The worst job interview I ever had

https://www.oliverio.dev/blog/the-worst-job-interview-i-had

Comments

gobdovanMay 27, 2026, 6:48 AM
I always wanted to tell the story of my weirdest interview. It's bad in a different way from OP's. This was for a "Machine Learning Engineer" contractor position.

- Hi, I'm gobdovan. How are you? says I.

The interviewer doesn't bite:

- How many prompting techniques do you know? (ok?..)

After a couple confused seconds, I respond with 2-3 techniques and ask if I should explain them, but the interview engine is already running at full speed:

- What is PEFT? How many PEFT techniques do you know?

I say I know LoRA and start to explain it, but the interview had no patience for answers longer than their acronyms. Before I knew it, I heard frantic clicking.

- He starts sharing his screen while I am still talking about LoRA in the background. Puts up an empty car from Google Images and commands: "Model the relationships between cars and people positioned inside the cars over time."

Uncertain of how to satisfy the inquiry, I start foolishly questioning what the task is supposed to be: vision? simulation? dataset labeling? self-driving cars?

But the interviewer doesn't budge. Doesn't give a specific task or context. Simply ignores the questions and stoically refuses to elaborate. The stars speak to me, and I guess he wants a relational mapping of some kind. Turns out I am right. This was supposed to test basic SQL table modeling.

At this point, I decide I'd sit through the interview just so I can collect all the questions. I am not disappointed:

- How many agentic frameworks do you know?

- What is the name of OpenAI's embedding model, and how many dimensions does it have?

- Then, the last ordeal lands: interviewer takes out a piece of cardboard that has "context engineering" written on it and asks: "What does this tell you?". His camera is unfocused, I ask if he could read what it says. Instead he repeats: "What does this tell you? What does this tell you? What does this tell you?".

I ask if he is the ML team lead. Turns out this absolute Chad is a mobile dev the client asked to interview candidates for the MLE role.

zeafoamrunMay 27, 2026, 7:15 AM
Holding up a cardboard board in a video interview? This is so deranged.
janussunajMay 27, 2026, 7:09 AM
It's also pretty sad that now "ML engineer" means prompting...
skrebbelMay 27, 2026, 7:06 AM
Did you get the job?
MattRogishMay 27, 2026, 12:04 AM
This… was a mistake on both you and the interviewer.

All interview questions - unless it’s impossible to twist your answer to fit this - is scoped to “… at work”. Nobody who asks “tell me about yourself” is asking you to talk about how you met your partner, how many cats you have, or that experience you had, that one time, at band camp. It would be redundant and awkward to literally say “… at work” at the end of every question. It’s totally 100% the intent of the interviewer.

This is interviewing 101 and unless this is your first ever interview I would find it odd, and stop you immediately and say “I meant, worst day at work”. They should’ve done that.

Unless they explicitly and unambiguously say “tell me about the day your mom and dog died in the same day when you found out you had cancer” they mean “tell me about your worst day _at work_.” And even if they ask about the time your dog died (they won’t), they are not asking you “tell me about the worst day you’ve had in your life”. They are asking “tell me about a time you experienced adversity and overcame it, exhibiting problem solving, resilience, and grit AT WORK. (Or - if you are operating in executive mode or you like to live dangerously - some non-work context that maps obviously and unambiguously to a work context).”

You failed the “knows how to interact with people in a professional setting” part of the interview. Or the “this person knows how to interview” part (which generally, but not always, correlates with experience and emotional maturity). Or the “read between the lines” part.

Yeah, inartfully asked questions - but also totally flubbed the answers.

Sorry, chalk it up to you had a bad interview or day or whatever, and never, ever forget the entire thing is scoped to “…. at work”.

victorbojicaMay 27, 2026, 5:38 AM
I was also part of this sort of interview once. They specifically asked personal questions - parents stuff, relationship, etc. Definitely not work related. It was indeed a very strange and exhausting experience. I could've definetly refused to answer some of the questions or drop out of the interview altogether, but not sure why I haven't.

So yeah, this type of interview exists so I highly doubt the interviewer interviewing OP was asking about work stuff...

olbeefyMay 27, 2026, 6:39 AM
At that point, I think I would have just started making things up or telling stories from other people I knew. Some random interviewer has literally no right to be asking me personal questions so I have no problem improvising some fun answers for them.
BugsJustFindMeMay 27, 2026, 6:35 AM
> They specifically asked personal questions - parents stuff, relationship, etc.

In the US any employer who asks you about personal relationships during an interview is opening themselves up to an illegal discrimination lawsuit.

wolfi1May 27, 2026, 7:08 AM
my father was a turd minet in virginia and his father was a goat ball licker (c) Stephen Colbert
idoMay 27, 2026, 6:37 AM
Doesn’t that open them to discrimination lawsuits?
anyfooMay 27, 2026, 12:23 AM
And even if, for the sake of argument, they legitimately did ask about your personal life instead of your work life... you normally wouldn't answer any of that. (In fact, it could very well mean the end of the interview, from the interviewee's side.)

That's vastly overstepping commonly accepted boundaries. Sure, some surface level smalltalk is normal and expected: "Any hobbies? Ah, you like hiking? Nice. Where do you like to hike? Oh, I did that, too. Might I suggest hiking there and there? I bet you'd like it. Anyway, moving on!" Common ground helps conversations flow.

But an employer asking about your personal relationships? Your needs, fears, and desires outside of any technical context? (My needs, fears, and desires from compiler toolchains are totally within scope.) Your traumata? That's a level of intrusiveness crossing into "rude" territory. They have no business of asking.

neilvMay 27, 2026, 1:11 AM
Some good points. Just a heads-up about something interesting I heard/read in training...

"Innocuous" icebreaker questions about hobbies, the weekend, or whatever, can be surprisingly problematic.

The questions and answers often inadvertently imply things about family status, religion, physical ability/disability, socioeconomic class, age, heritage, etc. that interviews are supposed to steer clear of.

For me, this was best illustrated by one of the https://www.linkedin.com/in/lornaerickson/ funny video skits, in which the interviewer character was using "innocuous icebreaker" chat aggressively to try to extract information all over the no-no list of things you aren't supposed to ask.

(Then the skit was funny again, after the fact, when I was in an interview with some barely-out-of-school founder, who was intentionally doing one of the things from the skit...)

ryandrakeMay 27, 2026, 2:41 AM
> The questions and answers often inadvertently imply things about family status, religion, physical ability/disability, socioeconomic class, age, heritage, etc. that interviews are supposed to steer clear of.

I had a bizarre interview (at an extremely well-known company with an eccentric, controversial founder) where the recruiter asked me directly questions that "BigTech interview training" explicitly taught me to never ask or even walk close to. I was actually shocked and stammered out an awkward "Uhh, I'm pretty sure it's fraught with risk to even ask those things" non-answer, but she seemed genuinely surprised I wouldn't go into personal family details during a professional job interview. So, it seems not everyone has gotten the memo...

anyfooMay 27, 2026, 1:22 AM
Good points. My hypothetical had the implicit assumption that the interviewer was acting in good faith when asking the weekend question. But that doesn't mean that interviewers necessarily are, of course.
neilvMay 27, 2026, 1:29 AM
Yeah, and even in good faith, the questions can be problematic.

Example: At the very start of the interview, candidate suddenly feels like they have to hide something about their religion, sexual orientation, or whatever, in how they answer. Or feels like their candid answer to the icebreaker was not received well.

Which is the opposite of what the interviewer intended, with an icebreaker, but their training didn't include how tricky casual icebreakers can be.

fsckboyMay 27, 2026, 12:34 AM
>Your traumata? That's a level of intrusiveness crossing into "rude" territory

OP didn't say that, he said "hardest day of my life, my biggest life challenges" and then characterized it (his opinion) 'similar “trauma-baiting” questions'

asking a young person (I don't know that he was young, just saying) "what was the hardest day of your life" is a pretty standard question. Like on a college application, they expect you to answer it. Young people often don't have enough other experience to fall back on, and in a context in which you are expected to make yourself look good, the filter that is expected is to emphasize something that you were successful/resourceful at.

freehorseMay 27, 2026, 12:48 AM
> asking a young person (I don't know that he was young, just saying) "what was the hardest day of your life" is a pretty standard question

Is that true? Is that a cultural thing that I do not get? I am in the same boat as OP and consider these questions, if intended for no-work specific context, very inappropriate. The age is irrelevant. If you are interviewing a young applicant who is not expected to have work experience, ask them about sth in the school context instead of work context.

Young people can still have really bad experiences. Especially when you interview a big number of people, you are guaranteed to fall upon some pretty bad. It seems to me that the right expected way to answer such a question is to find some personal experience that is bad, but not _that bad_, and then try to flip it and show you persevered. It seems to me that you are selecting for people who are better in making up stories this way, than anything else, because there is very often no way to answer such a question in any truthful, factual manner.

Personally I would only give answers in a work related context, and make sure to be clear that this is the way I interpreted the question.

