X." They're more similar than different. As for "punching down," yeah, chess/go probably have a lot more serious culture of public critical feedback, you could probably write a thinkpiece just on this, but factors include low ego culture and objectivity of sr->jr feedback.
One difference is with CEO is it's incomplete info. You may be surfacing something they don't know. Another difference is your interests are different. You're telling them they made you unhappy and you're upset about that; that's not really a thing in a board game where the cultural norm is "try to win." But if you really are talking to your CEO like "I know better than you" then you do sound like the novice Go player.
Also "omgz thank you for asking your incisive question" is not necessarily a compliment anymore than "your shoes look comfortable." One explanation is you have a better grasp that publicly punching up is OK and publicly punching down is not OK. Another explanation is they think you're insane, and you already know they're quite passive about critical feedback so that would be in character.
They might have a personal experience with someone above them harming them or somebody else for asking a question or something analogous.
Now and then, at work, we’ll have a CEO on from the megacorp that owns the company I work at. It’s a Zoom meeting with like 300 people, the guy is usually giving a speech that is harmless and nice (if a bit banal), and I’ll turn on my camera and ask a question about something that I feel is not going well.
Invariably, within 10 minutes, I receive messages from coworkers congratulating me on my boldness. You asked him? That question? So brave!
This is always a little strange to me. Of course I feel free to question the CEO!
What really makes me nervous is asking cutting questions to people newer to the company than me, who have less experience, and less position. If I screw up how I ask them a question, and am a little too thoughtless or rude, or imagine I was, I agonize about it for hours, and sometimes days.
This is because of how I view hierarchy. By hierarchy I mean: In any organization, be it a company, a friend group, or a board game meetup, there are people above you and there are people below you. These relative positions depend on differences in experience, skill, social ability, and how long each of you has been in the group. Your position relative to the person you’re talking to determines the kinds of things you can say to them, and how you can say them.
I think the people congratulating me on how bold I was in questioning a CEO have a rule like “In a corporation, you should not question, or seem to disagree with, those above you.” But I have long felt that the opposite rule is the obviously correct one: “Feel free to question those above you without worrying too much about how you come off, but be extremely careful when questioning those below you.” (In group settings. In private, just the two of you, many of these rules disappear).
Maybe it’s easier to see what I mean in a different example. Consider (male) friend groups. When I hang out with my friends, we talk shit to each other constantly. So imagine me, at the bar, in such a group, saying to a friend who’s been in the group for 2 years, “that’s the stupidest fucking thing I’ve ever heard!”. He’ll probably tell me I’m wrong to think so, and also that I’m the most ignorant nobody he’s ever met, and maybe call me ugly too.
Now imagine he’s invited his buddy along, it’s the buddy’s first time hanging out with us, and I tell him what he just said is the stupidest fucking thing I’ve ever heard. This can be really bad. Since he isn’t established - since most of us don’t know him - when I call him stupid, he’s suddenly in danger of being seen as actually being stupider than me and the other guys. And what kind of asshole calls a guy he just met stupid? So he’s probably not going to talk back and call me an idiot, but instead be surprised, hurt, and feel like he doesn’t want to hang out with us (me) next time.
When I’m talking to my friend - my peer in the friend group hierarchy - I can say viciously critical things, and he’ll double it and give it back to me and never think of it again. When I’m talking to the new guy - not yet established, and therefore less sure of his position - a serious insult is taken as a serious insult.
Back to corporate culture. Many in tech have imposter syndrome. They feel like others get things done faster and better than them (and they might be right! they’re less experienced, after all). If a senior statistician, who’s been working with everybody for years and is well-respected, is giving a talk, and I ask him why he used the mean instead of the median or whatever, he knows that whatever his answer is, he’s already so well-respected that he’ll still be socially-just-fine afterward. He can even say “I don’t know, it just felt right”, and people will probably think “lmao, alpha response, and honestly this guy does have great intuition, so he’s probably right”.
But if I ask the same thing to a stats guy one year out of college, and I ask it badly, in a way that puts him on the spot, he might think “agh, if I mess this answer up, people will think I don’t even know when I should use a median instead of a mean. I can’t believe Maxwell put me in this high-stakes situation in front of all my coworkers!”
Such questions still must be asked, but when someone is lower than me, I’ll take pains to phrase it very carefully: “I was wondering - perhaps - I’m not sure - maybe the median might be more appropriate than the mean here? I don’t know why I feel that way, I might be totally off track”
this in contrast to how I’d ask the same question to the senior statistician: “I worry the mean is a mistake here - a median feels like a better measure when the distribution is like this.”
