It doesn’t matter whether you are the interviewer or are being interviewed. There are ten questions you should ask yourself about any question you are thinking of asking.

Here they are:

 1. Is my question going to sound clichéd, stale or formulaic, rather than core?

You can find yourself impaled on the horns of a dilemma when it comes to asking formulaic, clichéd questions, such as “Where do you want to be in five years?” or “What are the prospects for advancement within your company?”

Of course, the reason that they are clichéd is that they target important information. However, if the person you are speaking with seems to be a think-outside-the-box type, you may want to hit the pause button on these kinds of questions.

That type will welcome and offer more offbeat, less predictable questions and answers.

2. Am I asking a question (in a way that) that will demonstrate competitiveness, or collegiality?

As a corollary to the principle that communication that emphasizes or is couched in terms of an explicit or implicit “we” is better than “me” or “you”, it can be argued that questions that convey a “we”-collegiality are much better than questions that suggest a “me”-competitiveness.

Note the difference between the following two questions:

  •  “Would I be promoted ahead of a coworker if I have seniority?”
  • “To what extent does the company factor in seniority in best allocating team talent?”

From one standpoint, the two questions are almost indistinguishable—the attempt to determine how much of a factor seniority is in promotion. However, the second question sacrifices explicitness for the sake of concealing dog-eat-dog competitiveness and conveying a commitment to being a team player, with the best interests of all, including the company, at heart.

On the other hand, a company may want a very competitive recruit—especially in one with planned attrition and rewards skewed to standouts. In that case, some variant of the more competitive question may be perfect, e.g., “As I pursue my ambition to rise like cream, will seniority count?”

3. Am I going to sound like I want really want important information, or more like I want to showboat? (To put this differently, will my question suggest I am seeking truth, or triumph?)

Be sure that your question and how you ask it make it sound sincere, rather than like self-aggrandizing, know-it-all horn-tooting. One way to tell in advance is whether the listener is likely to be better informed than you about the answer. If not, the question may come across as intimidating and contrived to make you look good (at the listener’s expense).

One precaution in this connection is to refrain from asking pedantic, esoteric, jargonized questions that are borderline incomprehensible.

On the other hand, one green light to ask precisely that kind of question is the listener’s use of the same kind of language prior to your asking, e.g., “non-linear vertically integrated, modularized and quasi-autonomous valued-added production steps”.

Apart from asking what all of that means, you should feel free to fire off a question couched in the same terms.

4. Is the question going to suggest that I am ignorant or stupid, rather than eager?

Never ask a question intended to demonstrate great interest and that you could easily find the answer for with the click of a mouse, e.g., “How global are your operations?” or “Is Harvard still all-male?”

In general this is a greater risk for applicants than recruiters, since displays of great interest are generally expected of the job seeker, not the job filler.

5. Will my question sound like informed acknowledgement, or like sucking up?

“How did the company become such a leader in the area of financial management?” is a craftily crafted question that incorporates a positive statement as a presumption, namely, “Your company is a leader in the area of financial management.”

(In logic this is called a “complex question”, and asking it when the presumption is incorrect is called the “fallacy of complex question”, the classic example being “Have you stopped beating your wife?”—asked when you’ve been doing no such thing.)

This can be risky, because it may be seen as blatant sucking up. Sure, on the surface, it conveys an awareness or at least belief that the company is a leader; but from just a rung down on the ladder of consciousness, it looks like classic brown-nosing.

6. Will I sound nosy, aggressive and invasive, rather than interested?

Beware questions that are may sound snoopy. To this end, you had better be able to judge whether a question expressed with a genuinely curious, but non-invasive intent will be perceived that way. One huge clue is how much “insider” or non-formulaic information the listener has been volunteering. The more of that, the smaller the risk.

A second indicator is how “open” the listener seems in other respects. The more casual the tone of voice, body language, etc., the more likely it is that (s)he isn’t so guarded as to take your question the wrong or worst way.

