20 Questions about Interviewing, with the World Experts on Hiring

Learn how to ace the interview and get hired to your dream job.

1. How “close to the vest” should I keep my cards during an interview?
   

   Not close at all. Losers hide the truth. Winners share information.

2. How much should I “butter up” my future boss?
   

   A 2 on a 10-point scale. A 0 or 1 makes you look selfish and un-interested. A 3 or more makes you look like a weak suck-up.

3. What should I do if the person interviewing me really stinks at interviewing?
   

   If they are your future boss, then find another future boss. Bosses that are bad at interviewing are bad at leading.

   If they are a “gatekeeper” like a peer or Head of HR, then go along with their lousy interviewing approach. Here are 5 versions of bad interviewing that you may encounter:

   • Sir Talks-A-Lot: This person has mistaken an interview with you as a confessional or a psychotherapy session or a Saturday Night Live monologue. Just let them talk. And reflect your understanding of their story so they know just how impressed you are with them. “It sounds like you have the ear of the CEO.” “It sounds like your college football success has translated into success in your job.” “It sounds like you have a different opinion about the strategy of this business than the board.” This person will hate you if you interrupt them, or if you change the subject to something productive or job relevant.
   • Serious Sally: This person takes their job too seriously. They frown at you. They try to “stump” you with meaningless technical questions—”What’s the square root of 120?” “How many bowling balls fit in the cargo hull of a 747?” The assumption of this type of interview is they will “test how you think” and derive insights about how you might perform on the job. It’s a flawed approach, proven non-predictive of performance in the field of Industrial Psychology 50 years ago. But Sally hasn’t gotten the memo.
   • Hypothetical Holly: She will give you “hypothetical scenarios,” and you get to speculate about what you “would do.” By the way, giving people hypothetical scenarios produces hypothetical answers, that have zero predictive validity. But just give her what she wants. “How would you get buy-in for an idea?” “Oh, Holly, first what I would do is to empathize with the other person. I’d find out what really motivates them. I’d find out what problems they are facing. Then I would offer to help, by sharing the idea. I’d listen to their reaction, and I’d probe for clarification. After demonstrating empathy and understanding for their needs, and thanking them for their feedback on the idea, I would modify the idea to include their feedback. Then I would circle back with them with the edited idea, and I’d let them know I was moving forward with *their* idea. They would thank me, and they would get credit in the eyes of their bosses and peers for coming up with a great idea. That’s how I’d get buy-in.”
   • Blank Bart: This person has no idea what they are doing. Their questions are pointless. They are just “making conversation.” So just make conversation back at them.
   • Best Friend Barb: This person wants to “friend” you. And they may actually send you a friend request minutes after the interview. This type of interviewer is highly insecure. They act like “testing your culture/chemistry match” is the point of the interview, but the point of this interview is really just for them to feel safe, that if you join you are not going to try to get them fired. So, be friendly. Don’t try to steer this interview into productive territory, or else they will complain to your future boss that you are too serious or not friendly enough.    
     
4. How much eye contact should I make during the interview?
   

   Some interviewing books tell you to maintain constant eye contact. Really? Constant? Like, 100%? How psycho is that? No, we find that about 25% eye contact is perfect.

5. How much “chit chat” should I make at the beginning of the interview?
   

   About as much as your future boss wants to make. Generally, 5 minutes of chit-chat is ideal. Then show a willingness to dive into more substantive topics.

6. Should I never cry during an interview?
   

   Right, you should never cry during an interview.

7. How much personal information should I reveal during the interview?
   

   Like a 6 out of 10. This includes your career goals, honest reporting of the number of hours or travel is acceptable to you, and anything else job-relevant that gives your future boss a sense of your motivations, parameters, and such. Sharing more gets weird. What, are you going to be like, “I have this fungal problem on my left foot. I’ve had it looked at several times but I have not pulled the trigger yet on a treatment.”
   

8. How should I change my approach if there is like a 5 on 1 interview?
   

   This is called a “panel interview.” They don’t work. But you can use them to your advantage. Answer questions directly, and completely. There will unlikely be follow-up questions, because how can you really follow up when there are 5 people all asking you questions? Appear calm and undaunted by 5 people asking you questions. They will conclude that you can “handle pressure.”

9. What if my future boss is being “tough” during the interview; is that a good sign or a bad sign?
   

   A bad sign. Ideal interviewers build rapport with their candidates. They are authentic, interested, and use a tone of “intense curiosity.” But it’s always respectful. In contrast, if you encounter a future boss who is trying to “make the candidate feel uncomfortable” during an interview, that’s likely because they are a lousy person, insecure, or stupid. There was one young CEO who came up to one of us after a speaking event we did at MIT. He was wearing a “muscle shirt” tank top and jeans. This entrepreneur asked us, “How do I hire more tough-minded people?” We found the question odd. So we probed deeper, and what we learned was that this boss was taking an extremely disrespectful “tough” tone during interviews. We asked for examples and he told us:

   “I like to be a tough interviewer.”

   “OK. So what does that look like.”

   “It looks like my making them wait, like 20 minutes. Just sitting there in my office as I work on emails, or run in and out of my office. I want them to know who’s boss.”

   “Mmm hmm,” we said.

   “And then once I start to interview them, I’ll start it like this. ‘Hey. Your resume is not that impressive. I only want to hire the best. Why should I think you are the best?”

   “Mmm hmm,” we replied.

   “But wait, it gets better.”

   “OK,” we said.

   “So then, as they are starting to talk, and justify their existence, I’ll ask them very specific questions. Like, ‘Really? You say you succeeded in selling into the enterprise space, but I bet you can’t even spell enterprise. Go ahead, spell it.'”