AurornisMay 27, 2026, 1:18 AM
> asking a young person (I don't know that he was young, just saying) "what was the hardest day of your life" is a pretty standard question. Like on a college application, they expect you to answer it.

This is not a standard job interview question at all.

In fact if you tried asking this at any company with a legal or HR team, you'd get pulled out of interviewing people until they could train you appropriate job interview questions.

cwnythMay 27, 2026, 5:43 AM
Keeping in mind the context of the original parent comment, yes it is 100% standard to ask about the "hardest day of your [working] life." I wouldn't ever put it like that, but asking about difficult challenges and how you overcame them is completely normal. The blog post reads to me as someone who is oblivious about the subtext of these questions.

When I ask that kind of question, I'm not asking you to share about a breakup, or death of a parent, or some other non-working issue, and I would think it very inappropriate for you to do so (thus, the quick rejection email). Instead, I'm asking about how you navigated losing all your code due to a backup issue or how you dealt with a difficult client or coworker or even some problem at work that threw you for a loop for weeks. That's the subtext of these questions, as the original commentator also made quite clear.

defrostMay 27, 2026, 6:07 AM
> Instead, I'm asking about how you navigated losing all your code due to a backup issue or how you dealt with a difficult client or coworker or even some problem at work that threw you for a loop for weeks.

Cubicle drama, hey?

Easy stuff. I've got a million+ SLOC behind me, no real cubicle stories worthy of note resulting, just had a few days at work clearing air strips at high altitude in Papua, had to work for a couple of weeks at gunpoint after one of our lovely clients detonated a nuclear device near enough our plane for the shock wave to affect the flight dynamics, nearly lost a whole boat to a fire under the kerosene filled float cables in the Spratly Islands region (after getting boarded constantly by various gunboats).

All good though.

albedoaMay 27, 2026, 6:41 AM
> Keeping in mind the context of the original parent comment, yes it is 100% standard to ask about the "hardest day of your [working] life."

The original comment says:

> Like on a college application, they expect you to answer it.

I don't know if that changes your interpretation, but if the other replies are any indication, yours is not the default.

anyfooMay 27, 2026, 12:45 AM
Well, I have no idea what they actually specifically asked or didn't ask, because the article is light on details. So I just elaborated on what I consider crossing into unacceptable (which I believe is based on commonly shared conventions), and everyone can draw their own conclusions for any particular situation.
AurornisMay 27, 2026, 1:03 AM
The job is described as "founding engineer at a mental health startup".

Generally getting called in for a "founding engineer" interview is code for a company that doesn't have money for a full salary but hopes they'll find someone willing to work for some token equity grant. These jobs usually come with amateur founders who aren't good at hiring. They could have really been pushing for life experiences, thinking they were doing some breaking-the-mold interview technique.

I do agree that every candidate should know to deliver answers in the context of a work interview. Even when the interviewer starts asking personal questions, you bring it back to something related to the job every time. Everything that comes out of your mouth should have a focus of showing how you'll work well at this company because you've worked well in the past at other companies.

The interviewers may have been shocked when someone didn't know this and actually unloaded their personal life struggles without a filter. I bet every other candidate they talked to had been giving interview-appropriate answers so they didn't realize how broken their questions were.

Chalk it up to a learning experience. I am certain you didn't miss out on any great opportunity with these amateurs. You will probably never see them again. We all have embarrassing work experiences at some point, but this is a good one to learn from and then promptly try to forget.

neilvMay 27, 2026, 12:30 AM
> Or the “this person knows how to interview” part (which generally, but not always, correlates with experience and emotional maturity).

I think that "generally..." is a little harsh.

The person might just not have worked in a stereotypical corporate drone environment before.

Or they might normally have been able to handle the corporate drone interview theatre, but are overextended by the context (e.g., laid off in this job market, which can easily be more stressful and existential than most actual work situations), and a bad interview hazing just yanks on that.

There's going to be more and more overstressed people showing up to tech job interviews, and people on the other side of the table will need empathy and understanding, if they're going to make good assessments despite the context.

MattRogishMay 27, 2026, 1:49 AM
Thank you; you’re right - context matters and now more than ever there are a ton of folks looking involuntarily. Grace is always needed, but now especially.
alanbernsteinMay 27, 2026, 6:09 AM
Do you experience many "life challenges" at work?
fsckboyMay 27, 2026, 12:29 AM
>It would be redundant and awkward to literally say “… at work” at the end of every question. It’s totally 100% the intent of the interviewer.

you are stating your opinion as fact, and I don't think there is a basis beyond your opinion, you simply don't know.

I agree with you the interviewee could have handled the questions better to not be so revealing about himself, setting boundaries the interviewer was crossing, but it might have been precisely the intent of the mental health company interviewer to elicit responses like that to stay away from emotionally wounded people.

dnnddidiejMay 27, 2026, 6:15 AM
Or at uni, at work-likes (volunteering, toastmasters etc.). It has to be in the pursuit of a commercial-like goal really. But yeah avoid friends, family, travel, pets...
sdenton4May 26, 2026, 10:49 PM
I fail to recall the exact wording of the discussion topics, but they were, in fact, non-technical — covering such lovely topics as the hardest day of my life, my biggest life challenges, and other similar “trauma-baiting” questions.

Ha, I don't think anyone who asks these questions expects that you'll respond in a fully unfiltered way... These kinds of questions are part and parcel of non-tech interview processes.

You can redirect with some subtlety "Well, my hardest ever day at work was..." to avoid talking about dead babies or whatever. Your interviewer doesn't get to look over your whole life history and determine whether your /truthfully/ chose the actual hardest ever day. So really it's a chance for you to say "Here's a [big] challenge I once faced, and here's how I survived/overcame it."

rsotoMay 26, 2026, 11:19 PM
Yeah, OP just unwinded himself, no filter. You can be truthful and open with friends and family, close people to you. You absolutely shouldn't when talking with strangers.
morkalorkMay 26, 2026, 11:57 PM
Then strangers shouldn't fucking ask questions that could have answers that make them uncomfortable. Just a thought.
anyfooMay 27, 2026, 12:27 AM
We weren't there, and the article is light on details, so we can only speculate. I see two options here:

a) The potential employer vastly overstepped commonly accepted boundaries.

b) It was totally implied that the questions were to be answered in the context of work. "What was the hardest challenge you had to overcome?" in that context relates to e.g. debugging a hard concurrency problem, not your divorce.

What stood out to me is that whatever interpretation is the correct one, the candidate was willing to give (apparently) deeply personal answers. That's just something to adjust for in upcoming interviews, we live and learn.

gherkinnnMay 27, 2026, 6:03 AM
"How are you?" "How was your weekend?"

It is common for people to ask a personal sounding question but expecting an impersonal answer.

thaumasiotesMay 27, 2026, 7:03 AM
And they should stop doing that. Who benefits?
interviewitisMay 27, 2026, 1:10 AM
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freehorseMay 27, 2026, 12:09 AM
But why ask about "the hardest day in your life" instead eg "the hardest day at work"?

Personally asking this kind of personal questions sounds very weird. You can evaluate soft skills and culture fit by asking more relevant, professional questions. Except if the reason to ask this kind of more personal questions was sth else.

cwnythMay 27, 2026, 5:47 AM
Notice that the blog post author did not provide exact quotes. In fact, they explicitly state they do not remember the wording. It's very likely that they did, in fact, ask about biggest challenges, and the author misunderstood.
TylerEMay 27, 2026, 12:14 AM
The cynic in me says because they want to select candidates whose work IS their life.
staredMay 27, 2026, 12:06 AM
If they ask questions but expect fake, censored or cherry-picked answers, it says a lot about their culture.

Pro tip (for life, not only interviewing): never ask a question you don’t want to hear answer to.

johnfnMay 27, 2026, 12:03 AM
You are technically correct. But you must admit it sounds pretty bad to say "Yeah, the idea of the behavioral technical interview is the interviewer asks questions that look like they admit honest answers, but you should actually lie to them, and they expect you to lie, and actually it's a charade you play with your interviewer, and if you don't understand this (which is never explained to you) then you will immediately be rejected."

I can definitely understand the perspective of someone who has done few interviews not understanding this and being upset/confused!

thaumasiotesMay 27, 2026, 6:52 AM
I paid for interview coaching at interviewing.io. This is the coaching I got about the behavioral interview:

- "There is no place for honesty in a behavioral interview. No one is going to check your story."

- Tell a story about a time when you got into a dispute, ideally with your boss, over a work-related issue, and you won the dispute.

- If you have no relevant story, I [the coach] will write one for you to memorize.

nsvd2May 26, 2026, 11:14 PM
In fact, being able to "play the game" so to speak is probably part of what the interviewer is looking for.
throwaway89864May 26, 2026, 11:18 PM
It is also possible that they were trying to see, if the person had traumas that would interfere with their ability to work with toxic content, do red-teaming / etc tasks.
rigonkulousMay 26, 2026, 11:01 PM
I was excited, it was a game company, and I'd wanted to get back into games - or more specifically, game engines - for a few years. The tech of this particular company was interesting, an in-house engine developed by wunderkind, of course, and they'd invited me for an interview because I had done a fair bit of low-level work, which would be handy for their rough edges. Apparently.

