The worst job interview I ever had | personal sitehomeprojectsblogbooksgithubcontactThe worst job interview I ever hadMay 26, 2026The worst job interview I ever had wasn’t a knowledge meltdown, coding assessment failure, or a complete language misunderstanding with the interviewer (although I’ve had all of those, too). No, the worst job interview I had was something I can only describe as an unsolicited psych evaluation.
I’m an engineer, primarily working for small startups. At a less-than-10-person company, especially in the earliest days, cultural fit is of singular importance. 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. All this is to say - I get why you’d want to prioritize this. But despite many quite normal culture fit interviews, there’s one I still replay in my confused head once in a while. And I think it’s worth sharing not because I want to shame the company or individuals (I’ve left them anonymous), but rather to suggest some reconsideration for founders and hiring managers in the same boat.
About 3 years ago, I responded to a message looking for a founding engineer at a mental health startup (their noble cause was improving therapy access for at-risk youth). The first interview was a quick conversation with a founder and their head of engineering — a fairly uneventful informational interview (“this is why we’re great join us blah blah”). The follow-up with the head of engineering was scheduled shortly afterwards.
The follow-up, they described over email, would be a bit non traditional - a ~90 minute culture fit chat. Note there was no technical assessment yet. Expecting little, I joined the video call. It was explained we’d just be getting to know each other based on some guiding questions.
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.
Now, to be clear, I can understand why these discussions might give deep insight into a candidate! It’s just that I think it’s frankly a little invasive when you’re basically meeting this person for the first time.
I’m a little ashamed remembering myself talking about failed relationships, family struggles, and interpersonal challenges in previous work environments. This person gave the impression that it was a safe space to share, divulging little of their own trauma.
By the end of the call I felt completely emotionally drained - and i hadn’t even opened my terminal! By the time I got the cursory one line “We won’t be moving forward” email 24 hours later that emotional exhaustion quickly turned into two new feelings: shame and anger.
I felt awful that i had shared such deeply personal things with the interviewer just to be cast off in a rejection email. I felt angry that I was rejected. I felt embarrassment that my soul was seemingly cracked open and judged “unworthy.” It wasn’t my skills they were rejecting. It was… me.. I felt confused that a mental health startup had consciously decided to choose an interview so capable of making candidates feel so vulnerable.
I don’t think this person was trying to be cruel. Honestly, that almost made it more confusing. The format itself created the problem.
Culture fit is important, make no mistake. Make sure the people you hire are good people with strong morals. But consider evaluating this in a way that doesn’t make candidates feel like they need to share their deepest experiences just to scrape and claw for employment.rss

The author recounts an experience they describe as the worst job interview, which was not characterized by technical failure or misunderstanding, but rather by an unsolicited psychological evaluation during a process for a founding engineer role at a mental health startup. The author establishes the context by noting that in small, early-stage companies, cultural fit is considered critically important, as the success of hiring depends heavily on establishing a strong human connection.

The interview process involved an initial conversation with the founder and the head of engineering, followed by a subsequent approximately ninety-minute culture fit chat that lacked any technical assessment. During this session, the interviewer deviated from typical cultural discussions and instead posed deeply personal and sensitive questions, such as inquiries about the hardest days of the candidate's life and personal challenges. The author acknowledges that while such discussions might provide insight into a candidate, they felt invasive, especially when meeting someone for the first time.

The author reveals the emotional impact of sharing this vulnerability, noting feelings of shame, as they had previously shared personal struggles in other professional settings. The atmosphere created by the interviewer led the author to feel emotionally drained. Upon receiving the subsequent rejection email, this emotional exhaustion transformed into feelings of shame and anger, rooted in the perceived injustice of having exposed deep personal material only to be rejected. The core confusion stemmed from the realization that the hiring process, intended to assess fit, had instead placed the candidate in a position where they felt they had to reveal their deepest experiences simply to gain employment.

The author suggests that while evaluating cultural fit is necessary to ensure hires possess strong morals, the methodology employed in this assessment is flawed. The experience leads to a critique that hiring managers and founders should reconsider the methods used to evaluate cultural fit, emphasizing the need to avoid pressuring candidates into divulging their most intimate personal histories merely to secure a job.