   “Goodness,” we observed.

   “So,” he continued, “I want to know how to hire tough-minded people.”

   “What, your approach is not working?” we asked.

   “Well, um, not really. I’ll get these pretty talented candidates—you know, perfect SAT scores and grades and such—and they won’t come back for the next round of interviews after they sit with me.”

   “Oh,” we said.

   “I just want you guys to tell me. Am I doing it wrong? I’m just trying to find winners—people who are going to be tough and work hard and not complain.”

   “Yes, you are doing it wrong,” we replied, dead pan.

   “OK. Um, really? It’s a style of interviewing I sort of invented. I didn’t know if it was too much.”

   “Well, we’d say it’s not enough.”

   “Not enough what?”

   “Not enough of the best practices of interviewing, and too much stuff that is putting a barrier between you and great candidates.”

   “Yeah. OK, that’s why I asked, I figured it was probably not the best approach. Someone. (Pause) Some candidate recently posted online that I’m a ‘douche.'”

   “Really?” we feigned surprise.

   “Yeah. It sort of sucked because it got forwarded around to my own employees, and some of them agreed. It’s been something I need to wipe off the internet. I hired this SEO company that specializes in reputation management, and …” his voice trailed off.

   Well, not actually in person it trailed off. He continued to talk loudly, like a bully. But in our minds, his voice trailed off because we turned our attention to the other dozen or so entrepreneurs who were standing in line waiting to ask us questions about hiring.

    

10. What kinds of questions should I ask during an interview?
    

    You should ask questions about what your future boss wants to achieve, and then show how you are great at delivering relevant results (if you are in fact great at delivering relevant results. If you are not, then that’s not your dream job).
    

11. How much should I talk during an interview?
    

    45% of the time.

12. What are interviewers really trying to look for during an interview?
    

    Good ones are trying to measure the magnitude and relevance of your accomplishments.

13. What about chemistry? How do I make my chemistry match the chemistry of my future boss?

    We think chemistry is over-rated. It’s a crutch. But your chemistry will be good, if you are authentic, and if they hire you. Don’t over-manage your chemistry or it will come off as fake.
    

14. How about culture? How do I try to make my personality and background fit their culture?
    

    Figure out what their culture is all about. Is it fast or slow? Is it top-down or bottom-up? Is it highly communicative, or less so? Are people encouraged to speak up or just be heads-down? Once you figure out the culture, if you feel like you want to work in that culture, then do three things. 1) In describing past cultures and bosses, emphasize the parts you really liked, which match the culture at this company. (“I really liked how people were encouraged to take initiative. I raised my hand one town hall meeting with an idea and my boss at the time said, ‘Awesome—why don’t you get three or four people to work on that idea with you and report back next month on your progress.’) 2) When they ask you what type of culture you want to work in, emphasize the parts of this culture that you really like. 3) When they ask you why you want to work there, again, emphasize the elements of culture you like there.
    

15. When to “push back” on my future boss?
    

    Not at all. That doesn’t mean roll over and play dead. We don’t like the term “push back” because it implies that you are some poor, weak soul, who needs to stand up to the man. Stand up to the system that is oppressing you. We view you as strong. Smart. And capable. And we think you want your boss to be successful in achieving her goals, right? So don’t “push back.” As in “I’m going to have to challenge you on that point, Sue.” That’s weird and annoying to act like that. Instead, what you want to do is say, “I think you might achieve your goal of opening a London office, if you considered a slightly different approach. Rather than staff it with Australians, as you mentioned, you might consider staffing it with people from London, who have worked in that market and who have been successful.”

16. What if I don’t remember, or can’t figure out, the answer to a question I’m asked during an interview?
    

    Relax. There is nothing more awkward during an interview than somebody who feels bad for not remembering a fact, and who squirms and shifts in their seat. AWKward. Instead, you can say, “My best guess is that the company shipped 3,000 to 5,000 dish washers to India the year before I was the Regional VP of Sales there. I can get the exact number if you would like. The first year I was in place, I know we shipped 8,420 units on a goal of 6,000, and the second year we shipped 10,400 on a goal of 7,000. So I’m very proud of the work my team and I got done during those two years. Our boss said it was a fantastic performance, beating the targets.”

17. What does it look like to be “too confident” during an interview?
    

    Ah yes, the balance between being too confident vs. not confident enough. Our recommendation is to be “quietly confident.” Successes are things that took hard work and were possible because of the talent of the team you hired. Failures are real, had consequences, and you are aware with 20/20 hindsight what you could have done differently to have been successful. That’s confidence.

    Talking loudly, steepling your hands in a power gesture, pointing at your future boss, using vague overly-confident expressions like “we ate our competitors for lunch,” will make you look over-confident, or at a minimum, lacking in the EQ department (Emotional Quotient—your emotional intelligence).

18. What’s the worst thing I can do to blow my interview?
    

    I don’t know, slapping your future boss in the face. That’s not a very useful question to ask us.
    

19. What’s the second worst thing I can do to blow my interview?
    

    There are so many bad things you can do in interviews. In no particular order, it’s failing to read your future boss’ bio before the interview, talking too much, failing to answer questions directly, and having no idea about what the priorities are of the company, what the culture is, or any sense of relevant facts from your past you can talk about.
    

20. When should I talk about salary?
    

    Sometime during the first Screening Interview. It’s respectful to do so. Here’s why. You should make sure your salary expectations are in line with the job. We were interviewing a great candidate once for a job with a starting salary and bonus of $350,000. He failed to ask about salary until he was far into the process. As it turns out, he earned $2m in the previous year. So, that was a bummer for him and for us because everyone’s time was wasted.
    

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