Half way through the interview, I had an epiphany. I really didn't want to work there. It was cultural, it just wasn't going to fit.

I didn't waste any more time. Half-way through a white-board challenge, I put down the marker and said, plainly, "okay, I've seen enough, I don't want to work here - thanks and let me not waste any more of your time", picked up my coat and left.

It wasn't a bad interview. It wasn't a terrible one. Nor was it because of the whiteboard question, or anything like that.

I just didn't like the guys. That's all it was. And I couldn't stand the idea of working for them - just the way the interview proceeded. I don't need to give details.

It was really the only time I ever got up mid-interview and left.

jval43May 26, 2026, 11:09 PM
Always trust your gut. Especially when it comes to people. Don't overthink, never rationalize it. Accept your feeling, it's valid.

If I learned anything from all my past mistakes in life, it's this.

torben-friisMay 26, 2026, 11:51 PM
I have never done what you did, but I am going to take note of the fact that it is something one can do. Because I've certainly had the same moment of realization a few times, and I went through the motions anyway.
mannanjMay 27, 2026, 6:39 AM
Good. and you saved time by doing this. It feels more the right thing.
elzbardicoMay 26, 2026, 11:35 PM
If it was Blizzard, I can completely understand you.
huflungdungMay 26, 2026, 11:37 PM
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pan69May 26, 2026, 11:28 PM
I had something similar years ago. I applied for a job at a company, size around 150 people. Did two rounds of interviews which were great. They wanted me to offer the role. However, as a third round, I was going to do a meet and greet with the CEO and he was going to yay or nay me. At point I dropped out. If a CEO can't trust his delegate managers to hire the people they see fit for a role, then thanks but no thanks. That's not a company culture I want to spend most of my waking hours in.
anyfooMay 27, 2026, 12:17 AM
I don't know your particular situation, so it might be totally different, but I think this is commonly just a formality and a friendly chat.

It's a chance for you to meet the actual CEO (or VP or whatever in a larger company), and also for them to get to meet you in advance, instead of effectively getting "blindsided" by a new person (to exaggerate a bit).

Usually, by the time you've gotten to that point, the decision to hire you has well and truly been made. I don't know what then would need to happen for the actually rather secondary function of giving the CEO the opportunity to veto to become relevant. I'd be curious hearing about anyone who's ever experienced it (on whatever side). I guess it can be a safeguard against vastly unaligned values, but I suspect it's very rare.

But primarily, and effectively, it's usually just a meet-and-greet. And it's hard for me to blame a CEO (or VP etc.) for at least getting to anyone who's going to enter a mutual contract to effectively become part of their company.

pan69May 27, 2026, 2:23 AM
> just a formality and a friendly chat

That was not the case in this scenario. I was told I would be offered the role if I came out favorable with the CEO (did he like me or not? did I jump when the said "jump"?). To me this meant that the CEO doesn't trust the people he hires. He clearly didn't trust the hiring manager's jugement and/or respected their position. The CEO delegated a task and responsibility but then felt to have to authority to override that, which maybe he does. However, that's not a culture in which I want to operate. If I was wrong, so be it, but I saw a red flag and I made a choice.

anyfooMay 27, 2026, 5:27 AM
You know better, as you have all the information and we merely have a shadow of it, but that in itself still sounds like “standard boilerplate” to me.

I remember from my friends who worked at Google at the time, that everyone’s always been told that “every new hire’s contract lands on Larry Page’s desk, he has to sign off on it”, and you can probably bet your bottom dollar that Larry Page didn’t spend a lot of time on each hiring package, if any.

conspMay 27, 2026, 6:46 AM
I'd argue I won't work there. "The buck stops here" is never true when shit hits the fan so it's just kabuki theatre in all other situations just to take credit.
gamblor956May 27, 2026, 1:01 AM
it's usually just a meet-and-greet.

Yes, it usually is. But in this case the problem was that the CEO could unilaterally override the decision made by everyone else, so it wasn't just a meet-and-greet.

ryandrakeMay 27, 2026, 2:52 AM
Yea, it's not a meet-and-greet, as in there can be no impact to the outcome of the interview. You're definitely still interviewing. But, in every case where I got to the point of "You're going to chat with the [Founder|CEO|BigTech VP]," at that point the job was mine to lose. They're not going to waste a VIP's time if they're not serious about making you an offer. You effectively have the offer. Your job when talking to the VIP person at the end is to "sound like a likable, competent person, who VIP would be cool with saying 'yea I hired this person'." That's pretty much all you need to do.

Generally the chat with the VIP means: "You have the job, but I (VIP) want to just double check that my underling hiring managers are not totally useless."

anyfooMay 27, 2026, 1:26 AM
That is exactly the assumption I was operating under, I even called it a "veto". Does not change anything I wrote.

(And of course the CEO can override any hiring decision anyway. The question is if they will.)

smcinMay 27, 2026, 12:44 AM
If you got to that point it's just a formality, and unless you somehow blow it the job is (probably) already yours, if you decide you still want it. You seem to have jumped to unwarranted assumptions about the company culture; quite possibly the CEO does want to make sure the culture is good and remains good. It's not necessarily a binary test of whether the CEO can't trust delegating to their managers; it's also your constructive opportunity to use that conversation to get more insight into where the company, strategy, product/service, customers etc. are going. A good question to ask the CEO is about the broader impact of your role: that should get you some useful insight, also you compare the delta between what the CEO says vs what the senior managers said vs what the recruiter said; they don't need to be identical but they should broadly agree, and it shouldn't reveal any fundamental disagreements or ambiguities (e.g. "your role is incremental support of product X" vs "totally rewrite it in language Y in the next 9 months"). Listening to their response should also give you subtle behavioral cues about who in the company does/doesn't have influence, credibility and where the pain points are: you can't generally get that from the previous interviews, and it can be a faux pas to explicitly ask.

(PS: if you find reasons to suspect the CEO isn't delegating effectively to managers, then ask the CEO an open-ended question "How much do you do yourself vs which tasks do you delegate to your managers?" then listen carefully to their answer. And it's still not necessarily a red flag, it may just be a new or inexperienced CEO, or maybe overcompensating for one or two bad hire experiences at current or previous company. Compare to their answer to "How do you assess new hires within the first 90 days?").

The only (minor) negative I'd take from this is that it still behaves like a small startup scaling quickly, and they haven't yet figured out how to to scale interviewing and hiring for when they get larger... but that's overall a good complaint, it shows they're still growing. It's much better that your signoff interview is with the CXO (or VP) than the Director of HR, or an AI bot. Honestly I'd pay more attention to how many days/weeks/months it takes them to make the hiring decision than how many management layers were involved; that's a bigger tell of organizational dysfunction.

Don't overthink.

gamblor956May 27, 2026, 1:03 AM
You made the right choice.

The only time a CEO should be meeting a hire is if the company is a tiny startup, or the role will be working regularly and directly with the CEO.

Otherwise, it's the worse kind of micromanagement. If the CEO wants to meet the new face they do so after the person starts, and this is the norm outside of tech.

donatjMay 26, 2026, 11:50 PM
I've been working as a dev for over twenty years now and have had my fair share of interviews. The very worst I ever had was about six months ago.

I'd had a fantastic initial interview, it seemed like a perfect fit and interesting tech. Overlapped a lot with some work I'd been doing recently. They made it sound like my experience was a great match and they were exited for me to move forward. I was the most excited I've ever been after a job interview.

The second interview a couple days later was a one-on-one with the CTO. After about five minutes of pretty friendly get-to-know-you chitchat he asks if I have any questions about the position. I ask about what my day to day would look like and he replies "I don't know, and that's the problem. I don't like to lead people on, I'll be honest I don't see a position for you here."

It was such a sudden slap in the face that my brain just completely shut off. I kind of just stammered out an "Oh... Um... Thank you for your time"

I didn't get to talk about my experience ... at all. Not a single mention of my twenty years of across multiple tech stacks my resume doesn't even begin to scratch. I've never been judged so quickly or so blindly.

Later that day, out of sheer frustration I email him back trying to explain that I'd felt like I didn't get a chance to talk about myself and all the ways I'd felt like I was a great fit based on the previous interview and how my experience applied.

I never heard anything back.

codemogMay 27, 2026, 12:08 AM
Seems like you dodged a bullet. Hard to hear when you’re looking for a job, but not every job is a good opportunity.
npodbielskiMay 27, 2026, 6:55 AM
He probably perceived you as a competition. If you do not like playing politics that probably was for the better.
atoavMay 27, 2026, 5:50 AM
Congrats on not working there I guess. Apparently that CTO wasn't worth working with anyways
p0w3n3dMay 27, 2026, 7:05 AM
I am sorry to hear this. If you were perceiving the space as safe and then you felt abused, I think this is something you should report. Maybe people working in mental health startup are experts in mental health, but there are very strict rules and guidelines that forbid abusing this "power" with other people, especially when unwanted, uncertain etc. During my therapy I've learned that the therapeutist is having monthly update on their actions with their supervisor, so they wouldn't do things that are for example unethical, or direct me in the wrong direction for some reason.

