Interviewing is highly stressful at the best of times – for everyone involved. Even when the candidate and the interviewer(s) put on their best performance, there’s always a chance that something said will hit a sour note and foul up the entire process. One of the ways to mitigate this risk is to understand your own level of sophistication first before trying to gauge the proficiency of the person sitting opposite you, then try to synch the answers with the questions.
[Keil’s aside: As I close on submitting my 400th online column, I want to revive some older pieces that meant the most to me (and, if feedback is to be believed, had the strongest positive impact on my readers). This column was the start of a trilogy on corporate interviewing that became the central core of my first book in 2014. This was originally published on 9th September 2013 on Business Reporter, and includes the edits applied to version 3 of Why Are You Here?]
My weekly message boards digest from LinkedIn had an interesting thread this week. A poster presented a question he’d been asked during an interview (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 your response, you have to judge the relative sophistication of the person asking you the question. The savvier they are at hiring and at interpersonal relations, the more likely you are to have just stepped on a land mine when that specific question gets presented. Proceed with extreme caution until you’re confident that you have a good lock on your adversary’s interviewing proficiency. Then give them the answer that best addresses their expectations.
For simplicity’s sake, let’s assume that all job candidates and interviewers fall somewhere on this 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 stock-standard ‘greatest weakness’ question, but each interviewer will have very different expectations of what constitutes a ‘good’ answer. That’s because interviewers at different proficiency levels 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 their candidates, and the higher the bar is set for what constitutes a savvy answer.
Many job seekers view pole vaulting as more enjoyable and less physically stressful than appearing before a hiring board.
I’ve read a lot of advice for job seekers that’s oriented strictly to the Amateur level. For example, experts warn us to expect this question and to have an answer ready. Having no answer prepared or blurting out something embarrassing is considered equally counterproductive. This isn’t wrong, necessarily. I believe that you should have answers prepared for this question; that is to say, one answer for each proficiency level, and deploy the answer that is at or one step above the level of the person interviewing you. Yes, that means having multiple answers ready. It also means knowing when and how to select the optimal one for your interviewer.
For orientation’s sake, here’s are the attributes and abilities that most interviewers are looking to evaluate through this common question:
- 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, and is not really about your weaknesses?
- Level 5 – Professional adult dialogue; are you mature enough to realize that the interviewer genuinely wants an honest assessment from you and will judge you on your candour and confidence rather than the theoretical utility of your claimed weakness?
Only offer a Level 5 answer to a Level 5 interviewer. If you display naked candor to nearly anyone else you may blow the entire interview.
I submit that the best answers, based on the above-listed proficiency levels, might sound like this:
- Level 1 – ‘I’ve never thought about it. Can I get back to you on that?’ (It’s good enough 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 pretends at disarming 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 deadlines.’ (It’s good, because it sells the candidate as an exploitable workaholic – one who will voluntarily make sacrifices for their boss’s benefit)
- Level 4 – ‘I don’t know – yet – what might be considered a weakness in this organisational 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. Yet.’ (It’s very good for an interviewer who’s on par, because it shows that the candidate understands interviewing, interpersonal dynamics, cultural differences, and the fact that this is usually a ‘trick’ question)
- Level 5 – ‘I loathe bullies. I won’t tolerate them in my organisation. If a colleague is going to use the power of their position to inflict harm on others, be assured that I’ll run them out of the organisation by whatever legal means I have at my disposal.’ (It’s good, because it tells an equally-mature colleague who you are and the values that motivate you)
I once went into a high-stakes military job interview dressed in my chemical battle-suit rather than the expected dress uniform. It was a Level 5 tactic that – by design – freaked out the Level 2 interviewers. Since it was for a job that I knew I wasn’t getting, I chose to amuse myself.
These are very different answers. Each one reveals interesting information about the candidate – if the interviewer is sophisticated enough to understand the answer. Here’s where interviews often get rough.
Consider the interviews that you’ve endured. Interviewers had asked (and will continue to ask) seemingly-simple questions like this in order to evaluate your level of maturity. Many don’t appreciate, however, that they evaluate you as a person based entirely on their own level of sophistication. A brand-new interviewer has very little ability to recognize and evaluate the nuances of a sophisticated, layered answer. An insecure, anxious, or untrained interviewer is also likely to balk at an answer that’s too far outside of their expectations. Remember: if you answer the question at too high a proficiency level, it can be 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 their mind. They’ll come away thinking you’re brilliant because you don’t know that your ‘weakness’ isn’t really a weakness. That’s why so many business writers urge their readers to improve their interviewing skills through careful preparation and cleverness. This tactic works. It’s reliable and effective.
On the other hand, if you give a Level 3 answer to a Level 4 or -5 interviewer, they’ll write you off as a smarmy lickspittle. A seasoned interviewer recognizes that you’re trying to dazzle them. Most experienced interviewers are savvy enough to never let you know that they see through your malarkey. I like to call candidates out on their gambit on the spot and demand an honest, unfiltered answer instead, but that’s strictly a personal preference.
I’ve read far too many advice columns that insist that interviewing is a game of preparation and misdirection; a grand con job based on mathematically-tuned keywords. It’s not. That’s how you game the LMS to get to the interview. The interview is a candid conversation between potential colleagues.
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 delivered a good answer. You might be viewed as ‘too intellectual,’ as ‘arrogant,’ or even get branded 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 simply because you intimidate them. 
The way to make sure that you give an 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, because it requires a very rare mind-set.
When you’re just starting out playing the corporate interview game, this business can seem like navigating a minefield; if you foolishly step in the wrong place, you can blow the entire interview (and with it, your chances of being hired). Interviewing can be frightening and it’s always stressful. As you gain experience in the process, though, the entire process changes. Different metaphors are required. We’ll get into that in the next column in this short series.
 This column is the extended-dance-remix version of the answer I posted on the forum, in that it’s longer, over-engineered, and distorted to the point where it could be argued that it only samples the original to create a derivative work. The first version went up on the LinkedIn management forums. The second went up on Business-Reporter.co.uk a week later. A third version went up as a standalone LinkedIn article that’s still available if you want to compare versions. The fourth, fifth, and sixth versions appeared in the first, second, and third editions of Why Are You Here? Respectively. This edition makes version #7 and I’m certain that I’m not finished messing with it.
 It’s very rare to meet an interviewer who actively seeks out people smarter than themselves and has no worries about being intellectually or technologically overshadowed by their people. Those are the leaders you want to work for at all costs.
POC is Keil Hubert, firstname.lastname@example.org
Follow him on Twitter at @keilhubert.
Keil Hubert is the head of Security Training and Awareness for OCC, the world’s largest equity derivatives clearing organization, headquartered in Chicago, Illinois. Prior to joining OCC, Keil has been a U.S. Army medical IT officer, a U.S.A.F. Cyberspace Operations officer, a small businessman, an author, and several different variations of commercial sector IT consultant.
Keil deconstructed a cybersecurity breach in his presentation at TEISS 2014, and has served as Business Reporter’s resident U.S. ‘blogger since 2012. His books on applied leadership, business culture, and talent management are available on Amazon.com. Keil is based out of Dallas, Texas.