Last week, I challenged readers to share the most difficult interview questions they’ve ever gotten – as interviewers. 

From the blunt (“What don’t you like about working for your company?”) to the bizarre (“If you walked into a room filled with jars and I was one of the jars, what would I have to contain to stand out from the others?”), the only thing more surprising than the actual questions our readers submitted were the surprisingly insightful lessons they gleaned from those questions.  

So without further ado, I present The Hiring Site readers’ nominees for the most difficult-to-answer interview questions they ever received from job candidates…and what they took away from the experience:

• “What is your company’s mission statement?” Seems like an innocent enough question, but Christina Thais was still relatively new to her company when a candidate asked her this during a phone interview, causing her to go blank. Another reader, Angie, had a similar experience when a candidate asked her to describe the company’s corporate culture. Since then, Angie writes, she has “taken the time to really think about how to communicate our corporate culture to future candidates.” Lesson learned: Both Christina and Angie’s experience highlight how important it is to ensure your employees understand the company vision, mission and values and constantly look for opportunities to communicate these things. Not only will the constant reminders keep you and your employees accountable for upholding these values and objectives, but the ability to recite these things off the bat is a sign to candidates that you actually “walk the walk.”  
• “What don’t you like about working for your company?” After being asked this question, reader Jessica writes, “I now prepare myself with potential similar difficult questions that may come up during the interview process.” Lesson learned: Alas, you can’t anticipate every difficult question that’s going to come your way, but you can anticipate that difficult questions will come up, and when they do, your best bet will be to simply tell the truth.  After all, if you’re dishonest or bend the truth, you risk the chance of setting false expectations for the candidate. A sugar-coated answer might help you fill the position, but it won’t stay filled very long. [Side note: This is also a good attitude to have if you, like one reader, Bridget, ever get a question like: “If you walked into a room filled with jars and I was one of the jars, what would I have to contain to stand out from the others?” “I’m still not sure how to answer that question,” Bridget writes.]
• “So what’s in it for me?” Another reader, NL, remembers being “appalled” when a potential candidate for an entry-level receptionist position asked this, the second in a line of questioning that began, “Why should I accept an offer to work for this company? Obviously, you’re not Google, with candidates sending you flowers, balloon telegrams or banging on your door to get it in.” Lesson learned: Not only did the candidate’s attitude reveal that she would not be a good fit for the company and that “phone screens are essential!” but it also seemed to confirm what NL already knew: It’s more than okay to not be Google. “Considering that every other candidate had heard about us prior to even applying…we are doing something right.”
• “Will you be keeping in touch? WILL you?”  It’s easy to forget how heavily candidates depend on that post-interview phone call from you…until one of them actually says so. Such is what happened to one commenter, J., who was met with bitter disbelief after promising to keep in touch with one candidate, who had apparently been (falsely) told one too many times by recruiters that she’d be called back.  Lesson learned: The confrontation taught J. ”that a response to a candidate is not a courtesy, it’s an essential part of the process and should never, ever be overlooked or taken lightly. We are dealing with real people with real lives and very real concerns and challenges. Every one of them deserves respect, and a response.” Couldn’t have said it better myself.
• “How many healthy choices do you offer in your vending machine?” When Eileen Hershkowitz received this question as well as many others about various working conditions at her company that promoted a healthy lifestyle, she realized that the candidate was seeking affirmation that her company not only talked about employee wellness, but truly executed that in its culture. Lesson learned: Eileen writes, “The candidate really had a valid point in my mind and made me re-think how important areas such as break rooms, and choices in vending machines and/or cafeterias can affect how your employees view your organization in the commitment to its most valuable resource.” In other words, it’s in the every day things things companies do – not just through quarterly bonuses, annual awards or periodic celebrations – that communicate to your employees that you sincerely value their efforts, support them and want to ensure their success. 
• “What are the specific steps you as my manager take to ensure my success in this position, and what are your procedures for preparing for my termination if I’m not?” After getting this question at the end of a sales position interview, reader James was understandably thrown off guard. After all, not many people ask about the firing process; however, James wrote that it made him consider how his accountability practices play into his goals for his team’s performance.   Lesson learned: “Interviews (especially for sales positions) need to include detailed expectations for success and ‘how’ the candidates will be held accountable for that success so that he/she knows exactly what will be expected of them should they get the job.”
• “Why isn’t anybody that works at your company happy?” Sure, it’s not the most eloquently phrased question, and perhaps a tad on the presumptuous side, but when a candidate  threw this question to one anonymous reader, rather than take offense and immediately dismiss the candidate, the interviewer instead took the opportunity to find out where the candidate had gotten such an impression and clarify any misconceptions about the company. Lesson learned: The interview process provides an opportunity to find out how well your company is executing its employment brand, and give insight into how to better execute it. 
• “What do you do if he (the owner) dies?” Despite its bluntness, reader Brett found this question to be smart once he realized that the candidate was thinking long term, and was concerned about the company’s viability should he be hired. Brett writes that this question “made me start to think – we prep for a lot of things like talking salary & benefits because we think about what we’d want to know… but you never know who’s sitting on the other side of the desk and what their wants/needs are…”  Lesson learned: Brett brings up a good point about the importance of doing the right research to understand candidate attitudes, behaviors and perceptions when recruiting and trying to sell your company to candidates.

The overall lesson?
At the very least, questions like these can give you insight into how an individual thinks and his or her motives for taking a job, as well as a glimpse into their soft skills, what kind of employee they will make and how, if hired, they would potentially sell your company to others, to name just a few additional benefits.

At the most, these questions can help prepare you for future interviews and give you insight into something about your company that needs to be addressed (see “Why isn’t anybody who works at your company happy?” above) – whether it’s better communication about the company mission statement, or the fact that you need to better manage or build your external employment brand.

What about you? Any questions of your own to add to the list? And if so, did you learn from the experience?