As other people mention in comment, this surely have been error of the interviewer, and in my opinion the feedback should be left.

BugsJustFindMeMay 27, 2026, 7:05 AM
The problem seems to be that you treated a professional job interview like a therapy session and showed yourself to be a person who brings up situationally inappropriate subjects without a filter.

> I’m a little ashamed remembering myself talking about failed relationships, family struggles

It sucks what happened, but, yeah, you need to establish filters for yourself. No matter what they ask you, it's an absolutely terrible idea to talk about your failed relationships in an interview. Something tells me they did not ask for that private information specifically and you just decided it would be a good idea to volunteer it, otherwise the story would have said so.

analogpixelMay 26, 2026, 10:47 PM
Would be funny if the interviewer wrote the exact same blog post; "I had the worst candidate interview today, I asked him a simple ice-breaker question before getting into more technical stuff, and he just went off about his family and relationships for an hour; weirdest interview I ever gave."
tibbarMay 26, 2026, 11:05 PM
The description of the interview seems like it was explicitly non-technical, though.
hluskaMay 26, 2026, 11:32 PM
“He kept talking about dead babies, failed relationships and the time he cheated in an exam in grade five. Fifteen minutes in and I wondered not whether I would hire him, but if he would kill me and wear my skin if I didn’t. Or did. Little difference.”
genewitchMay 26, 2026, 11:05 PM
you think that's what it was? The people with 100% of the power in this situation did everything 100% correct and you're not victim-blaming at all?
atoavMay 27, 2026, 6:07 AM
It was a textbook example of the double contingency of communication¹. In communications it doesn't only matter what each side is objectively saying. It matters what the other side expects them to hear. And that goes both ways.

In this case the interviewer asked these questions to get to know the candidate in a professional setting, so they expected a diplomatic or professional answer. The candidate however misjudged the interviewer intention behind the questions, took them literally and answered them truthfully. Neither of these people is technically sporting a wrong position, yet the communication broke down.

That being said, the idea that you can choose not to talk about certain things is pretty basal when it comes to communications. If you have a trauma nobody can force you to talk about it and you should also not talk to everybody and their dog about it (and I know people who constantly do this and have a tendency to regret it afterwards). It costs you nothing to say that you can't think of any specific day, or talk about a day where a old boss at a shitty student job abused you, to frame it in work terms. To talk strategically or diplomatically is a skill that is needed in many positions. And that candidate displayed a total lack of that ability.

That being said I am not particularly fond of that type of question myself. Both as an the person carrying out an interview and the person going to one. I am more interested to see how a person tackles certain situations than to have them tell me stories about it.

¹: see https://www.orientation-philosophy.com/glossary/double-conti...

conspMay 27, 2026, 6:51 AM
> In this case the interviewer asked these questions to get to know the candidate in a professional setting, so they expected a diplomatic or professional answer

And there is no bias in this assumption whatsoever?

bitbasherMay 27, 2026, 12:17 AM
My worst interview was at Uber (their security team).

The screening and technical interviews on site were all fine and dandy. At the end of the onsite interviews I spoke with the director in charge of the team. I asked some general questions like, "What's the team's work-life balance like?"

He chuckled and said something like they work 60+ hour works. I looked at him and said flatly, "Yeah, I'm not doing that."

The HR person called me after the onsites and was completely puzzled. She said she never seen a candidate pass technicals and not get an offer. She suggested sending me to another team (I declined).

OutOfHereMay 27, 2026, 12:19 AM
I feel you. I once had a second-level manager interviewer suggest that I work through the lunch hour while on the job. I terminated that interview process the same day.
kxrmMay 26, 2026, 11:15 PM
Let me preface this by saying, I know this might be a privileged take. However, I've had some bad interview experiences but one thing I have never had happen and I never will do is cross the "just business"/"personal" line with anyone I may or am working with.

> hardest day of my life, my biggest life challenges, and other similar “trauma-baiting” questions.

I would take these types of questions as "from a professional standpoint". If the interviewer corrected and wanted personal answers, the interview would be over.

WatchDogMay 27, 2026, 12:00 AM
> ...I never will do is cross the "just business"/"personal" line with anyone I may or am working with.

Just in an interview situation, or you will just never be open to a personal friendship with anyone you ever work with?

kxrmMay 27, 2026, 12:23 AM
> you will just never be open to a personal friendship with anyone you ever work with?

Building relationships with colleagues is possible but I have tried to be careful. I have made some friends over time that were once co-workers. However, they were only able to move to full friend once they moved on to other teams or companies. I don't see someone I work with day-to-day as a personal friend. I compartmentalize them, keep the relationship professional and cordial.

Moving someone to a personal friend has risks, especially if there is a chance you may work for or with them again. Some personal friendships may be able to outlast work drama, but so far I haven't had that happen for me. I've lost a few along the way due to negative conditions at work.

Have you had a personal friend that stayed around after leaving a bad situation at work? Any pointers?

genewitchMay 27, 2026, 2:34 AM
My best friend is someone i worked with, and we hit it off immediately. He also was one of the people who interviewed me before hire, too. I left the company because of medication induced issues with co-workers (long boring story... careful with SSRIs kids!)

and we still ... actually he just called so i gotta cut this short we talk 5 hours a week on the phone plus we run a PBX and chat server and stuff so we're constantly in contact.

simgtMay 27, 2026, 12:37 AM
Thanks for that sensible answer, had to scroll down quite a while to find you there.

The real problem is that for many people it takes a while to realize you're being abused, in that case it was only a while after.

I highly recommend learning the basics of persuasion and how to manipulate people. It helps identifying the signs early.

tsukikageMay 27, 2026, 6:59 AM
Genuinely opening up is a mistake. The incentives for these clearly mean that they actually select for candidates who are capable of glibly blagging their way through an extended conversation without saying anything inconsistent, weird, compromising or of substance.

This isn’t usually a required engineering skill. I’m guessing the interview was designed for salespeople and/or middle management.

talkingtabMay 26, 2026, 10:34 PM
There is, and should be, a red flag for these situations. No make that RED flag. If you go into an interview that leaves you feeling the least bit helpless or at someone's mercy then run screaming. Not politely, not quietly. Just say to calmly to the person that you find the situation abusive. It is. As you go out, if you see anyone or have a chance to talk to anyone, just tell them you found that your interviewer to be personally abusive. That you will not be willing to take the position if it is offered, that you will share you perception with others around you and expect an apology.

Then fall down and appreciate that you did not end up in that situation. And tell everyone you know not to apply or work there.

robocatMay 26, 2026, 10:42 PM
Are you being glib or unrealistic?

You're going to find many red flags for any job, perhaps severe flags.

But you need a job.

Or you have to roll the dice because you have deep knowledge of the red flags for your current job.

Who finds 10/10 perfect jobs via an application process?

Note: I probably shouldn't be commenting since I don't need to apply for jobs and conditions here are likely different from yours.

jvanderbotMay 26, 2026, 10:49 PM
I disagree that you'll find "many red flags for any job"

I've interviewed at dozens of companies, received and accepted or rejected at least 20 job offers in my life, and rarely encountered true red flags. This is very different than saying it's a perfect 10/10, all life is about tradeoffs. What GP is saying is that "there are things that are not worth any tradeoff, and you'll know them by ... ", which is good advice, esp for young people, who might be willing to make uncomfortable personal sacrifices to obtain a job.

We may be there someday, but we're not there yet.

MaulingMonkeyMay 26, 2026, 11:12 PM
> I disagree that you'll find "many red flags for any job"

If they're hiding the many red flags, that's the biggest red flag of all!

genewitchMay 26, 2026, 11:07 PM
i agree with you, i've interviewed at a lot of companies, too, and seen only 1 red flag in retrospect. the flag was "we need to hire for budgetary reasons"
roadside_picnicMay 26, 2026, 11:36 PM
There's a difference between "red flags" and "imperfections". Every team has faults, which if you're experienced at interviewing/working many places, are usually pretty easy to figure out. These are distinct from "red flags".

Early in your career it can be hard to distinguish the two, but once you've joined a company where there really were "red flags" you quickly learn to differentiate.

Many people are reading the author's interview uncharitably as simply misunderstanding how to answer non-technical question, but I have absolutely been through loops (thankfully rare ones) that did have a "let's press on sensitive issues and see how tough this candidate is" round (one place brought in a consultant who bragged about his experience working with hardened criminals and terrorists to build out a true psych profile on candidates, I declined after learning he had had some "trouble" at a previous high profile job)

Sounds like you've never worked for a truly toxic org, which is great. But, especially if you're interviewing with smaller startups (as the author mentioned), there is a lot more variance and some truly messed up teams (and some truly remarkable ones as well) out there. I've noticed that HN increasingly doesn't have people that work at startups any more, so many people are probably less familiar with what's out there.