A third test is whether the answer could, by any stretch of the imagination, compromise the listener or you by being invasive, e.g., through “betrayal” of confidences, embarrassment, overstepping of authority, borderline illegality (“So, you’re not married?”) or pressure (“How am I doing in this interview?” or “Are you prepared to sign with us today?”) or “complex questions” that, in making factual presumptions that may be politically or factually incorrect, are offensive (“When your colostomy bag leaks at work, how do you cope with that emergency?”).

If your question fails that test, ask something else.

7. Will the question suggest I am asking in order to express, explore, or elicit something and is my actual intention clear?

None of these three is an improper purpose of a question. But you should be sure of your objective in asking it and that the specific objective is OK with the listener or perceived as intended.

For example, you may be asking “Does your company prefer M.B.A.s with science backgrounds like mine?” to elicit the information the question seems to be posed to get.

But the listener may think that your purpose is really to express or brag about having both an M.B.A. and a science background—possibly resenting the further presumption that (s)he hasn’t read your resume.

Likewise, asking in a hospital interview with the oncology department, “Have you considered replacement of your laparoscopic surgery with a da Vinci robotic surgery system?” as a genuinely exploratory or information-eliciting question may be perceived as expressing a bias or pressure favoring robotic systems.

8. Is the question (likely to be seen as) a trap or a switch-and-bait set-up for something else?

A recruiter asks the candidate, “Would you prefer to telecommute, or work in the office?”—asked before letting the candidate know that telecommuting will be introduced (no sooner than) a year and a half later.

When that news is broken, (s)he may feel tricked and trapped—tricked into divulging a potential disqualification if the answer given was “telecommute” and trapped as a caught, caged and labeled non-conformist telecommuterist.

Even if the “correct” answer is given, the candidate may be left with the impression that the recruiter is (being) devious, which can influence the decision to take the job or not, if it’s offered (after that answer).

9. Will my question be seen as an evasion?

If you answer a question with a question, you will run a high risk of being seen as evasive—as dodging the initial question. For example, the candidate asks, “What is the company policy on working from home?” The recruiter replies, “How do you feel about working exclusively from the office?”

This response accomplishes two things—neither good: 1. It dodges the question, thereby making the recruiter seem evasive and not forthright; 2. It creates an uncomfortable ambiguity—uncertainty about whether the question-as-answer means “no”, whether it’s a test of candidate flexibility, whether it’s a kind of counter-proposal, whether it’s pressure to conform to existing company culture, or whether it’s simply an off-the-cuff expression of curiosity.

10 .Does the question convey a sense of entitlement or presumption in its content, timing or tone?

To complicate matters, what makes a question good or bad, wise or unwise is not always its content. It may be its timing, the status differences between the questioner and the listener, the tone with which the question is asked or even the body language, e.g., “steepling”—finger tips of one hand pressed against those of the other to form a triangle that looks like a church steeple worthy of an infallible pontiff.

“Can I switch shifts with a coworker for my daughter’s birthday party?” is not something to be asked until after being hired.  Timing counts here. To ask it before that is to communicate presumptuousness and an irritating sense of entitlement.

If that birthday party is scheduled for the first day of work (assuming being hired is very likely) and some variant of the question must be asked, it could be put this way: “Forgive me if this seems premature or presumptuous—I feel awkward asking—but, if I were to be given this job opportunity, would I be able to request—as a one-time emergency request—that someone fill in for me or that I have time off for my daughter’s backyard birthday party?”

Even if this wording doesn’t appeal to you, it does illustrate a fundamental principle of question asking: When you want to ask a favor in or outside of an interview, without conveying a sense of entitlement or presumption, use a lot more words.

For some reason, when asked this way, most people regard the verbiage as an investment and humble deference, much as Wimpy’s (the Popeye cartoon character’s) “I’d gladly pay you Tuesday for a hamburger today”, although bolder than a question, seems softer and more polite than “Can I put it on my tab?”

Having put this principle of prolixity into practice, I can say that, judging from the substantial length of this article, I may have reason to hope you’ll be so kind as to judge what I’ve said favorably and patiently…

…at least until next Tuesday.

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