Asking them an esoteric question will make them uncomfortable but a personal question that addresses specific members of their family by name is going to put th

Asking them an esoteric question will make them uncomfortable but a personal question that addresses specific members of their family by name is going to put them at ease? This reminded me of the episode of The Office where Dwight steals Micheal's Rolodex to get information on his clients and it leads to him asking, "How's your gay son? ... Tony? The homosexual sophomore?" If you don't know someone intimately don't try to fake an intimate connection. The very next part of this quiz encouraged me to be upfront and honest instead of hiding behind excuses and managerial tricks. What if he were upfront and honest in response to the personal question and told you that his wife calls him a poor father and insults his manhood, are you ready to pivot to that subject? Can you reasonably expect him to answer that question dishonestly and if he needs to do so in order to avoid an awkward conversation then hasn't the question failed its purpose of opening an honest dialogue? What if this is a performance review and the result is somewhat negative? Is he to understand that his poor relationship with his wife had some bearing on his negative performance review? If not then why would you bring it up in that context? A relationship can thrive on one of two things: complete honesty or respectful boundaries. Maybe I am too sensitive about personal questions but that question doesn't seem appropriate. Also, esoteric conversation starters are great. I would much rather talk about why I would want to be a sunchoke than give a generic response without actually thinking about my answer.