ChrisMarshallNYMay 27, 2026, 12:32 AM
I don't know if they still do it, but the fashion, back in the 1980s, was to give a Myers-Briggs-type test to candidates.

Maybe I'm wrong, but given the type of company it was (and likely, the C-suite people), I guess that they were doing something similar. I assume that they really did want to know about the person's non-worklife stuff.

I would consider that crossing boundaries. It's also possible that some of the questions might have been illegal (in the US).

chapsMay 26, 2026, 10:52 PM
Sure, but there are some jobs that are so bad that this advice readily applies to. The sort of job that takes you away from your life, family and friends in a way not entirely unlike poverty does. It's good to recognize whether working somewhere will turn into this because it's... hell... working at those places.
hluskaMay 26, 2026, 11:35 PM
Wacky question. But if you shouldn’t be commenting, why did you? Or was that one of those fake ‘I shouldn’t say anything’ that people do when they’re being jerks and don’t want to get called out?

I’d like some clarity. :)

trusted_broMay 26, 2026, 10:49 PM
Similarly, if you find yourself working for a manager who uses power and fear as a lever, stand up to them or walk away.
ChrisMarshallNYMay 26, 2026, 10:22 PM
I have a lot of interaction with mental health professionals, due to an organization in which I participate. Have, for the last 45 years.

Many, many of them are "Doctor, heal thyself" type folks. Definitely non-boring people. I am quite sure of this, for reasons that I won't go into, here.

Sorry it didn't work out, but you dodged a bullet. Take it from me.

goodrootMay 26, 2026, 10:28 PM
Yikes. Good thing you didn't wind up there.

The furthest I've gone in these jazz style culture interviews is asking people what they do outside of work for fun. This was for fully remote async positions. And it was important to know you had other stuff going on because the mental/personal health risk in failing at remote work is massive and life altering.

If, through wherever that discussion went, I wasn't 100% sure that you could stand on your own feet and wouldn't sink into the abyss, it was impossible to move forward. It was a tough line to walk sometimes because you don't want to pry personally. But that doesn't appear to be a universal opinion, it turns out.

nicbouMay 26, 2026, 10:32 PM
That question would not be received well in many places. What candidates do in their private time is none of your business.
nomelMay 26, 2026, 10:51 PM
Not sure why this is downvoted.

Even if I wanted to, these questions aren't allowed in the company I work for, along with feedback related to "team fit". This is dictated by execs, dictated by legal, because it has nothing to do with proving competence, and opens up for employment discrimination lawsuits since you're persuading them (you have to understand the power dynamic) to reveal potentially protected info. For example, if a man say "Oh, I go hiking with my boyfriend!", he could also say "They didn't hire me because I told them I was gay!". Or, even "I spend time with my kids." since familial status is a legally protected class where I am.

As a person who does interviews, I have exactly zero interest in what people do for fun. I just want competent people that are nice to work with (in a productivity sense), and I only have 45 minutes to prove that, knowing that nearly everyone fucking lies. I see it serving no purpose other than helping enforce some monoculture within the group, because, genuinely, why else would you ask about free time activities during an interview?

Related, the only time I've asked this was early on when I didn't know how to interview. The only time I've been asked this, and answered, was with people who had just started interviewing (small startups and new hiring managers).

ryandrakeMay 27, 2026, 3:08 AM
Great comment. It's really shocking how close to the legal line Silicon Valley tech companies get, and the extent to which many of them actually cross way over the line. A huge number of interviewers I've encountered are in extreme need of training so they don't so casually put their companies at legal risk. If I was Lawful Evil, I could probably make a career out of just suing companies for discriminatory hiring practices, due to the various landmines poorly trained interviewers routinely step into.

BigTech seems to be the best at it. They tend to have rigorous training, and often have a "safe question bank" that interviewers pull questions from, which are all vetted by lawyers and are known not to put the company at legal risk.

dnnddidiejMay 27, 2026, 6:23 AM
Hmmm. Maybe overindexing on anecdata. Did that one guy go a bit crazy once?

I think you gotta trust adults to be adults.

pjsmith404May 26, 2026, 10:39 PM
I think that's the best you can do for culture fit, cause at the end of the day it's just "can they shoot the shit and are they pleasant to be around". You can't really know a person technically or socially until they've been in the job for at least a little bit though.
pm90May 27, 2026, 6:01 AM
I believe the authors reading of the situation: its likely the interviewer wasn’t intentionally being cruel; most likely its this startups “unique thing that makes them stand out”; quirky twists that every startup attempts to make them stand out from the rest.

Honestly though, I think it ultimately worked out best for all parties. Its clear that the startup didn’t value someone that could be so vulnerable, and hopefully the author ultimately found a place that did.

My personal perspective is that for super early/founding engineer type roles you absolutely have to bring a greater part of yourself to work; you will be working over the weekends, working late, celebrating together and such… generally that environment is closer to a college club or fraternity than a corporation.

eximiusMay 26, 2026, 11:21 PM
Earlier this year I was told I failed an interview because when asked why I wanted to join a company, my answer "could apply to other companies in the same stage of life." They apparently required me to be _uniquely_ interested in their company. There were other oddities about their interview process.

Some interviewers just want to feel special.

not_the_fdaMay 27, 2026, 12:30 AM
Thats the thing I love about recruiters. I won't be looking for a job, and a recruiter calls me about one that sounds interesting.

Come interview time someone will ask why I want to work there. My answer is: "You called me, why should I want to work here."

elzbardicoMay 26, 2026, 11:40 PM
Assume that every singlemotherfucking breathing human you find in your life wants or at least likes to feel special, and that any company that asks you that question wants you to massage their ego a little bit.

Don't think much about it, just believe what I am telling you. It is going to save you a lot of grief.

toast0May 27, 2026, 12:12 AM
That question may be a little bit praise seeking (especially in other contexts), but it's also a way to ask if you did any research on the company, or do you just spray and pray.

If you took time to do a little research and validate that you fit more than 'i need a pay check and you have paychecks' that's valuable for the company. Your judgement may be poor, but you self screened, so that's an extra screening.

eximiusMay 27, 2026, 2:19 AM
1) They reached out to me. 2) My answer was applicable and accurate, but insufficiently _unique_ for them.
genewitchMay 27, 2026, 2:43 AM
Dale Carnegie floating around this thread a lot.

Remembering (and using!) someone's name is a magic spell, too.

simoncionMay 27, 2026, 5:49 AM
> Remembering (and using!) someone's name is a magic spell, too.

When it's done to me, it's the magic spell of "I Distrust You". A time or two is fine, as is its usage if one is -say- in a group conversation where it can be difficult to understand to whom one is speaking, or -say- one needs to get my attention when I'm focusing on something else.

In my many years of personal experience, I've found that people who behave as if speaking my name to me is a magic spell absolutely do not have my best interests at heart. At best, they want to manipulate me into doing something that I don't wish to do. I recognize that my opinion is not universal, but I am absolutely not the only person on earth who's like this.

icedchaiMay 26, 2026, 10:29 PM
I would've ended the interview. "I don't want to waste any more of your time. It's clear to me I won't be a good fit here. Thank you for the consideration." <end call>
psadauskasMay 26, 2026, 11:17 PM
I had an interview many years ago, that wasn't nearly as traumatic, but the interviewer asked me about my failures like 4 different ways.

- Tell me about a time you made a professional mistake. - Tell me about your biggest failure. - Tell me when you last shipped a bug. - Tell me when you took down production.

Never asked me about my accomplishments, or the positives. I'm prepared for being asked about making mistakes, and have a few examples ready to give depending on the job I'm interviewing for, but to get asked so many times in a row was just deflating.

I'm glad I didn't get that job.

shooMay 27, 2026, 12:20 AM
I conducted a few hundred software engineering interviews while working for a non-tech corp. Aside from technical problem solving & programming interviews we'd also ask a few behavioural questions -- including asking about times where the candidate had made a mistake at work, or a time at work where they were very frustrated.

What we were looking for

- people unwilling to admit they'd ever made a mistake -- red flag

- people who could reflect on the situation and say what they'd do differently in the future

- ideally, people who could use their mistake / failure / bad situation as an example of how they then took initiative to improve things by doing blah blah blah

People who were able to give an ideal response had clearly practised for this kind of question & knew how to play this part of the interview game.

Behaviours valued by one type of potential employer may not be valued by another. Small businesses & startups might value folks who take initiative and have a bias for action. In contrast, regulated megacorps might value folks who are great at consulting stakeholders and getting buy in before making changes, and steer clear of people they believe will go off and do stuff unilaterally.