It’s a question of how secure the person feels. An example of security-in-position: At work some groups do daily status updates. An intern I work with was recently laughing about how in these update meetings, he’ll describe everything he’s doing, partly in order to demonstrate what he’s been up to since yesterday, and when it’s the senior guys’ turn, the seniors will just be like “no updates from me”, without explanation. The senior guys know everybody knows they deliver, so they don’t bother trying to prove it every day. The new guy feels like he has to prove he’s working.
Back to asking tough questions of the CEO in a giant meeting: he is so powerful - so above me - that I know I can’t threaten him, he knows I can’t threaten him, everybody watching knows I can’t threaten him, and everybody knows that everybody knows this. Boldness has little to do with me asking him a hard question - if you view hierarchy and position how I do, it’s one of the least dangerous group situations in which to ask such a question!
The pressures on people higher-up in a corporation are interesting. At my old job, we had a director - in charge of our team of like 50 or 100 people - who would always make some kind of comment when he found himself up in the elevator with me or my coworkers. He was not great at thinking up these comments and would often default to saying something about your hair or clothes, so people would laugh about their awkward elevator ride with Amad where he asked if they got a haircut, even though their hair hadn’t changed at all.
I thought this was a quirky thing about a weird guy, until one day, a guy I worked with - call him David - started talking about Amad: “I rode the elevator with that dude and he didn’t say a word to me. It was like he was ignoring me. I can’t believe that guy - what did I do to him??” He was pissed.
This would never happen with a peer! If I’d rode the elevator with David and not said a word, he would have thought I was having a bad day and asked me later if I was alright. But when someone far above him in the hierarchy did the same thing, David saw it as a major insult. So I realized Amad’s comment obsession was probably a defense against this dynamic - “I have to say something to my juniors when I see them”.
A naive view of hierarchy is “people higher up get everything, and those below them have to bow and scrape and avoid offending them”. But this isn’t right. People higher up in the hierarchy often have as many responsibilities to their juniors as the juniors have to the seniors, but those responsibilities are different. (and if you’ve never been a senior in an organization, you might not realize this).
Another example: in Korea, age differences are a big deal, and there is even a different conjugation scheme in their grammar for when a junior is addressing a senior. There is a Korean New Year’s ritual where the young person stands in front of their grandma, and the grandma tells them encouraging things like
“why haven’t you been promoted recently?”
“why aren’t you married yet??”
“work harder!”
The junior just has to sort of put up with this. So - sucks for the junior, right, should’ve thought of that before you went and got yourself a grandmother. But they put up with this because, after this pep talk, the grandma gives them money. I don’t know enough to say for sure, but I imagine if the grandma did this berating and then walked away without giving the money, this would be a social mistake, violating the ritual. She probably has to give the money! No choice! So: juniors and seniors both have responsibilities to the other, but those responsibilities are very different.
In college I went to a math talk once, and in the middle of it, when I found myself badly confused, I asked the speaker - a mathematics professor I didn’t know - a direct question. He took it poorly, and rejected my question with a cutting remark, and many in the audience laughed.
Now… like… okay… I’m biased here. (Suuuuper biased. That bastard!). But I think this is a good example of a senior violating his responsibilities to his juniors. Undergraduates in your audience should be treated gently, and given some forgiveness when they phrase a question indelicately. Using your position to roll over him in front of everybody is a mistake of hierarchical responsibility.
Part of the problem is that it’s just too easy for the senior. Imagine an undergrad, giving a math talk, trying to do the same thing to a mathematics professor in the audience who asked a question. Be as cutting as you want - nobody is going to laugh at the mathematics professor! Awkward silence! Unhappy looks from the crowd! And thirty more minutes to go, with an audience who now thinks you’re a jackass! It doesn’t work.
Different groups have different hierarchy rules. I play Go (an Asian board game you can think of as being like chess) at a local club in the city. The rules of hierarchy there are something like “if Joe is much better than Gary, Joe can say Gary’s moves are wrong whenever he wants, and is allowed to launch into a short speech about why Gary’s mistake is such a major mistake.” (There are more cultural norms than that, and Go players reading this will find that a poor description, but for those outside of the culture, it’s close enough). On the other hand, when a weaker player thinks a stronger player’s move is weird, they’ll be very humble in their asking why the move is good. This is the opposite of the situation in corporate!
The same thing happens in the boxing gym. If you say a new boxer’s stance is wrong, he’ll adjust and probably thank you. If you say you think what the coach said is wrong, he might kick you out of the gym and tell you to come back tomorrow.
I am not exactly sure why this difference - a total inversion! - in how you talk to your seniors and juniors exists, between Go and Boxing on the one hand, and corporate on the other. Some ways in which they differ:
But I can’t quite pull these items together into a convincing story about why there’s such a difference between those cultures, when it comes to how you can talk to who.