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To name some: - "You have enough money you live the rest of your life in idle luxury. You could just go to the beach and never come back. If I had your money,

To name some: - "You have enough money you live the rest of your life in idle luxury. You could just go to the beach and never come back. If I had your money, that's what I would do. Why the heck are you still working?" (this is incredibly assuming) - "Will you share slides from the last board meeting?" (I think if you need this information you'd probably be on the board) - "Where do you see yourself in 5 years?" (this one made me chuckle but it's also insanely arrogant) - "When I leave here in 2-3 years, will it be because of the people, or because I haven't gotten a raise and/or promotion?" (someone who states up front that they will for a fact leave after a short period will not get hired by me. The tone also implies that he will leave because something bad will inevitably happen) - "What keeps you up at night?" (IDK, seems way too personal, none of the employee's business)

notjustanymike 8y ago
Totally agree with you on those. They're a great way to tank your chances at the final interview, on the basis of "not a good culture fit"
johnwheeler 8y ago
They’re not bad. They’re similar to questions asked by employers to candidates. The fact that you find them arrogant, to me, says that you hold yourself in higher regard than you hold your employees; that you feel superior in some way. If someone asked you to share some board slides, you could simply explain they’re company confidential then try to tease out what information they’re after with follow up questions. Or maybe consider that they care enough about the business (or want to appear to) to ask questions like that. Why is asking where you see yourself in 5 years arrogant? I own my own profitable company, no vc funding. I’ve never been asked that, but if I were, I’d be delighted to give an answer. Totally reasonable question. If someone asked me why I wasn’t relaxing on the beach, I’d explain to them that it gets old. Sitting idle is a terrible way to spend time, although it might not appear so if you haven’t had the experience. I’d tell them that I hope to get them to a place one day where they could see just how overrated it is and judge for themselves.
- threatofrain 8y ago
  Arrogance is about overreaching your station. What that means to people depends on how much and why they value those boundaries and violations. What should be the emotional response to that? Does arrogance arouse anger?
- nsgi 8y ago
  #1 and #4 read as trying to catch the employer out. If an employer asked me interview questions like that I would view it as a red flag. It's one thing to be challenging, it's another to sound like you're on a power trip.
awillen 8y ago
Every company I've worked at has shared board slides (usually slimmed down for time and to remove any personnel info, but with all the key financial info there). Transparency is a huge deal for me and tells me a lot about the value of the founders. Also, "if you need this information you'd probably be on the board" is just wrong - if you're compensating someone in equity, they need to understand the financials of the business to value your offer. "What keeps you up at night" is also a very common question... obviously within the context of an interview, the candidate isn't asking about problems with your marriage or your health or whatever other personal issue you might be thinking of. Typical answers I've heard are figuring out how to scale, hiring fast while maintaining a high quality bar and moving up market. Knowing what the CEO is concerned about is a totally reasonable and relevant piece of knowledge for picking a company.
- rsweeney21 8y ago
  Sure, you can share that with employees, but not with any person off the street who happens to be interviewing. They most likely haven't signed an NDA.
what-the-grump 8y ago
Seriously? 1. Is a poorly worded "what's your passion" question to the CEO 2. That's a red flag, you can redirect and say minutes are posted ... question to gauge transparency 3. No more arrogant than asking the employee 4. Poorly worded... "how do you plan to keep me here when the market turns in 2-3 years to the next fad" 5. Is a perfectly fine question, not asking about your wife Some of these are poorly worded, none of them are out of line. If you are not comfortable answering them speaks to your character greatly.
ghaff 8y ago
I only really disagree with the last one which I think you're taking in the wrong way. It's just a way of asking "What do you see as the real or existential challenges to the business?" Yeah, maybe it's a silly way to ask that taken literally but it's a common formulation. And that seems like an absolutely valid question. The rest would be real turnoffs to me.
fma 8y ago
I'd think the "What keeps you up at night" is in reference to what difficult problems are you encountering at work. I'd asked my previous CTO this question (when I was working for him already) and his response was "Finding the best people to hire" which I think is a fair response. He was trying to get me to refer people to join.
ummonk 8y ago
Okay yeah questions 1 and especially 4 seem like really hostile questions. On the other hand, asking for slides from the last board meeting is a good request from someone deciding whether to accept an offer, and "where do you see yourself in 5 years" and "what keeps you up at night" are both perfectly reasonable questions about how you view the potential development of your venture.
rdiddly 8y ago
"You have enough money you live the rest of your life in idle luxury. You could just go to the beach and never come back. If I had your money, that's what I would do. Why the heck are you still working?" A wordy, trying-to-be-cute way of saying "What motivates you to keep working?" or "Why do you keep working instead of retiring?" which is a pretty good question. "Will you share slides from the last board meeting?" A bit presumptuous maybe, but not quite into the realm of arrogance. I would verbally summarize the slides. "Where do you see yourself in 5 years?" Nothing arrogant about this one; a CEO should have a 5-year plan at least. Although this particular way of asking it has been used verbatim enough times since I first heard it in the 80s, that it now shuts down my mind immediately due to its blandly mind-numbing cliché quality. Which doesn't speak to the candidate's amazing creativity. Don't ask it this way if you're sitting with a Gen-Xer probably. "When I leave here in 2-3 years, will it be because of the people, or because I haven't gotten a raise and/or promotion?" I mean, you tell me. Are you more "I have a terrible personality and poor social skills" or are you more "I get childishly petulant when I don't get promotions and raises I think I deserve?" Both these things are within your control... and so is your exit from the company for that matter. If you were mature enough to take responsibility that is. Terrible question, don't ever say this. It conveys four negative things about you, all of which I would assume are true. "What keeps you up at night?" The question is again trying to be all folksy and cute bygoshdarn bygolly, but at its heart it's a pretty good question. In other words right now what's your biggest obstacle / thing you're worried about / thing that's giving you a pain. At work mind you... not your personal life!
Xelbair 8y ago
First one is worded arrogantly i agree, but the core idea of the question is very important. It is a variation of "what drives you? what motivates you?". It's purpose is to find a CEO that doesn't want to just sell out and cash in for himself - but to grow the company. Slides from board meeting are about transparency, i do not want to work at organization that is not transparent about fiances(and especially not at one which has high profits, but very volatile cash reserves). If it gets deflected, but a summary is provided ,it isn't a red flag - it means that employees potentially have access to this data. if you think asking about your future plans arrogant, why are you asking such questions to employees? this is a legitimate question about where you want to take this company towards. In most western tech jobs - changing job after a year is norm - not an exception. over here it is frowned upon, but 2-3 years is a long enough time in most cases. And there are two main cases of job hopping: increase in salary is way more significant than any rise given; toxic workplace; Last one isn't personal, but it has implied context of company itself. what are problems that you want to fix, and potential threats. those questions are even more important if company is paying in equity. I wouldn't want to work there if i didn't get the answer at least to majority of them. It would be a huge red flag - or i would assume that equity is 100% worthless when comparing compensations between offers. Relationships of power shifted - there is abundance of jobs, and scarcity of good developers. Quite frankly - there are plenty of bad companies, and few good ones - just like with candidates. You would hate to bring in a bad horrible person in. We would hate to invest time and effort into useless endeavor.