One rule of thumb for handling these kinds of behavioural questions is "STAR" -- situation, task, action, result. Use the prompt for the question as a way to pick an example, then figure out how to frame an answer that shows you doing something to improve the situation. There's a fair chance that your interviewers are trying to mash your response into a STAR format in their own notes, even if they don't hint for you to respond in this way.

psadauskasMay 27, 2026, 4:05 AM
Right, I'm aware, and like I said, I expect those questions, and I have several examples I'm prepared for, and can tailor it to the interviewer. Like if it was a devops role, I could talk about when I took down production and what I learned from it. Or I could talk about when I failed to properly manage a junior if the role was more management-oriented and what I learned from it. Or when I badly architected a feature, and what I learned from it, and so on.

What I _wasn't_ prepared for was 4+ of those questions in a row, and _zero_ questions about my experience, or strengths, or anything else. The questions were more of the type "when did you stop beating your wife?". In retrospect, I think the interviewer already had someone they wanted to hire, but were forced into it by HR due diligence or something.

y1n0May 27, 2026, 6:27 AM
Where I work we divide up topics and questions so we aren't all asking the same thing in an interview. This guy might have been given the "handling failures" scenario.

It's possible that's what happened here and the interviewer also just wasn't very good. Some people just really suck at interviewing.

throwaway271818May 26, 2026, 11:33 PM
I think a lot of technical people interpret interview questions literally. Like yes of course the prompt starts with a negative - but you don't actually have to answer the question fully and literally, this isn't a college exam.

You could for example start talking about how you thought something was a colossal failure only to realize looking back that it was an incredible learning experience and how sometimes the only way to learn big lessons like that is by trying the experiment. And how it's only a failure if you stop. But you kept going so it wasn't really a failure.

Honestly we should probably take a page out of politicians' or media trained people's playbooks and not even answer the question as asked but relentlessly steer towards what you really want to talk about.

strkenMay 27, 2026, 12:15 AM
I too am capable of waffling to an interviewer. My favourite "took down production" story is a segue into why, when your interns ask you to look over the command they're about to run against the prod environment because they're not 100% comfortable, you should do it, and a broader chat about infrastructure-as-code and review processes.

I don't think it's good practice for the interviewer to require the ability to dissemble from software engineers, though.

pacman128May 27, 2026, 12:21 AM
Is it too much to ask for interviewers not to ask questions where the "right" answer is to give a BS answer?
lz400May 26, 2026, 11:44 PM
Truth is, most people who interview people have no idea how to do it. I know because I've done hundreds and nobody ever trained me or explained to me how to do it properly. Over the years I've seen so many people on both sides of the table that I developed a method and I got semi-functional at it but so many people doing interviews shouldn't that bad experiences should be almost expected by now.
efortisMay 27, 2026, 12:09 AM
A hiring manager asked me a question like those. I said: "sorry I'm not prepared, I don't remember from the top of my head." Right before that interview I was a solo founder. He said something like: "ok, so you just focus on the work?" "Yes." I got the job.
badc0ffeeMay 26, 2026, 10:33 PM
> Even if you hire a cracked engineer, it’s probably not gonna be a good experience all-around if you can’t make a human connection.

"Cracked engineer" is throwing me, but maybe I've just never seen the word cracked used this way before. Should it be "crack", like "crack team"?

AvicebronMay 26, 2026, 10:37 PM
It's a fairly common english phrase that originated out of the gaming culture of the US in the mid 2000-2010s.

"He's so good (plays aggressively) he must be on crack" sort of became "he's cracked", etc. Now that the people who were killing CoD lobbies are writing code full time or running companies, its seeped out.

Actually I think "it's cooked" came from this as well.

stuxnet79May 26, 2026, 10:43 PM
I have heard this term and used it myself but wasn't aware of the etymology.

Funny enough, I've only ever heard 'crack team' used in a professional context.

If 'cooked' diffuses to corporate at the same rate then I'm very much looking forward to 'cooking the ops' during standup in 2035 :P

kbelderMay 26, 2026, 11:15 PM
"Crack team" long predates video games and even crack cocaine. I think it is related to the phrase "get cracking", i.e., "get working", but I wasn't able to find a clear etymological line. One possibility is it refers to gunfire, but I wonder if it refers to harvesting, cracking corn, etc.
defrostMay 27, 2026, 12:56 AM
What if it's actually Craic team though ?

IMHE everybody wants to be on the craic team - they play hard, work hard and go hard.

https://en.wikipedia.org/wiki/Craic

jszymborskiMay 26, 2026, 10:43 PM
Notably, if someone is "cooked", it's bad. If someone is "cooking", it's often (but not necessarily) positive, most commonly in the form "let him/her cook" or "he's/she's cooking".
dugidugoutMay 26, 2026, 10:52 PM
I believe it was emergent from FPS gaming culture, particularly following the popularity of Apex Legends. In Apex Legends you have an energy shield which serves as a buffer of hit points. When playing cooperatively it is useful to communicate when this energy shield is "cracked", thus the line "they are cracked" emerged. This originally meant a target player's shield is down in Apex Legend specifically, but it was then the Fortnite (and broader FPS) community which took this phrase and warped it to mean someone is precise or an excellent shot. Today it is certainly used in the context the original poster intended.

edit: Looking again, this may be overstated. Apex-era gaming culture likely helped popularize the usage, but considering older idioms like "crack shot," the actual etymological root is more likely there.

pibakerMay 27, 2026, 12:41 AM
I have never seen it used in this way before around 2021, but it has become popular since then among the Twitter and YouTube tech influencer circle. Maybe that's where OP picked it up.
sliechtyMay 27, 2026, 1:41 AM
same, i've heard "crack engineer/team/etc" but cracked sounds to me like u fucked em mate
OgreMay 26, 2026, 11:49 PM
I'm with you, came here to ask this too. This is how I would have read it:

"Crack engineer" someone who is an excellent engineer, I feel like this goes back to at least the early 20th century, certainly long before gaming culture.

"Cracked engineer" a damaged person who is an engineer

Shrug. Language changes all the time!

cbdevidalMay 26, 2026, 10:46 PM
Beats my worst interview. For some reason I mentioned that I like reading. The guy then demanded to list the last ten books I read. I just named ten random books that I had read at some point in my life, even in childhood. Pretty bizarre. Glad I didn’t get that job.
cmdoptescMay 26, 2026, 11:24 PM
Asking you to name a book or two to continue the conversation is fine, but 10 is ridiculous. That interviewer literally pulled the "oh you like _____ band?! name 5 of their albums" meme on you.
OJFordMay 26, 2026, 11:29 PM
I can imagine getting myself into a similar fix. I'd like to think I'd calmly clarify that while I enjoy it I don't get through as many as quickly as I'd like; I'm currently reading blah, and previously blah and blah, but I can't recall the last ten.

Because they're presumably just trying to call bullshit, since it can sound like such an easy probably oft-recomended 'hobby' to say you have, so it's 'oh yeah well what have you actually read recently then', not actually 'I now therefore expect you to have perfect recall over your read catalogue'.

dylan604May 26, 2026, 10:52 PM
Asking for a list of 10 is a pretty specific version of a natural conversational follow up "what have you read lately?" Sounds like a coder with bad social skills. Like a bad sitcom where I could totally see a Sheldon asking that as a response
cbdevidalMay 26, 2026, 11:04 PM
The little bit I knew about the guy, coder with bad social skills does seem to be a fit.
nitwit005May 26, 2026, 11:14 PM
I got "tell me what you're passionate about" last time, and I'm curious what a bad reply would be, because I showed them a silly comic I drew on my phone. Apparently that was fine.
ungreased0675May 27, 2026, 12:18 AM
A pattern I’ve noticed on high performing teams is that individuals were or are excellent at something, anything. I suppose that could be an interview question, but people may not want to share their competitive barbershop quartet videos with a stranger.
TurdF3rgusonMay 26, 2026, 10:49 PM
I mean, what's the cutoff for something like that. The last book you read seems innocent enough. The last 3? No red flag yet... 10 though is kind of a lot.
cbdevidalMay 26, 2026, 10:50 PM
I couldn’t even tell you the last ten I’d read recently, and I thoroughly enjoy reading.
stavrosMay 26, 2026, 10:53 PM
I'm not sure I could name ten books, period.
sdenton4May 26, 2026, 10:51 PM
"Actually, I just pulled up your goodreads profile, and it looks like your eighth-most recent book was 50 shades of grey. In addition to having a faulty memory, you're reading work-inappropriate material. Finally, you read that in 2021, so clearly you don't care about reading /that/ much. Dismissed!"
dylan604May 26, 2026, 10:53 PM
I just said I enjoy it, not that I do it often.
elzbardicoMay 27, 2026, 12:02 AM
I would go by something like:

"The industrial society and its future" - Theodor Kaczinski.

"The communist manifesto" - Karl Marx.

"Rules for Radicals" - Saul Alinsky

"Hitler's War" - David Irving

"The Souls of Black Folk" - W.E.B. Du Bois

"Capital in the Twenty-First Century" - Tom Pickety

"Las venas abiertas da America Latina" - Eduardo Galeano

"The question of Palestine" - Edward Said.

"Grapes of Wrath" - John Steinbeck.

