Job interviews are stressful enough before you factor in the common ‘gotcha!’ questions. Business Technology’s resident U.S. blogger Keil Hubert deconstructs one popular ambush question and reveals that there’s a lot more danger hidden in it than you’d normally expect.
My weekly message boards digest from LinkedIn had an interesting thread this week. The poster presented a question about an interview board question (and I’m paraphrasing, here): ‘when asked,“What is your greatest weakness?” how do you respond?’ 
This is an intriguing problem, because the ‘best’ answer for one interviewer can (without changing a single syllable) also be the worst answer for another interviewer. Before you offer up a response, you have to judge the relative sophistication of the person asking you the question. The savvier they are at hiring and interpersonal relations, the more likely you are to have just stepped on a land mine when that question gets presented. Proceed with extreme caution until you’re confident that you have a good lock on your adversary. Then give them the answer that best addresses their expectations.
For simplicity’s sake, let’s assume that job candidates and interviewers both fall somewhere on a five-level proficiency spectrum:
Level 1 – Amateur
Level 2 – Novice
Level 3 – Experienced
Level 4 – Proficient
Level 5 – Expert
An interviewer at each level of proficiency will ask you the ‘greatest weakness’ question, but will have very different expectations of what constitutes a ‘good’ answer. That’s because interviewers at different levels of proficiency usually have very different objectives for the interviewing process. As a general rule, the more sophisticated the interviewer, the higher the expectations they have for the candidate, and the higher the bar is set for what constitutes a savvy answer.
I’ve read a lot of advice for job seekers that’s oriented strictly to the Amateur level. For example, experts warn you to expect this question and to have an answer ready.  Having no answer or blurting out something embarrassing is counterproductive. The same holds true as you advance up the proficiency spectrum; you should have an answer prepared for this question that is at or above the level of the person interviewing you. Yes, that means having multiple answers ready.
Here’s what I’ve found the interviewers are looking for:
Level 1 – Rudimentary communications skills; can you answer the question?
Level 2 – Basic self-awareness; can you articulate a reasonable answer?
Level 3 – Basic other-awareness; can you craft an answer that sounds like a self-deprecating weakness, but will actually be considered to be a strength?
Level 4 – Interview process meta-awareness; do you understand that the question the interviewer asked you is actually a test of how well you understand the hiring process, not about your actual weaknesses?
Level 5 – Professional adult dialogue; are you mature enough to realize that the interviewer genuinely wants an honest assessment and will judge you on your candour rather than the character of your claimed weakness?
Best answers, based on the above-listed proficiency chart, might sound like this:
Level 1 – ‘I’ve never thought about it. Can I get back to you on that?’ (It’s good, because it’s a complete sentence)
Level 2 – ‘I have a hard time waking up when my alarm goes off.’ (It’s good, because it shows some basic introspection and honesty)
Level 3 – ‘I hate to leave work undone. I’ll always stay late, on my own time, to finish my work so that I don’t miss any deadlines.’ (It’s good, because it sells you as a workaholic who will voluntarily make sacrifices for the boss’s benefit)
Level 4 – ‘I don’t know – yet – what might be considered a weakness in this corporate culture. I can talk about behaviours that weren’t optimal in my last employer’s culture, but I don’t know how they’ll translate here.’ (It’s good, because it shows that you understand interviewing, interpersonal dynamics, cultural differences, and the fact that this is a trick question)
Level 5 – ‘I loathe bullies. I won’t tolerate them in my organization. If you’re going to use the power of your position to inflict harm on others, be assured that I’ll run you out of the organization by whatever legal means I have at my disposal.’ (It’s good, because it tells an equally mature colleague who you are and what you stand for)
These are very different answers, and each one reveals interesting information about you as a candidate – if the interviewer is sophisticated enough to understand the answer. Here’s where it gets rough: interviewers ask the question in order to evaluate your level of sophistication, but they evaluate you and your answer based entirely on their own level of sophistication. The trouble is, if you answer at too high a level, it’s just as counterproductive as it would be if you answer at too low a level.
Giving a Level 3 answer to a Level 1 or 2 interviewer is likely to blow her mind. She’ll think you’rebrilliant because you don’t know that your ‘weakness’ isn’t really a weakness. On the other hand, if you give a Level 3 answer to a Level 4 or 5 interviewer, she’ll write you off as a smarmy lickspittle, since she recognizes that you’re trying to snow her, but aren’t savvy enough to know that she knows the game as well or better than you do.
Similarly, if you give a Level 4 or 5 answer to a Level 1-3 interviewer, you may induce an aneurism, but you won’t score ‘points’ for having a good answer. You may be viewed as too intellectual, or even get branded as an idiot because your answer went right over the interviewer’s head. If your interviewer feels intellectually overawed by you, and they lack the maturity to appreciate your value, they may invent specious reasons to disqualify you as a candidate.
The way to make sure that you give the optimal answer is to assess where the person asking the question falls on the proficiency spectrum. The idea is to figure out where they’re at, and then give them the answer that’s on par with what they’re looking for. It’s quite a challenge, and it requires a very different mind-set.
When you’re just starting out in the interview game, this whole business seems like navigating a minefield; if you foolishly step in the wrong place, you can blow the entire interview. It’s frightening, and it’s stressful. As you gain experience in the process, though, the entire process changes. Different metaphors are required. We’ll get into that in next Monday’s column.
 This column is the extended-dance-remix version of the answer I posted on the forum.
 Um … duh?