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.

(Now… everybody has the experience of being in a talk where there’s that one guy in the audience asking things barely related to the topic at hand, without consideration for what the audience is there to hear, and asking it over and over again, even when the speaker looks increasingly unhappy with each of their questions. This is a case where it’s appropriate for the speaker to be like “talk to me afterwards - my focus is this specific topic”. And if that doesn’t deter them, the speaker should start rolling them over with their position as speaker. But this should be reserved for extreme cases. With great power…)

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!

(This is not to say seniors at Go club have no responsibilities to their juniors. A strong player who never gives any teaching games to their juniors is probably making a social mistake. As a senior, maybe 1/5 of my time is spent teaching players much weaker than me. So maybe the hierarchical responsibility split there looks something like: “A stronger player will be willing to spend a lot of time teaching you, but in exchange, you need to be easy to teach, and polite about it.”)

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:

• Go and Boxing are 90%+ male, while corporate cultures have more women. A strong sense of hierarchy is more of a male trait, so maybe it manifests one way in all-male groups, but less in mixed-gender spaces? But this doesn’t explain why I need to be more careful when talking to the new guy in the friend group at the bar.
• 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.

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.