"The conquest of Bread" - Kropotkin

"Problems of Leninism" - Josef Stalin

If adventurous, I'd cite another one I've read that should not be mentioned amongst educated XXI century folks, as they think reading a book means you agree with the author.

Not the last 10 books I've read, but books I've read along my life and that would maybe make the guy think twice before considering making me an offer.

dnnddidiejMay 27, 2026, 6:33 AM
Non zero chance you make a friend by citing the list! Or you get the boot. Especially when the Atlas Shrugged reading startup founder is deciding.
niraj898May 27, 2026, 7:09 AM
My first interview was the weirdest one, as i was so panicked that i started lying to the interviewer.
mcvMay 26, 2026, 10:55 PM
> covering such lovely topics as the hardest day of my life, my biggest life challenges, and other similar “trauma-baiting” questions.

> talking about failed relationships, family struggles, and interpersonal challenges in previous work environments.

I think that's an interpretation that wasn't necessary (though I agree they're terrible and risky interview questions). I'd stick to hard challenges is my professional life, hard problems I had to solve, etc. My personal life is none of their business.

And I think there's the possibility you may have been rejected for sharing too much. But I agree that kind of question does invite sharing too much.

tombertMay 26, 2026, 11:28 PM
Not the OP, but having been in many similar interviews, I feel like it's an easy trap to fall into, especially if you've not developed a good bit of curmudgeonly cynicism.

At least when I've done these interviews, they will be extremely friendly, and they will at least act interested in everything you have to say. It's very easy to overshare when you think the audience is actually interested in what you have to say.

sbinneeMay 27, 2026, 12:47 AM
I can share mine. It was a job interview with one of the fastest growing companies. They were expanding sales positions in APEC region, specifically Korea. I am not really into sales, but I thought okay because it was such a big opportunity to work for this company.

I got three rounds of interviews including technical ones, then I had an interview with my potential team lead. The first thing he asked was about my MBTI personality test, which I hate and didn't pay much attention to learn mine. It seemed every encounter in Korea began with this MBTI test, but common in a job interview? I honestly answered him that I don't know my MBTI and just described my personalities in general. Then he started describing his MBTI and told me that I may not be the best fit with him because this and that.

A few days after, I got an email "... sorry". I don't want to believe that his MBTI question attributed a lot to this decision.

gabolaevMay 26, 2026, 11:08 PM
It’s kinda ironic that after interviewing with a mental health startup, you ended up so emotionally disturbed that you might now need some actual mental health support to tackle the thoughts it brought up. I’m sorry you had to go through that.
mawadevMay 26, 2026, 11:39 PM
I think the author was reading too much into these questions. I bet these people came up with random questions they thought were deep, especially coming from a mental health lens, but struck a nerve in the author. They essentially weren't prepared for the raw human experience that was shared here.

I think regardless of whatever you face during an interview, true mastery is to let your humanity at the door and pull up a facade. If you cannot do it in that context, you dodged a bullet imho.. you wouldn't be able to recognize yourself a few years down the line working there with them daily.

esperentMay 26, 2026, 11:46 PM
> true mastery is to let your humanity at the door and pull up a facade

Or say "screw that" and go find work that lets you be a human, not a repressed shell. I'm in my 40s now and have followed that my whole life to great benefit. Barring about two months in a open-plan hell hole in my mid twenties which I still look back on and shudder, mostly out of empathy for people who spend their whole working lives that way.

awesomeusernameMay 26, 2026, 11:43 PM
I know many people like you. Don't project your mentality onto someone else.

People who can "pull up a facade" are a subset of the population

steelframeMay 27, 2026, 1:07 AM
I had an eerily similar situation in a behavioral interview I had with a company where I had a very strong internal referral from a very senior person. I didn't have any time at all to prepare for the interview and was super stressed out that week because of a cascade of work and personal problems all hitting me at once. In hindsight I probably should have asked for the interview to be postponed by a couple of weeks.

In short, I hadn't prepared at all for the interview loop, so I didn't have any of the standard responses "ready to go" for the behavioral interview. We ended up meandering into a bunch of stuff from my personal life, and I didn't have the presence of mind to course-correct it myself. It didn't help that the interviewer actively encouraged me to keep talking about the personal non-work experiences. I got the impression that the interviewer was self-deluded into thinking that they could do some kind of psychological evaluation of me, even though they clearly (in hindsight) had no formal education or training in doing that sort of thing.

Anyway, same story. After a few days, generic rejection letter, and no more communications. I can only imagine my interview loop feedback must have been horrific to overcome what I am certain was a strong internal referral by a very senior and well-respected employee at said company who I had worked with closely for several years (and he'd sung my praises at our previous company many a time when giving perf feedback). I keep replaying the behavioral interview in my mind and realize I must have come across really awkwardly to the hiring manager. In the end I felt much like the author of this blog post did, personally rather than professionally rejected.

I'm resolved no longer suffering pseudo-psychological behavioral interviews. If I get any questions that I feel cross the line between professional and personal, I'll firmly respond that I do not feel comfortable discussing non-work-related issues in a job interview.

KholinMay 27, 2026, 12:08 AM
I've met the same type interview recently, but not on the phone, it's a online web forms. I just write those not that important and positive memories, because I don't trust them from the start. Also, on the next step of the form, there's a statement shows they will use AI to analyze my personality. I feel uncomfortable and told them I don't like their way of interview and just end it.
ryukopostingMay 26, 2026, 11:57 PM
This is hazing, and OP is right to be upset. They were put into a Catch-22 by the interviewer and I see no reason to believe that was accidental.

I see a lot of replies that accuse OP of oversharing, and that's bullshit. In any job interview, the expectation is that you answer questions to the best of your ability. If "I'm not comfortable answering that" is an acceptable answer, that is an exception to the norm and it should be made clear ahead of time.

justomsharmaMay 27, 2026, 12:51 AM
After reading your blog : I would say : interview depend totally on candidate on how he/she wants to drive, its never like an QnA, unless you are giving a HR round. its like : you say something : other person asks more about it : you explain more. and this is how an interview is driven.

The feeling you expressed is a true feeling of a candidate after the interview : but you are thinking that you did everything best : I would suggest to think from interviewer's shoes as well : how you gave interview : if you are someone taking interview : and candidate gave this responses : would you hire him or not

if not then what could he/she do better...

Reflect like this...

garrickvanburenMay 26, 2026, 11:34 PM
My worst job interview ever - in-house creative team at telecom company in downtown Chicago.

I walk into a darkened cubicle farm, down to the only lit corner office for a 'lunch interview'.

Interviewer is sitting at their desk eating a hot pocket on a paper plate.

Didn't even offer me any.

First interview I walked out of.

Not the last.

lokarMay 26, 2026, 10:48 PM
I had one job, where at the very end of the process there was a multi-hour evaluation by a psychologist / consultant they used. Went over my full life history, school, jobs, etc.

It was all disclosed up front, so no surprises. Not really that bad.

mbf1May 26, 2026, 10:33 PM
Sounds like a behavioral interview that silicon valley sometimes uses - the questions are designed to ascertain how you deal with difficulty, stress, and certain situations which they absolutely can't legally ask about directly - they are looking for you to discuss challenging times where you succeeded by working harder, doing more than peers, etc. It's not about shaming you, and understanding what they are looking for and why is key - they want people who stick with them through difficult times that they anticipate having.

For interview questions like these, they can only tease about what they are really after - finding employees who "go the extra mile" or "stay late" or "don't give up in the face of adversity". They are looking for you to find evidence of these patterns to corroborate your story. If they drove you to the answer they were after, it wouldn't be a passing score in their interview summary write-up.

bcynMay 26, 2026, 10:57 PM
Agreed. Reading the rest of these comments are makes me feel crazy / like I’m missing something. It doesn’t sound like the interviewer was making the candidate divulge traumatic information - but rather assessing how they deal with adversity.
hyperhelloMay 26, 2026, 10:24 PM
Are you quite sure it was a real business and not just some weirdo pretending to be a business for fun?
robertclausMay 26, 2026, 10:35 PM
I think the post said early stage startups... So maybe both?
livealifeMay 26, 2026, 11:20 PM
Name and shame company: Canonical

They make us write essays and life stories and reject in 24hrs.

Felt the exact same frustration.

comrade1234May 27, 2026, 12:34 AM
I've had that kind of interview. I kept avoiding the questions because it's not their business. He kept asking. I didn't get the job but that's fine.

