I'm not sure why, but a lot of candidates think asking deeply personal questions will get them high marks on the interview. I'm sure that most professionals enjoy sharing their career journey, but I've had some candidates ask me what the hardest part of my job is, or how I got here, etc, and it always seems a little out of place for me. What do you think of such questions? I'm happy to change my perspective, but as of now, I find it slightly weird.

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Many candidates want to know if there’s genuine transparency and whether leaders are relatable. It’s less about prying and more about understanding fit. So I never see it as a red flag or find it weird. I think I actually encourage when I'm being asked less than normal questions... helps me feel out the candidate too!

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There’s a lot of content circulating as well that encourages this as a means of “building rapport” but it’s always subjective at the end of the day.

I don’t agree that those kinds of questions are “deeply personal.” It’s still career related. It’s not like they’re asking you anything about your life outside of work.

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Those questions you mentioned as examples seem quite reasonable. You may find them to be personal or invasive but these people are trying to make an incredibly important decision and they only have 30min (or so) to get everything they need to know out of the conversation. A lot of the pleasantries get accelerated in that process. If you were in their shoes, you would want to know the answers to questions around transparency, culture, upward mobility, daily-in-the-life, etc. It’s hard to get it without being direct.

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I don't think it's weird! I think they are still career related. Personal to me would be asking about your dating life lol

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"What's the hardest part of your job" is not a deeply personal question to me.
"Honestly, it's purchasing the stuff I need to do my job efficiently," or "attending all my required meetings while still covering my responsibilities," is incredibly valuable data.
If it's "coming up with innovative solutions" or "doing the math" then it says the organization and the culture is doing a good job not getting in your way.
IMHO, it's one of the most important things a prospect can ask. And it would do everyone good to answer it honestly.

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Depending on your line of work and what type of role, & who you’re asking, it can be. But it’s still important for the candidate to ask as well.

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How is asking the hardest part of your job "deeply personal"? It's a reasonable question, and it's work related. People want to understand what to expect and knowing what someone in a hiring position finds challenging can be insightful for them.

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yes especially if the candidate is going to be working under this person, they want to know how they can help or what to expect!

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These are similar to questions candidates are often asked. As an interviewer, you have to be comfortable answering the same questions you are comfortable asking candidates. Interviews are a two-way street, and candidates are looking for as good of fit as the company interviewing them.

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