notjustanymike 8y ago

Totally agree with you on those. They're a great way to tank your chances at the final interview, on the basis of "not a good culture fit"

johnwheeler 8y ago

They’re not bad. They’re similar to questions asked by employers to candidates. The fact that you find them arrogant, to me, says that you hold yourself in higher regard than you hold your employees; that you feel superior in some way. If someone asked you to share some board slides, you could simply explain they’re company confidential then try to tease out what information they’re after with follow up questions. Or maybe consider that they care enough about the business (or want to appear to) to ask questions like that. Why is asking where you see yourself in 5 years arrogant? I own my own profitable company, no vc funding. I’ve never been asked that, but if I were, I’d be delighted to give an answer. Totally reasonable question. If someone asked me why I wasn’t relaxing on the beach, I’d explain to them that it gets old. Sitting idle is a terrible way to spend time, although it might not appear so if you haven’t had the experience. I’d tell them that I hope to get them to a place one day where they could see just how overrated it is and judge for themselves.

threatofrain 8y ago
Arrogance is about overreaching your station. What that means to people depends on how much and why they value those boundaries and violations. What should be the emotional response to that? Does arrogance arouse anger?
nsgi 8y ago
#1 and #4 read as trying to catch the employer out. If an employer asked me interview questions like that I would view it as a red flag. It's one thing to be challenging, it's another to sound like you're on a power trip.

awillen 8y ago

Every company I've worked at has shared board slides (usually slimmed down for time and to remove any personnel info, but with all the key financial info there). Transparency is a huge deal for me and tells me a lot about the value of the founders. Also, "if you need this information you'd probably be on the board" is just wrong - if you're compensating someone in equity, they need to understand the financials of the business to value your offer. "What keeps you up at night" is also a very common question... obviously within the context of an interview, the candidate isn't asking about problems with your marriage or your health or whatever other personal issue you might be thinking of. Typical answers I've heard are figuring out how to scale, hiring fast while maintaining a high quality bar and moving up market. Knowing what the CEO is concerned about is a totally reasonable and relevant piece of knowledge for picking a company.

