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Unfortunately, this sort of thing is a soft skill and doing it well requires a lot of expertise. It's comparable to being a good interviewer, which is also a rarity.

You can't just ask hard, probing questions baldly and expect to get accurate answers. More so, you can't expect to do that and expect it to not affect your interviewer's appraisal of you as well. You need to build up a rapport first and then you need to ask some leading questions that give your interviewer the opportunity to reveal some perhaps unsavory truths about their workplace. Granted, it might be hard to generate a rapport, or they might be too wary to tell you anything of substance or anything negative about the company, but that alone provides a lot of information regardless. If you have a hard time connecting with interviewers then maybe culture fit would be a problem. And if they won't open up about problems then that might be a sign of a dysfunctional corporate environment that discourages honesty and openness.




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