I've always worked with people I don't mesh with. We fight with each other. We even yell sometimes. But that's ok. We don't need to be a family and in fact I feel major ick at the thought (weird polyamory shit) - they're gross. But they are competent and consistently bring us more customers.

phacker007May 27, 2026, 12:11 AM
You dodged a bullet my fren.
jimt1234May 27, 2026, 12:08 AM
One thing I've done in the past when interviewing candidates is to create a hypothetical situation where the candidate doesn't know how to proceed, like some difficult technical issue. I'd also tell the candidate that their manager and peers are all unavailable. Then, I'd ask how they'd go about trying to resolve the issue and proceed. Honestly, I was never looking for the correct resolution. Rather, I was just looking that the candidate had some basic process for troubleshooting and figuring stuff out on their own. If someone said, "I'd search Stack Overflow until I found the solution.", that was usually good enough. However, all too often, candidates just couldn't understand what was being asked, like they independent troubleshooting was an unrealistic skillset. I'd say, "Just walk me through how you'd approach solving this issue." Some candidates would fully melt down, saying, "I don't know. I can't proceed."
tamimioMay 26, 2026, 11:59 PM
Boy oh boy, the shenanigans I saw when it comes to job interviews are enough to write a book, not even joking, it was easier to start a business than getting hired as an employee, because building a business you talk with mature, goal oriented adults, who only care about what value that business will add. In jobs, that’s the last they care about nowadays, from morons in the HR, to power hungry managers, to contracts that I would say borderline exploitation with minimum regulations to protect the employees.

One job they got offended to ask for a negotiation, despite it was them who changed the original job posting. Another job took 4 interviews (plus one redundant, as it seems they forgot they had that interview with me) over 4 months only to send a generic “thank you” email. Another job, the interviewer seems was hostile just to have the interview. Another one the questions in the first interview were stupid, supposedly technical but extremely shallow, like tabs or spaces.. yeah, I got asked that! Another one refused to change a word in the contract because it’s a “template”, it felt like applying to a service rather than a job. And many other stories, like a company sent me a ticket for an interview in another country, only to find the team is disconnected from what the recruiter wants, they paid for the trip tho.

European companies seem slightly better than North American ones, but for some reasons bringing up the money talk early is a taboo topic? Had few calls and noticed that, they got shocked asking such question, even though it’s great to know so we don’t waste our time.

I never negotiated money, funny how that sounds, but it isn’t my no1 priority, all I wanted is a mature workplace and working with goal oriented people where nothing else matters that much than delivering the results, it seems it was impossible.

booleandilemmaMay 26, 2026, 10:38 PM
I was asked what my hobbies are during an interview once and it made me believe they were just looking for a personality hire or a pretty face.
freehorseMay 26, 2026, 11:48 PM
The mirror side of this is when almost all the intern applications/cover letters we used to receive contained a paragraph about the hobbies of the applicant (all domain-irrelevant). I find that weird but I guess it is sort of common nowadays?
toast0May 27, 2026, 12:24 AM
I was involved with picking a candidate for an internship in 1999, we had three candidates and they all mentioned basketball on their resumes. I think it's just something to help the resume fill one page. And help provide a direction for a 'validate the resume' interview.

Sometimes, if the hobby shows leadership etc, it might be relevant even if the domain isn't.

bobanrockyMay 26, 2026, 11:19 PM
Umm .. pretty standard & generally lame line of questioning at many companies/countries. Sounds like you were offended or surprised by it?
dbgrmanMay 27, 2026, 12:25 AM
had a similar unsolicited psych evaluation interview back in 2017 in twitter. There was a VP (or maybe director), who started with "go back in history and tell me what your boss at position X would say about you", and this kept happening for an hour.
siliconc0wMay 26, 2026, 11:10 PM
These are essentially sociopath screens where they expect you to memorize some STAR stories and regurgitate them on demand. And I don't mean screen out.
pureagaveMay 26, 2026, 11:30 PM
I came here expecting it was a yet another story about Canonical.
tombertMay 26, 2026, 11:01 PM
I have a two way tie for the worst interviews I've ever had, for very different reasons.

First, in 2023 I interviewed for a startup as a lead architect.

They had me do some virtual whiteboard stuff, and so I was drawing rectangles and cylinders and mentioning things like "database" and "message queues" as generically as I could.

They would interrupt me and say stuff like "Which message queue? Where do you download that?". The interview went on for a long time, with many bizarrely-specific questions for a whiteboard interview, but I figured that it was just their way to make sure that candidates didn't bullshit them by handwaving away important details.

They did make me an offer a few days later, but not for as much as I wanted. That's fine, no hard feelings over that.

But then a week later the CEO emails me asking for technical help on a question. I was on the train when I got it. I don't remember the exact question but it was something to do with RabbitMQ and Redis, and it was pretty easy, so I just typed out a quick answer to my phone and replied without even really thinking about it. Then another half-hour later he responds back to my reply asking for more detail on everything.

After his last reply I sent a response like "I am happy enough to continue this conversation but I'm afraid I will need to start billing the time it takes for me to reply. Give me a call and we can discuss the rate.

He didn't reply.

And then I realized something: this company was using interviews as unpaid consulting. That's why they were asking for bizarrely-specific stuff during the interview, and that's why the CEO was still trying to get free consulting out of me even afterward.

Really pissed me off, and I am very glad I didn't accept their offer. I am generally a person who is happy to help answer technical questions for free [1], but I felt like my trusting nature was kind of weaponized.

---------

Second was last year at a big bank.

I was really excited for this job, so I showed up to the interview in my best (and only) suit, made sure everything looked nice, and had studied for many of the technical questions I thought they were likely to ask the previous night.

Off to a bad start, it was one of the hottest days in NYC of the year, and I sweat a lot by nature, so in combination with the full suit, by the time I got to the building I was already kind of drenched in sweat.

Once I get in, they start giving me some conceptual algorithm questions on the whiteboard. I don't remember the exact question, but I remember they asked the runtime complexity of my solution and I said "Looks like O(n + log m) where n is the length of list A and m is the length of list B". One of the interviewers very confidently corrects me an says "You got your n and m backward".

I look at the board, go through my solution, and, no, I actually hadn't gotten the variables backward.

I have no idea what you're supposed to do in a situation where you're right and the interviewer is wrong [2], so I just do a trace through my solution and explain that, no, my variables were appropriately assigned. He still confidently "corrected" me again.

At this point I really don't know what I'm supposed to do, because I'm not going to just lie and say "oh you're right", but if I'm wrong, then I do want to know why so I don't repeat the mistake in the future. So I ask him "Ok, let's trace through this again because I really don't think my understanding is wrong here".

It was this bizarre gaslighting experience, because he would agree with every premise of why I thought the answer was O(n + log m), and every reasoning step along the way, but then still insisted I got the answer wrong. I do really know my Big O complexity, I have been doing this for a very long time, so eventually I just said something like "I guess we need to agree to disagree" because my time for that interview was almost up.

Then there was another interview immediately afterward. The interviewer started asking me very specific questions about Java Spring MVC (like about which annotations to use and whatnot)

Now, I don't have Java Spring on my resume, I haven't touched Java Spring in more than a decade, and Java Spring was not in the job listing. I didn't even consider studying Spring MVC because the listing didn't even mention that this would be web-based.

So I tell the guy something like "umm, I don't really know Spring. I know how a web request works so I'm happy to answer conceptual questions on the whiteboard, but I'm afraid I would have to learn the specific syntax".

And he responded "Well this is not a junior role. You shouldn't have to learn."

So of course I get the specific Spring questions wrong, and fine, if they wanted a person who knew Spring, that's ok, even if they should have put that in the job posting.

But then he asked me to, on the whiteboard, design a basic web request where there was a global counter [3]. I use an AtomicLong, which to my understanding is what pretty much every human who writes Java uses for counters.

He asked me why I used an AtomicLong, and I said "because it's what everyone uses, and because it doesn't block and because compare and swap for a small surface area like that is pretty cheap".

The guy then, corrected me, and told me to use a mutex. I said "I don't think a mutex is necessary here, if it's just a counter I think an atomic is fine."

He was very insistent, and told me to rewrite it with a mutex, and at this point I am starting to question my own competence, so I yield and just rewrite it with a ReentrantLock, which he again "corrected" me saying that I should use `synchronized`, and at that I push back and say "no, ReentrantLock is fine".

I left the interview feeling like a moron; I was so sure about this stuff before, but maybe I didn't have the understanding I thought I did.

I'm friends with a few graybeard C and C++ programmers on Discord, so when I got home I told them the questions and asked them how they'd solve them, and they solved the problems in the same way I would have.

Then I realized that this interviewer, who was principal level, didn't know what an atomic was, and I think he also had no idea how to use ReentrantLock, and so when I used them he just assumed I was wrong. Moron.

[1] And that's still true; feel free to email me if you want to geek out about software :)

[2] And it seems like the answer I get for that varies between each person. I'm not sure anyone knows.

[3] With, to be clear, no further arithmetic or anything being applied to it, before someone asks.

trusted_broMay 27, 2026, 5:48 AM
Dodged a bullet. There are good banks (eg Goldman) and shitty banks (eg Bank Of $Large_North_American_Country) and not a lot in between.
offerccMay 27, 2026, 6:20 AM
[flagged]
huflungdungMay 26, 2026, 11:37 PM
[dead]
ctdinjeu5May 26, 2026, 10:26 PM
[flagged]
padolseyMay 26, 2026, 10:35 PM
>covering such lovely topics as the hardest day of my life, my biggest life challenges, and other similar “trauma-baiting” questions.

And this was for a mental health startup!? Please name-and-shame them. Awful.