rsweeney21 8y ago
Sure, you can share that with employees, but not with any person off the street who happens to be interviewing. They most likely haven't signed an NDA.

what-the-grump 8y ago

Seriously? 1. Is a poorly worded "what's your passion" question to the CEO 2. That's a red flag, you can redirect and say minutes are posted ... question to gauge transparency 3. No more arrogant than asking the employee 4. Poorly worded... "how do you plan to keep me here when the market turns in 2-3 years to the next fad" 5. Is a perfectly fine question, not asking about your wife Some of these are poorly worded, none of them are out of line. If you are not comfortable answering them speaks to your character greatly.

ghaff 8y ago

I only really disagree with the last one which I think you're taking in the wrong way. It's just a way of asking "What do you see as the real or existential challenges to the business?" Yeah, maybe it's a silly way to ask that taken literally but it's a common formulation. And that seems like an absolutely valid question. The rest would be real turnoffs to me.

fma 8y ago

I'd think the "What keeps you up at night" is in reference to what difficult problems are you encountering at work. I'd asked my previous CTO this question (when I was working for him already) and his response was "Finding the best people to hire" which I think is a fair response. He was trying to get me to refer people to join.

ummonk 8y ago

Okay yeah questions 1 and especially 4 seem like really hostile questions. On the other hand, asking for slides from the last board meeting is a good request from someone deciding whether to accept an offer, and "where do you see yourself in 5 years" and "what keeps you up at night" are both perfectly reasonable questions about how you view the potential development of your venture.

rdiddly 8y ago

"You have enough money you live the rest of your life in idle luxury. You could just go to the beach and never come back. If I had your money, that's what I would do. Why the heck are you still working?" A wordy, trying-to-be-cute way of saying "What motivates you to keep working?" or "Why do you keep working instead of retiring?" which is a pretty good question. "Will you share slides from the last board meeting?" A bit presumptuous maybe, but not quite into the realm of arrogance. I would verbally summarize the slides. "Where do you see yourself in 5 years?" Nothing arrogant about this one; a CEO should have a 5-year plan at least. Although this particular way of asking it has been used verbatim enough times since I first heard it in the 80s, that it now shuts down my mind immediately due to its blandly mind-numbing cliché quality. Which doesn't speak to the candidate's amazing creativity. Don't ask it this way if you're sitting with a Gen-Xer probably. "When I leave here in 2-3 years, will it be because of the people, or because I haven't gotten a raise and/or promotion?" I mean, you tell me. Are you more "I have a terrible personality and poor social skills" or are you more "I get childishly petulant when I don't get promotions and raises I think I deserve?" Both these things are within your control... and so is your exit from the company for that matter. If you were mature enough to take responsibility that is. Terrible question, don't ever say this. It conveys four negative things about you, all of which I would assume are true. "What keeps you up at night?" The question is again trying to be all folksy and cute bygoshdarn bygolly, but at its heart it's a pretty good question. In other words right now what's your biggest obstacle / thing you're worried about / thing that's giving you a pain. At work mind you... not your personal life!

Xelbair 8y ago

First one is worded arrogantly i agree, but the core idea of the question is very important. It is a variation of "what drives you? what motivates you?". It's purpose is to find a CEO that doesn't want to just sell out and cash in for himself - but to grow the company. Slides from board meeting are about transparency, i do not want to work at organization that is not transparent about fiances(and especially not at one which has high profits, but very volatile cash reserves). If it gets deflected, but a summary is provided ,it isn't a red flag - it means that employees potentially have access to this data. if you think asking about your future plans arrogant, why are you asking such questions to employees? this is a legitimate question about where you want to take this company towards. In most western tech jobs - changing job after a year is norm - not an exception. over here it is frowned upon, but 2-3 years is a long enough time in most cases. And there are two main cases of job hopping: increase in salary is way more significant than any rise given; toxic workplace; Last one isn't personal, but it has implied context of company itself. what are problems that you want to fix, and potential threats. those questions are even more important if company is paying in equity. I wouldn't want to work there if i didn't get the answer at least to majority of them. It would be a huge red flag - or i would assume that equity is 100% worthless when comparing compensations between offers. Relationships of power shifted - there is abundance of jobs, and scarcity of good developers. Quite frankly - there are plenty of bad companies, and few good ones - just like with candidates. You would hate to bring in a bad horrible person in. We would hate to invest time and effort into useless endeavor.